Location: Winter Garden
Do Not Show Listings
11400 LOVERS LN, WINTER GARDEN, FL 34787
$1,250,000393 Days on yellowkey MLS ID: O6295587
1 Days Off yellowkey (back on 3/28/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2517 Built: 1999 Tax: $6,673 (2024)Community: Avalon EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,673
Elementary School: Lost Lake Elem
High School: East Ridge High
Tax Year: 2024
Middle School: Windy Hill Middle
Remarks: Under contract-accepting backup offers. If you've ever dreamed of country living, but don't want to give up your conveniences, then welcome to your DREAM property in desirable Winter Garden! This spacious 2,571 sq ft custom home sits on 4.6 acres and includes a 3 stall horse barn with a tack room, as well as an additional 10x20 garage. The home has so much natural light and views out of every window. The kitchen has been recently updated and it's a showstopper! Relax in the sparkling pool and enormous outdoor entertainment space. Property like this is a rare find! Avalon Estates is located close to several shops and restaurants, the Florida turnpike, 429 and 408 expressways, 11 miles from Disney World, 12 miles from Universal Studios, and is an easy 23 miles from Orlando International Airport. Reserve a private viewing of this exceptional country home and begin building memories today. Pool built in 2023 with a state-of-the-art heating and cooling system.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brad Bolton, Llc (407-797-8875)
1408 SPRING RIDGE DR, WINTER GARDEN, FL 34787
$459,00048 Days on yellowkey MLS ID: O6390610
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1614 Built: 1991Monthly Fee: $25 Tax: $1,722 (2025)Community: Crown Point SpgsSingle Family
Taxes:$1,722
Elementary School: Dillard Street Elem
High School: Ocoee High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom single-story home in highly desirable Winter Garden, Florida! This light and bright residence features an inviting open floor-plan with soaring high ceilings that create a spacious and airy feel throughout. The cozy wood-burning fireplace serves as a beautiful focal point in the main living area—perfect for relaxing evenings at home. The property sits on a spacious corner lot with a fully fenced backyard, offering privacy and plenty of room for outdoor entertaining, pets, or play. A large storage shed (10x16) designed to match the home provides excellent space for tools, hobbies, or additional storage. Located within Winter Garden’s popular golf-cart district, you’ll enjoy easy access to the vibrant historic downtown area. Cruise over to the shops, restaurants, and the beloved weekly farmers market, or take part in the many community festivals and events that make Winter Garden such a special place to live. With its desirable location, open layout, and charming features, this home offers the perfect blend of comfort, convenience, and small-town charm. Call today as these opportunities tend to go fast!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
12566 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$609,90049 Days on yellowkey MLS ID: O6389532
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2420 Built: 2024Monthly Fee: $96 Tax: $2,162 (2024)Community: Osprey Ranch-Ph 1Single Family
Taxes:$2,162
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: PRICE IMPROVEMENT! Welcome to 12566 Westhaven Oak Drive in the desireable Osprey Ranch community of Winter Garden. This beautifully designed 4-bedroom, 3-bath home offers the perfect blend of modern comfort and luxury finishes, featuring an open-concept layout ideal for everyday living and entertaining. The gourmet kitchen shines with quartz countertops, a spacious island and stylish cabinetry, flowing seamlessly into the main living and dining areas. A convient downstairs guest suite offers flexability for visitors or a home office, while the upstairs primary retreat provides a relaxing escape with a spa-like bathroom and generous walk-in closets. Residents of Osprey Ranch enjoy a welcoming community athomsphere with a scenic walking paths, convenient access to Horizon West's shopping, dining, top-rated schools and world class attractions. Experience luxury, comfort and the best of the Winter Garden lifestyle in this exceptional home. Call to schedule a private tour today!
