Maitland FL Real Estate, Homes with Pool for Sale - Pinecrest Real Estate Management

4 Beds ⋅ 2 Baths ⋅ Forest Brook 4th Sec SubDv. ⋅ 32751 Zip Code

Updated 4-bedroom, 2-bath heated pool home situated on a .27-acre corner lot in the sought-after Forest Brook neighborhood. From the moment you arrive, you’ll notice the paver driveway, mature landscaping, pops of color, and warm wood accents that give the home great curb appeal. Step inside to an open floor plan with soaring ceilings and plenty of natural light. The spacious living room features vaulted ceilings and offers plenty of flexibility for different furniture layouts. At the center of the home is the updated kitchen, highlighted by a level 3 stone countertop island with breakfast bar seating and pendant lighting. Shaker-style cabinetry, a dry bar, tile backsplash, decorative molding, single-basin sink, and updated cabinet hardware complete the space. Just off the kitchen is a bright dinette with sliding glass doors leading to the covered patio. The split-bedroom floor plan places the primary suite on one side of the home, with bedrooms 2, 3, and 4 and the second bathroom on the opposite side. The primary bedroom features a beautifully updated ensuite bath with marble tile flooring, dual-sink vanity, level 3 stone countertops, and a spacious frameless glass walk-in shower with upgraded tile and dual rainfall shower heads. A large walk-in closet provides plenty of storage. The secondary bedrooms have also been updated and include built-in closets. The indoor laundry room offers additional space for shelving and storage. Outdoor living is a big part of this home. Sliding glass doors open to a screened and covered patio with tile flooring overlooking the fenced backyard and solar-heated pool. The pool was resurfaced in 2017, and the pool pump was replaced in 2021. Make this space your own personal outdoor oasis. Major updates include a NEW ROOF in 2025, HVAC in 2024, and newer exterior paint. Forest Brook has a optional HOA and offers a convenient Maitland location with easy access to Winter Park, Baldwin Park, Audubon Park, Winter Springs, Oviedo, SR-417, UCF, shopping, dining, and more. A move-in-ready pool home with plenty of updates, indoor space, and outdoor living!

812 Woodside Road, Maitland

$115,000

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Welcome to 484 Banyon Tree Circle, Unit #100, Maitland, a well-updated 1 bedroom, 1 bathroom FIRST-FLOOR condo offering 759 square feet of comfortable living space. This move-in ready unit features a functional layout, a modern kitchen with granite countertops, and an IN-UNIT WASHER AND DRYER COMBO for added convenience. The spacious primary bedroom offers a walk-in closet. The living room has sliding glass doors that provide direct access to the front porch, creating a great space to enjoy your morning coffee or relax outdoors. Enjoy resort-style community amenities including a community pool, fitness center, clubhouse, and playground. The first-floor location provides easy access with no stairs, making everyday living simple and convenient. Ideally located in Maitland, close to shopping, dining, entertainment, major highways, and everything Central Florida has to offer. Whether you're looking for a comfortable primary residence or an investment opportunity, this condo is a great place to call home. Schedule your showing today!

484 Banyon Tree Circle Unit 100, Maitland

$218,400

2 Beds ⋅ 2 Baths ⋅ Building 14 Visconti West SubDv. ⋅ 32751 Zip Code

Auction Property. Auction Property. AUCTION/OCCUPIED. Buyers will be required to sign a occupancy declaration. 2-bedroom 2-bathroom condominium in gated community of Visconti West situated off Lake Shadow. Quick access to interstate 4 and Florida turnpike. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or guarantee occupancy status. NO VIEWINGS of this property. Please DO NOT DISTURB the occupant. Buyer is responsible for obtaining possession of the property upon closing.

1225 Lake Shadow Circle Unit 14102, Maitland

$350,000

3 Beds ⋅ 2 Baths ⋅ Floridahaven 1st Add SubDv. ⋅ 32751 Zip Code

Rare opportunity in desirable Maitland! Bring your builder and your vision to this approximately .40-acre homesite located directly across the street from Lake Seminary. Situated in an established residential area, this property offers an excellent opportunity to create a custom home in a highly desirable Central Florida location. Home has lake access & Community Park. The existing structure is in poor condition with known mold present and is being marketed primarily for its land and redevelopment potential. Buyers should anticipate demolition or substantial redevelopment of the existing home. The backyard also features an existing in-ground swimming pool that has been drained. No representations are being made regarding the condition, functionality, or future usability of the pool. With approximately .40 acres, there is plenty of room to envision a beautiful new residence and outdoor living space designed to take advantage of this desirable Maitland setting. Enjoy being directly across from Lake Seminary while remaining convenient to Maitland, Winter Park, shopping, dining, recreation, and major roadways. Build new. Create your vision. Take advantage of a hard-to-find .40-acre homesite in an established Maitland location. Property is being sold AS-IS. Buyer and Buyer’s Agent are responsible for independently verifying all information important to Buyer, including zoning, lot dimensions, building requirements, utilities, demolition requirements, permitting, pool condition, and intended use. Do not enter the existing structure without authorization.

265 Lake Seminary Circle, Maitland

$650,000

3 Beds ⋅ 4 Baths ⋅ Bretton Woods SubDv. ⋅ 32751 Zip Code

Elegant Pool Home with Classic Florida Charm & Modern Comfort in Bretton Woods. Discover timeless charm and modern convenience in this stunning brick ranch, ideally situated on an expansive lot in desirable Bretton Woods. Thoughtfully updated for today’s lifestyle, this one-of-a-kind home combines character, comfort, and exceptional functionality. It’s easy to fall in love with this special property from the moment you arrive. Mature oak trees frame the front yard, while a welcoming porch sets the stage for the beautifully updated interior, featuring engineered hardwood flooring and a gourmet kitchen outfitted with top-of-the-line stainless steel appliances, including an induction Bosch cooktop, GE Monogram French door wall oven, GE Advantium microwave/oven, GE French door refrigerator, and KitchenAid dishwasher. A butler’s pantry provides exceptional storage and a seamless extension of the gourmet kitchen, making entertaining and everyday living effortless. The spacious owner’s suite offers a private retreat with an en-suite bath and cedar sauna. French doors open to an enclosed spa for the ultimate relaxation experience. A generous guest suite includes its own full bath and walk-in closet. A centrally located half bath provides added convenience for family and guests, while a separate full pool bath offers easy access from the outdoor living spaces. Recent improvements provide added peace of mind, efficiency, and year-round comfort. These include a newer roof, kitchen and powder room remodel, new Trane HVAC system with new ductwork featuring three separate zones, each with its own thermostat, new windows, pool pump, irrigation controls, and exterior paint. Step outside to your own private oasis. The expansive, fully fenced backyard features a sparkling pool framed by a large screened lanai, offering the perfect setting for entertaining, relaxing, or enjoying Florida’s beautiful weather. A large double gate provides convenient side-yard access for boat parking, while an outdoor shower adds to the poolside experience. Practicality is just as impressive, with a sizable laundry room, abundant storage, a circular driveway, and a two-car garage. A dedicated parking pad in front of the garage can accommodated an RV. Blending the warmth and character of old Florida with thoughtful modern updates, this exceptional property offers space, privacy, and convenience just minutes from I-4 and all that the Orlando area has to offer. A truly distinctive home with an unforgettable combination of charm and amenities to accommodate your lifestyle.

1501 Oranole Road, Maitland

$215,000

3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Need Room! Welcome home to this spacious 1612 S.F. first-floor condominium featuring three bedrooms and two full baths in a well-maintained community conveniently located near shopping, dining, and Full Sail University. Step inside to find brand-new luxury plank flooring throughout the living and bedroom areas, ceramic tile in the kitchen and bathrooms, and absolutely no carpet! Blinds on all windows and ceiling fans add to the comfort and convenience of this inviting home. The kitchen comes complete with refrigerator, range, microwave, and dishwasher, while a brand-new washer and dryer are also included. Relax and enjoy Florida's beautiful weather year-round from your private screened-in lanai, with the community pool and playground conveniently located nearby. The HOA offers exceptional value by covering water, sewer, trash, building insurance, roof, grounds maintenance, and the community pool. With its desirable first-floor location, fresh updates, generous three-bedroom floor plan, and convenient location, this condo offers easy Florida living and is ready for you to make it home!

