Location: Winter Garden , 34787
Do Not Show Listings
15161 CANOE PL, WINTER GARDEN, FL 34787
$1,200,0009 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
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)
17162 INGRAM BLUFF DR, WINTER GARDEN, FL 34787
$699,9709 Days on yellowkey MLS ID: G5110993
0 Days Off yellowkey (back on 4/14/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3122 Built: 2026Monthly Fee: $122Community: Hamlin Meadows At HamlinSingle 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. 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.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
7550 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$701,3409 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.
408 S BOYD ST, WINTER GARDEN, FL 34787
$815,00023 Days on yellowkey MLS ID: O6394810
REDUCED by $20,000 (2.4%) on 04/15/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2295 Built: 1939 Tax: $2,572 (2025)Community: G T Smith Sub 3Spa: NoSingle Family
Taxes:$2,572
Elementary School: Dillard Street Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Charming home located just blocks from Winter Garden's historical downtown in the highly sought-after GOLF CART DISTRICT! This 3 bedroom, 3 Bath house blends timeless character with modern living, featuring hardwood floors, vintage tiled bathroom, built-ins, and a traditional layout with separate dining room. The kitchen opens to a comfortable family room, ideal for everyday living. The primary suite offers a spacious, spa-like bath with freestanding tub, walk-in shower, and custom vanity. A recent addition includes an oversized two-car garage , HVAC , large pantry, and bathroom to the third bedroom, creating a private en-suite with separate exterior entrance, ideal for guests or flexible living. Situated on a fenced, .41-acre corner lot, enjoy the screened-in back porch, expansive yard with mature landscaping, and the pavered pool area-perfectly designed for entertaining. Live the Historical Downtown Winter Garden Life-Style with convenient access to dining, shopping, farmer's market, Lake Apopka sunsets, and more.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787
$475,00029 Days on yellowkey MLS ID: O6391856
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1670 Built: 2016Monthly Fee: $148 Tax: $657 (2025)Community: Watermark Ph 1BSingle Family
Taxes:$657
Remarks: One or more photo(s) has been virtually staged. Experience the perfect blend of modern upgrades and an unbeatable location in this move-in-ready 3-bedroom, 2.5-bathroom home within the premier Watermark community. This residence has been meticulously maintained, boasting exterior paint (2023), a new garage lift (2024), and a brand-new water heater (2025). The home welcomes you with a huge covered front porch and an open-concept first level featuring tile flooring throughout, a chef-inspired kitchen with stainless steel appliances, rich cabinetry, and a breakfast bar. Upstairs, a versatile loft and convenient laundry room connect the primary suite to two generously sized guest bedrooms. Residents enjoy world-class community amenities including a resort-style pool, fitness center, tennis courts, and playground, all while being walking distance to the brand-new "The Mark" shopping center. Perfectly situated for families and commuters alike, zoned for Top Rated Schools, and just minutes from Hamlin Town Center, the 429 expressway, and Disney property. With alley-access parking and easy access to Winter Garden’s unique charm, this home offers the ultimate Horizon West lifestyle. Tour today!
