Location: Winter Garden , 34787
Do Not Show Listings
15280 MARITIME PINE DR, WINTER GARDEN, FL 34787
$988,539271 Days on yellowkey MLS ID: G5102291
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3550 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$0
Elementary School: Hamlin Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: Virtually Staged. Pre-Construction. To be built. The Ellington is a spacious two-story home offers 3,550 square feet of elegant living, featuring 5 bedrooms and 3.5 bathrooms, along with a generous 3-car garage. The primary suite is conveniently located on the first floor, alongside the laundry for easy access. Upstairs, you’ll find four additional bedrooms and a massive game room—perfect for family fun! Relax and unwind outside under the covered lanai. Enjoy ample space with an additional flex room, café, and walk-in closets throughout the home.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
3351 HANGING TIDE ST, WINTER GARDEN, FL 34787
$635,00033 Days on yellowkey MLS ID: O6407746
0 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2741 Built: 2021Monthly Fee: $152 Tax: $7,521 (2025)Community: Lakeview Preserve Ph 2Single Family
Taxes:$7,521
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this move in ready home newly built in 2021 in the gated Lakeview Preserve community. This single story home is offering 4 bedrooms, 3.5 bathrooms, with split bedroom layout and a spacious open floor plan. Step inside to find a bright and airy living space that seamlessly connects the kitchen, dining, and living areas. The gourmet kitchen is the centerpiece of the home, featuring sleek quartz countertops, a large center island ideal for gatherings, and ample cabinetry for storage. Whether you're hosting guests or enjoying a quiet night in, this layout delivers both comfort and functionality. The split bedroom design provides added privacy, with a generously sized primary suite offering a peaceful retreat. Additional bedrooms are well appointed and versatile, perfect for guests, a home office, or growing families. This gated community features resort style amenities including a clubhouse, zero entry pool, splash pad, playground, fitness center, and a private dock with kayak launch on John’s Lake, offering the ideal setting to experience the best of Florida living. Located just minutes from the charm of Downtown Winter Garden, you’ll enjoy access to boutique shopping, local dining, farmers markets, and the popular West Orange Trail for biking and outdoor recreation. Food lovers will appreciate nearby favorites like The Hangry Bison, Chef's Table at the Edgewater, and Crooked Can Brewing offering everything from casual bites to upscale dining. Convenient access to Florida State Road 429 and Florida State Road 408 makes commuting to Orlando and nearby attractions a breeze. Don't miss out on this opportunity and schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Devon Sobers (407-341-4720)
7808 WINTER WREN ST, WINTER GARDEN, FL 34787
$579,00054 Days on yellowkey MLS ID: O6400269
REDUCED by $9,000 (1.5%) on 06/04/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2274 Built: 2015Monthly Fee: $252 Tax: $8,119 (2025)Community: SummerlakeSpa: NoSingle Family
Taxes:$8,119
Elementary School: Summerlake Elementary
Remarks: Under contract-accepting backup offers. Welcome to resort-style living in the highly sought-after Summerlake Community of Winter Garden! Enjoy Disney fireworks and Space Coast Rocket launches from the front porch or across the pond in front of the house. This beautifully situated home on a corner lot is MOVE IN READY and features: 4-bedrooms, 2.5-baths with an upstairs office loft, offers space, style, and flexibility in one of Horizon West’s premier neighborhoods. The inviting covered front porch sets the tone as you step into this light-filled home featuring granite countertops throughout, freshly painted both inside and out, and tile flooring across the main living areas. The open-concept design is perfect for both entertaining and everyday living. The kitchen flows seamlessly into the living and dining areas, and opens to a covered and screened in rear patio lanai, creating an ideal indoor-outdoor living experience. The main floor also includes a convenient half bath, perfect for guests. The primary suite is a relaxing retreat, featuring dual sinks, granite countertops, a soaking tub, a separate walk-in shower, and ample closet space. Three additional bedrooms are well-sized and thoughtfully arranged with easy access to the remaining full bath. This is truly a rare opportunity to experience both tranquility and park like setting right outside your front door! Residents of Summerlake enjoy exceptional amenities including a lakeside clubhouse with fitness center, party room, resort-style pool, fishing pier, walking trails, parks, playgrounds, and tennis courts makes this the perfect area for the active lifestyle — all just minutes from SR-429, top-rated schools, Winter Garden Village, downtown Winter Garden, golf courses, and major theme parks. Lawn care, sprinkler maintenance, and irrigation water are all included in the low HOA fee, making maintenance a breeze. Schedule your private tour today and make this exceptional property yours!