2308 Haywood Court Unit 100, Maitland

$749,000

3 Beds ⋅ 3 Baths ⋅ Bretton Woods SubDv. ⋅ 32751 Zip Code

LAKEFRONT LIVING IN THE HEART OF MAITLAND WITH EAST/WEST EXPOSURE! Set on approximately .68 acres with an impressive 115 feet of frontage on beautiful Wood Lake, this gorgeous updated 3-bedroom, 3-bath residence offers the perfect blend of timeless character, modern updates, and effortless Florida living with the potential to add your own private dock. From the moment you step inside, expansive windows and skylights fill the home with natural light while framing tranquil views of the water. Beautifully restored terrazzo floors bring vintage character back to life, complemented by fresh interior paint, renovated bathrooms, and new LED lighting throughout. At the heart of the open living spaces, a striking double-sided fireplace creates a dramatic focal point connecting the living and dining areas. The spacious kitchen offers an incredible opportunity to create a custom chef's kitchen tailored to your style. The waterfront primary suite is a true retreat, featuring floor-to-ceiling windows overlooking the lake and a private en-suite bath with large closet and dressing room. Two additional generously sized bedrooms, one with an en-suite provide flexibility for family, guests, or a dedicated home office. Step outside and discover your own private waterfront oasis. A new saltwater pool, added in 2023, overlooks the lake and creates a spectacular backdrop for entertaining, relaxing in the sun, or enjoying peaceful evenings by the water. With approximately 115 feet of lake frontage, there is plenty of room to embrace the lakefront lifestyle bring your paddleboard, kayak, canoe, or other non-motorized watercraft and launch your next adventure right from your backyard. Thoughtful improvements include a 2020 roof, 2021 HVAC, and updated electrical and plumbing within the last 10 years, offering added peace of mind while preserving the home's distinctive character. Ideally positioned with convenient access to Winter Park, Maitland, and Altamonte Springs, as well as exceptional dining, shopping, medical facilities, parks, and major roadways, this one-of-a-kind property delivers the rare combination of space, privacy, character, and waterfront living all in the heart of Central Florida.

255 Wood Lake Drive, Maitland

$415,000

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome to beautiful Montacino, Enclave at Maitland, a well maintained Mediterranean inspired gated community. This well appointed town home features three bedrooms and two and 1/2 bathrooms. The first floor is a desirable open floor plan with a welcoming foyer, 1/2 bathroom, fully tiled living/dining room, kitchen with bar top and access to the first floor covered patio. The kitchen has beautiful rich cabinetry, dark granite countertops with newer stainless steel appliances as well as pantry for additional storage space. The second floor features all three bedrooms, two bathrooms and ideally located central laundry closet with 2 year old (high capacity) washer and dryer included. The primary bedroom features a private ensuite bathroom with an updated double vanity, gorgeous walk-in shower with rain shower option, a walk in closet with built-in storage cabinets and a private balcony overlooking community green space. The flooring on the second floor is luxury vinyl plank in the bedrooms and hallway and tile in the bathrooms. (carpet only on stairwell). The interior was just freshly painted and new fans were added in the living room and primary bedroom, allowing for a turnkey move-in ready experience. Additionally there are high end plantation shutters throughout! There is an attached one car garage and private paver driveway as well as open community parking. Montacino features a resort style community pool and beautiful sidewalks overlooking Lake Charity perfect for an evening stroll. All this with exceptionally easy access to I-4 and Maitland Blvd allow for convenient shopping and dining and commuting. Schedule a tour today!

1257 Blessing Street, Maitland

$130,000

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

**LOCATION, LOCATION!** Welcome to this charming and cozy 1-bedroom, 1-bathroom condo, ideally located in a convenient and desirable area near Semoran Blvd and Howell Branch Rd. This move-in-ready second-floor unit offers comfort, convenience, and easy access to everything you need. Enjoy being just walking distance from shopping, restaurants, supermarkets, and everyday essentials. The community offers a refreshing swimming pool, perfect for relaxing or enjoying quality time with family and friends, as well as ample parking for residents and guests. The property is also conveniently located near schools and educational institutions, including Rollins College, making it an excellent opportunity for professionals, or anyone looking for a convenient Central Florida location. HOA includes water, adding even more value and convenience. Whether you're looking for your next home, a low-maintenance place to live, or an investment opportunity, this condo is one you won't want to miss! Schedule your showing today and come see all this property has to provide.

2520 Caper Lane Unit 204, Maitland

$200,000

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Welcome to 2637 Legacy Villas Drive, a spacious 2-bedroom, 2-bath residence located in the gated Visconti community in Maitland. Offering 1,280 square feet of living space, this home features a comfortable and functional floor plan along with the added convenience of a private 2-car garage. Enjoy everything the Visconti community has to give, including a resort-style swimming pool, clubhouse, fitness center, tennis courts, basketball courts, playground, and gated entry. The community's recreational spaces and amenities provide plenty of opportunities to enjoy the Central Florida lifestyle. Conveniently located in Maitland with easy access to I-4 and major roadways, the property offers a short commute to Downtown Orlando and convenient access to shopping, dining, entertainment, and employment centers throughout the Orlando area. Whether you're looking for a primary residence or an investment opportunity, this 2-bedroom, 2-bath home combines generous living space, a private 2-car garage, desirable community amenities, and a convenient Maitland location.

2637 Legacy Villas Drive Unit 2637, Maitland

$229,000

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

LOCATION LOCATION LOCATION! The Park Lake Townhome Community is Maitland's hidden treasure! Offering for sale this well-maintained townhome with 2 levels of comfortable living, a one-car garage, a nice sized laundry room under air, along with a private screened back patio. As you step inside, look over your shoulder at the community pool that is literally steps from your front door! Once inside you will immediately fall in love with the wood-look easy care tile throughout the first floor. The large living room has the cutest window seat, streaming in tons of natural sunlight, with room for many different seating configurations. A convenient half bath to your left leads you into the kitchen and dining areas of the home. The large open concept kitchen features new appliances and shiny granite countertops with plenty of counterspace for the chef in the family. Off the dining area you'll find a set of sliding glass doors leading out to a private screened-in patio, perfect for morning coffees, grilling or entertaining friends and family. The patio also provides access to the attached one-car garage with garage door opener. This garage leads into the oversized indoor laundry room complete with a washer and dryer and a large storage area. As we head up the stairs, you'll notice the brand-new carpet in a lovely neutral color running on the stair treads and into the first bedroom for comfort and style. The 2nd bedroom features the wood-look flooring for added convenience. Both bedrooms share a well-appointed en-suite bathroom with a newly reglazed tub and shower. Freshly painted inside makes this home truly turn-key. Residents of the Park Lake Townhome Community not only enjoy the sparkling community pool, but your HOA also covers trash collection, exterior maintenance (including the roof!) and lawn care! Low Maintenance Living at it's Best! And have I mentioned this AMAZING LOCATION? This lovely townhome community is less than 1 mile from N Park Avenue and less than 1/2 mile to 17/92 (Orlando Avenue)! The convenience to Maitland City Center, Rollins College, shops, restaurants, and the ease of commuting to work is 2nd to none. Make an appt to see this home, it is a gem and won't last! Note, some photos have been virtually staged for furniture placement.

856 Park Lake Circle Unit 51, Maitland

$460,000

3 Beds ⋅ 2 Baths ⋅ Floridahaven 1st Add SubDv. ⋅ 32751 Zip Code

Charming 3-bedroom, 2-bath pool home in Maitland with tons of potential! This home is ready for a buyer with the vision to renovate, restore, and make it their own. The property needs substantial TLC throughout, but offers a wonderful opportunity to customize it to your personal style. Features include a private pool, screened patio, spacious yard, and covered parking. Conveniently located near shopping, dining, schools, and major roadways. Property is being sold AS-IS. Seller will not make repairs. Cash or conventional financing only.

