Location: Winter Garden
Do Not Show Listings
6159 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$699,74528 Days on yellowkey MLS ID: G5111054
0 Days Off yellowkey (back on 4/15/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2235 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: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria, an award-winning single-story, open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, ample counter space, and an open layout that connects directly to the living areas, making it perfect for everyday living and entertaining. The owner’s suite and additional bedrooms are thoughtfully placed to maximize privacy and comfort. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
6050 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$712,63428 Days on yellowkey MLS ID: G5111051
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2515 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Carter, a thoughtfully designed bungalow that combines style, comfort, and modern functionality. This brand-new home offers 4 bedrooms, 3.5 bathrooms, and 2,520 sq. ft. of living space. The inviting front porch creates charming curb appeal, while inside, abundant natural light enhances the open-concept layout. The first floor features a bedroom with private bath, perfect for guests or multi-generational living, while the upstairs showcases spacious secondary bedrooms and a well-appointed primary suite. Outdoor living shines with a covered breezeway and private courtyard, ideal for gatherings, dining, or quiet relaxation. Located in Avalon Woods, residents will enjoy proximity to top-rated schools, Hamlin Town Center, Hwy 429, and Disney, all just minutes away.
15142 TEA TREE DR, WINTER GARDEN, FL 34787
$858,12028 Days on yellowkey MLS ID: G5111049
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3498 Built: 2026Monthly Fee: $150 Tax: $298 (2025)Community: Avalon WoodsSingle Family
Taxes:$298
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite bathroom, offering privacy and convenience. A flex room with walk in closet and a half bathroom are also located on the first floor, along with direct access to the garage and additional storage. The second floor includes additional secondary bedrooms with access to full bathrooms, a central loft providing flexible living space, and a dedicated laundry area. A secondary primary bedroom is also located on the second floor, featuring its own en-suite bathroom and walk-in closet, making it ideal for multi-generational living or extended stays.
15359 MARITIME PINE DR, WINTER GARDEN, FL 34787
$828,10529 Days 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
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!
14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787
$749,00050 Days on yellowkey MLS ID: O6392994
REDUCED by $46,000 (5.8%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2027 Built: 1989Monthly Fee: $322 Tax: $4,924 (2025)Community: Woodbridge On GreenSingle Family
Taxes:$4,924
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Drew Ross (407-383-6497)
1035 CHASE DR, WINTER GARDEN, FL 34787
$465,00033 Days on yellowkey MLS ID: O6396474
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1793 Built: 1995Monthly Fee: $44 Tax: $3,337 (2025)Community: Island Pointe SubSpa: NoSingle Family
Taxes:$3,337
Elementary School: Dillard Street Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to a home that feels right the moment you arrive. Set beneath the shade of mature oak trees on a 100-foot-wide lot in Winter Garden’s golf cart district, this beautifully maintained single-story home in Island Pointe invites you to slow down, breathe a little deeper, and truly enjoy where you live. The wide, covered front porch stretches across the entire front of the home, creating the perfect place for morning coffee, evening conversations, and everything in between. Step inside and you’re greeted by soaring vaulted ceilings and natural light that pours in from every angle, giving the home an open, airy feel that lives larger than its footprint. The layout flows effortlessly with multiple living and dining spaces designed for both connection and flexibility. At the center of it all is a generously sized kitchen with abundant counter space and a center island that opens seamlessly to the family room. This is where life happens. Holidays, casual dinners, and late-night conversations all find their place here. The split floor plan offers privacy and comfort. The owner’s suite is tucked away and serves as a peaceful retreat with a walk-in closet and a spacious en-suite bath featuring dual sinks, a garden tub, and a separate shower. On the opposite side of the home, two additional bedrooms provide the ideal setup for family, guests, or a home office. This home has been lovingly cared for and offers something buyers are always searching for but rarely find: solid construction with major system updates already done, including a newer roof, updated HVAC, and a brand new water heater. The finishes reflect its original character, giving you the opportunity to modernize at your own pace and build meaningful equity along the way. But what truly sets this home apart is the lifestyle. Located in the highly sought-after Golf Cart District of historic Downtown Winter Garden, you are just minutes from everything that makes this area so special. Hop on your golf cart or bike and head to Plant Street where you’ll find charming boutiques, incredible dining, live music, festivals, and the beloved Saturday Farmers Market. Enjoy local favorites like Crooked Can Brewery and Food Hall and Scoops Ice Cream only a quick ride away. Spend your weekends exploring the West Orange Trail or relaxing at nearby Newton Park, the City Pool, playground, fishing pier, and public boat ramp. Whether it’s a morning ride, an afternoon on the water, or an evening out, everything you need is right at your fingertips. Daily convenience is just as impressive, with multiple grocery options nearby and shopping along Highway 50. You are also close to top-rated schools, Winter Garden Village, AdventHealth, and have easy access to the 429 and Florida Turnpike. All of this, paired with low HOA dues and a welcoming, established neighborhood, makes this home not just a great purchase, but a smart investment in both lifestyle and long-term value. Homes like this do not come around often. A single-story layout, a prime location, strong bones, and the chance to make it truly your own. Come see it in person. Walk the space. Feel the openness. Sit on the front porch and imagine life unfolding here.