Listing is courtesy of: BROOKSHIRE HOMES REALTY (303-838-0434)
Listing Agent: Robert Larosa (303-489-2019)
16848 HAMLIN VISTA ALY, WINTER GARDEN, FL 34787
$525,000103 Days on yellowkey MLS ID: O6387459
REDUCED by $15,000 (2.8%) on 05/17/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 Built: 2024Monthly Fee: $200 Tax: $8,210 (2025)Community: Hamlin PointeSingle Family
Taxes:$8,210
Remarks: Virtually Staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Discover the timeless appeal of the Newbury floor plan in the exclusive Hamlin Pointe community! This 2024-built two-story home offers 4 bedrooms, 3 full bathrooms, and 2,088 sq ft of thoughtfully designed living space. A versatile first-floor bedroom serves perfectly as a guest suite, home office, or multi-generational retreat. The open-concept great room and dining area are anchored by a gourmet kitchen featuring quartz countertops, upgraded cabinetry, stylish backsplash, and a built-in cooktop, oven, and microwave — ideal for both casual family meals and effortless entertaining. Upstairs, three additional bedrooms surround a spacious owner’s suite with a generous walk-in closet, plus a conveniently located laundry room. Outside, enjoy a covered patio for relaxing or dining al fresco, and the privacy of a detached two-car garage on a low-maintenance lot. Nestled in the heart of Hamlin within Horizon West — one of Orlando’s fastest-growing areas — Hamlin Pointe delivers walkable resort-style living at its best. Stroll or bike to the vibrant Hamlin Town Center along scenic Lake Hancock for dining, shopping, entertainment, and year-round events. Families love the top-rated schools, abundant parks, trails, and new medical facilities. Just minutes to Walt Disney World, downtown Winter Garden, Winter Garden Village, SR 429, and Florida’s Turnpike, this boutique community of only 53 homes offers the perfect blend of modern convenience, low-maintenance luxury, and long-term investment value in a location where others vacation every day.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Tyler Somers (561-713-8728)
642 MEDORA WAY, WINTER GARDEN, FL 34787
$1,137,1507 Days on yellowkey MLS ID: O6413483
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2995 Built: 2026Monthly Fee: $155 Tax: $993 (2025)Community: Lakeview Village EstatesSingle Family
Taxes:$993
Elementary School: Dillard Street Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, quartz countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Tatiana Souza (407-467-9914)
650 MEDORA WAY, WINTER GARDEN, FL 34787
$1,157,1907 Days on yellowkey MLS ID: O6413464
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2902 Built: 2026Monthly Fee: $155 Tax: $993 (2025)Community: Lakeview Village EstatesSingle Family
Remarks: Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.
17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$534,90048 Days on yellowkey MLS ID: G5111718
1 Days Off yellowkey (back on 6/12/2026)
REDUCED by $5,000 (0.9%) on 06/02/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2148 Built: 2019Monthly Fee: $215 Tax: $7,499 (2025)Community: Waterside/Johns Lk-Ph 2ASingle Family
Taxes:$7,499
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Looking for a move-in-ready home in Winter Garden with the upgrades already done? NO CDD!! This 3-bedroom, 3-bath home with a loft in The Cove at Waterside offers stylish finishes, flexible living space, and a location close to shopping, dining, and downtown Winter Garden. Inside, you’ll find luxury vinyl plank flooring, fresh interior paint, granite countertops, solid maple 42-inch cabinetry, a double wall oven, and a custom dry bar with wine refrigerator and mini refrigerator. The loft adds extra space for a home office, media room, playroom, or guest retreat. Other highlights include new carpet, a tankless gas water heater, Low-E dual-pane windows, 15 SEER HVAC, utility room cabinets with sink, new attic insulation, and a screened lanai for outdoor living. Community amenities include a resort-style pool, upgraded fitness center, and private community lakefront park near Johns Lake. Ask for full list of upgrades and features
Listing is courtesy of: TOWERSIDE REALTY INC (407-454-9800)
Listing Agent: Jennifer Roberts (407-456-2124)
14501 GROVE RESORT AVE #1703, WINTER GARDEN, FL 34787