315 Lake Seminary Circle, Maitland

$825,000

3 Beds ⋅ 3 Baths ⋅ Oakland Shores SubDv. ⋅ 32751 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this gorgeous, move-in-ready 3-bedroom, 2.5-bath POOL home in the desirable Oakland Shores neighborhood of Maitland! Situated on an oversized, beautifully landscaped lot, this exceptional home welcomes you with mature landscaping, a large circular driveway, and additional side parking ideal for a boat or RV. Inside, you’ll immediately appreciate the light and bright open feel, luxury vinyl flooring, and crown molding throughout the main living areas. The formal living room flows seamlessly into the dining and family rooms, all overlooking the spectacular resort-style pool and backyard. The expansive sparkling pool is surrounded by a custom pavered patio with multiple spaces for lounging, dining, and entertaining, while the generous green space and privacy create your own backyard retreat. The beautifully appointed kitchen features quartz countertops, white shaker cabinetry, stainless steel appliances, a center island with sink, walk-in pantry, and a charming dining nook with custom seating. The spacious primary suite offers direct pool access, a huge walk-in closet with a custom organizing system, and a spa-like ensuite bath complete with dual sinks, vanity, garden tub, and separate glass-enclosed shower. Two generously sized secondary bedrooms share an upgraded full bath, while an additional upgraded half bath provides convenience for guests. A well-designed interior laundry room includes built-in cabinetry and direct access to the yard. One of the home’s most versatile features is the large bonus room, complete with a spacious walk-in, air-conditioned storage room. Whether you envision a home gym, classroom, office, creative space, or potential mother-in-law suite, the possibilities are endless. Recent updates provide additional peace of mind, including a roof and septic system replaced in 2017. The septic was recently cleaned in 2025 with the filter replaced. Additional upgrades include electrical, fencing, water heater, pool pump, interior paint, HVAC, irrigation pump, plumbing, and windows. Oakland Shores offers a wonderful neighborhood setting for walking and includes deeded access to Lake Faith, a non-motorized lake great for paddle boarding and kayaking, with a community access point on Lake Shore Drive. Conveniently located near shopping, dining, major roadways, and the newly planned Maitland Trader Joe’s, this home combines comfort, versatility, privacy, and an ideal Maitland location. With its beautiful pool, oversized lot, extensive updates, and flexible living spaces, this is one you won’t want to miss!

505 Oak Lane, Maitland

$699,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

This move-in-ready 4-bedroom, 3-full-bath pool home is located in the beautiful Dommerich Estates! (A NEW ROOF is scheduled to be installed in late September/early October.) Enjoy a waterfront lifestyle just steps from your front door, with access to a private community boat ramp, fishing pier, picnic tables, built-in grills, social events, and endless sunset views along the shoreline of Lake Minnehaha. Lake Boat access is available to Dommerich Estates residents for just $150 annually. Walk or bike to Dommerich Elementary and Maitland Middle. High school is Winter Park High. Beyond the community amenities, you’ll love exploring the multiple nearby resident parks (Maitland Community Park is just a short walk away from the home) featuring canopied tree-lined walking and biking trails, playgrounds, tennis courts, lush gardens, and so much more. Inside, this spacious home offers a desirable split-bedroom floor plan, with the over-sized private primary suite thoughtfully separated from the three additional bedrooms. Build in surround sound speakers. There is no carpet—the home features beautiful travertine and tile flooring throughout. Step outside to your own private oasis! The huge swimming pool is the centerpiece of the expansive screened-in outdoor living area, complete with an oversized paver lanai—perfect for relaxing, entertaining, and enjoying the Florida lifestyle year-round. Additional features include a 2-car garage and paver driveway. A NEW ROOF is scheduled to be installed in late September/early October. A wonderful opportunity to enjoy the comfort of a move-in-ready home with exceptional community amenities. (Throughout the home are pieces of Stickley furniture that are available for sale)

431 Arapaho Trail, Maitland

$175,000

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Welcome to 1150 Lake Shadow Circle, Unit 3305, a 2-bedroom, 2-bath condominium located in the gated Visconti community in Maitland. Situated on the third floor, this 1,048-square-foot residence offers a functional floor plan with comfortable living spaces, luxury vinyl flooring, crown molding, ceiling fans, and the convenience of an in-unit washer and dryer. Step outside onto your private balcony or take advantage of the community's extensive amenities. Visconti residents enjoy access to a swimming pool, clubhouse, fitness center, tennis courts, playground, sidewalks, and gated entry. Conveniently located in Maitland with easy access to major roadways, the property is a short commute to Downtown Orlando and close to shopping, dining, entertainment, and everything Central Florida has available. Whether you're looking for a primary residence or an investment opportunity, this 2-bedroom, 2-bath condo combines a convenient location, desirable community amenities, and comfortable Florida living.

1150 Lake Shadow Circle Unit 3305, Maitland

$699,000

4 Beds ⋅ 3 Baths ⋅ Hidden Estates Unit 3 SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. RARE OPPORTUNITY! Nestled on .68 acres in one of Maitland‘s most established and beautiful neighborhoods, Hidden Estates, this single story 4 bedroom, 2.5 bath pool home is filled with loads of character and charm. Once you enter the handsome foyer with brick flooring, you will notice the spaciousness of this home, which is one of its greatest features. The beautiful mature landscaping and plenty of room to enjoy the outdoors provides this property with an incredible sense of privacy that is so increasingly hard to find! The great room with brick fireplace and adjacent living room, as well as the kitchen, overlook the large pool and expansive deck just perfect for entertaining or simply relaxing in your own backyard retreat. The inside utility room and half bath are conveniently located right off of the kitchen. The large game room/office/workout room has lots of cabinetry for wonderful storage space. The home’s layout offers tremendous potential for a buyer ready to renovate while preserving its unique warmth and character. Convenient access to shopping, dining, schools, and medical facilities adds to it’s desirable location. This long time, family home awaits its next chapter, offering it’s new owner an exceptional setting to preserve or create something truly special. Look forward to seeing you there!

212 Flame Avenue, Maitland

$375,000

2 Beds ⋅ 2 Baths ⋅ Maitland House SubDv. ⋅ 32751 Zip Code

LOCATION, LIFESTYLE & LOW-MAINTENANCE LIVING IN THE HEART OF MAITLAND/WINTER PARK! Welcome to Maitland House, a hidden gem perfectly positioned between Maitland and Winter Park, where convenience, character and an unbeatable lifestyle come together. Located just steps from the iconic Enzian Theater and its lush Eden Bar, and minutes from Winter Park Village, Lake Lily and Park Avenue, this beautifully updated second floor 2 bedroom, 2 bath condo puts some of Central Florida’s best dining, entertainment, shopping and nightlife right outside your door. Inside, you’ll find a bright and inviting open floor plan with thoughtful updates throughout. The spacious living area features a wood burning fireplace, granite countertops, plantation shutters and custom-built closet systems with abundant shelving, drawers, shoe storage and hanging space. Step outside to your screened, pool view porch, the perfect spot for morning coffee, an evening glass of wine or simply enjoying the peaceful surroundings. The kitchen is equipped with a 2025 dishwasher, 2021 refrigerator, range and microwave, while the home also features a BRAND NEW water heater. The 2019 HVAC system includes electrostatic filtration and a UVC air purification system, with air ductwork replaced in 2024. Additional improvements include updated windows and attic insulation replaced in 2021. Maitland House offers the kind of amenities and conveniences that make everyday living easy. Enjoy a tranquil pool and clubhouse, community bathrooms, Weber Genesis grill, covered dog walk area, community laundry room with three large washers and three dryers, covered assigned parking and an assigned storage unit. The community itself has been well maintained, with exterior painting completed in 2025 and the parking lot resurfaced in 2026. And the HOA delivers exceptional value. Included with the association are water, sewer, exterior maintenance, and an impressive Spectrum entertainment and connectivity package. Schedule your showing today!

