Maitland FL 2 Bedroom Real Estate, Homes, Condos for Sale

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

Welcome to Lake Maitland Terrace! A serene neighborhood perched beautifully on Lake Maitland offering a lakefront pool & clubhouse. Enjoy this first floor corner home with screened porch & lake view. Delight in the retro vibe of this original unit OR renovate to your heart's content. One assigned parking space steps from your front door. Welcome Home!

1140 S Orlando Avenue Unit G8, Maitland

$199,900

2 Beds ⋅ 2 Baths ⋅ Visconti East 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

$225,499

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

Why pay Winter Park prices when you can live minutes away? Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhouse in the heart of Maitland, where location, lifestyle, and value come together. From the moment you walk in, you'll appreciate the many upgrades already completed, including a gorgeous kitchen with quartz countertops and stainless steel appliances, luxury vinyl plank flooring throughout, new energy-efficient windows and sliding glass doors, updated lighting, an updated half bath, and a new A/C (2022). The home features a spacious, fenced private courtyard. You have a partial garage/carport area, or you can utilize the entire space for outdoor living. Picture a patio furniture set, an outdoor TV, a grilling station, and a safe place for the kids to play or the pets to run around. Upstairs, you will find two HUGE bedrooms joined by a Jack-and-Jill bathroom. You cannot find bedrooms this big in newer homes. Each bedroom easily fits a king-sized bed and all furnishings needed. Both bedrooms have dual closets, and then there is an additional closet on the upstairs landing, so storage space will not be an issue. Outside, you'll discover one of the community's hidden gems—an expansive open green space and Park Lake just steps from your front door. Whether you're walking the dog, enjoying time with the kids, or spending a quiet evening outdoors, you'll love the sense of space and tranquility. And then there's the location, because your lifestyle should be just as important as the features of your home. Imagine grabbing coffee in Winter Park, spending Saturday mornings at Lake Lily, or meeting friends on Park Avenue, all without paying Winter Park prices. With easy access to I-4 and several major healthcare campuses nearby, this home is ideally situated for professionals, commuters, and anyone looking for a low-maintenance lifestyle close to everything. Most of the heavy lifting has already been done. All that's left is for you to move in and make it yours. This one won't last long, so schedule your showing today!

820 Park Lake Circle Unit 11, Maitland

$420,000

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

Welcome to Lake Maitland Terrace, where this beautifully renovated condominium offers a rare opportunity to enjoy Chain of Lakes living. Included with the property is a leased boat dock on the Winter Park Chain of Lakes, paid through 7/31/2027, with the lease transferable to the new owner and renewable. This stunning 2-bedroom, 1.5-bath residence features picturesque lake views from both bedrooms as well as the screened front porch. The screened-in front porch is the perfect place to relax while overlooking the expansive lakefront campus, complete with a sparkling pool, fishing dock, putting green, and shuffleboard courts. From the moment you step inside, you'll appreciate the exceptional quality of the modern renovation, thoughtfully designed with both style and function in mind. The beautifully updated kitchen is ideal for entertaining, featuring premium finishes, generous workspace, and a party-size ice maker. It flows seamlessly into the dining area, where abundant built-in storage provides both convenience and organization. The spacious primary suite serves as a private retreat, complete with a walk-in closet, an updated half bath, and tranquil lake views to wake up to each morning. Whether you're looking for a full-time residence or a weekend escape, this move-in-ready home offers an exceptional lifestyle in one of Winter Park's most desirable waterfront communities. This is a rare opportunity you won't want to miss.

1140 S Orlando Avenue Unit K15, Maitland

$199,000

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

Experience resort-style living in the heart of Maitland at the highly desirable gated community of Visconti. This beautifully maintained three-story townhome offers 1,280 square feet of thoughtfully designed living space plus an oversized attached garage, providing the perfect combination of comfort, functionality, and low-maintenance living. The open-concept main living level features luxury vinyl flooring, soaring ceilings, abundant natural light, and a spacious kitchen with stainless steel appliances, updated countertops, tile backsplash, breakfast bar seating, and generous cabinet space. The spacious primary suite offers a large walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or growing families. A full-size interior laundry room, ample storage, and neutral finishes make this home truly move-in ready. Visconti residents enjoy an impressive collection of amenities including a gated entrance, resort-style swimming pool, a state-of-the-art fitness center, playground, scenic walking paths, car wash station, and beautifully landscaped grounds shaded by mature oak trees. Conveniently located just minutes from I-4, Winter Park, Downtown Orlando, AdventHealth, RDV Sportsplex, shopping, dining, and entertainment, this home offers the perfect blend of convenience, lifestyle, and value.