$299,00071 Days on yellowkey MLS ID: O6394100
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1396 Built: 2016Monthly Fee: $998 Tax: $6,709 (2025)Community: Grove Residence & Spa Hotel CondoCondo
Taxes:$6,709
Remarks: RARE opportunity to own a TOP-FLOOR UNIT with SWEEPING LAKE VIEWS! This 3-bedroom, 2-bathroom Jasmine floor plan is located in The Grove Resort & Spa, one of Central Florida’s premier vacation investment communities. Just minutes from Disney World, with Universal Orlando and SeaWorld also nearby, this resort offers an unparalleled combination of luxury and convenience. Enjoy incredible amenities, including theFlowRider® surf simulator, a lazy river with waterfalls, multiple water slides, a zero-entry resort-style pool, private cabanas with poolside food and drink service, and an activity pool. Beyond the waterpark, the resort also features three large pools and a jacuzzi conveniently located near the unit’s building. After a day of excitement, guests can unwind at the Longboard Bar & Grill or take advantage of the resort’s many luxurious amenities. The unit itself boasts a beautifully designed, well-equipped kitchen, an open-concept layout, and comes FULLY FURNISHED for a seamless move-in or rental experience. The great room, master bedroom, and one of the additional bedrooms all feature stunning LAKE VIEWS, with the great room opening to a private balcony where you can relax and take in the scenery. The master suite offers a spa-like ensuite bathroom with a garden tub, separate tiled shower, and dual vanities. The split-bedroom layout ensures privacy, and the unit comes equipped with four large-screen TVs for entertainment. As a turn-key investment, this condo includes all bookings upon purchase, with on-site management handling hotel operations and maintenance, a truly hassle-free opportunity that generates immediate income. Schedule your showing today!
Listing is courtesy of: REALTY ONE GROUP INSPIRATION (321-233-2300)
Listing Agent: Blake Blahut (239-691-9519)
205 HORSTFIELD DR, WINTER GARDEN, FL 34787
$310,00025 Days on yellowkey MLS ID: O6410222
REDUCED by $5,000 (1.6%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1048 Built: 1998Monthly Fee: $40 Tax: $1,983 (2025)Community: Park Ave EstatesSingle Family
Taxes:$1,983
Elementary School: SunRidge Elementary
Remarks: **WINTER GARDEN SINGLE FAMILY HOME** **HVAC (2023) + ROOF (2018) + EXTERIOR PAINT (2024)** **ALL NEW ENERGY EFFICIENT WINDOWS & SLIDING DOOR (2025)** **LARGE FULLY FENCED PRIVATE BACKYARD** **NATURAL GAS** **TILE THROUGHOUT -- NO CARPET** Welcome to this adorable, affordable & move-in-ready single family home in the PERFECT LOCATION. Purchase with CONFIDENCE & PEACE OF MIND…recent updates & special features include: all new energy efficient windows and sliding door (2025), updated kitchen cabinetry (2018), updated bathroom vanities (2024), roof (2018), HVAC (2023), freshly painted exterior (2024), new garage opener (2023), custom hurricane shutters for windows & doors, fully fenced (2022)…and MORE! NO CARPET -- tile throughout the entire home. Lots of NATURAL LIGHT throughout. The fantastic & FLEXIBLE floor plan features a large living space open to the kitchen, THREE bedrooms, TWO full bathrooms -- all one ONE LEVEL. The primary suite includes a large walk-in shower, updated vanity and walk-in closet with shelving. All appliances STAY -- including washer & dryer. Enjoy the Florida lifestyle outdoors with the extended paver patio and large backyard space that is fully fenced & private with additional open community easement behind the home for added privacy buffer. Extended driveway for ample parking space. LOW UTILITY BILLS with newer roof, HVAC & windows! The LOW HOA includes a community pool. The PERFECT location -- conveniently located to both Winter Garden & Clermont with easy direct access to the FL Turnpike (less than three miles) and HWY 429 (less than two miles). Just ONE MILE to historic Downtown Winter Garden -- enjoy the West Orange Trail, HUGE weekly farmer's market, festivals, shopping, dining, art, the Crooked Can Brewery & Plant Street Market. Easy access to ALL shopping (Costco, Target & more), dining, medical & conveniences in both Winter Garden & Clermont along HWY 50 and Winter Garden Village. WELCOME HOME!