210 Magnolia Road Unit 207, Maitland

$950,000

5 Beds ⋅ 4 Baths ⋅ Oakleigh Third Add SubDv. ⋅ 32751 Zip Code

Coveted Maitland Location – Renovate or Build New! A rare opportunity to create your dream home in one of Maitland’s most sought-after communities. Situated on nearly half an acre along a quiet, beautiful street, this 5-bedroom, 3.5-bath home offers a spacious floor plan, an oversized pool, and endless potential. Renovate the existing home and make it your own or take advantage of the incredible homesite and build the home you’ve always envisioned. With the property already replumbed and rewired, there’s a great foundation for a thoughtful renovation. And then there’s the location—you simply can’t beat it. Enjoy the charm and convenience of Downtown Maitland, with its local restaurants, shops, farmers market, parks, and community events all nearby. Stroll to neighborhood favorites, spend a morning at the Maitland Farmers Market, or enjoy the beautiful grounds, museums, and gardens of the Art & History Museums of Maitland. Winter Park and Park Avenue are just a short drive away, along with convenient access to major roadways and the airport. Whether you choose to reimagine the existing home or start fresh, this is a special opportunity to create something truly your own in a community you’ll never want to leave.

60 Oakleigh Lane, Maitland

$250,000

3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Move-in ready 3-bedroom, 2-bath condo in the heart of Maitland! This beautifully maintained home features an open-concept layout, abundant natural light, and ceramic tile flooring throughout. The updated kitchen offers generous cabinetry, stylish countertops, decorative backsplash, stainless steel appliances, breakfast bar, and views of the community pool. The spacious primary suite features a walk-in closet and private ensuite bath, while two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy the convenience of a full-size stacked washer and dryer, ample storage, and generous closet space. Community amenities include a sparkling pool, picnic areas, BBQ grills, and mature landscaping. Ideally located within walking distance of Casselberry Commons, offering Publix, Starbucks, shopping, dining, and more, with easy access to major highways and Central Florida attractions.

416 Banyon Tree Circle Unit 108, Maitland

$184,900

2 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

**Welcome to Carrington Park, a beautifully maintained community in the heart of Maitland!** This spacious **2-bedroom, 2-bathroom condo** offers **over 1,200 square feet** of comfortable living space and has been lovingly cared for as a seasonal winter home, reflecting its exceptional condition throughout. Step inside to discover a bright and inviting floor plan featuring **vaulted ceilings**, **no carpet throughout**, and **newer kitchen appliances**, creating a clean, low-maintenance living environment. The home is being offered **mostly furnished**, making it an ideal opportunity for a primary residence, seasonal retreat, or investment property. Enjoy the convenience of a well-maintained community with a beautiful swimming pool and peaceful surroundings, all while being just minutes from abundant shopping, popular restaurants, entertainment, and major roadways for easy access throughout Central Florida. Located in one of Maitland's most established and desirable areas, this move-in-ready condo combines comfort, convenience, and exceptional value. **Whether you're looking for a full-time residence, a winter getaway, or an investment opportunity, this is a home you won't want to miss. Schedule your private showing today!**

2305 Haywood Court Unit 203, Maitland

$130,000

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Discover comfort, style, and convenience in this beautifully renovated and tastefully furnished first-floor condominium in the centrally located Carrington Park community. This inviting home features brand-new tile flooring throughout and a thoughtfully updated kitchen with wood cabinetry, stainless steel appliances, granite countertops, and a spacious pantry for excellent storage. The generously sized bedroom includes a walk-in closet, offering plenty of room for organization. The updated bathroom features a walk in shower, new toilet and vanity. Carrington Park provides a desirable lifestyle with multiple swimming pool areas, a fitness facility, playground, and a peaceful courtyard for relaxation. Ideally located just steps from shopping and near the intersection of Howell Branch Road and 436, this condo offers easy access to major destinations, including UCF, Valencia, and Full Sail. A great opportunity for those seeking a move-in ready home in a convenient central location.

476 Banyon Tree Circle Unit 104, Maitland

$425,000

3 Beds ⋅ 2 Baths ⋅ Forest Brook 2nd Sec SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Waterfront potential on Brookside Circle! Classic 3-bedroom, 2-bathroom property situated directly on peaceful Howell Creek with canoe access to Waumpi Lake. Renovation opportunity! The interior layout includes a living room with a window nook, a dedicated dining area, and a primary suite located off the dining room. The kitchen features a breakfast nook and opens directly into the main living area. A split floor plan places two secondary bedrooms on the opposite side of the home, alongside an indoor, air-conditioned laundry room. The second full bath opens directly to the screened pool deck to serve as a dedicated pool bath. The property sits on an expansive lot featuring a wide side yard and a deep backyard running along the creek. Filled with warmth and pride of ownership, the home showcases unique, hand-painted artistic touches throughout that reflect years of love—ready for the next owner to bring their own style. Ready for a complete transformation, this property presents an exceptional waterfront renovation opportunity. Schedule your tour today!

535 Brookside Circle, Maitland

$340,000

3 Beds ⋅ 2 Baths ⋅ Sierra Condo Ph 2 SubDv. ⋅ 32751 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom condo in the desirable Sierra Condominium Association, offering a comfortable split-bedroom floor plan, private attached garage, exceptional curb appeal, and a serene outdoor setting. The meticulously maintained landscaping features a stunning bougainvillea plant, adding vibrant color and charm to the home's inviting exterior. Inside, wood flooring extends through the family room, hallway, and primary bedroom, adding warmth and character to the living spaces. The spacious family room features a wood-burning fireplace and additional storage closet space, providing both a cozy gathering area and convenient functionality. The kitchen offers 42-inch wood cabinetry with ample storage and provides a functional space for everyday cooking and entertaining. The open flow into the main living areas makes it easy to stay connected with family and guests. The split-bedroom floor plan provides added privacy, with the spacious primary suite thoughtfully separated from the additional bedrooms. The primary bedroom features wood flooring, while both full bathrooms are equipped with walk-in showers and porcelain tile flooring, adding a clean, durable, and stylish finish. The HVAC system was replaced in 2020 and has been routinely serviced for added peace of mind. Enjoy the tranquility of your private outdoor space with a paver patio and covered pergola overlooking a peaceful creek—an ideal spot for morning coffee, outdoor dining, or unwinding at the end of the day. The property also includes a private attached one-car garage, providing convenient parking and additional storage. Residents of the Sierra Condominium Association enjoy desirable community amenities, including a community swimming pool and tennis courts, with cable and internet included in the association fees for added convenience and value. Conveniently located near shopping, dining, entertainment, and major roadways, this home provides easy access to Orlando and surrounding communities while offering a peaceful retreat to call home. Combining low-maintenance living, beautiful landscaping, thoughtful storage, desirable amenities, and a tranquil creekside setting, this Sierra condo is an opportunity you won't want to miss.

2362 Sierra Lane, Maitland

$239,000

3 Beds ⋅ 3 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Welcome to this beautiful 3-bedroom townhouse in the desirable gated community of Visconti East in Maitland! This spacious townhouse features three levels, an open-concept living and dining area, a well-appointed kitchen, and plenty of natural light. The primary suite and additional bedrooms are located upstairs, along with a convenient laundry area. The third bedroom offers flexibility as a home office, den, or guest room. The attached two-car garage provides convenient parking and additional storage. Residents of Visconti East enjoy resort-style amenities, including two swimming pools, a 24-hour fitness center, tennis, basketball and pickleball courts, a clubhouse, and beautifully maintained grounds. Ideally located near I-4 and major roads, with easy access to shopping, dining, Winter Park, Downtown Orlando, and Central Florida's many attractions. This home is an excellent opportunity for a primary residence or investment property with strong rental potential. Schedule your private showing today!

1807 Shadow View Circle Unit 1807, Maitland

$184,900

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

Look at that NEW Price! You decide to move in Now and upgrade as you go, benefitting from this below market price point, or Fix it up as little or as much as you want and keep the added Equity. 2 Bedroom, 1.5 Bath Townhouse with Living and Dining Rooms, Single Car Garage, Inside Laundry Room, and Oversized Fenced Patio. Located between 17-92 & I-4 with short commute to Winter Park, Downtown Orlando, or Maitland Center. Community Features include Swimming Pool less than 50 yards from Unit as well as Dock on Lake in Community. All Appliances in Unit. All Electrical Panels replaced July 2026, Alumicons to satisfy insurance for aluminum wiring added July 2026, Air Conditioning Replaced in 2016, Hot Water Heater in 2018, Garage Door in 2021. Sold As Is, Priced based on current condition.