1952 Legacy Cove Drive Unit 1952, Maitland

$140,000

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

Welcome to Carrington Park — one of Maitland’s most conveniently located communities! This ground-floor 2-bedroom, 2-bathroom condo offers 1,200+ square feet of comfortable living space at an unbeatable price point, making it an ideal primary residence or a smart addition to any investment portfolio.The open living and dining area flows naturally to a private screened patio perfect for enjoying Florida’s year-round weather without the bugs. Both bedrooms are generously sized, and the split-style layout offers privacy for owners and guests alike.Residents enjoy access to community amenities including a sparkling pool, fitness center, and more, all just steps from your front door. Situated at the corner of Howell Branch and SR-436, you’re minutes from shopping, dining, and major employers, with easy access to UCF, Full Sail, and Downtown Orlando.Whether you’re looking for a place to call home or a turnkey rental opportunity in a high-demand corridor, this one checks all the boxes. Priced at $140,000, schedule your showing before it’s gone.

2329 Coawood Unit 103, Maitland

$419,900

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

Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!

1140 S Orlando Avenue Unit H3, Maitland

$295,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo Ut 1 SubDv. ⋅ 32751 Zip Code

Ground-floor 2BR/2BA in the gated, lake-access community of Sun Bay Club in Maitland, FL — updated and move-in ready! The kitchen was renovated in 2023 with new cabinets, quartz countertops, and updated appliances (microwave 2024, dishwasher 2025). Both bathrooms were updated in 2026: the primary with a new double-sink vanity, modern lighting, and a pocket door for privacy, and the hall bath with a new vanity, mirror, and lighting. Durable wood-look tile and wood flooring throughout — no carpet. This is a two-story building, which falls outside Florida's SIRS and milestone inspection requirements that apply to condos three stories and taller. The open-concept living space extends through sliding glass doors to an enclosed sunroom overlooking the pond, ideal as a home office or morning coffee spot, and each bedroom opens to its own private screened patio. The primary suite adds a walk-in closet with built-in shelving; the second bedroom offers double closets with built-in shelving as well. HOA fee includes cable/internet, lake access for boats and jet skis, a large lakefront pool, a tennis court, and all exterior maintenance, including the roof. Minutes to Maitland and Winter Park shopping and dining, and easy access to highway I-4. Great option for low maintenance living as a primary residence or an investment opportunity. Schedule a viewing today!

1000 Winderley Place Unit 141, Maitland

$184,900

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

If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.

1440 Lake Shadow Circle Unit 8201, Maitland

$210,000

2 Beds ⋅ 2 Baths ⋅ Visconti East Bldg 27 SubDv. ⋅ 32751 Zip Code

Visconti Condo - Gated Community with lots of amenities only 8 miles from Downtown Orlando. This community situated on the north shore of Lake Shadow offers swimming pool, fitness center, clubhouse, tennis and basketball courts. Conveniently located close to I-4 and Maitland Blvd. Multi level home features an open floor plan with kitchen living/dining and office on main 2nd floor and 2 bedrooms 2 bathrooms on the 3rd floor. This home also features an attached 2 car garage with plenty of room for your vehicles or extra storage. HOA includes exterior maintenance, landscaping, valet trash, water, sewer and pest control.

2847 Shadow View Circle Unit 2847, Maitland

$129,000

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

Under contract-accepting backup offers. Bright and well maintained 2 bedroom, 1 bath condo located in a desirable shopping and dining area! This inviting home features abundant natural light, a spacious walk-in closet in the primary bedroom, and a relaxing enclosed patio perfect for additional living space or entertaining. The HOA includes water for added convenience. Residents also enjoy access to a community pool and low-maintenance living close to everything you need. Great opportunity for homeowners or investors alike!