Listing is courtesy of: TARA MOORE REAL ESTATE (407-738-5588)
Listing Agent: Tara Moore (407-765-3700)
648 ORANGE BELT LOOP, WINTER GARDEN, FL 34787
$499,990110 Days on yellowkey MLS ID: S5144591
REDUCED by $25,010 (4.8%) on 04/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1688 Built: 2018Monthly Fee: $338 Tax: $4,171 (2024)Community: Heritage/Plant StreetTownhouse
Taxes:$4,171
Tax Year: 2024
Remarks: Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Heritage at Plant Street in the GOLF CART DISTRICT. This beautiful 3-bedroom, 2.5-bath home offers nearly 1,700 square feet of thoughtfully designed living space in an unbeatable setting. Step inside to an expansive great room featuring stylish wood-look tile and an open-concept layout that seamlessly connects the living, dining, and kitchen areas—perfect for entertaining. The kitchen is designed for both function and style, offering abundant stylish cabinetry, gorgeous backsplash, elegant gold hardware, granite countertops, NEW Refrigerator, NEW microwave, NEW dishwasher, GAS stove and generous prep space. A screened courtyard with pavers creates a more private/secure outdoor retreat between the home and the detached 2-car garage. Whether you envision an outdoor lounge, garden oasis, or entertainment space, the possibilities are endless. Upstairs you will find upgraded- low maintenance flooring through out and your own private owner’s retreat. The spacious primary suite features a walk-in closet and an impressive ensuite bath designed to impress. Two additional bedrooms share a full bathroom, offering flexibility for guests, family, or a home office setup. A convenient half bath is located downstairs for visitors. Enjoy your summer months cooling off in the COMMUNITY POOL which is located just a couple of minutes from your front door. This community is ideally positioned between the West Orange Trail Park and the Winter Garden Branch Library, and just minutes from the 429 for easy commuting. If you like to run or bike this home is the perfect place for you since it is located along the West Orange Trail. Walk—or hop on your golf cart—to downtown Winter Garden where you’ll enjoy the vibrant atmosphere of Plant Street Market, known for its local food vendors, craft brews, artisan goods, and year-round community events. Located close to the community pool and surrounded by everything that makes Winter Garden special, this home truly offers the lifestyle buyers are searching for. Lower utility bills since it's an inside unit, double pane windows and a Instant Hot Gas Water Heater. Schedule your private showing today and experience why this location is so highly sought after.
Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)
Listing Agent: Milinda Knollinger (321-624-7384)
1503 COLUSO DR, WINTER GARDEN, FL 34787
$473,00024 Days on yellowkey MLS ID: O6410109
REDUCED by $7,000 (1.5%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2187 Built: 1988 Tax: $1,952 (2025)Community: Magnolia Wood Fifth AddSpa: NoSingle Family
Taxes:$1,952
Remarks: Ideally located in Winter Garden's Magnolia Wood neighborhood, this single-story block-and-stucco home offers quick access to the SR-429 entrance for an easy commute, with historic Downtown Winter Garden and the West Orange Trail — and its shops, dining, and miles of paved path — within close reach. Set on a landscaped 0.32-acre lot, the home features 3 bedrooms, 2 baths, and 2,187 heated square feet of comfortable living space. Inside, the popular split floor plan places the primary bedroom on the main floor, while vaulted ceilings and an open layout create a bright, airy feel throughout. A wood-burning masonry fireplace anchors the family room, and a Florida room adds flexible space to enjoy year-round. Outdoor living is easy here, with a screened front porch overlooking the garden and a private backyard featuring a workshop and shed, plus an attached 20x24 two-car garage. Situated in Orange County with low annual taxes of approximately $1,952 and in low-risk Flood Zone X, this property also allows leasing with a one-month minimum and no association approval required — offering flexibility for owners and investors alike. Schedule your showing today.
