Location: Winter Garden
Do Not Show Listings
15161 CANOE PL, WINTER GARDEN, FL 34787
$1,200,000Listed 04/14/2026 1:43PM MLS ID: O6398949
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3816 Built: 2019Monthly Fee: $385 Tax: $13,235 (2025)Community: Lakeshore Preserve Ph 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,235
Elementary School: Panther Lake Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Welcome to this beautifully appointed home in the highly desirable Lakeshore community in Winter Garden, offering an exceptional combination of space, comfort, and location. Situated in a prime area close to top-rated schools, shopping, dining, and major roads, this residence is ideal for buyers seeking both convenience and an outstanding lifestyle. This spacious home features 5 bedrooms, 4 full bathrooms, and 1 half bath, with a highly functional and attractive floor plan. Upon entry, you are welcomed by a private first-floor suite, perfect for guests, in-laws, or a home office with added privacy. Upstairs, you will find the remaining bedrooms, including the generous primary suite, along with a huge loft that offers endless possibilities for a media room, playroom, second living area, or home workspace. The home also features a formal dining room, while the kitchen, breakfast area, and family room flow seamlessly together in an open-concept layout that is ideal for both everyday living and entertaining. Step outside to enjoy the brand-new outdoor gourmet area, creating the perfect setting for gatherings, weekend barbecues, and relaxed Florida living. Residents of Lakeshore enjoy access to excellent community amenities, including a well-appointed clubhouse, fitness center, and playground, all contributing to a vibrant and welcoming neighborhood atmosphere. This is a rare opportunity to own a spacious, well-located home in one of Winter Garden’s most attractive communities.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Maqueli Gewehr (863-258-5656)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,900Listed 04/14/2026 1:24PM MLS ID: O6398208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1988 Tax: $2,702 (2025)Community: East Garden Manor Add 03Single Family
Taxes:$2,702
Elementary School: Maxey Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.
Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)
Listing Agent: Rosa Rodriguez (407-832-1185)
16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787
$495,0006 Days on yellowkey MLS ID: O6397108
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 2019Monthly Fee: $127 Tax: $5,006 (2025)Community: Hawksmoor-Ph 1Single Family
Taxes:$5,006
Elementary School: Water Spring Elementary
Remarks: Welcome to 16716 Wingspread Loop, a beautifully maintained single-story home in the highly sought-after Hawksmoor community of Winter Garden. Built in 2019 and cared for by its original owner, this 3-bedroom, 2-bath residence is move-in ready with thoughtful upgrades throughout. The open layout creates an easy flow between the kitchen, dining, and living areas. The kitchen features warm honey-toned cabinetry, granite countertops, and generous storage. The spacious primary suite serves as a private retreat with a large bedroom, walk-in closet, and an en-suite bath with quartz countertops. Additional highlights include built-in cabinetry in the laundry room, with the washer and dryer conveying for added convenience. Enjoy Florida living outdoors on the private patio, perfect for relaxing or hosting friends. The two-car garage includes a durable epoxy-coated floor, and the paved driveway enhances the home’s curb appeal. All kitchen and laundry appliances are included. Located along Avalon Road, this home places you just minutes from Hamlin Town Center, Flamingo Crossings, Walt Disney World, FL-429, Orange County National Golf Center, Clermont, Windermere, and top-rated Orange County schools. Residents of Hawksmoor enjoy a variety of resort-style amenities, including a clubhouse with rentable event space, fitness center, pool and splash pad, outdoor summer kitchen and grill, yoga lawn, shaded playground, dog park, and scenic walking paths. Schedule your private showing today and experience everything this Winter Garden home has to offer. Transferable lifetime termite contract from Massey available.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
13282 SERENE GLADE RD, WINTER GARDEN, FL 34787
$456,49746 Days on yellowkey MLS ID: S5144831
0 Days Off yellowkey (back on 3/4/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2026Monthly Fee: $225 Tax: $500 (2025)Community: Serenade At OvationTownhouse
Taxes:$500