Listing is courtesy of: UPWELL REALTY LLC (407-926-9960)
Listing Agent: Kyle Madorin Pa (407-504-9247)
14423 WABASSO LOOP, WINTER GARDEN, FL 34787
$899,999126 Days on yellowkey MLS ID: O6368408
1 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3630 Built: 2023Monthly Fee: $217 Tax: $12,742 (2024)Community: Tilden Place/Winter GardenSingle Family
Taxes:$12,742
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2024
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. PRICED TO SELL! Welcome home to this stunning two-story residence in the gated community of Tilden Place, ideally located in the heart of Winter Garden. Just minutes from Winter Garden Village with its abundant shopping, dining, fast-casual options, hospital access, and everyday conveniences—and only a short drive to Walt Disney World Resort, this home offers the perfect blend of luxury, comfort, and location. Built by MI Homes, known for exceptional energy efficiency, this 5-bedroom, 4-bath home showcases sleek, modern upgrades throughout. The pavered driveway and porch set the tone, opening to a thoughtfully designed floor plan that includes a first-floor bedroom with a full bathroom, ideal for guests, multigenerational living, or a private home office. The main living areas feature LVP flooring, striking iron stair railings, and incredible custom trim work along the staircase. The gourmet kitchen will keep even the pickiest of chefs happy, featuring dark cabinetry that beautifully contrasts with a bright white waterfall island, pendant lighting, stainless steel appliances, gas cooking, and stunning upper cabinetry that elevates the space. A built-in pocket office offers the perfect spot for quick correspondence, bill pay, remote work, or a homework station. The family room is anchored by a dramatic wall of custom built-in shelving with accent lighting and a fireplace, creating a warm and inviting focal point for everyday living and entertaining. Upstairs, a spacious loft continues the custom design theme with floating shelves and integrated storage. The expansive upstairs primary suite features LVP flooring, generous space, and access to a private balcony, perfect for morning coffee or evening relaxation. With no rear neighbors, enjoy a private backyard retreat complete with an extended lanai, while the coastal-style balcony off the loft provides even more opportunities for entertaining and unwinding. The intimate gated community is centered around a beautiful pond with a fountain, and just a short walk down the street brings you to the community green space and playground. This stunning home truly offers modern luxury, functional living, privacy, and an unbeatable Winter Garden location. WELCOME HOME!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Amy Kidwell Pa (407-848-8042)
1923 JEAN MARIE DR, WINTER GARDEN, FL 34787
$580,000116 Days on yellowkey MLS ID: G5106903
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2916 Built: 2007Monthly Fee: $90 Tax: $4,275 (2024)Community: Carriage Pointe A-I & LSingle Family
Taxes:$4,275
Remarks: GATED COMMUNITY !! ENTICING CURB APPEAL !! 3 CAR GARAGE !! Welcome home to Carriage Pointe !! One of the most highly desired communities in Winter Garden !! This home has beautifully manicured lush landscaping and complimented by a BRICK PAVER DRIVEWAY AND WALK leading to the COVERED FRONT PORCH with DOUBLE LEADED GLASS ENTRY DOORS !! ROOF 2022 !! This 4 bed/ 3 bath VERSATILE FLOOR PLAN boasts 2,916 climate controlled sq. ft. The grand foyer with SOARING CEILINGS opens to the formal Living Room and the elegant trey ceiling Dining Room both providing plentiful NATURAL LIGHT !! The chef friendly kitchen has ABUNDANT CABINETRY, granite counters, tasteful backsplash, SS appliances, BREAKFAST BAR ISLAND and spacious Dinette/Nook that flows seamlessly into the oversized Family Room that overlooks the lanai. The EXPANSIVE PRIMARY ENSUITE has a trey ceiling, bay window-sitting area, an enormous walk-in closet, dual vanities, garden tub and large shower stall. The opposite side of the home has two additional bedrooms with a shared bath, and a GUEST SUITE complete with full bath and separate entry. The SCREENED LANAI overlooks the backyard with a HOT TUB !! The community has a tennis court, playground, soccer field and walking path. Location benefits include close drive to Disney/Theme parks, shopping, Toll 429, and numerous activities in downtown HISTORIC WINTER GARDEN !! Make this home your new address !!