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Kendra Wallace (407-457-7069)
2450 DAHLGREN WAY, WINTER GARDEN, FL 34787
$1,950,00059 Days on yellowkey MLS ID: TB8481106
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 4365 Built: 2007Monthly Fee: $225 Tax: $8,970 (2024)Community: Bronsons Lndgs F & MSingle Family
Taxes:$8,970
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-style living in this one-of-a-kind gated lakefront home in the heart of Winter Garden. Nestled on a quiet, tree-lined cul-de-sac, this 5-bedroom, 5-bathroom, 4,365 Sq Ft home offers a smart layout designed for both everyday living and entertaining. The first-floor bedroom and full bath are ideal for guests or multi-generational living, while upstairs includes a loft, media room, and three additional bedrooms, including one en-suite and a Jack-and-Jill setup. Enjoy endless lake views from the screened pool with grotto seating and waterfall, or entertain indoors in the Florida Grill/Bar room featuring a refrigerator, freezer, deep fryer, griddle, bar sink, dishwasher, and full pool/guest bath. The primary suite is a true retreat with double walk-in closets, spa-style bath, garden tub, walk-in shower, and dual water closets. Lake enthusiasts will love the boathouse, covered dock, and boat lift, complete with power and water, along with multiple watercraft options including a pontoon slip (~20’), jet ski slip for 2, power lifts, and additional space for non-powered boats. Additional bonus spaces include a garage under air with a separate gym/rec room. Outdoor living abounds with a beachfront-style area, wood-burning fireplace, granite bar-top seating, and spectacular sunset views. This is a rare opportunity to own the only home on Lake Luntz with grandfathered boat access, offering a private lakefront lifestyle you won’t find anywhere else.
Listing Agent: Keegan Siegfried (813-670-7226)
1226 PORTMOOR WAY, WINTER GARDEN, FL 34787
$650,00075 Days on yellowkey MLS ID: O6381941
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2856 Built: 2003Monthly Fee: $243 Tax: $7,279 (2024)Community: Stoneybrook West 44/134Single Family
Taxes:$7,279
Elementary School: Whispering Oak Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to 1226 Portmoor Road in the highly sought-after, manned-gated Golf community of Stoneybrook West! This stunning 5-bedroom, 3-bath golf-view home offers over 2,800 square feet of beautifully updated living space. Designed for both comfort and entertaining, the home features formal living and dining rooms, a spacious family room, and a desirable first-floor guest bedroom with a full bath. The chef’s kitchen shines with granite countertops, stainless steel appliances, and an extra refrigerator in the garage. Upstairs, enjoy new laminate flooring, generously sized bedrooms, and a luxurious primary suite with tray ceilings and a private balcony overlooking the course. Step outside to your upgraded screened lanai and low-maintenance turf backyard—perfect for relaxing or hosting gatherings. A NEW ROOF (2021), A NEW A/C (2022), and A NEW Water Heater (2023) add peace of mind. Residents enjoy a Jr. Olympic pool, fitness center, clubhouse, dock, tennis, basketball, playground, high-speed internet, cable, and discounted golf—all minutes from Winter Garden Village, major highways, hospitals, theme parks, and Orlando International Airport.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Shirley Botansky (407-704-0874)
8256 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$675,000214 Days on yellowkey MLS ID: O6346538
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2557 Built: 2016Monthly Fee: $290 Tax: $10,027 (2024)Community: Waterleigh Ph 1BSingle Family
Taxes:$10,027
Elementary School: Panther Lake Elementary
Remarks: PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon West! Welcome to this 4-bed, 3.5-bath, with an upstairs loft residence in the highly sought-after Waterleigh community of Horizon West. Perfectly positioned on a corner lot in quiet Marina Bay of Waterleigh, this home impresses inside and out with a private pool, fenced yard, and modern designer finishes. A stacked-stone entry and covered front porch create standout curb appeal. Inside, you’ll find luxury vinyl flooring, custom finishes, and thoughtful updates throughout. The gourmet kitchen features a large island with pendant lighting, stainless steel appliances, updated backsplash, granite countertops, updated lighting, a dry bar, abundant cabinetry, and a custom pantry. The kitchen and breakfast nook flow seamlessly into the family room, where a custom fireplace with natural-wood mantel and built-in shelving provides a warm, modern focal point. Both spaces overlook the screened and covered lanai with views of the pool and fenced yard. A first-floor bedroom with an en-suite full bath and walk-in closet is ideal for guests, while a custom drop zone adds everyday organization. A powder bath and extra storage complete the first level. Upstairs, a custom wood child gate and coordinating handrail lead to a versatile loft/bonus area—perfect for a second living room, home office, or playroom. Built-in shelving and a media wall create a showcase for books, art, and collectibles. The spacious primary suite offers designer touches and a spa-inspired bath with oversized dual-sink vanity, walk-in shower, private water closet, and a beautifully customized