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Step into style and serenity with this stunning townhome that perfectly blends modern living with picturesque pond views. This home is a haven for comfort and convenience. The open-concept main floor is designed for both everyday living and effortless entertaining, featuring upgraded finishes throughout—from sleek countertops and solid wood cabinetry to premium luxury vinyl flooring that exudes sophistication. Upstairs, you'll find a tranquil primary suite with a spa-like ensuite bath, offering a private retreat to unwind after a long day. Two additional bedrooms provide plenty of space for family, guests, or a home office. And let’s not forget the breathtaking pond views—whether you're sipping coffee on your patio or enjoying the natural light streaming through your windows, the serene backdrop adds a touch of calm to every moment. Only 20 minutes to Magic Kingdom (NO highway driving needed for access!), less than 3 miles to Flamingo Crossing Shopping area, less than 10 miles to Hamlin Town Center, and 30 minutes to all that Millenia and the Outlet Malls, this home provides all that Orlando Living has to offer.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Marissa Crawford (407-361-7400)
14501 GROVE RESORT AVE #1310, WINTER GARDEN, FL 34787
$230,0007 Days on yellowkey MLS ID: O6397317
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1265 Built: 2016Monthly Fee: $608 Tax: $6,200 (2025)Community: Grove Resort And Spa Hotel CondoCondo
Taxes:$6,200
Elementary School: None
High School: None
Middle School: None
Remarks: Fully Furnished & Turn-Key Ready! Welcome to your dream vacation retreat at the highly sought-after Grove Resort & Spa—a full-service luxury resort just 10 minutes from Disney World! This spacious 2-bedroom, 2-bathroom Jasmine Model is located on the 3rd floor and offers 1,265 sqft of comfortable living space, including a screened-in balcony with serene views. Enjoy the ultimate resort lifestyle with incredible on-site amenities: a full water park with dual water slides, a FlowRider® double surf simulator, lazy river, splash zones, multiple pools, private cabanas, restaurants, spa, fitness centers, arcade game room, mini golf, walking trails, and more. The resort also features a convenient alfresco market and offers complimentary shuttle service to Disney for your added ease. The unit is fully furnished with a king-sized bed in the primary suite and a queen bed in the secondary bedrooms—perfect for families or guests. Located just off I-192, you’re minutes from shopping, dining, and all of Orlando’s top attractions. Truly turn-key and resort living at its best—call today to schedule your private showing!
Listing Agent: Vinny Apolinario (407-371-2227)
1209 CASTLEPORT RD, WINTER GARDEN, FL 34787
$664,90032 Days on yellowkey MLS ID: O6390760
REDUCED by $10,090 (1.5%) on 04/14/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 2001Monthly Fee: $243 Tax: $4,030 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$4,030
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.
Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)
Listing Agent: Angela Magac (407-744-5557)
604 FOSTER AVE, WINTER GARDEN, FL 34787
$400,0004 Days on yellowkey MLS ID: O6389095
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1975 Tax: $1,633 (2024)Community: Westchester PlaceSingle Family
Taxes:$1,633
Elementary School: Tildenville Elem
Tax Year: 2024
Remarks: Situated just two blocks outside the Golf Cart District and directly across from Veterans Memorial Park, this property offers a lifestyle that blends convenience, privacy, and outdoor living. BRAND NEW ROOF JUST INSTALLED! (April 2026, 10-yr warranty) Set on a rare double lot, the home welcomes you with mature landscaping, an orchid tree in the front yard, stylish Bermuda hurricane shutters, and a covered front porch that provides a charming place to relax and enjoy the neighborhood. Inside, the spacious layout features durable porcelain wood-grain tile flooring installed in 2017, a bright living area, and a generous kitchen designed for everyday functionality and gathering. Major updates provide peace of mind, including all new double-pane windows installed in 2021, a water heater replaced in 2020, HVAC from 2019 (installed 2021) under warranty with American Air & Heat, and upgraded WiFi. Outside is where the property truly shines. The fully fenced backyard offers exceptional privacy with mature landscaping, fruit trees including kumquat, green apple, mango, and pineapple, along with bananas, plantains, pecan, and raised herb beds featuring aloe, basil, spearmint, and Italian oregano. Entertain or unwind on the recently resealed paver patio or under the pergola, while the powered shed with custom shelving and ramp provides flexible space for hobbies or storage. Additional features include a large private driveway, gutters, double weather-stripped front doors, and a chicken coop. With extensive updates, functional living space, and a backyard designed for gardening, relaxing, and entertaining, this home offers a unique opportunity to enjoy both comfort and outdoor lifestyle.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Jackie Isham (407-917-8954)