550 Flemming Way Unit 100, Maitland

$225,000

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

Under contract-accepting backup offers. Maitland's Hidden Gem! Discover comfort, style, and convenience in this BEAUTIFULLY MAINTAINED 2-bedroom, 1.5-bath condo in the desirable Park Lake Townhouses community of Maitland with NEW A/C 2026 and NEW Water Heater 2026. Located minutes from Park Ave, Trader Joes, Lifetime Fitness and all Winter Park/Maitland has to offer! Offering the FEEL OF A TOWNHOME with two spacious levels, a private patio, and a one-car garage, this home is tucked away in a QUIET LOCATION with PEACEFUL GREEN SPACE VIEWS from the front. Step inside to find EASY-CARE TILE FLOORING throughout the main level and a bright, welcoming Living Room filled with NATURAL LIGHT from the large front window. A convenient half bath and SPACIOUS CLOSET are located just off the hallway before the home opens into the Dining and Kitchen areas. Perfect for both everyday living and entertaining, the Dining area features sliding glass doors leading to a PRIVATE FENCED PATIO, creating a wonderful outdoor space for morning coffee, grilling, or relaxing evenings. The patio also provides direct access to the ATTACHED ONE-CAR GARAGE. Just off the Dining area, you'll find a DEDICATED LAUNDRY ROOM complete with an included washer and dryer. The beautiful Kitchen is sure to impress with its abundance of cabinetry, GRANITE COUNTERTOPS, stainless steel appliances, CHIC TILE BACKSPLASH, and center island that adds both functionality and style. Upstairs, two generously sized bedrooms provide comfortable retreats. The Primary Bedroom features ATTRACTIVE HARDWOOD FLOORING, while the second bedroom is carpeted for added comfort. Both bedrooms offer DOUBLE MIRRORED CLOSET DOORS and share a well-appointed en suite bath. FROSTED GLASS-PANELED INTERIOR DOORS throughout the home add a modern and distinctive touch. Adding even more value and peace of mind, the home features a NEW AC SYSTEM and NEW WATER HEATER. Residents of Park Lake Townhouses enjoy a SPARKLING COMMUNITY POOL along with HOA-covered trash collection, lawn care and exterior maintenance, including the roof, making for a LOW-MAINTENANCE LIFESTYLE. Ideally located, you're just minutes from the boutiques, restaurants, and cafés of PARK AVENUE IN WINTER PARK, as well as CULTURAL DESTINATIONS such as Rollins College, Morse Museum of American Art, and Winter Park Scenic Boat Tour. Nearby shopping, dining, and entertainment options abound at MAITLAND CITY CENTRE, while commuters will appreciate EASY ACCESS to I-4, SR 414, and downtown Orlando. With its STYLISH UPDATES, private outdoor space, attached garage access, and EXCEPTIONAL LOCATION near some of Central Florida's most beloved destinations, this CHARMING residence is ready to welcome you home. Act quickly—this GEM won't last long!

892 Park Lake Circle Unit 69, Maitland

$325,000

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

One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.

1140 S Orlando Avenue Unit I14, Maitland

$215,000

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

Under contract-accepting backup offers. Virtually Staged. Resort-style amenities, low-maintenance living at a reasonable price, and a move-in ready home come together at 1927 Legacy Cove in beautiful Maitland. As you approach this GATED COMMUNITY, you will feel at ease with the added layer of security. Parking at the condo, you will see an extremely rare feature - an ATTACHED 2 CAR GARAGE! Inside, your eyes will be immediately drawn to the kitchen features: NEW STONE COUNTERTOPS, updated cabinets, STAINLESS STEEL APPLIANCES, pantry, tile backsplash, and breakfast bar. FRESH INTERIOR PAINT and tall ceilings throughout the home give it a clean, bright feel. Laminate floors and crown molding give the main living spaces a special touch. Upstairs, you will find NEW CARPET and a walk-in closet in both bedrooms. The conveniently-located 2nd floor laundry area is situated near the main bedrooms for everyday ease. The HOA provides exceptional value with a comparatively low monthly fee that includes: water/sewer, concierge trash pickup, and exterior maintenance, and resort-style amenities including a gorgeous COMMUNITY POOL, fitness center, clubhouse, playground, a basketball court, fishing pier, and tennis courts. They also just replaced the roof on this building within the last year or so. Conveniently located less than 1.5 miles from I-4 and approx 1 mile from SR-414, this home offers easy access throughout Greater Orlando. Historic Park Avenue in Winter Park is just 5 miles away, and Lake Eola in Downtown Orlando is approx 8 miles away. Altamonte Mall, multiple hospitals, Seminole State College, Rollins College, and even Orlando’s famed theme parks are all within easy reach.