walk-in closet. Two additional bedrooms share a full bath with dual sinks and one of the secondary bedrooms boasts a walk-in closet with extra storage. The upgraded laundry room includes cabinetry, open shelving, a folding station, and washer/dryer. The oversized garage offers a workbench area, custom shelving, and an additional refrigerator. Outdoors, the custom pebble-finish pool invites year-round enjoyment, while the fenced yard provides additional space for play, pets, or gardening. Waterleigh residents enjoy resort-style amenities: 3 pools, 2 clubhouses, 2 fitness centers, tennis courts, sand volleyball, mini-golf, dog parks, playgrounds, walking trails, and scenic lakes with a fishing pier and BBQ areas. HOA dues include lawn care for a truly low-maintenance lifestyle. Marina Bay has its own waterfront clubhouse with pool and fitness center overlooking Hickory Nut Lake and the walking trails capture the serene views. Ideally located near the new the Waterleigh Publix, Hamlin Town Center, Disney, dining, and shopping. Enjoy the charm of Winter Garden with the historical downtown Winter Garden having boutiques, restaurants, farmer's markets and social activities. Also, enjoy easy access to the 429, 417, and 408 expressways. Zoned for highly rated schools, this home is turn-key and move-in ready—schedule your private showing today! View the video tour: http://bit.ly/42HCqhG
Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)
Listing Agent: Deb Schroeder (407-234-2256)
9312 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787
$1,100,00076 Days on yellowkey MLS ID: S5143665
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3077 Built: 2015Monthly Fee: $165 Tax: $11,481 (2024)Community: Watermark Ph 2ASingle Family
Taxes:$11,481
High School: None
Middle School: Hamlin Middle
Remarks: Located in the highly sought-after Watermark community in Winter Garden, this stunning 4-bedroom, 3 full bath, and 1 half bath home offers the perfect blend of luxury, comfort, and functionality. Step inside to find beautiful wood flooring, tile, and plush carpet thoughtfully placed throughout the home. The chef-inspired kitchen features gourmet stainless-steel appliances, ample cabinetry, and modern finishes—ideal for both everyday living and entertaining. Elegant details elevate the interior, including crown molding, upgraded baseboards throughout, and a tray ceiling in the spacious primary suite. The home also offers a versatile bonus room perfect for a media room, office, or playroom. The laundry room is equipped with built-in cabinets for added storage and convenience. A 2-car garage completes the home, while the community offers exceptional amenities and a prime location close to shopping, dining, and major roadways. Schedule your private showing today and experience the best of Winter Garden living!
Listing is courtesy of: K REALTY (407-668-4310)
Listing Agent: Karine Nascimento (508-259-8853)
17134 LAKE INGRAM RD, WINTER GARDEN, FL 34787
$775,00084 Days on yellowkey MLS ID: G5107793
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1924 Built: 1959 Tax: $400 (2025)Community: Mt Park Orange GroveSingle Family
Taxes:$400
Elementary School: Hamlin Elementary
Remarks: Welcome to 17134 Lake Ingram Rd, which offers LAKEFRONT living with NO HOA on Lake Ingram, The property is 1.16-acres and has 118 feet of waterfront. WALT DISNEY WORLD is approximately 15 minutes away, while Orlando College of Osteopathic Medicine is just minutes away. Opportunity awaits for the current home and pool to be updated to suit the buyer’s personal style and taste. Zoned A-1, the parcel may appeal to buyers seeking space for a custom home or long-term investment. Property sold as-is. Due diligence recommended regarding zoning and development options. Call today to see this unique property in the desirable area of Horizon West.
Listing is courtesy of: OPTIMA ONE REALTY, INC. (352-243-6784)
Listing Agent: Cynthia Griffin (321-438-8203)
8066 BOWERY DR, WINTER GARDEN, FL 34787
$589,90069 Days on yellowkey MLS ID: O6384210
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2579 Built: 2017Monthly Fee: $195 Tax: $5,185 (2024)Community: Lake Hancock PreserveSingle Family
Taxes:$5,185
Elementary School: Summerlake Elementary
Remarks: Prime location in the heart of Horizon West, Winter Garden. This modern 4-bedroom, 3.5-bathroom with office/flex space home offers an open layout with plenty of natural light and smart home features. The heart of the home features a great room, informal dining, kitchen combo that has too many upgrades to list including: custom lighting, wood plank floors, wood stairs, gourmet kitchen with granite counters, stainless appliances, contemporary cabinets, and many custom options throughout just to name a few. Even energy-efficient upgrades like a hybrid water heater, and smart home systems, including thermostats, locks, and a security alarm. All bedrooms, including the laundry room, are located upstairs to add family convenience. Outside, an outdoor OASIS awaits to entertain friends and family from an extended, covered lanai with plenty of room to enjoy the Florida outdoor lifestyle and a private, fenced-in backyard that is large enough to add a future pool. This home is just minutes away from Historic Downtown Winter Garden, Hamlin Town Center, shops, dining, entertainment and Disney-including firework views. A must see!