12055 BRACCO ST, WINTER GARDEN, FL 34787
$429,000126 Days on yellowkey MLS ID: O6366675
REDUCED by $11,000 (2.5%) on 04/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1668 Built: 2023Monthly Fee: $105 Tax: $6,881 (2024)Community: Highland RidgeSpa: NoSingle Family
Taxes:$6,881
Remarks: Welcome to Your Florida Retreat! Step into a bright and breezy lifestyle in this seldom-offered home that captures the essence of Florida living year-round. Built in 2023, this well-maintained, energy-conscious single-family residence offers 3 bedrooms, 3 bathrooms, and approximately 1,668 sq ft of thoughtful living space on a 7,468 sq ft lot. Inside, enjoy a generous open-concept floor plan designed for comfort and ease — perfect for morning coffees, island-style dinners, or casual gatherings. The home features new lighting and energy-efficient windows to let in Florida sunshine while helping with energy savings. All bedrooms are upstairs, offering privacy and quiet; the attached garage adds convenience for everyday living. Outside, the property sits in a community that embodies that laid-back, sunny Florida vibe. Located in Winter Garden, FL, you’re just minutes from vibrant shopping, dining and entertainment options — from the historic charm of downtown Winter Garden and its weekend farmers’ market, boutiques, cafés, and arts scene to larger retail centers around Daniels Road and SR-429. For families or anyone valuing convenience, this home is within the public school zone of Water Spring Elementary School (PK-5), Water Spring Middle School-0482 (6-8), and Horizon High School (9-12) — all within a few miles of the home. Whether you’re relocating from out of state and seeking a home that offers easy maintenance, comfort, and solid investment value, or you’re a local buyer drawn to Winter Garden’s charm and amenities — this property combines practicality, modern updates, and that unmistakable Florida lifestyle.
Listing is courtesy of: POWERHOUSE REAL ESTATE NETWORK (305-409-6835)
Listing Agent: Luciana Figueiredo (781-635-2712)
14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787
$2,999,990203 Days on yellowkey MLS ID: O6346469
REDUCED by $333,389 (10.0%) on 04/14/2026
Bed: 6 Bath: 7.0 Gar: 4 Liv Area Sq Ft: 6442 Built: 2025Monthly Fee: $112 Tax: $6,673 (2024)Community: Shorefront CoveSingle Family
Taxes:$6,673
Remarks: Exquisite Luxury Estate in Shorefront Cove at Horizon West. Presenting a rare opportunity to own a premier residence in the sought-after Shorefront Cove community of Winter Garden’s Horizon West. This elegant two-story estate offers 6,442 square feet of impeccably designed living space, showcasing refined luxury, modern convenience, and breathtaking views of Huckleberry Lake. Boasting 6 spacious bedrooms, 6 full bathrooms, and 2 half baths, this home features dual primary suites, one on the main level and one on the upper level, bonus room, wet bar, theater, large lanai, and 4-car garage offering ample storage and convenience. This residence provides easy access to major highways, premier shopping, dining, entertainment, and top-rated schools, all within one of Central Florida's most desirable communities.
Listing is courtesy of: PARK SQUARE REALTY (844-774-4636)
Listing Agent: Suresh Gupta (844-774-4636)
15359 MARITIME PINE DR, WINTER GARDEN, FL 34787
$828,1051 Day on yellowkey MLS ID: G5110994
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,726 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The Arlington is perfect for families of all sizes!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
17162 INGRAM BLUFF DR, WINTER GARDEN, FL 34787
$699,9701 Day on yellowkey MLS ID: G5110993
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3122 Built: 2026Monthly Fee: $122Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model by Dream Finders Homes. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with a walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Above the garage hosts a wonderful apartment with a private entrance. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location.
7550 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$701,3401 Day on yellowkey MLS ID: G5110990
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2515 Built: 2026Monthly Fee: $122Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model by Dream Finders Homes. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with a walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways.