895 Park Lake Circle Unit 75, Maitland

$219,900

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Impressive - 2 bedroom 2 bath condo on first floor in resort style community of Visconti Maitland. This recently remodeled unit features designer paint throughout, berber carpet, new ceramic tile, a gourmet kitchen with contemporary light grey cabinets, stainless steel appliances and laundry room with w/d hook ups. Community offers its residents 2 tropical pools overlooking Lake Shadow, a fitness center, tennis - and basket ball court and car wash area. Located within minutes to major shopping, entertainment and I-4.

1475 Lake Shadow Circle Unit 6105, Maitland

$239,000

2 Beds ⋅ 2 Baths ⋅ Park Lake Villas Condo SubDv. ⋅ 32751 Zip Code

Virtually Staged. Rare updated 2/2 | | Top-Rated Schools Welcome to peaceful Park Lake Villas! This fully updated single-story condo has spacious living, major energy-efficient upgrades, and an unbeatable location zoned for Dommerich Elementary, Maitland Middle, and Edgewater High. Key Features Brand New A/C (2025) & Updated R-38 Insulation Low-E Thermal Pane Windows & Slider Door replaced throughout Remodeled Kitchen with updated cabinets, appliances, paint, and a cozy dinette space Fully Remodeled Bathrooms (2024) including a private primary en-suite Private Outdoor Space: Second bedroom opens via slider to a fenced yard & patio Convenience: Indoor laundry room with washer/dryer included, pull-down attic storage, and designated parking right out front. Community & Location: Enjoy a tranquil, well-maintained neighborhood with a community pool just steps away. Walk or bike to Lake Lily Park & Farmers Market, Downtown Maitland, Enzian Theater, and local dining. Minutes to SunRail, I-4, Winter Park Village, and Park Ave!

1711 Grove Street Unit 519, Maitland

$315,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Completely renovated and move-in ready, a desired first-floor unit in the sought-after Lake Maitland Terrace! This impeccably updated two-bedroom, 1.5-bath condominium blends modern style with an unbeatable lakeside location in the heart of the Maitland/Winter Park area. Thoughtfully redesigned throughout, the home showcases a new kitchen with fresh cabinetry, granite countertops and stainless steel appliances. The baths have been tastefully reimagined with contemporary finishes, and stylish updates continue across the entire unit, delivering a turnkey home you can move into with confidence. The comfortable two-bedroom layout features a full bath in the hall plus a convenient half bath tucked within one of the bedrooms. Sunlight pours through large windows, and the easy first-floor accessibility makes everyday living a breeze. A space-saving washer/dryer combo is conveniently inside the unit, and a dedicated parking space adds day-to-day ease. Set within Lake Maitland Terrace, residents enjoy an amenity-rich community on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Take in the sparkling community pool with beautiful lake views, gather at the clubhouse with a full kitchen, and enjoy lake access from the private dock and fishing pier, plus kayak racks and tree-lined sidewalks throughout. Ideally just minutes from the charming shops, restaurants, and entertainment of downtown Maitland and Winter Park, you can walk to Lake Lily Park's popular events and the Enzian Theater, and reach Winter Park Village and Park Avenue in no time. Zoned for top-rated schools Dommerich Elementary, Maitland Middle and Winter Park High, this beautifully updated home is ready to impress. Whether you're seeking a primary residence or a seasonal retreat, don't miss your chance to claim this exceptional lakeside gem as your own.

1140 S Orlando Avenue Unit G3, Maitland

$225,000

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

Welcome to 820 Park Lake Circle, a beautifully updated two-bedroom condo tucked into one of Maitland’s most convenient locations. Offering the charm and space of a townhouse with the ease of condominium living, this inviting home is just minutes from Downtown Maitland, Park Avenue, Winter Park Village, Lake Lily, major healthcare campuses, I-4, and some of Central Florida’s best shopping and dining. Inside, the home feels fresh, comfortable, and move-in ready. Newer energy-efficient windows and sliding glass doors fill the interior with natural light, while updated flooring creates a clean, cohesive look throughout. The renovated kitchen features quartz countertops, stainless steel appliances, updated cabinetry, and a functional layout that makes everyday cooking and entertaining easy. A convenient half bath completes the main level. Step outside to a spacious, fenced courtyard offering a rare amount of private outdoor living space. Create a comfortable lounge area, grilling station, container garden, or a secure place for pets to enjoy the outdoors. The partially covered area provides additional flexibility for parking, storage, or an expanded patio. Upstairs, two remarkably spacious bedrooms provide room for king-sized furniture, home office space, or a comfortable guest retreat. Each bedroom offers generous closet storage and direct access to the shared Jack-and-Jill bathroom. An additional upstairs closet adds even more practical storage. Just beyond the front door, residents can enjoy the community pool, expansive green space, and the peaceful surroundings of Park Lake. Whether spending a sunny afternoon by the pool, taking a morning walk, or simply unwinding outdoors, the community offers welcome opportunities to relax and enjoy the Florida lifestyle. With an updated interior, private outdoor space, oversized bedrooms, newer A/C, community pool, and an exceptional Maitland location, Unit 11 offers a compelling combination of comfort, convenience, and value.

820 Park Lake Circle Unit 11, Maitland

$219,900

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Exceptional - 2 bed 2 bath condo on 1st floor in resort style community of Visconti. Featuring designer paint throughout, plush carpeting, a gourmet kitchen with newer appliances, laundry room with full size washer/dryer hook ups and screened in patio with outside storage. Community offers its residents 2 tropical pools overlooking Lake Shadow, Gym, Tennis - and basketball court, play ground and clubhouse. Located within minutes to major shopping, entertainment and Interstate 4. Call and schedule your private showing today !

1100 Lake Shadow Circle Unit 2103, Maitland

$394,000

4 Beds ⋅ 2 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code

Opportunity awaits in the established English Woods community! This 3-bedroom, 2-bath pool home is full of potential and ready for its next owner to bring it back to life. Originally designed as a 4-bedroom, the home can easily be converted back, offering added flexibility and living space. Featuring a spacious floor plan, private pool, and hot tub, this property is an excellent opportunity for investors, renovators, or buyers looking to customize a home to fit their vision. Roof is 2006, water heater is 2015, and A/C is 2001. Conveniently located near shopping, dining, schools, and major roadways, this is your chance to create your dream home or add a promising investment property to your portfolio. Bring your ideas and unlock the potential this home has to offer! HUD Case #:094-528168 A Property is HUD owned & subject to HUD rules. FHA eligibility-Insured With Escrow. Sold As-Is, no post-contract repairs or credits. Buyer to independently verify square footage and all measurements, condition, and HOA information if any. The buyer is responsible for activating utilities for inspection. Investors must complete inspections prior to bidding.

2467 Fieldingwood Road, Maitland

$959,000

4 Beds ⋅ 4 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code

Tucked at the end of a quiet cul-de-sac beneath a canopy of mature oaks, this beautifully maintained Maitland home offers space, privacy, and thoughtful updates throughout — all within a top school zone just minutes from Winter Park and downtown Orlando. A paver driveway winds through lush, established landscaping to a covered entry framed by an arched transom window, with a tile roof crowning the home. Inside, the open floor plan unfolds around a striking floor-to-ceiling tile fireplace anchoring the family room, with vaulted ceilings, skylights, and French doors that flood the space with natural light and open directly to the screened lanai. The kitchen is a true centerpiece — rich wood cabinetry, granite countertops, a tile backsplash, and stainless steel appliances including a French door refrigerator, all overlooking the family room. A bright, bowed breakfast nook wrapped in windows offers the perfect everyday dining spot, while a separate formal dining room and living room provide room to entertain. This is a true split floor plan, with the primary suite privately tucked away from the secondary bedrooms for maximum peace and quiet. The primary retreat features a spacious layout, built-in bookshelves, and an oversized walk-in closet with custom shelving. The en-suite primary bath features dual vanities, a walk-in glass shower with a bench, and elegant lighting throughout. A versatile bonus room/loft with a full wall of built-in shelving and columned entry adds flexible space for a home office, playroom, or media room. A separate storage loft offers abundant built-in shelving — ideal for keeping everything organized and out of sight. Three additional bedrooms host generous closet space, and a well-appointed powder bath rounds out the main living areas. The oversized utility room impresses with abundant cabinetry, a utility sink, and stone countertops — plenty of room for laundry, storage, and more. Step outside to your own private oasis: a screened, covered lanai wrapping a sparkling pool, all enclosed by mature landscaping and a fully fenced yard — perfect for Florida indoor-outdoor living, entertaining, or simply relaxing under the trees. Located in a sought-after Maitland neighborhood with easy access to top-rated schools, shopping, dining, and major roadways.