Listing is courtesy of: FL PRO BROKERS LLC (407-790-7341)
Listing Agent: Michael Blank (407-595-0144)
15506 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787
$899,000230 Days on yellowkey MLS ID: O6343579
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3408 Built: 2018Monthly Fee: $110 Tax: $8,619 (2024)Community: Highlands/Summerlake Grvs Ph 2Single Family
Taxes:$8,619
Elementary School: None
Middle School: None
Remarks: Stunning 5BR/4.5BA home on the largest corner lot in Highlands at Summerlake Groves. This beautifully upgraded residence features new high-end laminate flooring, a redesigned kitchen with updated cabinetry, and built-in closets in every bedroom. The office is enhanced with custom built-ins, and the home is equipped with a whole-house water purifier system. The spacious living room offers a wet bar with ice maker and refrigerator, perfect for entertaining. An in-law suite provides a private retreat with its own en-suite bath and walk-in closet. Upstairs, the second-floor balcony overlooks the community and delivers breathtaking views of Disney’s nightly fireworks, creating the ultimate Florida lifestyle. The property is fully fenced for added privacy and outdoor enjoyment. Community amenities include a resort-style pool and cabana, tennis courts, dog park, two playground for families, walking and biking trails, and a mini soccer field. Ideally located next to Orange County National Golf Center, and just minutes from Hamlin Town Center, Disney parks, shopping, dining, and top-rated A-schools.
Listing is courtesy of: VALSTAR REALTY LLC (407-270-5000)
Listing Agent: Otto Solis Parraga (407-431-1789)
12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$639,90036 Days on yellowkey MLS ID: O6393606
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1860 Built: 2022Monthly Fee: $192 Tax: $7,965 (2025)Community: Encore At OvationSingle Family
Taxes:$7,965
Remarks: Welcome to this impeccably maintained single-story residence offering serene water and conservation views in desirable Encore at Ovation. Thoughtfully designed with three bedrooms and two baths, this home blends comfort, style and effortless living. From the moment you arrive, charming curb appeal sets the tone with a welcoming front porch, shaker-shingle accents, stone detailing and carriage-style garage doors. Inside, an open-concept layout creates a seamless flow ideal for everyday living and entertaining. At the heart of the home, the chef’s kitchen impresses with a spacious island, upgraded apron-front farmhouse sink and natural gas range, balancing beauty and functionality. The kitchen overlooks the dining area, family room and extended covered lanai, all positioned to capture peaceful water views and enhance indoor-outdoor living. Elegant tile flooring runs throughout, offering sophistication and easy maintenance. The private owner’s suite serves as a relaxing retreat, featuring a spa-inspired bath with dual vanities, a soaking tub, separate shower and a generous walk-in closet. Two secondary bedrooms are thoughtfully on opposite side of the home and share a full bath, providing privacy for family or guests. A spacious laundry room adds everyday convenience. Modern upgrades include fiber-optic internet, a security system and exterior cameras, delivering seamless connectivity and smart home peace of mind. Residents of Encore at Ovation enjoy resort-style amenities including a clubhouse, fitness center, sparkling pool and lawn maintenance services. Ideally just minutes from shopping, dining, entertainment and world-renowned attractions like Disney, this home offers a blend of lifestyle and location. Don’t miss the opportunity to own this move-in-ready gem in one of the area’s sought-after communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Megan Byers (407-457-7131)
13665 KILLEBREW WAY, WINTER GARDEN, FL 34787
$939,00094 Days on yellowkey MLS ID: O6376754
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3909 Built: 2017Community: Cypress Reserve Ph 1Single Family
Taxes:
Tax Year:
Remarks: This stunning 4-bedroom, 3.5-bath residence offers an impressive 3,909 sq ft of thoughtfully designed living space, making it one of the best family floorplans available in Winter Garden. The open and airy layout features high ceilings and spacious rooms that create a welcoming, light-filled atmosphere perfect for everyday living and entertaining. The primary bedroom is conveniently located downstairs for privacy and ease, while the remaining bedrooms are upstairs—each boasting a generous walk-in closet for ample storage. Throughout the home, you'll enjoy durable and stylish tile and laminate flooring, providing a clean, low-maintenance look that flows seamlessly from room to room. Step outside to the spacious fenced backyard—ideal for safe play, gardening, pets, or relaxing in your own private outdoor oasis. The yard also has plenty of space for a custom pool. Additional standout features include a dedicated office (ideal for remote work or