Listing is courtesy of: FLA REAL ESTATE SERVICES (321-436-4911)
Listing Agent: John Tilton (407-955-2759)
14989 APOLLO BOND DR, WINTER GARDEN, FL 34787
$405,000122 Days on yellowkey MLS ID: O6378685
REDUCED by $10,000 (2.4%) on 06/12/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1789 Built: 2019Monthly Fee: $241 Tax: $3,914 (2024)Community: Watermark Ph 3Townhouse
Taxes:$3,914
Elementary School: Panther Lake Elementary
Remarks: Welcome to this beautifully maintained townhome offering stylish finishes, functional space, and a prime location with serene views. Step inside to an open-concept layout featuring a spacious kitchen with light cabinetry, granite countertops, stainless steel appliances, a large center island with bar seating, and a walk-in pantry. The kitchen flows seamlessly into the dining and living areas, creating the perfect space for entertaining or everyday living. Natural light fills the home, highlighting the neutral tones and tile flooring throughout the main living areas. Upstairs, the generous primary suite features a designer accent wall, large windows, and a spacious walk-in closet with built-in organization. The en-suite bath offers dual vanities with granite counters and a walk-in glass-enclosed shower. Secondary bedrooms are well-sized and share a full bath with granite countertops. A convenient upstairs laundry room adds to the home’s thoughtful layout. Additional highlights include a private office/flex space, a powder bath downstairs, ample storage throughout, and a charming covered front porch overlooking peaceful green space. Enjoy outdoor living on the private paver patio. Enjoy low-maintenance living with community-maintained exteriors and close proximity to Hamlin’s shops, restaurants, lakefront trails, events, and community recreational amenities, including a nearby basketball court — all just minutes from your front door. Convenient access to FL-429, top-rated schools, and downtown Winter Garden adds to the appeal. This is a fantastic opportunity to own in a vibrant, walkable area that blends convenience, lifestyle, and charm. Schedule your showing today!
Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)
Listing Agent: Jasmine Reierson (407-630-3336)
15419 UGLIS ALY, WINTER GARDEN, FL 34787
$555,00047 Days on yellowkey MLS ID: O6403047
REDUCED by $10,000 (1.8%) on 06/12/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2270 Built: 2018Monthly Fee: $60 Tax: $8,121 (2025)Community: Highlands/Summerlake Grvs Ph 2Single Family
Taxes:$8,121
Remarks: Welcome to 15419 Uglis Aly, a uniquely positioned Horizon West home offering rare privacy, lifestyle, and convenience just minutes from Disney. This property faces open green space with no immediate front neighbors, creating a rare sense of privacy and openness. Enjoy nightly Disney fireworks views from home, with Grand Floridian approximately 12 minutes door to door. Built by K. Hovnanian, this open-concept home features surround sound, full ethernet wiring throughout, a bright sunroom, double ovens, stainless appliances, and flexible living spaces ideal for modern family life. Upstairs offers 3 spacious bedrooms, a dedicated laundry room, and a versatile loft—an option many similar homes in the area have converted into a 4th bedroom. The primary suite includes dual walk-in closets and an en-suite bath. The backyard is designed for low-maintenance entertaining with premium artificial turf, a covered lanai, and extended pavers. An oversized 20’ x 24’ garage plus one of the longest driveways in the neighborhood provide exceptional parking and storage. Just steps from the playground, green space, and mailboxes without crossing a street, plus access to resort-style amenities including pool, tennis, dog park, grills, and golf-cart-friendly access to shops, dining, and top-rated schools. A rare move-in ready opportunity combining privacy, smart upgrades, and the Horizon West lifestyle.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Evan Caulfield (407-432-9767)
17125 STILLNESS ALY, WINTER GARDEN, FL 34787
$580,9335 Days on yellowkey MLS ID: G5113666
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2083 Built: 2026Monthly Fee: $121Community: Serenade At OvationSingle Family
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Virtually Staged. Under Construction. Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The gourmet kitchen is a standout feature, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized , ensuring that everyone in the family has their own comfortable space. This home is guaranteed to exceed your expectations with its blend of spaciousness and functionality. Sample Image
181 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$600,00017 Days on yellowkey MLS ID: O6412174
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2940 Built: 2002Monthly Fee: $67 Tax: $7,609 (2025)Community: Lakeview ReserveSingle Family
Taxes:$7,609