1889 Berkeley Court, Maitland

$325,000

3 Beds ⋅ 3 Baths ⋅ Lake Faith Villas Condo SubDv. ⋅ 32751 Zip Code

Welcome to Lake Faith Villas, an established lakefront community in Maitland. This spacious 3-bedroom, 3-bathroom condominium offers 1,860 square feet with an open floor plan, abundant natural light, and views of the community's landscaped grounds. The layout includes a first-floor bedroom and full bathroom, offering flexibility for guests, a home office, or everyday living. Upstairs, the primary suite features a walk-in closet and en-suite bath, while the third bedroom also has its own full bathroom. Recent updates include a new Washer and Dryer (2025), HVAC System (2022), Hot Water Heater (2022), and the roof replaced by the HOA (2022). Enjoy your garden patio or take advantage of the community's lakefront clubhouse, swimming pool, and direct views of Lake Faith. Located just minutes from Winter Park, SunRail, and major highways, the home is also close to Maitland's growing selection of restaurants, shopping, and fitness options, including the newly opened Crunch Fitness. Schedule your private showing today!

283 W Lake Faith Drive Unit 146, Maitland

$249,000

2 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo Ph C SubDv. ⋅ 32751 Zip Code

Welcome home to this beautifully updated two-story condo nestled in one of Maitland's most established communities, where lush mature landscaping, winding sidewalks, a community pool, lake access and a private dock create a peaceful setting just minutes from some of Central Florida's favorite restaurants, shopping and entertainment. Enjoy easy access to Enzian Theater, Winter Park Village, Trader Joe's, Whole Foods, Park Avenue and countless local dining favorites all within minutes. Inside, you'll immediately notice one of this home's most unique features. The floor plan was thoughtfully reimagined to create an expansive open-concept living space centered around a beautifully enlarged kitchen—offering a layout rarely available within the community. Warm cabinetry, stainless steel appliances, a center island, under cabinet lighting, recessed lighting and abundant workspace make this kitchen equally suited for everyday living and entertaining. Ceramic tile flooring flows throughout the entire first floor, while upstairs features durable laminate wood flooring throughout both bedrooms. Each bedroom serves as its own private primary suite with an ensuite bathroom, providing exceptional flexibility for guests, roommates or multi-generational living. One suite features a tub/shower combination while the other offers a walk-in shower. A third full bathroom downstairs with a walk-in shower adds additional convenience for visitors. Additional highlights include a re-roof (2021), energy-efficient double-pane windows and sliding glass door (updated 2023), a dedicated interior laundry room complete with cabinetry and folding counter, attractive 5¼-inch baseboards throughout the main living area, and a private rear courtyard that connects to the garage—perfect for grilling, outdoor dining, container-gardening or additional storage. Combining an exceptional location, a one-of-a-kind floor plan, and low-maintenance living in the heart of Maitland and minutes from Winter Park, this home offers a rare opportunity to enjoy both convenience and comfort in one of Central Florida's most desirable areas.

1713 Gulfview Drive Unit 435B, Maitland

$287,000

2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

PRICE IMPROVEMENT! WELCOME HOME to LAKE MAITLAND TERRACE! This beautifully remodeled 2 bedroom, FIRST FLOOR CORNER condo is truly move in ready and perfectly located in the heart of Maitland/Winter Park! Step inside to discover a stylish, completely updated interior featuring a BRAND NEW KITCHEN with NEW CABINETRY, COUNTERTOPS, and APPLIANCES, a beautifully RENOVATED BATHROOM, NEW LIGHTING and NEW INTERIOR DOORS, newer AC system and newer Hot Water Heater. Plus, you will love the convenience of an HOA approved stackable WASHER AND ventless DRYER inside the unit. Enjoy your morning coffee or unwind after a long day on your PRIVATE SCREENED IN PORCH, offering the perfect extension of your living space. As a desirable first floor corner unit, you’ll enjoy easy accessibility, added privacy, and CONVENIENT PARKING. Lake Maitland Terrace offers wonderful amenities, including a private lakefront dock for fishing and enjoying the water, community pool, and clubhouse. HOA includes water, sewer, valet trash pickup 3 days/week, all lawn services. You are just minutes from the charming shops, restaurants, parks, and entertainment of downtown Maitland and Winter Park. Whether you are looking for a full time home, a Florida getaway, or a low maintenance lifestyle, this beautifully renovated condo checks all the boxes. Updated, Convenient, Waterfront Community. Prime Location. Nothing to do but move in! Come see why this one won’t last!

1140 S Orlando Avenue Unit E1, Maitland

$340,000

2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Experience the perfect blend of Mid-Century Modern charm and contemporary living in this beautifully renovated 2-bedroom, 1-bath condominium in the highly sought-after Lake Maitland Terrace community. Nestled on the shores of Lake Maitland with access to the renowned Winter Park Chain of Lakes, this waterfront community offers an exceptional lifestyle in one of Central Florida's most desirable locations. Inside, you'll find a thoughtfully redesigned interior featuring a stunning chef-inspired kitchen with classic shaker cabinetry, quartz countertops, a spacious pantry, and a large center island offering storage on both sides. The open-concept layout creates a bright and inviting living space that's perfect for entertaining or relaxing at home. The generous primary bedroom features a large closet, while the beautifully updated bathroom boasts a spacious walk-in shower and modern finishes. Additional conveniences include an in-unit washer and dryer, a private storage room located behind the unit, and access to the community's updated laundry facilities. Lake Maitland Terrace offers outstanding amenities, including a new lakefront swimming pool, community dock, clubhouse, putting green, and direct access to Lake Maitland and the Winter Park Chain of Lakes. Ideally located just moments from Lake Lily, the Enzian Theater, and the vibrant Independence Lane District, you'll enjoy easy access to local restaurants, breweries, shopping, and the popular farmer’s market. Winter Park Village, Park Avenue, and major roadways are also just minutes away. Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School districts, this move-in-ready home offers an unbeatable combination of style, location, and convenience. Don't miss this incredible opportunity. Schedule your private showing today!

1140 S Orlando Avenue Unit B-7, Maitland

$535,000

4 Beds ⋅ 2 Baths ⋅ Roosevelt Place SubDv. ⋅ 32751 Zip Code

Move-in ready and full of charm, this one-story Maitland home offers 4 bedrooms, 2 bathrooms, and an array of desirable features. Enjoy Florida living with your own in-ground pool, or relax by the cozy wood-burning fireplace in the front living room. The updated kitchen (2019) features granite countertops and modern finishes, while the primary bathroom includes a beautifully tiled walk-in shower. Additional highlights include a spacious Florida room, a two-door, two-car garage, fresh interior paint, and a roof replaced in 2014. Conveniently located just minutes from Altamonte Springs, Winter Park, shopping, dining, and I-4, this home offers both comfort and an ideal location.