study), a fun playroom, and a versatile media room—perfect for movie nights, gaming, or family gatherings. These bonus spaces enhance the home's appeal for growing families. Nestled in a family-friendly neighborhood that's centrally located in Winter Garden, this home offers easy access to top-rated schools, shopping, dining, and major roadways. Families love the convenience of a beautiful community pool just steps away from the home. Kids can safely ride their bikes to nearby schools (only .2 miles away), fostering independence and community connections. The community amenities provide plenty of opportunities for recreation and relaxation, including parks, playgrounds, and green spaces that encourage outdoor play and neighborly gatherings. Don't miss this exceptional opportunity to own a move-in-ready gem in one of Winter Garden's most desirable family-oriented areas. Schedule your private showing today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Paulo Silva (407-790-1649)
14187 JOMATT LOOP, WINTER GARDEN, FL 34787
$949,90036 Days on yellowkey MLS ID: O6393373
Bed: 6 Bath: 3.5 Liv Area Sq Ft: 4181 Built: 2019Community: Cypress Reserve Ph 2Single Family
Remarks: Rare opportunity to own a 6-bedroom, 4,181 sq ft home with water views in Winter Garden's Cypress Reserve community. Built in 2019, this spacious residence sits on a premium homesite with expanded distance from neighboring properties, providing privacy rarely found in newer construction neighborhoods. The home features a gourmet kitchen with two oversized islands, ideal for entertaining and everyday living. The open-concept layout flows seamlessly into large living and dining spaces filled with natural light and scenic water views. With six bedrooms and 3.5 bathrooms, this home offers exceptional flexibility for multigenerational living, guest accommodations, or dedicated work-from-home spaces. Located just minutes from Downtown Winter Garden, residents enjoy easy access to award-winning restaurants, boutique shopping, the popular Winter Garden Farmers Market, and miles of outdoor recreation along the West Orange Trail. The property is also near the highly anticipated Tucker Ranch Park development, which will bring new green spaces, trails, and community amenities to the area. Homes offering over 4,000 square feet with water views in Winter Garden are rarely available, making this an exceptional opportunity in one of Central Florida’s most desirable communities.
Listing is courtesy of: ELEVATE REAL ESTATE BROKERS (954-772-3870)
Listing Agent: Kelly Roth (352-514-5045)
14126 LAKE TILDEN BLVD, WINTER GARDEN, FL 34787
$1,490,00057 Days on yellowkey MLS ID: O6386648
0 Days Off yellowkey (back on 3/16/2026)
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3517 Built: 1995Community: Country LakesSingle Family
Remarks: Under contract-accepting backup offers. Tucked away on 2.5 private lakefront acres in the heart of Winter Garden, this exceptional 4-bedroom, 4 full + 2 half bath estate offers privacy, space, and the ultimate retreat lifestyle. In this beautiful home, you can start your day drinking morning coffee on your screened-in lanai overlooking Lake Tilden, enjoy a mid-afternoon swim in the saltwater, heated pool, and end your evening with Disney fireworks lighting up the sky from your backyard. Inside, the home features fresh interior paint, a dedicated home office, a spacious great room, and formal living and dining areas perfect for both entertaining and quiet relaxation. Custom built-ins throughout the home provide charm, function, and plenty of storage. Three newly remodeled bathrooms include a spa-like master bath with a soaking tub, multi-head shower, and finished walk-in closet, bringing luxury and comfort to daily living. Updated interior and exterior lighting enhances the home while honoring its timeless character. A new electrical panel ensures modern reliability. A versatile ADU adds endless possibilities as a home gym, private office, guest suite, creative studio, or man cave, giving flexibility for multigenerational living or working from home. Recent upgrades include a new well pump, whole-home water filtration system, new septic drain field, two new HVAC units, brand-new pool equipment with iAquaLink automation, and a newly epoxied garage floor. Outdoors, fresh exterior paint, updated landscaping, and a newly fenced backyard with puppy picket fencing create an inviting environment for kids, pets, and entertaining. This rare lakefront property combines acreage, character, and thoughtful updates just minutes from downtown Winter Garden, top-rated schools, dining, and shopping. With space to spread out, enjoy the outdoors, and live a lifestyle others only dream about, this home is meant to be lived in, loved, and enjoyed for years to come.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lisa Kirsch (678-373-8917)
13037 SANDCASTLE DR, WINTER GARDEN, FL 34787
$994,29556 Days on yellowkey MLS ID: O6387932