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Jo Holton (307-690-7219)
8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$555,00018 Days on yellowkey MLS ID: O6394975
1 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2489 Built: 2015Monthly Fee: $332 Tax: $8,849 (2025)Community: WaterleighSingle Family
Taxes:$8,849
Elementary School: Water Spring Elementary
Remarks: Must see and make your new home today!! Situated in front of a most beautiful, sweeping lakefront view, it's the perfect place to wind down or just relax. It has A+ rated school district. Waterleigh provides a perfect blend of activities, amenities, trails, nature, parks, Tennis, clubhouse pools, fitness, parks, lush landscaping, parks & playgrounds allwing activities for everyone. Beautiful views of spectacular sunsets, & Disney Fireworks at night. You are close to several shopping districts, farmers markets, restaurants, luxury theaters, schools, hospitals, and (of course) at Disney's back door. Inside this beautiful and meticulously maintained home, there is a spacious en suite bedroom downstairs with walk in closet and lake view. A vast great room with large dining area adjacent to an open kitchen plan with plenty of cabinet space and walk in pantry. The appliances, including under counter water purifier and dispenser, are all in excellent condition with a brand new samsung dishwasher. A drop zone from the rear entry attached two car garage (with workbench/countertop). The large pavered screened in lanai is both private and large enough for outdoor sofa and dining al fresco. Upstairs is a bright loft with lake view, and two additional guest bedrooms, one with a beautiful lake view. The master bedroom has a huge double sink vanity, two linen closets, large walk in closet, private privy, and luxury no maintenance shower. This home has it all... except carpets... no carpet anywhere in the home. All flooring is either tile or luxury vinyl plank in a modern birch tone. Weeks and Months Available
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Karan Wienker (310-890-8687)
17326 BAL HARBOUR DR, WINTER GARDEN, FL 34787
$774,00028 Days on yellowkey MLS ID: O6393857
REDUCED by $11,000 (1.4%) on 04/14/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3196 Built: 2018Monthly Fee: $215 Tax: $11,210 (2025)Community: Waterside/Johns Lk-Ph 2BSingle Family
Taxes:$11,210
Remarks: Stunning lake-view home in Waterside at Johns Lake, overlooking Lake Avalon in Winter Garden! This spacious 5-bedroom, 3-bath residence offers 3,196 sq ft of open-concept living with a desirable downstairs primary suite featuring a spacious, well-appointed bathroom along with a customized walk-in closet. A second downstairs bedroom is paired with a beautifully RECENTLY renovated full bath showcasing a newly upgraded walk-in shower—ideal for guests or multi-generational living. Step inside to a welcoming entry that opens to a versatile sitting area—perfect for a home office or library—leading into a large family room, dining area, and well-appointed kitchen with natural gas range—perfect for entertaining. Enjoy the clean, modern feel of a completely carpet-free interior with durable vinyl flooring throughout the main living areas. The highlight of this home is the oversized screened lanai, perfectly positioned to capture serene Lake Avalon views—an ideal space for morning coffee, outdoor dining, or relaxing sunset evenings. Upstairs features a versatile loft, three additional bedrooms, and a full bath. Residents of Waterside at Johns Lake enjoy resort-style amenities including a lakeside pool, clubhouse, fitness center, scenic walking trails, playground, and community dock. Conveniently located just minutes from Winter Garden Village with easy access to 429, Florida’s Turnpike, downtown Orlando, theme parks, and Orlando International Airport.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Rema Perras (802-233-5292)
5401 BOWMAN DR, WINTER GARDEN, FL 34787
$1,250,00012 Days on yellowkey MLS ID: O6390128
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4044 Built: 2015Monthly Fee: $214 Tax: $9,108 (2025)Community: Overlook At HamlinSpa: YesSingle Family
Taxes:$9,108