112 Roosevelt Place, Maitland

$925,000

4 Beds ⋅ 3 Baths ⋅ Druid Isle SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Welcome to your private lakefront retreat on one of Maitland's most coveted streets—Druid Isle. Tucked away on a quiet peninsula surrounded by water on every side, this exclusive one-way-in, one-way-out street offers an unmatched sense of privacy and tranquility. Situated at the end of the cul-de-sac, this beautifully updated 4-bedroom, 3-bathroom pool home combines modern finishes with an incredible waterfront lifestyle. Inside, you'll find a bright, open floor plan featuring brand-new luxury vinyl flooring throughout, fresh interior paint, and thoughtfully updated spaces designed for both everyday living and entertaining. Every detail has been carefully refreshed, making this home completely move-in ready. Step outside to your own private oasis where a sparkling pool overlooks the water, creating the perfect setting for relaxing or hosting family and friends. The exterior has been transformed with all-new professional landscaping, a brand-new paver driveway, and a newly paved walkway leading to a dedicated fire pit area—an ideal place to gather and enjoy breathtaking sunsets over the lake. Whether you're looking for peaceful waterfront living, exceptional privacy, or a home that's been completely updated from top to bottom, this Druid Isle gem offers a rare opportunity to own one of Maitland's most desirable lakefront properties. Experience the beauty, serenity, and lifestyle that only Druid Isle can provide. ROOF - 2017 HOT WATER HEATER - 2026 AC - 2012 PLUMBING - Updated 2018 ELECTRICAL - Updated 2018

1301 Druid Isle Road, Maitland

$965,000

4 Beds ⋅ 4 Baths ⋅ Sybelia Place SubDv. ⋅ 32751 Zip Code

Beautiful two-story home nestled on a quiet cul-de-sac in desirable Maitland, FL right off of Lake Sybelia. Featuring a private pool, spacious layout, luxury kitchen, high ceilings and an ideal location. Sub-Zero Pro refrigerator, Wolf duel-fuel range, quartzite counter tops, custom cabinetry, gas tankless water heater. Walking distance from Lake Sybelia, Maitland farmer's market, library and restaurants. This 4 bedroom, 3 1/2 bathroom home offers the perfect blend of comfort and privacy in this perfect neighborhood!

313 Macarthur Place, Maitland

$830,000

5 Beds ⋅ 4 Baths ⋅ Dommerich/Maitland Highlands SubDv. ⋅ 32751 Zip Code

Fantastic Maitland location! Situated on quiet cul-de-sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary, Maitland Middle and Winter Park High. This one-story home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in kitchen opens to the cozy family room anchored by the wood-burning fireplace. Expanded in 2008, the attached 900 sq ft in-law suite has a bedroom, living room, kitchenette and bath - ideal for an elderly parent or returning college grad. This flex space would also be ideal as an exercise room or home office. Primary bedroom has screened patio access and a walk-in closet. Three secondary bedrooms with access to two additional baths. Living areas have wood and tile flooring and the bedrooms have luxury vinyl plank. Out back is a sparkling screened pool overlooking the wooded back yard. Recent improvements include all new interior paint throughout (7/26) and roof ('22). Conveniently located near I-4, several parks, and excellent neighborhood restaurants. Charming library with books to share. No HOA. Welcome home!

2051 Dyan Way, Maitland

$549,000

4 Beds ⋅ 2 Baths ⋅ Forest Brook Sec 2-A SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Virtually Staged. Welcome home to this spacious 4-bedroom, 2-bath pool home in Maitland. From the moment you arrive, you'll appreciate the attractive brick exterior and inviting curb appeal. Inside, a welcoming foyer is flanked by a large formal living room with parquet flooring and abundant natural light, while the formal dining room features classic wainscoting and connects directly to the updated kitchen. The kitchen offers granite countertops, wood cabinetry, stainless steel appliances, a breakfast bar, and overlooks the generous family room with French doors leading to the backyard. The split-bedroom floor plan provides plenty of privacy. Two spacious secondary bedrooms with engineered hardwood flooring are located on one side of the home and share a hall bath. The primary suite is tucked away on the opposite side and features engineered hardwood floors, a walk-in closet and an ensuite bath with a walk-in shower. A fourth bedroom is centrally located, making it an ideal guest room, nursery, or home office. Just off the kitchen, you'll also find a large laundry room with built-in cabinetry for extra storage and access to the oversized two-car garage, which offers additional storage space. Step outside to a fully fenced backyard with an updated vinyl fence, a large pool ready for your personal finishing touches, and plenty of yard space for entertaining, pets, or play. Whether you choose to resurface the pool right away or customize it over time, this backyard offers great potential to create your own private outdoor retreat. Conveniently located just off Howell Branch Road, you're only minutes from I-4, Downtown Maitland, Winter Park, shopping, dining, and everyday conveniences. Call today to schedule your private showing!

564 Brookside Circle, Maitland

$649,000

3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add Maitland SubDv. ⋅ 32751 Zip Code

**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

553 Arapaho Trail, Maitland

$299,000

3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

Virtually Staged. Welcome to this beautifully updated two-story townhouse in the heart of Maitland, offering a well arranged floor plan, stylish finishes, and exceptional functionality. Featuring three bedrooms and two and a half bathrooms, the thoughtfully designed layout separates the living room from the kitchen and dining area, creating distinct yet connected spaces that feel open, organized, and highly functional. Walk into the fully renovated kitchen, showcasing elegant Calacatta quartz countertops, updated cabinetry, stainless steel appliances, and modern finishes that make it the centerpiece of the home. Waterproof luxury vinyl plank (LVP) flooring extends throughout the entire residence, complemented by updated lighting and fixtures that give the home a fresh, contemporary feel. Upstairs, the spacious primary suite offers a generous walk-in closet and private access to a screened balcony—the perfect place to enjoy your morning coffee or unwind in the evening. Step outside to your private courtyard, an inviting outdoor retreat perfect for relaxing or entertaining. Residents also enjoy access to a sparkling community pool, perfect for cooling off during Florida's warm summer months. Ideally situated with quick access to I-4 and Orange Avenue, this home places you just minutes from Downtown Orlando, top-rated hospitals, shopping, dining, and entertainment. Nearby attractions such as the Orlando Science Center and Orlando Museum of Art provide endless opportunities for culture and recreation, while schools and everyday conveniences are all within easy reach. With tasteful updates throughout, modern finishes, and an unbeatable Maitland location, this move-in-ready townhouse offers the perfect combination of style, comfort, and convenience. Schedule your private showing today!

812 Park Lake Circle Unit 7, Maitland

$252,000

3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo SubDv. ⋅ 32751 Zip Code

Welcome home to this spacious 3-bedroom, 2.5-bath condo in the desirable Park Lake Grove community. Enjoy peaceful lake views from your living room, and the convenience of an attached 1-car garage. The thoughtfully designed floor plan offers generous living space, 2 primary bedrooms with en suites upstairs, natural light, and plenty of storage. Community amenities include a pool and lake access. Conveniently located near shopping, dining, major highways, and downtown Orlando.

603 Waverly Lane Unit 405B, Maitland

$435,000

3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home featuring a sparkling pool and exceptional curb appeal! Nestled among lush landscaping, the backyard is a true private oasis—perfect for relaxing or entertaining. Inside, you'll be greeted by vaulted ceilings, abundant natural light, upgraded flooring, high-end countertops, and a beautifully designed kitchen that's both stylish and functional. The thoughtfully designed split floor plan offers privacy, with the spacious primary suite situated in its own wing and two additional bedrooms on the opposite side of the home. Additional highlights include a charming breakfast nook, a large living room, a dedicated office area, and a convenient indoor laundry room with the washer and dryer included. The attached garage provides ample storage and parking. Currently has a tenant with a lease ending on Nov 19th. Ideally located near the thriving Maitland business district, this home is just minutes from shopping, dining, Altamonte Mall, Winter Park, and offers easy access to I-4 and SR 414, making commuting throughout Central Florida a breeze. Don't miss the opportunity to make this exceptional home your own—schedule your private showing today!