2 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2902 Built: 2022Community: Del Webb OasisSingle Family
Remarks: Experience the perfect blend of luxury and convenience with Mystique Grand home. Formerly a model home, this two-story home offers a thoughtfully designed layout featuring 3 bedrooms, an enclosed flex room, 3 bathrooms, in ground pool and spa with an outdoor kitchen, and a 2-car garage with tandem storage. The owner's suite is conveniently located on the first floor, offering a private retreat with a spa-inspired en suite bathroom. The heart of the home is the open-concept kitchen, café, and gathering room, where natural light floods the space, creating a welcoming and airy atmosphere. Tall ceilings, expansive windows, and a pocket sliding glass door leading to the extended covered lanai seamlessly blend the indoor and outdoor living areas, ideal for effortless entertaining. Step outside and enjoy your back yard oasis complete with an inground pool and spa, as well as an outdoor kitchen. Inside, the gourmet kitchen is a true highlight, featuring a Whirlpool built-in natural gas cooktop, microwave, oven, and refrigerator, white soft-close cabinetry, quartz countertops, and a decorative tile backsplash. A spacious walk-in pantry, granite single-bowl sink, and upgraded faucet complete this culinary space, which is both stylish and functional. The owner's suite is designed for relaxation, with an en suite bathroom that includes a walk-in shower with a built-in bench, dual vanity with quartz countertops, a linen closet, and an enclosed toilet for added privacy. On the first floor, you’ll also find a conveniently located spare bedroom, full bathroom, and enclosed flex room that can easily serve as an office, hobby room, or guest retreat. Upstairs, the expansive loft provides additional space for leisure, and the third bedroom features its own walk-in closet and private bathroom. Throughout the home, designer-curated finishes enhance the sense of luxury, including matte black hardware, wood-look luxury vinyl plank flooring throughout the first floor, tile flooring in the bathrooms and laundry room, and plush Shaw carpet adds warmth to the upstairs bedroom and loft. This home is also equipped with the latest in home technology, including surround sound pre-wire, digital IP camera pre-wire, security system pre-wire, and LED downlights. Don’t miss the opportunity to own this beautifully designed home with unparalleled functionality and elegance. Schedule your tour today!
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
707 GRASSY STONE DR, WINTER GARDEN, FL 34787
$550,00097 Days on yellowkey MLS ID: O6376356
0 Days Off yellowkey (back on 3/23/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2398 Built: 2014Community: Covington ChaseSingle Family
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this single-story home in the highly sought-after Covington Chase community, perfectly positioned on a quiet cul-de-sac hilltop with peaceful lake views. The fully fenced .25-acre yard offers space, privacy, and room for a future pool or patio expansion, while the large covered lanai and expansive outdoor back patio seating areas create the ideal setting for entertaining, relaxing, or enjoying Florida sunsets. Step inside to discover an open and functional floor plan featuring four bedrooms plus a versatile den or office with glass French doors and a built-in Murphy bed, perfect for a home office, guest room, or additional living space. Natural light floods the interior through triple sliding glass doors in the family room and additional sliders in the primary suite, highlighting the bright, airy design. Elevated ceiling heights enhance the spacious feel throughout the main living areas. Premium features include hurricane-proof glass front doors, tile flooring throughout main living areas, and laminate in the dining room. The oversized three-car garage (approx. 32 x 26) provides abundant space for vehicles, storage, a workshop, or a golf cart. The exterior was freshly painted just five years ago, adding to the home’s curb appeal. Covington Chase offers a community pool, park, and low HOA. The West Orange Trail runs directly through the neighborhood, ideal for walking, jogging, biking, or simply enjoying the outdoors. Living in Downtown Winter Garden means embracing a vibrant, walkable lifestyle with award-winning farmers markets, annual festivals, Plant Street Market, Crooked Can Brewery, boutique shopping, eclectic dining, and lively entertainment all within golf cart distance. Convenient access to Winter Garden Village, Highway 429, and the surrounding Orange County attractions puts everything you need right at your doorstep. This home perfectly combines lake views, elevated outdoor living spaces, and an active Downtown Winter Garden lifestyle, making it a true gem in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
4230 REX DR, WINTER GARDEN, FL 34787
$2,500,000455 Days on yellowkey MLS ID: O6274608
0 Days Off yellowkey (back on 3/26/2026)
