Between $500,000 - $600,000 Winter Garden FL Real Estate, Homes, Condos for Sale

4 Beds ⋅ 4 Baths ⋅ Watermark Ph 3 SubDv. ⋅ 34787 Zip Code

Welcome to your new townhome in the always desirable Watermark Terrace community in Winter garden FL! Built in 2019 the two story property stuns upon entry with its open floor plan, double height and beautiful and unique style that was meticulously selected by the owners when they had it built. Enjoy fireworks from the clubhouse viewing deck, a few sets of tennis or a summer afternoon at the community's resort-style swimming pool. Schedule your showing today!!!!

9803 Amber Chestnut Way, Winter Garden

$548,000

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.

12911 Westhaven Oak Drive, Winter Garden

$564,900

3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code

Beautiful modern single-family home featuring 3 bedrooms and 2.5 bathrooms, thoughtfully designed for comfort and style. The open-concept kitchen showcases quartz countertops, a breakfast island, luxury backsplash, and tall gray cabinets, creating a sleek and functional space.The first floor offers elegant tile plank flooring, a versatile flex space ideal for a home office or study, a convenient half bath, and extra storage with a closet under the stairs.Enjoy outdoor living in the extended screened patio, perfect for BBQs and gatherings, plus additional green space with the option to add a fence for extra privacy. Spacious bedrooms throughout, with a bright and inviting primary suite.Amazing Winter Garden location on Avalon Rd, just minutes from Hamlin, Flamingo Crossings, theme parks, FL-429, Orange County National Golf Center, Clermont, Windermere, and top-rated schools.The community features clubhouse, resort-style pool, fitness center, splash area, trails, playground, dog park, and soccer field perfect for the whole family.

16461 Olive Hill Drive, Winter Garden

$539,000

3 Beds ⋅ 2 Baths ⋅ Lakeview Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Built in 2021, this stunning single-family, single-story home is located in the highly sought-after gated community of Lakeview Preserve, in one of Winter Garden's most desirable areas. The property features 3 bedrooms and 2 bathrooms, plus a huge office that can easily be converted into a 4th bedroom, offering rare flexibility and adding immediate value to the home. The open, integrated floor plan creates spacious, light-filled living areas, ideal for everyday living and entertaining. A standout feature of this property is the already-installed solar panel system, which delivers real energy savings and lowers monthly utility costs from day one. Living in Lakeview Preserve means enjoying a full resort-style lifestyle, with a swimming pool, complete fitness center, clubhouse for events, splash pad, lake access with a dedicated kayaking area, and beautiful outdoor green spaces, all within a secure, gated community surrounded by nature. The location is strategic, with easy access to major roadways, top-rated schools, shopping, and dining. A home with this combination of features won't stay on the market long, making it an excellent choice for homeowners and investors seeking long-term value in one of Central Florida's fastest-growing areas.

4620 Gliding Wave St, Winter Garden

$529,990

3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16840 Hobe Sound Court, Winter Garden

$595,000

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful 4-bedroom, 3.5-bath home located in the highly sought after community of Waterleigh in Winter Garden. This residence features tile throughout the first floor main living areas and has an open floor plan with sleek finishes and quartz countertops, creating a modern and stylish atmosphere. There is one bedroom on the first floor that can serve as an in-law or guest bedroom, while upstairs you'll find three additional bedrooms, including a spacious Primary bedroom. The upstairs includes a versatile loft area, perfect for a home office, playroom, or additional living space. This home offers not just a comfortable living space but a vibrant lifestyle within a master planned community. Enjoy access to a resort style clubhouse, multiple pools with a fitness center, playgrounds, and sports fields. Additional amenities include mini golf, walking and nature trails, beach volleyball, and all concrete block construction for durability. The home features smart home technology, and all landscaping is included for your convenience. The community is family friendly with an elementary and middle school located right inside, while the high school is just minutes away. As you arrive, you'll be greeted by a beautiful waterfall entrance. Waterleigh is golf cart friendly and conveniently located with a Publix at the front of the neighborhood. Situated in a prime location, you're just minutes from all that Orlando showcases. Enjoy nightly views of the Disney fireworks, with easy access to Disney World. Explore the heart of Horizon West, including Hamlin Town Center and Flamingo Crossings, both offering a wide variety of shopping, dining, and entertainment options. With quick access to the Turnpike, commuting around Orlando is a breeze. This is truly a fantastic place to live!