Remarks: Virtually Staged. Experience elevated living in the gated WATERFRONT community of Lakeview Reserve, ideally situated in the heart of historic downtown Winter Garden in the GOLF CART DISTRICT with LOW HOA. This impressive FIVE-bedroom, THREE-bath residence with dining space and LOFT offers an exceptional combination of space, comfort, and versatility, thoughtfully designed to accommodate both everyday living and grand-scale entertaining. Boasting a generous floor plan with expansive living areas and well-proportioned bedrooms, the home provides ample room for growing families, multigenerational living, or those seeking dedicated spaces for a home office, fitness room, or media retreat. Situated on a premium homesite spanning nearly one-quarter of an acre (.19), the property presents endless possibilities for outdoor enjoyment. Whether you envision creating a private backyard oasis, adding a custom pool, designing an outdoor kitchen, or simply enjoying the abundance of open green space, this oversized lot offers the flexibility to bring your vision to life while still providing plenty of room for recreation and relaxation. Upon entering, you are welcomed by a thoughtfully designed open-concept floor plan enhanced by new flooring and a freshly painted interior (2023-2024), creating a bright and inviting atmosphere throughout. The beautifully appointed and newly UPDATED gourmet kitchen serves as the heart of the home, featuring stainless-steel appliances, quartz countertops, shaker style cabinets, and two pantries. The living area is adjacent to the kitchen and presents a great opportunity to expand into the outdoor space creating an indoor-outdoor vibe. Designed with flexibility and comfort in mind, the main level offers a generously sized guest bedroom and a full bathroom, ideal for visitors, a home office, or multigenerational living. The laundry room and dining space are also located on the main level. Upstairs, the spacious primary suite provides a private retreat, while three additional bedrooms, full bath, and loft offer abundant space for family and guests. The primary suite includes a garden tub with separate shower, vanity, linen closet, and walk-in closet. Enjoy picturesque views of Lake Apopka from multiple vantage points throughout the home, creating a serene backdrop for everyday living. ADDITIONAL UPDATES: roof (2018), water heater (2025), downstairs AC (2024-2025), Just moments away, residents enjoy exclusive access to a private community dock overlooking the lake—an idyllic setting for morning coffee, fishing, or taking in spectacular sunset views. Located within the golf-cart district, this remarkable home places you just minutes from the charming boutiques, acclaimed dining, farmers market, and year-round events that make downtown Winter Garden one of Central Florida’s most sought-after destinations. Convenient access to major highways (Turnpike, 429, East-West Expressway) further enhances the lifestyle, placing world-renowned attractions such as Walt Disney World, Universal, and downtown Orlando within easy reach. You can access the 22 mile long WEST ORANGE Trail just footsteps outside of the community to take in cycling and exercising. Move-in ready, this exceptional residence offers a rare opportunity to enjoy luxury, convenience, and a true sense of community in one of Winter Garden’s sought after gated neighborhoods. Measurements are approximate. Buyer is responsible for verifying information.
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Ashley Boyd (321-209-5540)
16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787
$435,000111 Days on yellowkey MLS ID: O6383709
REDUCED by $25,000 (5.4%) on 05/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1662 Built: 2021Monthly Fee: $284 Tax: $6,683 (2024)Community: Hawksmoor-Ph 3Townhouse
Taxes:$6,683
Remarks: Welcome to 16425 Prairie School Drive, a beautifully maintained 2021 townhome located in the highly desirable Hawksmoor community of Winter Garden. This move-in-ready home offers 3 bedrooms, 2.5 bathrooms, a rear-entry two-car garage, and 1,662 square feet of modern living space designed for comfort and convenience. Step inside to an open-concept floor plan featuring tile flooring throughout the main living areas, a spacious living and dining room, and a bright, stylish kitchen complete with a large center island, stainless steel appliances, and ample cabinet space—perfect for entertaining or everyday living. Upstairs, the spacious primary suite features a walk-in closet and private en-suite bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy low-maintenance living and access to Hawksmoor’s resort-style amenities, including a community pool, fitness center, clubhouse, playground, walking trails, and scenic lakes. Conveniently located near Downtown Winter Garden, Flamingo Crossings, major highways, shopping, dining, and Walt Disney World, this home offers an exceptional opportunity to enjoy one of Central Florida’s most sought-after communities. Schedule your private showing today and experience the lifestyle that makes Winter Garden one of the area’s most desirable places to call home.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nairobi Rondon (786-935-0365)
16217 LAKE JOHNS CIR, WINTER GARDEN, FL 34787
$1,200,00028 Days on yellowkey MLS ID: O6409098