4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787
$585,00044 Days on yellowkey MLS ID: S5144794
REDUCED by $6,000 (1.0%) on 04/14/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2149 Built: 2021Monthly Fee: $281 Tax: $6,500 (2024)Community: Enclave At HamlinSingle Family
Taxes:$6,500
Remarks: Welcome to 4642 Prairie Creek St, an exceptional 2021-built residence nestled in the highly desirable Enclave at Hamlin in Winter Garden. Perfectly positioned in one of Central Florida’s fastest-growing and most vibrant areas, this meticulously upgraded two-story home offers approximately 2,149 square feet of refined living space on a 4,250 sq ft lot, combining modern luxury, energy-conscious enhancements, and functional design. This thoughtfully designed floor plan features 4 bedrooms (including a convenient main-floor bedroom ideal for guests, multigenerational living, or a private office), 2.5 bathrooms, and a private rear-load 2-car garage that enhances curb appeal and provides additional driveway functionality. From the moment you enter, you are welcomed by an expansive open-concept layout filled with natural light. The seamless flow between the living, dining, and kitchen areas creates an ideal setting for both everyday living and entertaining. Upgraded flooring throughout, fresh interior paint, and contemporary light fixtures elevate the home’s clean, modern aesthetic. The chef-inspired kitchen serves as the heart of the home, fully enhanced with Level 5 quartz countertops, a spacious island wrapped in custom porcelain tile creating a dramatic focal point, stainless steel appliances, and abundant cabinetry for optimal storage. The layout is designed for both functionality and visual impact, making it perfect for hosting gatherings or enjoying quiet evenings at home. Upstairs, the spacious primary suite offers a private retreat complete with a custom walk-in closet and a beautifully upgraded en-suite bath featuring a quartz countertop. Secondary bedrooms are generously sized, and the second full bath is finished with durable ceramic tile for both style and longevity. The remodeled laundry room adds efficiency and thoughtful design to daily routines. This home stands out with premium system upgrades that add tangible long-term value and comfort, including: Whole-home water filtration and softener system, APCO-X Ultra air purification system (improves indoor air quality and extends HVAC lifespan), Five Arlo security cameras that convey with the home, Pre-wiring for additional coverage and connectivity. The 4,250 sq ft lot provides usable outdoor space for entertaining, storage, and parking flexibility while maintaining low-maintenance appeal. Residents of the Enclave at Hamlin enjoy close proximity to Hamlin Town Center, offering premier shopping, dining, entertainment, and waterfront amenities, along with access to top-rated schools and major roadways for convenient commuting. Blending contemporary finishes, high-end upgrades, smart home enhancements, and an unbeatable location, 4642 Prairie Creek St is truly move-in ready and delivers both immediate comfort and lasting investment value. This is a rare opportunity to own a turn-key home in one of Winter Garden’s most sought-after communities. Schedule your private showing today and experience the lifestyle this exceptional home offers.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Shanta Navarro (407-747-0549)
16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787
$1,459,90051 Days on yellowkey MLS ID: S5144064
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4263 Built: 2017Monthly Fee: $178 Tax: $16,938 (2024)Community: TwinwatersSingle Family
Taxes:$16,938
Remarks: Experience refined elegance in this beautifully maintained residence located in one of Winter Garden’s most desirable communities. Designed for modern living, the home offers bright open spaces, a stylish kitchen, and inviting bedrooms that blend comfort with sophistication. Step outside to a private, resort-style backyard with over $200,000 invested, creating an exceptional outdoor oasis perfect for entertaining or unwinding in total privacy. Ideally positioned near top-rated schools, upscale dining, shopping, major highways, Downtown Winter Garden, Disney attractions, and Orlando—this home delivers luxury, location, and lifestyle at its finest.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Yuliana Naim (818-434-9717)
15828 SHOREBIRD LN, WINTER GARDEN, FL 34787
$900,000Listed 04/14/2026 12:15PM MLS ID: O6398059
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3058 Built: 2020Monthly Fee: $360 Tax: $11,042 (2025)Community: Lakeshore Preserve Ph 5Spa: NoSingle Family
Taxes:$11,042
Remarks: Welcome to 15828 Shorebird Lane — a beautifully upgraded Toll Brothers home built in 2020, featuring 4 bedrooms, 3.5 baths, and more than $200,000 in thoughtful enhancements throughout. From the moment you walk in, the home feels bigger, brighter, and more open. The expanded layout adds extra space where it matters most — in the main living areas, bedrooms, and the upstairs loft — giving the whole home an easy, comfortable flow. The kitchen sits right at the heart of the home with upgraded cabinetry, premium appliances, and a large island that makes cooking, gathering, and entertaining feel effortless. It opens directly to the living room and backyard, so everything stays connected. Step outside and you’ll find a space designed to be enjoyed. The screened-in pool and outdoor gas kitchen create a true backyard hangout — perfect for hosting friends or relaxing on a quiet evening. Upstairs, the loft offers a flexible second living area that works as a media room, office, or play space. The three additional bedrooms are well-sized and tucked away for privacy. Details like open stair railings and an extended lanai add to the home’s open, airy feel. Beyond the visible upgrades, the home includes a security system, water softener, epoxy garage flooring, built-in speakers, gutters, and a transferable termite bond for added peace of mind. Located in the Lakeshore community, you’ll enjoy included lawn care and access to amenities along Panther Lake — a zero-entry pool, clubhouse, fitness center, playground, beach volleyball court, dock, and kayak launch. Plus, you’re just minutes from Hamlin Town Center, Orange County National Golf Center, major highways, and Walt Disney World.