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to Horizon West living at its finest in the highly sought-after Overlook at Hamlin community, home of top-rated schools. This exceptional pool home is perfectly positioned on a premium oversized lot offering over 4k SF with lake views in the front and fireworks views in the back. The thoughtfully designed living space has a northwest-facing orientation, allowing you to enjoy breathtaking sunrise views from your backyard oasis and stunning sunset views from the front. This luxurious and meticulously maintained upgraded home features 4 to 6 bedrooms, 3.5 bathrooms, and a highly desirable first-floor primary suite designed for comfort and privacy. The open-concept floor plan is enhanced by a spacious loft and multiple flex spaces, including dedicated offices or additional bedrooms on both levels, each with elegant French doors. The expansive living area is anchored by a custom 20-foot entertainment wall complete with built-ins, a fireplace, and integrated sound, creating the perfect setting for both relaxation and entertaining. The chef’s kitchen is a true showpiece, upgraded with brand-new commercial-style Café luxury appliances (2026), gas cooktop, custom cabinetry with soft-close features, designer backsplash, upgraded lighting, and an oversized custom pantry with a butler’s area. Multiple dining spaces, including a formal dining room and eat-in kitchen, offer versatility for gatherings both large and intimate. Additional major upgrades provide peace of mind and modern efficiency; two brand-new Carrier AC systems (2026) with a 10-year warranty, whole-house water purification and softener system, and new LED lighting in the pool. The home also includes 2 tankless gas water heaters and features high-end finishes throughout, including commercial-grade luxury vinyl flooring, premium carpeting, fresh interior paint, designer lighting, and smart home enhancements such as remote-controlled window treatments and extensive wall-mounted TV connections. Step outside to your private resort-style retreat, featuring a custom 600-square-foot saltwater pool with marble decking, sun shelf, waterfall features, and panoramic screened enclosure designed to maximize views of Disney fireworks. A separate spa, added in 2024, creates the ultimate relaxation experience. The outdoor living space is complete with a fully equipped summer kitchen, built-in bar, tongue-and-groove ceilings, and professionally designed landscaping with privacy hedges and palm trees. With no direct rear neighbors and a dry retention pond behind, this home offers exceptional privacy and serene surroundings. Additional exterior highlights include an extended driveway, oversized two-car garage with space for a golf cart, full fencing with multiple access points, exterior lighting, gutters, and security features, including cameras and motion lighting. Located just a half-mile from Hamlin Town Center, this home is accessible via walking trails, golf cart, or a 1-minute drive to shopping, dining, and entertainment. Residents of the Overlook community enjoy resort-style amenities, including a clubhouse, fitness center, community pool with splash area, walking trails, dog park, playgrounds, fishing pier, and private boat ramp access to Lake Hancock. This is a rare opportunity to own a move-in-ready luxury home in one of Winter Garden’s most desirable locations, where you can experience elevated Florida living at its best. Set up a showing today before it's gone.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
15050 GROVESIDE RD, WINTER GARDEN, FL 34787
$492,67062 Days on yellowkey MLS ID: O6384403
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 2026Monthly Fee: $247 Tax: $1,375 (2026)Community: Parkview At HamlinTownhouse
Taxes:$1,375
Tax Year: 2026
Remarks: Under Construction. Ready in June! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed to your spacious flex space. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
131 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787
$235,00028 Days on yellowkey MLS ID: O6393946
REDUCED by $15,000 (6.0%) on 04/14/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 738 Built: 2005Monthly Fee: $309 Tax: $2,176 (2025)Community: Southern Pines CondoCondo
Taxes:$2,176
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Welcome to Southern Pines in the heart of Winter Garden. This well-maintained 1-bedroom, 1-bath upper-level condo offers a bright and functional layout with abundant natural light. The kitchen features granite countertops, ample cabinetry, and a practical layout that connects to the living and dining areas, creating a comfortable flow for everyday living. The open layout and high ceilings help maximize the space and give the unit an airy feel. The bedroom is comfortable and well-sized, offering a quiet and private retreat. This unit also includes an attached 1-car garage and additional storage, a valuable feature within the community. Southern Pines is a gated community with resort-style amenities including a pool, fitness center, tennis courts, basketball, racquetball, sand volleyball, playground, and clubhouse. The HOA covers lawn care, water, cable, and internet for added convenience. Ideally located near Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail, with easy access to SR-429, Florida Turnpike, SR-408, and SR-50. Daily conveniences are just minutes away, including Publix (approx. 3 minutes) and Costco (approx. 8 minutes). Make this property your home today.