16031 Scarpetta Street, Winter Garden

$550,000

Bray J W F Add 01 SubDv. ⋅ 34787 Zip Code

Prime Vacant Land in the Heart of Downtown Winter Garden. Rare opportunity to own a 16,338 sq. ft. vacant lot perfect to build a custom home, two single family homes or a duplex. in the picturesque downtown Winter Garden area. Just a short walk to Plant Street, this property is ideally situated near the vibrant heart of the city, offering unmatched convenience and charm. This spacious lot provides endless possibilities in one of Central Florida’s most sought-after communities. Downtown Winter Garden is known for its welcoming atmosphere, featuring award-winning restaurants, boutique shops, theaters, local events, and a lively cultural scene. Enjoy walkability, historic character, and modern amenities all in one location. Whether you envision a private residence or an investment opportunity, this property offers an exceptional chance to build in a thriving area.

47 Oak Street, Winter Garden

$515,000

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2a SubDv. ⋅ 34787 Zip Code

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence with a bonus room/office, built in 2018 and thoughtfully designed for both comfort and functionality. From the moment you step inside, you’ll appreciate the open-concept layout and high ceilings that create a light, airy feel—perfect for hosting gatherings or enjoying quiet evenings at home. This move-in-ready home features brand-new carpet throughout the upstairs and all bedrooms, along with fresh interior paint (December 2025) and new exterior paint (May 2025), giving it a clean, modern feel throughout. Upstairs, all three bedrooms and two full bathrooms give you a private retreat, highlighted by a spacious primary suite with a walk-in closet featuring custom built-ins designed to keep everything organized and within reach. Enjoy Florida living year-round on the covered outdoor patio, ideal for morning coffee or winding down at the end of the day. A separate laundry room adds everyday convenience, while HOA-maintained landscaping allows you to spend more time enjoying your home and less time on upkeep. Located in a vibrant community offering parks, a resort-style pool, and clubhouse, this home combines lifestyle, comfort, and convenience in one exceptional package. Don’t miss your chance to make this inviting Winter Garden home your own.

16330 Brisk Breeze Alley, Winter Garden

$519,000

5 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code

(3D tour link attached!) Motivated seller, just reduced $20K. Welcome to this well-appointed single-family home offering 2,455 sq. ft. of living space in the desirable Winter Garden area. Featuring 5 bedrooms and 3 full bathrooms, this residence provides generous space and flexibility for comfortable everyday living, guests, or work-from-home needs. All the bedrooms upstairs and the stairs are laminate flooring. Only the bedroom downstairs is carpet. The thoughtfully designed floor plan includes multiple living areas and a layout well suited for both relaxation and entertaining. With five bedrooms, the home offers versatility for growing households or those seeking additional space. Situated within a welcoming residential community, residents enjoy sidewalk-lined streets, green spaces, and a neighborhood-friendly atmosphere ideal for outdoor enjoyment and daily walks. When using our preferred lender, the buyer will receive a 1 percnt lender credit of the loan amount, which can be applied toward closing costs or an interest rate buydown. Conveniently located near major roadways, this home offers easy access to shopping, dining, parks, and schools, and is just a short drive from Walt Disney World, making it an excellent option for a primary residence, vacation home, or investment opportunity. This property presents a wonderful opportunity to enjoy space, location, and community living in one of Central Florida’s most sought-after areas.

15401 Porter Road, Winter Garden

$515,000

3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterlerigh, the Cordale includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16821 Hobe Sound Court, Winter Garden

$515,000

3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16845 Hobe Sound Court, Winter Garden

$555,000

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

Welcome to this stunning Clearden model, offering 4 bedrooms and 3.5 bathrooms in one of Horizon West’s most desirable neighborhoods — Waterleigh! The thoughtful floor plan features a spacious primary suite upstairs, along with two guest bedrooms and a versatile loft area, perfect for a home office or playroom. Downstairs, you’ll find a guest suite with a private bath, ideal for visitors or multigenerational living. The modern kitchen boasts stainless steel appliances, granite countertops, and opens to a large family room, creating the perfect space for entertaining. The primary bathroom includes dual vanities with granite tops and a large walk-in closet. This home also includes the Smart Home Package, offering convenience and peace of mind with the latest in home automation technology. Located in the resort-style Waterleigh community, residents enjoy exceptional amenities including two beautiful clubhouses, two resort-style pools, two fitness centers, mini golf, tennis courts, beach volleyball, dog park, and scenic lakefront picnic areas with BBQs. Experience the perfect blend of comfort, style, and Florida lifestyle living at its best — schedule your private showing today!

17098 Water Spring Boulevard, Winter Garden

$591,830

4 Beds ⋅ 3 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code

Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Berkley, a thoughtfully designed bungalow that blends charm, functionality, and modern comfort. This brand-new home offers 4 bedrooms, 3 bathrooms, and 2,102 sq. ft. of living space. The inviting front porch sets the tone, while inside, abundant natural light flows through thoughtfully placed windows. A bedroom and full bath on the first floor provide flexibility for guests or multi-generational living, while the upstairs keeps the remaining bedrooms together for privacy. Enjoy seamless indoor-outdoor living with a covered breezeway and private courtyard, perfect for gatherings or a quiet retreat. Nestled in Avalon Woods, you’ll love the convenience of being just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.