2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$750,000Listed 04/14/2026 12:28PM MLS ID: O6398720
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3747 Built: 2000Monthly Fee: $90 Tax: $10,152 (2025)Community: Wintermere PointeSpa: NoSingle Family
Taxes:$10,152
Elementary School: Lake Whitney Elem
Remarks: Located in the GATED community of Wintermere Pointe in Winter Garden, FL, this spacious .25 acre, 5-bedroom, 3-bath pool home for sale in Winter Garden offers nearly 3,750 square feet of well-designed living space just minutes from Winter Garden Village, Windermere, Walt Disney World, AdventHealth Winter Garden, SR 429, and the Florida Turnpike. Designed for both everyday living and entertaining, the home features an open-concept layout with formal living and dining rooms, a large family room, and a centrally located kitchen that flows seamlessly into the main living areas. A DOWNSTAIRS BEDROOM and full bath provide flexibility for guests, multi-generational living, or a private home office, while upstairs, the expansive primary suite offers a true retreat with a soaking tub , separate shower, dual vanities, and two walk-in closets. Additional bedrooms are generously sized, and both a LOFT and a large BONUS ROOM create endless possibilities for a media room, game room, home gym, or additional living space. High ceilings and natural light enhance the open feel throughout the home, while the layout offers both functionality and comfort. Step outside to a screened-in PRIVATE POOL, covered lanai and extended paver patio, perfect for enjoying Florida living in Winter Garden year-round, all set on a .25 ACRE LOT with mature landscaping and a FULLY FENCED backyard for added privacy. Wintermere Pointe is a well-established gated community in Winter Garden, Florida offering tennis courts, a playground, and a LOW HOA, and is zoned for Lake Whitney Elementary, SunRidge Middle, and West Orange High. If you’re searching for homes for sale in Winter Garden FL with a pool, gated community, and flexible layout, this home offers space, location, and lifestyle in one of Central Florida’s most desirable areas.
Listing is courtesy of: EXP REALTY LLC (407-392-1800)
Listing Agent: Alexis Bress (407-900-0771)
14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787
$545,00014 Days on yellowkey MLS ID: O6395079
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2049 Built: 2014Monthly Fee: $252 Tax: $3,824 (2025)Community: Summerlake Pd Ph 1B-A RepSingle Family
Taxes:$3,824
Elementary School: Summerlake Elementary
Remarks: Welcome to this well maintained home in the highly sought after community of Summerlake in Horizon West, known for its convenient access to shopping, dining, parks, and major roadways. This property offers a thoughtful layout with an open concept design connecting the kitchen, living, and dining areas, creating a comfortable space for everyday living and entertaining. The interior has been freshly painted and features 18 inch tile flooring throughout, providing a clean and cohesive look with easy maintenance. The kitchen is equipped with granite countertops, tall cabinetry, and ample storage, while both bathrooms also feature Corian surfaces and double vanities for added convenience. The primary suite includes a tray ceiling, a spacious bathroom with both a garden tub and separate shower, and a private water closet. Additional interior features include custom blinds throughout, cabinetry in the laundry area, and an upgraded front door with a stained glass insert that adds character and curb appeal. Outdoor living is enhanced by a full side patio with both covered and open areas, offering flexibility for relaxing or entertaining. The side patio has a natural gas line for your future grill outs. The side yard is partially fenced with a railing design that complements the front porch, and the property includes a two car carriage style garage along with a third parking pad accessed from the rear alleyway. The home is fully guttered and features newly installed landscaping, adding to its overall appeal.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Vanessa Scotland, Pa (407-217-4580)
15659 JUNGLE ALY, WINTER GARDEN, FL 34787
$360,00025 Days on yellowkey MLS ID: S5143684
REDUCED by $85,000 (19.1%) on 03/31/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1732 Built: 2021Monthly Fee: $203 Tax: $6,265 (2024)Community: Winding Bay Ph 2Townhouse
Taxes:$6,265
Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Beautifully maintained town home 3 bed and 3 bath in the desirable Horizon West area of Winter Garden! This charming alley-facing property features an open-concept floor plan with spacious living and dining areas, a modern kitchen with solid surface countertops, stainless steel appliances, and a large island perfect for entertaining. Upstairs offers generously sized bedrooms, including a private primary suite with walk-in closet and en-suite bath. Enjoy low-maintenance outdoor living with a private patio and rear-entry garage. Conveniently located near top-rated schools, shopping, dining, and major roadways. A fantastic opportunity to own in one of Central Florida’s most sought-after communities! Offers may be entered ONLINE through Tuesday, April 14, 2026 at 3:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Dinorah Navarro (407-625-7522)