Listing is courtesy of: EXIT REALTY TRI-COUNTY (352-385-3948)
Listing Agent: Steven Boone (352-430-4144)
1710 E BAY ST, WINTER GARDEN, FL 34787
$249,99071 Days on yellowkey MLS ID: O6376343
REDUCED by $5,005 (2.0%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 972 Built: 1957 Tax: $958 (2025)Community: Joe Louis Park First AddSingle Family
Taxes:$958
Remarks: WALK INTO $45,000+ OF INSTANT EQUITY! Appraised at $295,000 but priced for a lightning-fast sale at only $249,995, this fully renovated 3-bedroom, 2-bathroom Winter Garden home is the deal of the year. The seller must close before April 29, 2026, offering you a rare opportunity to secure a move-in-ready luxury property significantly below market value. This home provides total peace of mind with a BRAND NEW ROOF, new HVAC, and complete re-piping, all accented by a designer interior featuring large-format flooring, a gourmet kitchen, and spa-like bathrooms. Outside, the property shines with fresh stucco, a massive driveway, and a private fenced backyard, just minutes from the charm of Historic Plant Street. Best of all, this deal offers total financing flexibility: while the base price is set for a clean sale, the seller is happy to include any amount of closing cost credits or a furniture package by simply adjusting the price above $250,000. Act now to claim this built-in wealth before the deadline passes!
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Jose Villafana (407-705-8014)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,90029 Days on yellowkey 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
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)
17222 DANCY ORANGE CT, WINTER GARDEN, FL 34787
$965,00082 Days on yellowkey MLS ID: O6383910
REDUCED by $25,000 (2.5%) on 04/06/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3787 Built: 2023Monthly Fee: $83 Tax: $11,862 (2024)Community: Northlake/Ovation Ph 1Single Family
Taxes:$11,862
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Exceptional Upgraded Home on Premium Conservation Lot in Winter Garden Welcome to this beautifully upgraded two story residence located in one of Winter Garden’s most desirable communities, zoned for highly rated A schools and surrounded by convenience, lifestyle, and long term value. Featuring 5 bedrooms and 4.5 bathrooms, this home offers a spacious and functional layout designed for both everyday living and entertaining. The primary suite provides a private retreat with a generous walk in closet and a spacious primary bath with an oversized shower, dual vanities, and elevated finishes throughout. The additional bedrooms offer comfort and well planned storage. From the moment you enter, the dramatic double height ceilings create an impressive sense of space and natural light. A custom floor to ceiling wood paneled TV feature wall serves as a stunning focal point in the main living area, adding warmth and architectural presence. Throughout the home, custom made window treatments have been thoughtfully installed and will remain with the property, an elegant and valuable enhancement rarely included. The open concept kitchen blends timeless finishes with modern functionality, featuring upgraded cabinetry, quartz countertops, refined plumbing fixtures, and carefully selected design details throughout. Over 115,000 dollars in builder design upgrades were invested into this home, in addition to custom improvements completed after construction. Adding even more value and comfort, the home is equipped with a whole house water filtration system, providing filtered water throughout the entire property for enhanced quality, convenience, and peace of mind. The covered lanai has been pre plumbed and equipped with electrical planning for a future summer kitchen, offering flexibility for outdoor entertaining and long term customization. Set on a premium conservation lot, this property offers exceptional privacy with no rear neighbors and no future development behind the home. The fenced backyard provides a peaceful outdoor setting ideal for relaxing or hosting gatherings. Additional highlights include an expanded driveway, a two car garage, and a location just minutes from major roadways, shopping, dining, and entertainment. With a low HOA and positioned in one of Winter Garden’s strongest appreciation corridors, this is a rare opportunity to own a thoughtfully upgraded home that combines privacy, quality, and strategic location. Don't miss this opportunity to live with quality, comfort, and style. Schedule your visit!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Adriana Pl Franzoi (407-924-0872)