1 Days Off yellowkey (back on 5/29/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4659 Built: 1973 Tax: $3,817 (2025)Community: Lake Johns ShoresSingle Family
Taxes:$3,817
Remarks: 16217 Lake Johns Circle is a rare modern farmhouse retreat where luxury, craftsmanship, and family-centered design come together in extraordinary fashion. Positioned on a quiet cul-de-sac of only 15 homes with no HOA, this fully reimagined Winter Garden residence offers front-porch views toward Johns Lake and backs to protected green space, creating a setting that feels private, peaceful, and deeply connected to nature. Completed in 2025, the home underwent an extensive renovation and expansion with remarkable attention to detail and quality. Unlike typical luxury renovations, much of the craftsmanship was personally completed by the homeowners themselves-resulting in a residence that feels intentionally built rather than simply remodeled. Inside, the home unfolds with warm modern farmhouse design, engineered hardwood flooring throughout, soaring ceilings, custom millwork, curated lighting, and expansive gathering spaces designed for both everyday living and elevated entertaining. The chef's kitchen serves as the architectural centerpiece of the home, featuring professional-grade appliances, custom cabinetry, quartz surfaces, a hidden butler's pantry, beverage station, and an oversized gathering island wrapped in authentic character and texture. The floorplan was thoughtfully designed to accommodate multigenerational living and large gatherings with uncommon flexibility. Unique design moments include custom built-in bunk spaces, a secondary bedroom designed with three built-in beds, and a truly exceptional owner's retreat featuring vaulted ceilings, a private sitting area, spa-inspired bath, oversized custom closet room, and peaceful views toward Johns Lake. The upstairs loft creates an additional lifestyle space ideal for media, gaming, reading, or relaxation, while the nearly 1,500-square-foot insulated garage/workshop offers incredible versatility for vehicles, boats, hobbies, fitness, or storage. Major infrastructure improvements completed in 2025 include a new roof, new HVAC systems, new windows, new plumbing, tankless water heater, septic system, and extensive mechanical upgrades. Located minutes from Downtown Winter Garden, Oakland, the West Orange Trail, and major roadways, this is a rare opportunity to own a highly customized modern farmhouse retreat in one of Central Florida's most desirable lifestyle corridors.
Listing is courtesy of: HOMEFIRST REAL ESTATE (689-340-3007)
Listing Agent: Ed Vasquez (689-340-3007)
18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787
$724,900100 Days on yellowkey MLS ID: O6388830
0 Days Off yellowkey (back on 5/1/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2924 Built: 2024Monthly Fee: $280 Tax: $10,366 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$10,366
Remarks: **POND VIEW 4-BEDROOM IN WATERLEIGH!** Don’t miss this opportunity to own a spacious 4-bedroom, 3-bath home with nearly 3,000 sq ft in one of Winter Garden’s most sought-after communities, now aggressively priced to sell quickly. Situated on a premium **pond-view lot with no rear neighbors**, this home offers peaceful water views and added privacy. The open-concept layout provides generous living space, a large kitchen ideal for entertaining, and flexibility for everyday living. Why wait months and pay more for new construction? This home is **move-in ready now** no delays, no added upgrade costs, and priced below comparable homes in the area, making it one of the **best values in Waterleigh**. Nearly 3,000 sq ft; 4 bedrooms / 3 full bathrooms; Pond view with no rear neighbors; Open-concept layout with spacious living areas; Located in amenity-rich Waterleigh **Seller is motivated. Bring all offers.** LEASE WILL BE CONSIDERED. Opportunities like this don’t last. Schedule your showing today.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Linda Morgan (404-625-5256)
706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,259,00078 Days on yellowkey MLS ID: O6394059
REDUCED by $28,000 (2.2%) on 05/28/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4019 Built: 2018Monthly Fee: $298 Tax: $17,895 (2025)Community: Canopy Oaks Ph 1Single Family
Taxes:$17,895
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Experience a lifestyle defined by elegance, privacy, and exceptional design in this luxury residence within the gated community of Canopy Oaks in Winter Garden. Built by A.R. Bailey Homes, this highly sought-after Delray floor plan offers nearly every feature today's discerning buyer desires, blending sophisticated architecture with functional living spaces designed for entertaining, multigenerational living, and everyday comfort. Nestled within an intimate enclave of just 49 homesites, this residence enjoys a premier location, minutes from Historic Downtown Winter Garden, Winter Garden Village, top-rated schools, dining, shopping, recreation, and major commuter routes. A striking exterior presentation sets the tone with a paver driveway, concrete tile roof, stone-accented