Bed: 9 Bath: 6.0 Liv Area Sq Ft: 7505 Built: 2003Community: Lake Avalon Grvs 2Nd RepSingle Family
Remarks: Under contract-accepting backup offers. **A RARE OPPORTUNITY YOU WON’T WANT TO MISS!!** 9.75 PRIME ACRES IN THE HEART OF WINTER GARDEN ~ MAIN HOME CUSTOM BUILT BY HANNIGAN HOMES 5BD/4BA/3-CAR- 5,423 SQFT, INCLUDING AN ABOVE GARAGE APARTMENT WITH 1/BD/1/BA/+KITCHENETTE ~ SECOND HOME ON PROPERTY INCLUDES 4BD/2BA/2-CAR - 2,082SQFT ~ 10-STALL + TACKROOM HORSE BARN - 2,592 SQFT, 3 PASTURES ~ FENCED IN RIDING RING AND MUCH MORE! This countryside estate is an exclusive opportunity to own two homes, a horse barn, an adorable chicken coop, Koi pond, paver fire pit, built-in playground and so much more in the heart of the sought-after Winter Garden! Bring your horses and enjoy all that this massive CORNER LOT has to offer and being just minutes from the 429 gives you easy access to every convenience including neighboring HORIZON WEST and DISNEY THEME PARKS. Being sold all as one gives you endless opportunities in the ADDITIONAL SINGLE FAMILY HOME with the main home ready with charm for a family to make it their own. The long covered front porch welcomes you home and gives you front row seats to the riding ring. Built by Hannigan Homes, the main home was modeled after Disney’s Grand Floridian, and the thoughtful and unique features throughout are the perfect blend of comfort and quiet luxury. The roof was updated in 2019, the office space can serve as an additional bedroom, light and bright with views of the property, there is a movie/media room currently being used as an indoor trampoline park, WALK-IN WINE CELLAR for the adults, a fun HIDDEN WALK-IN PANTRY for ample kitchen storage and an energy saving SOLAR WATER HEATER. The new owner will absolutely fall in love with the PRIVATE PRIMARY SUITE that takes up the entirety of the second floor with sweeping views overlooking your estate, large WALK-IN CLOSET and well appointed ensuite bath. The additional bedrooms on the main floor give room to grow, and the additional home and garage apartment graciously allow for multi-general living. This gorgeous property is best experienced in person (stunning sunsets included!) so it can speak for itself - call today to schedule your private tour today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
17261 HEARTWOOD LOOP, WINTER GARDEN, FL 34787
$1,999,000182 Days on yellowkey MLS ID: O6354268
15 Days Off yellowkey (back on 3/26/2026)
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 6400 Built: 2002Community: Avalon EstatesSingle Family
Remarks: Discover Winter Garden’s best-kept secret in Avalon Estates, a peaceful, horse-friendly enclave where timeless country charm meets modern luxury. This custom-built residence offers an impressive 6,400 sq. ft. under air and nearly 10,000 sq. ft. under roof, set on 4.6 picturesque acres surrounded by nature and serenity. From the moment you arrive, the inviting curb appeal and sprawling front porch set the tone for what awaits inside. Step through the double entry doors into a grand living space filled with soaring ceilings, abundant natural light, and an airy, open feel that defines Florida living at its finest. The modern farmhouse kitchen is a dream for entertaining, featuring two expansive islands, generous counter space, and seamless flow into the family room, where a wood-burning fireplace adds warmth and charm. French doors open to the pool area, complete with two oversized covered lanais, creating an ideal setting for relaxing or hosting guests. The downstairs primary suite is both spacious and inviting, featuring a private fireplace, large walk-in closet, and a magazine-worthy en suite bath. A private office sits just off the primary suite, offering a quiet retreat for work or study. Upstairs, you’ll find a large bonus room with kitchenette, three additional bedrooms, and two full bathrooms—perfect for family or guests. Don’t miss the panoramic views through the large windows—on clear nights, you can watch Disney fireworks sparkle in the distance and even catch NASA rocket launches from the east coast. Built with poured concrete tilt-wall construction, this home is as strong and resilient as it is beautiful. The laundry room doubles as a safe room, featuring metal doors, bullet-resistant glass, and reinforced concrete walls and ceiling. Additional highlights include a new roof (2025), an attached three-car garage, plus a detached 2.5-car garage with studio and full bath—ideal for guest quarters, an office, or hobby space. Located just minutes from shopping, dining, and major highways (Florida Turnpike, 429, and 408), this estate is 11 miles from Disney World, 12 miles from Universal Studios, and 23 miles from Orlando International Airport. With its combination of space, craftsmanship, and location, this property also offers excellent potential as a luxury short-term rental. Experience the tranquility and grandeur of Avalon Estates—schedule your private tour today and start creating lifelong memories in your new home.