15161 CANOE PL, WINTER GARDEN, FL 34787
$1,200,00029 Days on yellowkey 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
Taxes:$13,235
Elementary School: Panther Lake Elementary
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 Agent: Maqueli Gewehr (863-258-5656)
17162 INGRAM BLUFF DR, WINTER GARDEN, FL 34787
$699,97029 Days 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
$701,34029 Days 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.
1209 CASTLEPORT RD, WINTER GARDEN, FL 34787
$664,90060 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)
14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787
$2,999,990231 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)
15312 GILLIGAN CT, WINTER GARDEN, FL 34787
$1,150,000111 Days on yellowkey MLS ID: O6372954
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3652 Built: 2020Monthly Fee: $102 Tax: $9,787 (2024)Community: Winding Bay Ii LlcSpa: YesSingle Family
Taxes:$9,787
Remarks: Set within one of Winter Garden’s most loved communities, this thoughtfully designed two-story home offers a lifestyle shaped by ease, connection, and everyday enjoyment in Winter Garden, Florida. Morning walks along sidewalks, friendly neighbors, nearby parks, and resort-style amenities create a rhythm that feels relaxed yet vibrant. With top-rated schools, convenient access to shopping and dining, and Walt Disney World Resort just minutes away, the location blends Central Florida convenience with the feeling of being tucked into something special. From the moment you step inside, the home invites you to slow down and take it all in. Natural light fills the space, drawing your eye through the open living area to peaceful pond views and the private pool. Beyond the pond, a wooded area owned by Disney provides a protected natural backdrop that will never be built on, preserving privacy and tranquility. Oversized white tile spans the first floor, creating an open, airy atmosphere that feels clean and welcoming. At the center of the home, the kitchen is designed for real life and real gatherings. White cabinetry, granite countertops, a double oven, and a statement range hood anchor a space that works effortlessly for weeknight dinners or hosting friends. A large walk-in pantry keeps everything organized and within reach. Just beyond, the family room feels warm and grounded, with a stone accent wall, electric fireplace, and custom shelving creating a comfortable place to relax. The first floor offers flexibility to suit your lifestyle. A dedicated den or home office provides a quiet place to focus, while a formal dining room invites shared meals and conversation. A drop zone near the garage keeps daily routines running smoothly. Toward the back of the home, a spacious downstairs bedroom with a full en suite bath offers privacy, ideal for guests or multi-generational living. Upstairs, an open loft serves as a central gathering space for movie nights or game days, enhanced by a stone wall and theater-style seating. The owner’s suite feels like a true retreat with a tray ceiling, spa-inspired bath featuring a rain shower, dual sinks, generous storage, and two oversized walk-in closets. A private balcony overlooks the pond and wooded preserve, offering a peaceful place to enjoy morning coffee or unwind. Three additional upstairs bedrooms provide ample space for family or guests. Two share a hall bath, while one enjoys its own en suite for added comfort and privacy. Outside, the backyard feels like a private Central Florida escape. A resort-style saltwater pool with a lounging platform and in-water loungers overlooks the serene pond, creating an inviting setting for relaxing afternoons or entertaining. The screened enclosure allows for year-round enjoyment, and the community dog park directly across the street adds everyday convenience for pet lovers. With fresh interior paint and plantation shutters throughout, this move-in ready single-family home is ready for its next chapter. Community amenities include a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and a dog park. This is more than a house — it is a place to settle in, build memories, and truly feel at home in Winter Garden.
Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)
Listing Agent: Gretchen Carlson (407-484-0005)
17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787
$606,44056 Days on yellowkey MLS ID: G5109791
0 Days Off yellowkey (back on 3/18/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2102 Built: 2026Monthly Fee: $140Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 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 15' 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 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.
14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787
$1,390,00097 Days on yellowkey MLS ID: O6379808
3 Days Off yellowkey (back on 4/14/2026)
Bed: 7 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5001 Built: 2017Monthly Fee: $215 Tax: $9,308 (2024)Community: Overlook 2 At HamlinSpa: YesSingle Family
Taxes:$9,308
Elementary School: Independence Elementary
Remarks: Under contract-accepting backup offers. Experience refined Florida living in this exceptional 7-BEDROOM POOL HOME located in the prestigious West Lake Hancock Estates, perfectly positioned on an OVERSIZED CORNER LOT. The light-filled interior showcases a modern, open-concept floor plan with expansive living and gathering spaces ideal for both everyday comfort and elevated entertaining. At the heart of the home is the gourmet DOUBLE-ISLAND kitchen, offering generous prep space, abundant cabinetry, and a layout designed to host with ease. A rare and highly desirable feature, this home offers TWO PRIMARY SUITES on the FIRST FLOOR, each complete with private en-suite bathrooms and spacious walk-in closets, providing exceptional flexibility for multi-generational living, extended guests, or a private home retreat. The additional bedrooms are generously sized and thoughtfully placed, offering versatility for guest accommodations, a home office, fitness room, or creative space. Step outside to your private backyard oasis, where a sparkling POOL and OUTDOOR KITCHEN create the ultimate setting for relaxing, entertaining, and enjoying Florida’s year-round sunshine. Whether hosting summer gatherings or quiet evenings at home, this outdoor space is designed for elevated living. Additional highlights include a 3-car attached garage, ample storage throughout, and a pet-friendly neighborhood. Residents of West Lake Hancock Estates enjoy access to resort-style amenities, including a stunning clubhouse overlooking Lake Hancock, community pool, fitness center, playground, amphitheater, scenic walking and biking trails, canoe access, and a full calendar of organized social activities. Ideally located just off SR-429, this home offers convenient access to downtown Orlando, major highways, shopping, dining, and entertainment—while still providing the tranquility of an upscale, lake-centered community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jason Asa (407-337-7702)
14788 FIELD DAISY DR, WINTER GARDEN, FL 34787
$617,50030 Days on yellowkey MLS ID: O6398754
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1992 Built: 2026Monthly Fee: $229Community: Harvest At OvationSingle Family
Remarks: Under Construction. What's Special: Game Room | Dedicated Study | Covered Lanai | North Facing Lot. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Ashwood at 14788 Field Daisy Drive in Harvest at Ovation! This welcoming new home blends spacious living with thoughtful design, featuring a bright great room that flows seamlessly into a beautifully appointed kitchen with quartz countertops and designer kitchen cabinets. Luxury vinyl plank flooring runs throughout the main living area, creating a warm and cohesive feel that is easy to enjoy every day. Just off the kitchen, the lanai extends your living space outdoors, while a versatile flex room and convenient powder room sit near the foyer. Upstairs, the primary suite offers a comfortable retreat with an en-suite bath and a large walk-in closet, alongside two secondary bedrooms that share a full bathroom and an upstairs laundry room. The rear two-car detached garage includes stairs leading to a spacious game room complete with a wet bar, full bathroom, and walk-in closet, giving you even more room to live and entertain. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Bedroom in place of loft, game room, wet bar at game room, full bathroom at game room, 8' interior doors, oak treads and painted risers. Photos are for representative purposes only. MLS#O6398754
Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)
Listing Agent: Michelle Campbell (407-756-5025)
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