1927 Legacy Cove Drive Unit 1927, Maitland

$139,900

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

Sought-after Visconti community of Maitland. The lowest 2-2 entry point currently available. This third-floor, 2-bed, 2-bath, 1,048 sqft condo features updated flooring, designer paint, LED lighting, new ceiling fans, updated faucets, and a screened patio with exterior storage. Community amenities include two pools overlooking Lake Shadow, tennis courts, lakeside walking paths, dog stations, and car wash stations, minutes to I-4, 429, downtown Orlando. Sold as-is, priced to sell.

1150 Lake Shadow Circle Unit 3304, Maitland

$215,000

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

A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new water heater (2026) and the electrical panel upgraded within the past couple of years. The A/C system was replaced in 2022. This wonderful unit is at a great price and will not last long.

814 Park Lake Circle Unit 8, Maitland

$169,900

2 Beds ⋅ 1 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code

Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

1375 Lake Shadow Circle Unit 11203, Maitland

$190,000

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

Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

1100 Lake Shadow Circle Unit 2307, Maitland

$467,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

204 Quayside Circle Unit 201, Maitland

$175,000

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

Welcome to Visconti! A Gated Waterfront Community in the Heart of Maitland. Step into an easy, low-maintenance living with this move-in ready 2-bedroom, 2-bath condo located on the third floor, offering added privacy and a peaceful, elevated feel. With all new flooring and fresh interior paint, this home is completely refreshed and ready for its next owner. The split floor plan layout offers a comfortable and functional flow, ideal for both everyday living and entertaining. Natural light fills the space, creating a bright and inviting atmosphere throughout. Whether you’re starting your day or winding down in the evening, this home delivers a relaxed, low-stress environment that truly feels like home. Located within the highly desirable Visconti community, residents enjoy resort-style amenities including a sparkling pool, fitness center, clubhouse, tennis and basketball courts, playground, and scenic walking paths with a waterfront gazebo. The gated entry and beautifully maintained grounds enhance both privacy and curb appeal. The HOA includes water service and valet trash, helping simplify your monthly expenses and making condo living even more convenient. Positioned in one of Maitland’s most central locations, you’ll have quick access to I-4, 414, and 434, with nearby shopping, dining, and entertainment options including Maitland Promenade, Winter Park Village, Cranes Roost Park, and Uptown Altamonte. Downtown Orlando is just a short drive away. If you’re looking for a fully updated, move-in ready condo in a gated community with strong amenities and an unbeatable location, this one checks all the boxes.

1440 Lake Shadow Circle Unit 8305, Maitland

$299,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

$599,000

2 Beds ⋅ 2 Baths ⋅ West Cove Condo SubDv. ⋅ 32751 Zip Code

TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

1100 S Orlando Avenue Unit 306, Maitland

$325,000

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

This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.

1140 S Orlando Avenue Unit F11, Maitland

$427,400

2 Beds ⋅ 1 Baths ⋅ Sunset Ridge SubDv. ⋅ 32751 Zip Code

Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida. The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners, builders, or investors seeking a property in a desirable and established area. The adjacent property to the west (210 Alpine) is also available for purchase. Contact the listing agent for additional information and pricing on the neighboring parcel.

220 Alpine Drive, Maitland

$749,900

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

LAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse with million-dollar water and above treetop views, and beautiful panoramic sunrises from multiple rooms. This 9th-floor, 1,685 SF residence features 2 bedrooms, 2 baths, 2 multi-purpose rooms, and an open-concept kitchen, dining, and living area. Centered on the west cove of Lake Maitland, the largest of the Winter Park Chain of Lakes. The primary suite offers a spacious bath with an oversized walk-in shower and walk-in closet. The second bedroom includes guest bath access and a 6-ft soaking tub. Interior features include engineered wood flooring, plantation shutters, grand crown molding, and custom built-ins, display areas and doors. Three sets of French doors open to two balconies overlooking the lake. Balcony features electric hurricane shutters and a private 6’x5’ storage closet. A place of serenity, peace and beauty; with an energy of quiet, expansiveness and closeness to nature. Community amenities include resort-style pool and spa, boat docks, kayak racks, fitness center, clubhouse, and on-site management. Walk to Enzian Theater, Lake Lily Park, community center, library, dining, farmers market; minutes to Park Ave, Whole Foods, Winter Park Village, and major roads.

1100 S Orlando Avenue Unit 956, Maitland

$850,000

2 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code

Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

219 Quayside Circle, Maitland

$395,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!

204 Quayside Circle Unit 304, Maitland

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