1531 HAWKESBURY CT, WINTER GARDEN, FL 34787
$575,00045 Days on yellowkey MLS ID: O6388237
0 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2141 Built: 1995Community: TuscanySingle Family
Remarks: Under contract-accepting backup offers. Tucked away at the end of a quiet cul-de-sac in the highly sought-after Tuscany community of Winter Garden, this pool home offers the rare combination of privacy, space, and lifestyle that buyers are searching for. Set on an oversized pie-shaped lot shaded by mature oak trees, the property welcomes you with beautiful curb appeal and lush landscaping before opening to a backyard retreat designed for everyday enjoyment and effortless entertaining. A screened pool with a natural rock waterfall and expansive lanai creates the ultimate outdoor living space, while the fully fenced yard extends well beyond the enclosure, offering abundant green space for pets, play, gardening, or future possibilities. Inside, the thoughtfully designed split-bedroom floor plan blends comfort with functionality. Upon entry, you’ll find a flex space enclosed with elegant French doors, currently used as a private home office—perfect for today’s work-from-home lifestyle. Across the foyer sits a formal dining room ready for gatherings and celebrations. The heart of the home flows seamlessly between the family room with a cozy wood-burning fireplace, the breakfast area, and the well-appointed kitchen featuring granite countertops, generous cabinetry, pantry storage, breakfast bar seating, and newer appliances. Sliding glass doors frame beautiful pool views and bring in natural light, creating a warm and inviting atmosphere. The owner’s suite is a peaceful retreat with room for a sitting area and direct access to the pool and lanai. The spa-inspired primary bath features dual vanities, a soaking tub, separate shower, and walk-in closet. Three additional bedrooms and an updated guest/pool bath are thoughtfully positioned on the opposite side of the home for privacy. Beyond the home itself, the location delivers the best of the Winter Garden lifestyle. Tuscany is a beloved neighborhood with limited turnover, situated just moments from the West Orange Trail and the vibrant shops, dining, and charm of Historic Downtown Winter Garden. With its oversized lot, cul-de-sac setting, private pool oasis, and prime location, this property offers a rare opportunity to own a home where space, serenity, and community come together.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Silvia Kinkela, Pa (407-284-9254)
13900 FOX GLOVE ST, WINTER GARDEN, FL 34787
$669,00078 Days on yellowkey MLS ID: S5143671
1 Days Off yellowkey (back on 3/25/2026)
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 3887 Built: 2004Community: Stoneybrook West Ut 04 48 48Single Family
Remarks: Under contract-accepting backup offers. Lowest Priced square foot in Stoneybrook West by more than $20 sq ft! Aggressively priced for this large home by motivated seller! Brand new roof June 2025! Beautiful spacious family home well maintained, southern views over the golf course! Welcome to your new home in the sought-after Stoneybrook West Golfing Community! The lovely 5-bedroom, 3-bathroom home is situated in St Andrews. Walking inside this spacious residence with over 3800 sq ft of space, you'll be welcomed and see the open plan and brightness of the home. You have a large open plan family room which leads to the kitchen and dining area, also accompanied by a formal dining room and a formal living room. From the kitchen dining area there are double sliding doors and triple sliding doors from the family room to the screen room. The screen room has a dining area, seating area and an outside covered area great for grilling. The downstairs has a convenient bedroom with an en-suite bathroom, featuring a large walk-in shower. Head upstairs and find 4 additional bedrooms and a huge bonus room ideal home office, man cave or games room. Double doors open into a spacious master bedroom complete with a sitting area, tray ceiling, two walk-in closets and en-suite bathroom. The owner's bathroom offers dual sinks, a large tub, and a walk-in shower. The three additional bedrooms with ample closet space and an additional shared bathroom ensure comfort for the whole family. The bonus room spans over the 3-car garage and has a multitude of uses. This home was designed with family living and comfort in mind, the back yard has sun all day. There is a 3-car garage with plenty of front parking for your family and visitors. Two new A/C units were installed in 2017 which are very well maintained with a biannual service since install and a new Hot water heater in 2023. Stoneybrook West has it all, catering to all types of families with its extensive range of amenities. The town center and clubhouse boast a large outdoor pool, fitness center, tennis courts, playground, volleyball court and basketball courts. Stoneybrook West is fully guarded 24/7. Included in your dues is also cable TV and internet for your convenience. The newly renovated 18-hole golf course now open. Situated just minutes away from Fowlers Grove shopping center and the charming Downtown Winter Garden area, you’ll be spoiled with the choice of dining and shopping options.
Listing is courtesy of: SELECT ESTATES, LLC (407-705-2330)
Listing Agent: Donna Ramsden (321-279-5233)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.