2180 Tortoise Shell Drive, Maitland

$189,900

2 Beds ⋅ 2 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code

Welcome home to this beautifully updated and maintained 2-bedroom, 2-bath corner unit condo at Visconti West in Maitland! Located on the third floor, this light filled home features vaulted ceilings and an open, airy floor plan designed for comfortable living. The spacious primary suite includes an en-suite bathroom, while both bedrooms offer generous walk-in closets. The kitchen and bathrooms feature upgraded granite countertops and luxury vinyl plank flooring throughout the entryway, kitchen and bathrooms. Enjoy your morning coffee or unwind in the evening on the screened balcony. Additional highlights include an in-unit laundry room with washer and dryer, AC unit (2023), and hot water heater (2025). Residents enjoy gated access and resort style amenities including a pool, fitness center, clubhouse, tennis court, basketball court, valet trash pickup Monday through Friday, and a scenic pond and lake. Conveniently located just minutes from I-4, shopping, dining and entertainment, this home offers the perfect blend of style, comfort, and an unbeatable location.

1475 Lake Shadow Circle Unit 6307, Maitland

$585,000

4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome home to a rare find, one of the largest floor plans in the community, sitting right on Lake Charity. This Mediterranean style townhome greets you with sweeping water views, mature landscaping, and a peaceful stillness that is hard to find this close to everything. Inside, wood floors and tile carry you through the first level. Plantation shutters run throughout the home and you'll find real wood cabinetry, a detail that speaks to the quality of this build. A large family room and dining room combo with a half bath offers plenty of space to entertain. The kitchen features newer appliances and granite countertops, opening into a bright and functional living space. The primary suite is located on the first floor and is oversized, with double vanities, a jacuzzi tub plus separate shower, and a walk in closet. Head upstairs to a spacious landing area that connects three additional bedrooms, featuring walk in closets with closet systems, along with two full bathrooms. Step outside to the true showstopper. Townhomes rarely feel private, but this courtyard is your own Mediterranean oasis. Grow plants, entertain, or simply enjoy the quiet. Another great feature of this home is the all new energy efficient windows and new AC unit, keeping utilities low without sacrificing comfort. Walk through the covered entry to your oversized two car garage, a rare find, offering plenty of room for both vehicles plus storage. As a resident, you'll enjoy a resort style community pool overlooking Lake Charity, all within a gated neighborhood. Minutes from Maitland Boulevard and I4, you're close to Downtown Orlando, Maitland, and Park Avenue. If you're looking to be in the heart of Maitland with the space, privacy and lake views to match, this is the home for you.

1132 Charming Street, Maitland

$549,000

3 Beds ⋅ 2 Baths ⋅ Druid Hills Estates 1st Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Welcome home to this charming 3-bedroom, 2-bath pool home nestled in the highly sought-after Druid Hills Estates, one of Maitland’s most desirable neighborhoods. Set on an oversized wide lot along a picturesque street lined with majestic oak trees, this beautifully maintained home offers timeless character, thoughtful updates, and exceptional indoor-outdoor living. Inside, you’ll be welcomed by original hardwood floors that flow throughout the home, creating warmth and charm from the moment you step inside. The beautifully updated kitchen, renovated in 2019, is both stylish and functional, featuring propane service to the stove, newer appliances replaced in 2023, and an open flow into the living and dining area—perfect for everyday living and entertaining alike. Just beyond the main living space, the expansive Florida room is filled with natural light and features French doors that open to your private backyard oasis. Whether you’re hosting weekend gatherings or enjoying a quiet evening at home, the outdoor space is sure to impress with a sparkling pool, outdoor shower, fully fenced backyard, dedicated boat parking, and plenty of room for gardening, pets, or play. All three bedrooms are conveniently located together down the hall, creating a comfortable and private retreat. The bathrooms were tastefully remodeled in 2023, and additional updates provide peace of mind, including a BRAND NEW tankless water heater, new HVAC system (2023), a roof that’s just three years old, and a propane water heater. The septic drain field was replaced in 2019, and the septic system was professionally flushed just one year ago. Storage is abundant with an inside laundry room, built-in garage shelving, and a spacious attic for all your storage needs. Ideally located in a quiet pocket of Maitland with no HOA, you’ll enjoy easy access to the shopping, dining, parks, and entertainment of both Winter Park and Altamonte Springs while coming home to the peaceful charm of this established neighborhood. With the new Trader Joe’s planned just five minutes away, this location continues to become even more desirable. Blending classic character with modern updates and an incredible outdoor lifestyle, this move-in-ready Maitland pool home is one you won't want to miss!

1055 Druid Drive, Maitland

$799,890

3 Beds ⋅ 2 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code

Discover a rare waterfront, pool-home in the desirable Dommerich Hills neighborhood. This exceptional property offers the ideal combination of family-friendly living, modern convenience, and breathtaking natural beauty. The open floor plan welcomes you with vaulted ceilings and natural light in the living room, dining room, kitchen, and family room. Bamboo flooring enhances the bedrooms and living room, while cool and durable tile flooring extends throughout the remaining living areas. The family room features a wood-burning stone fireplace, French doors to lanai, walk-in closet, Just outside, a lakeside fire pit is perfect for relaxing with family and friends while taking in peaceful water views and sunsets. The 12-foot-deep lanai overlooks the screened swimming pool and the 120 feet of lake frontage. Across the water lies a protected nature preserve, providing a backdrop of trees and nature. Whether hosting holiday gatherings, celebrating special occasions, or enjoying quiet evenings at home, the layout provides flexibility and comfort. Imagine your own pineapple patch and fruit trees! You’ll have seasonal oranges, Key limes, plums, and kumquats. Whether you're enjoying your morning coffee overlooking the lake or spending evenings under the stars, the outdoor spaces invite you to slow down and savor every season. The original 1968 home was replaced with a new home in 1998, including new electrical and plumbing and incorporating the updated building codes that required hurricane-resistance structures. In 2026 the home was connected to the new City of Maitland sewer system. The home has fresh paint throughout, new fixtures, and new water heater. This is more than just a home; it's a lifestyle. Here, families have room to grow, creating lasting memories, and nature is always just outside the door. This home has an exceptional waterfront setting and is situated very close to the Maitland and Winter Park Chain of Lakes. With a bright and inviting interior, thoughtful features, and an outstanding location, with A-rated schools, this property offers a rare opportunity to enjoy peaceful lakeside living without sacrificing convenience.

2624 Tuscarora Trail, Maitland

$735,000

6 Beds ⋅ 3 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code

HONEY STOP THE CAR! This Maitland POOL home has EVERYTHING you need and MORE under one roof! Welcome to one of Maitland's most desirable neighborhoods English Estates. This 6 Bedroom, 3 Bathroom estate offers over 2,600 square feet of living space with a Split Bedroom Floor Plan and a Private Pool. This home is Move-In ready and provides comfort with modern style and top of the line updates by offering the perfect combination of luxury and space which is ideal for Large Families, Multi-Generational households, and working professionals seeking a premium residence. Once you step inside, you'll find an Open Concept showcasing the Kitchen, Living Room, and Dining Room with lots of natural light down to the fine details of Wainscoting and Crown Molding. The Kitchen is the Heart of the Home and this Kitchen is surely that! Great space for the whole family to enjoy and gather around the Extra Large Island. The Kitchen comes equipped with Real Wood Cabinets, Granite Countertops, and all major Stainless Steel Appliances including a Gas Stove with Hood Vent, Dishwasher, Fridge, and Microwave. Located off the Kitchen, the Living Room opens up to the Florida Room that leads out to your own Private Pool with Screen Enclosure. The Split Bedroom Floor Plan in this home features 3 Bedrooms on each side of the home, a true even split, giving you a thoughtful layout for everyday living, entertaining, and working from home. The ROOF and AC by Trane with Nest Thermostat are all from 2021. This home comes with Natural Gas at the Stove, Tankless Water Heater, and Dryer. The Extra Long Driveway with Additional Parking on the side provides ample parking for all your vehicles, boats, RV's and toys. Residents enjoy access to A-Rated Schools and a voluntary low-cost HOA. This location is ideal and conveniently located near 1792 which is a short distance to Maitland Community Park and Maitland City Centre where there are local dining spots and recreation activities. This home is also close to Winter Park, Rollins College, AdventHealth, and 10 minutes to Downtown Orlando. Whether you're looking for more space or a new lifestyle, this home delivers! Come enjoy one of Maitland's most established sought-after neighborhoods.

2462 Carolton Road, Maitland

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