431 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787
$319,9005 Days on yellowkey MLS ID: O6397663
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1499 Built: 2005Monthly Fee: $576 Tax: $4,273 (2025)Community: Southern Pines CondoCondo
Taxes:$4,273
Remarks: Welcome to one of the largest condo floor plans in this highly desirable Winter Garden community. This 3-bedroom, 2-bathroom condo offers spacious, low-maintenance living with no carpet throughout, fresh interior paint, and an updated AC system for added comfort and efficiency. A rare find in the area, this condo with a private garage includes upgraded electrical—perfect for storage, hobbies, or added functionality. Enjoy resort-style living with access to a pool, fitness center, basketball and pickleball courts, recreation center, on-site movie theater, and car wash station. Ideally located just minutes from Downtown Winter Garden and Plant Street’s popular restaurants, weekly farmers market, and community events, plus convenient access to shopping and dining at Winter Garden Village at Fowler Groves. If you’re searching for a condo in Winter Garden with a garage, modern updates, and unbeatable amenities, this is one you don’t want to miss.
931 KYLEE ALY, WINTER GARDEN, FL 34787
$849,00041 Days on yellowkey MLS ID: O6387922
REDUCED by $26,000 (3.0%) on 04/14/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2831 Built: 2022Monthly Fee: $401 Tax: $9,637 (2025)Community: Oakland ParkSingle Family
Taxes:$9,637
Remarks: There is a specific frequency to life in Oakland Park that exists nowhere else in Central Florida. It is a rare, rhythmic harmony between the nostalgia of Old Florida and the crisp, clean lines of modern luxury. As you cross into the community, the atmosphere shifts. The air feels lighter, filtered through the canopy of ancient oaks and manicured greenery of a village designed for connection. This is not just a residential development. It is an intentional ecosystem where the 22-mile West Orange Trail serves as the community’s main artery, pumping vitality into every cul-de-sac and alleyway. At 931 Kylee Alley, this lifestyle reaches its peak. On a commanding corner lot, the David Weekley Stoneybrook residence stands as a testament to timeless architecture. One of the greatest luxuries of this exterior is what you do not have to do. In Oakland Park, your time is reclaimed. The homeowners association provides comprehensive landscaping maintenance and care, ensuring your estate remains in a perpetual state of magazine-ready perfection. Imagine the freedom of a Saturday morning where the scent of freshly cut grass is a sensory delight rather than a chore on a list. Going across the threshold, you are greeted by a masterclass in sightlines. Built in 2022, the home possesses a groundedness that only thoughtful design can provide. The soaring ceilings act as a canvas for the Florida sun, which pours through windows dressed in custom plantation shutters. The heart of the home is the gourmet kitchen. The oversized central island is topped with solid-surface counters that feel like cool silk to the touch. It serves as the natural gathering point for evening wine tastings or slow Sunday brunches. The floor plan is a brilliant response to the modern need for connection and solitude. On the main floor, the layout offers a sophisticated executive wing feel. Whether you utilize the first-floor bedroom as a guest en-suite or a high-powered home office, the separation of space ensures privacy. Ascending to the second level, you enter the private quarters. The primary owner’s retreat is a voluminous space anchored by a spa-inspired en suite where stresses of the day dissolve. Life here is defined by proximity to the West Orange Trail. This is your private gateway to the best of Winter Garden. Within minutes, you can cycle toward the historic charm of Plant Street or explore the renowned Saturday Farmers Market. Back within the gates, the amenities rival those of a five-star resort. Three sparkling swimming pools, a social clubhouse, and a dog park ensure every member of the family enjoys a sense of belonging. This is a lock-and-leave lifestyle in its purest form. The Investment Thesis. From an investment perspective, 931 Kylee Alley represents a blue-chip asset. Oakland Park is recognized as one of the stable and appreciating communities in the region. As Winter Garden evolves into a premier luxury destination, the scarcity of newer construction on premium corner lots creates a natural ceiling for appreciation. This is a strategic land-hold in a community where demand consistently outpaces supply. Check out the virtual tour video!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Barbara Vance Pa (407-947-6236)
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