6339 Wild Persimmon Way, Winter Garden

$575,000

Briley Farm SubDv. ⋅ 34787 Zip Code

Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room—airy yet cozy and ready for your personal touch. Enjoy the perfect balance of indoor and outdoor living, set against serene scenery while remaining close to shopping, restaurants, and major highways. Briley Farm offers comfortable countryside living under a canopy of welcoming trees, crafted to embody the lifestyle you’ve been searching for. Stop by our sales office today to start building your dream home with Pioneer Builders!

514 N Pollard Street, Oakland

$599,000

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

A home full of charm, comfort, and practicality. It features four bedrooms, including a spacious master suite, three full bathrooms, and a powder room, distributed in a clever layout that enhances each room. Right at the entrance, the balcony invites you to slow down and enjoy the home's cozy atmosphere. The kitchen is modern and functional, equipped with all essential appliances and a central island perfect for quick meals or family time. The laundry room is also fully equipped and ready for everyday use. Upstairs, a spacious loft opens up to new possibilities—it could be a TV room, office, or leisure space—in addition to three bright and comfortable bedrooms. Sliding doors connect the interior area with the private backyard, where the covered balcony offers stunning views. With no neighbors in the back, the environment is quiet, private, and ideal for relaxation. The condominium offers a complete infrastructure, with swimming pools, gyms, and leisure areas for the whole family. The location is strategic, with supermarkets, schools, and various amenities nearby, as well as easy access to the region's main attractions. The house is currently occupied, but you can schedule a viewing. A rare opportunity to live well, with tranquility and quality of life.

17865 Adrift Road, Winter Garden

$505,000

3 Beds ⋅ 3 Baths ⋅ Hamilton Gardens Ph 2a & 2b SubDv. ⋅ 34787 Zip Code

Welcome to 5963 Glory Bower Drive, Winter Garden, FLorida a beautifully Home 3 bedroom, 2.5 bathrooms, plus office space, offering over 2,120 square feet of thoughtfully designed living space. This modern residence features an open-concept layout perfect for both everyday living and entertaining. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, ample cabinetry, and a gas range. The home also features a gas water heater, providing efficiency and convenience. Enjoy the Florida lifestyle just minutes from Disney.

5963 Glory Bower Drive, Winter Garden

$585,000

4 Beds ⋅ 3 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code

WATERFRONT--2 ACRES--NO HOA 7 Miles west of Disneys' main entrance...Winter Garden address with "A rated" schools listed on tax records. Close to many restaurants, shopping and other amenities. This is considered the 4 Corner Area because across Hwy 192 is Kissimmee, Hwy 27 is just a couple blocks west and if you go North it is Clermont and going south on Hwy 27 is Davenport. Piece of Paradise..Spacious..Upgraded...MOVE IN READY.. Expansive 2 car garage..workshop...storage...oversized.. Also approx 19X11 shed with an upper loft area ..The property is partially fenced. --..French doors open to a deck overlooks Lake Chapin in the rear of the property with fruit trees, banana trees, .. You will absolutely need to see to appreciate this home...even driving by, it is deceivingly large from just outside appearance.(almost 3400 Living sq ft). Beautifully maintained and Quality throughout.--Double Paned, tilt-out Windows with Marble sills--Well Maintained Bamboo Flooring (quality thicker boards ).Loads of Storage throughout and lighted closets...extra insulation in attic..Ceiling fans with wall controls and remotes..-French doors..-the list continues... A Central Kitchen that will delight the Chef --It has been thought out from past years of wants and needs and implemented. A WALL of Cabinetry..Corner Lazy susans upper and lower , pull out drawers ..under counter lights ..Convection oven and island cooktop with grill. Bar area opening into the Living room/ Dining room.. Split bedrooms plan and Master Suite has an extra room adjoining,which could be a exercise room, office, sitting room just to name a few. Large (approx 16x15) Suite has 3 solid core barn doors to close off the double walk in closet ROOMs and for the entrance door. Beautifully done Master Bath. (approx 13x9) Inside Laundry room with additional outlet for another refrigerator ..freezer. More than expansive (approx 16x13 sq ft) with a prestine pool table that can stay or go...your call.. This home makes a fantastic home for entertaining and/or family life with room to grow .. Come and see this home and you will want to make it yours..There is not another like it around. and it's so rare to find

14902 Arrena Road, Winter Garden

Browse All Winter Garden FL Between $500K - $600K Properties for Sale

Between $500K - $600K Winter Garden Real Estate