elevation, wood-look garage doors, and grand solid wood double-entry doors. Beyond the entry, thoughtfully designed interiors showcase expansive gathering spaces, architectural ceilings, elegant finishes, and abundant natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring a natural gas cooktop with exterior venting, built-in oven, upgraded appliances, pot filler, 42-inch cabinetry with crown molding, under-cabinet lighting, tile backsplash, walk-in pantry, and an oversized island overlooking the spacious great room with coffered ceilings. Adjacent to the living areas, a gated wine cellar creates a memorable entertaining feature rarely found in homes at this price point. The first-floor primary suite offers a private retreat with a spa-like bath featuring dual granite vanities, a soaking tub, oversized walk-in shower with dual shower heads and bench seating, and a custom-designed closet system. A separate first-floor en-suite bedroom provides ideal flexibility for guests, extended family, or a dedicated home office. Upstairs, the versatile layout continues with a second primary suite, two additional en-suite bedrooms, a generous loft, guest powder bath, and a covered balcony, creating multiple private living spaces throughout the home. Designed to embrace Florida's year-round outdoor lifestyle, the residence seamlessly connects indoor and outdoor living through a dramatic corner-opening glass wall and expansive stackable sliding doors. The covered lanai, enhanced by a motorized retractable screen, creates an ideal setting for entertaining, relaxing, or enjoying peaceful evenings outdoors. The oversized backyard, with stucco privacy wall, offers ample space to create a custom pool, outdoor kitchen, and private resort-style retreat. Additional features include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, a mudroom, reading nook, and extensive storage throughout. Residents of Canopy Oaks enjoy access to community nature trails and a playground while remaining conveniently located near Downtown Winter Garden, Winter Garden Village, the Roper YMCA, Orlando Health facilities, and major transportation corridors including the Florida Turnpike, SR 429, SR 408, and Interstate 4. Offering luxury, flexibility, and an exceptional Winter Garden location, this beautifully maintained home presents a rare opportunity to enjoy elevated Central Florida living in one of the area's most desirable gated communities. Virtual pool rendering shown for illustrative purposes only. Also listed for lease MLS #O6416527
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Lisa Rutkowski (407-793-2416)
1019 PORTMOOR WAY, WINTER GARDEN, FL 34787
$595,0005 Days on yellowkey MLS ID: O6414940
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2401 Built: 2001Monthly Fee: $243 Tax: $646 (2025)Community: Stoneybrook West Unit 1Spa: NoSingle Family
Taxes:$646
Elementary School: Whispering Oak Elem
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1019 Portmoor Way in Winter Garden, a 2-story home offering 3 bedrooms, 3 bathrooms, a balcony, and a layout designed for comfortable everyday living. All bedrooms are located on the upper floor, creating separation between the main living areas and private spaces. Inside, the home offers a functional floorplan with room for relaxing, dining, and entertaining. The primary suite features upgraded walk-in closet space and French doors added in 2022, while the guest half bath was fully upgraded in 2022. Additional improvements include a new garbage disposal in 2024, new upstairs windows installed in 2020 by the previous owner, a new boiler in 2025, and a new HVAC system in 2026. Outdoor living is a standout feature, with a covered patio overlooking the screened in-ground pool. The pool was installed in 2020 by the previous owner, with a new pool pump added in 2024 and a new motor in 2026. The balcony adds another outdoor space to enjoy fresh air, while the covered patio and screened pool area provide a comfortable setting for lounging, dining, and entertaining. The exterior has also been thoughtfully maintained, with the home sealed and painted in 2026, new landscaping completed in 2026, and a roof installed in 2018 by the previous owner. These updates add to the home’s overall appeal and help support a move-in-ready feel. The community offers a strong amenity package, including a pool, park, clubhouse, fitness center, and restaurant, giving residents convenient options for recreation, gathering, dining, and everyday enjoyment close to home. Located in Winter Garden, the home is set in one of Central Florida’s most desirable areas, known for shopping, dining, parks, trails, community events, and access to major roadways. The location provides convenient connections to Horizon West, Hamlin, Windermere, Walt Disney World, and the greater Orlando area while maintaining a residential neighborhood setting. Be sure to ask about the assumable VA loan opportunity with a low interest rate, offering potential savings and added value for qualified buyers.
Listing Agent: Thomas Nickley, Jr (407-629-4420)
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