Listing is courtesy of: EC REAL ESTATE INVEST.& RENTAL (954-775-4221)
Listing Agent: Elsy Camacho (954-775-4221)
8955 LAKESHORE POINTE DR, WINTER GARDEN, FL 34787
$639,990237 Days on yellowkey MLS ID: O6337042
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2539 Built: 2018Monthly Fee: $600 Tax: $8,886 (2024)Community: Lakeshore Preserve Ph 1Townhouse
Taxes:$8,886
Tax Year: 2024
Remarks: Reduced price! Welcome to this elegant and beautiful townhome, designed by an architect. SELLER JUST REPAINT THE WHOLE INTERIOR HOME! This property is being offered for the first time since its original purchase in 2018. It has an open concept, full of upgrades and details. Wall papers bring a cozy atmosphere and elevate harmony. This home has ceiling speakers, security camera and ring door bell. As you walk in you feel the modern layout with a charming patio to enjoy family, friends and Florida weather. Main level with kitchen, 1/2 bath, living and dining area. At the living area you can enjoy the natural light, lovely crown-molding, blinds for privacy and Wine Refrigerator. Dining area with wall paper and Borserie. An extra graceful environment with wall paper at the 1/2 bath . Sophisticated gourmet kitchen with granite, backsplash, gray color cabinets, double sink and double kitchen island for extra seating. Sliding doors bring extra natural light and take you to back patio, blending space, nature and elegant paver to appreciate life. The upgraded stairs add a refined touch to the second floor with a cozy carpet. A spacious hall with nice double door closet for linens. Second floor Master Bedroom with wall paper at main wall, shade and walk in closet. Master Bathroom with 2 sinks, niche, shower inclosure, shower tiles upgraded to ceiling, private commode, and handheld private bided. Second floor tasteful 2 bedrooms, with wall paper, brand new custom closets, blinds and curtains. Second floor full bathroom with niche, shower enclosure, creme color stylish cabinet, 2 sinks and handheld toilet bidet. Laundry room with granite, cabinet and laundry sink. The surprise is the additional bonus apartment on top of garage with mini kitchen, full bathroom, wall paper at the main wall, blinds and walk in closet. To wrap this masterpiece listing, a 2 car garage with epoxy. This home was a vacation home for sellers, as they never lived, and only used for a few days during the year. Seller is giving a new kitchen refrigerator as credit at closing. Schedule a tour as you will fall in love! There is a you tube link with a video of the property!
Listing is courtesy of: ANA TEIXEIRA REALTY (321-624-4325)
Listing Agent: Ana Paula Teixeira (321-624-4325)
14501 GROVE RESORT AVE #1310, WINTER GARDEN, FL 34787
$230,00015 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
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
$664,90040 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
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
$2,999,990211 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)
4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787
$585,00052 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)
931 KYLEE ALY, WINTER GARDEN, FL 34787
$849,00049 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
Elementary School: Tildenville Elem
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)
12112 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$540,000133 Days on yellowkey MLS ID: O6366467
REDUCED by $10,000 (1.8%) on 04/14/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2801 Built: 2021Monthly Fee: $192 Tax: $9,460 (2025)Community: Encore At OvationSpa: NoSingle Family
Taxes:$9,460
Remarks: Gorgeous Brand new 4-bedroom 3.5 bath home across the street from the pool and fitness center, Off Western Way on the west side of Disney. This home has a covered and paved front porch with direct views across the street to the community clubhouse, fitness center, pool and open park. When you want a little more privacy, you can sneak off to the small side covered patio. As you enter into the home, you are greeted by a wide foyer which opens to the main Great room, the stairs, and the first-floor spare 4th bedroom with full private bath. Walk past the partially open staircase with beautiful iron Rail, into the main Great room featuring Family, dining and kitchen. The family room is very large, over 18x16 feet and has a great storage closet under the stairs. The dining room has a window and large slider to the side covered patio and is completely open to the kitchen. The amazing Kitchen has tons of cabinets, counter space, huge pantry, Large flat island with Stone counter bar top, cabinet crowns, all SS appliances and Gas stove. Just past the kitchen is the half bath powder room and drop zone from when you enter into from the rear facing garage. First floor is tile throughout except for bedroom. Upstairs has carpet in all bedrooms and open loft. The Master Bedroom has 2 very large walk-in closets, and nice large bath with two separate vanities with extra cabinet space, a walk-in shower, and private toilet. The Master has more privacy split away from the other bedrooms by the laundry room. Laundry room has extra space for an ironing board, and laundry sink next to the provided washer and dryer. Bedrooms 2, 3 are separated by a full bath with double sinks and shower/tub. Tankless water heater saves in efficiency and constant hot water. This home is in a great and quite community just a few miles off the 429 west of Disney. While this home sits across from the clubhouse and pool area, the community offers other areas of interest to explore and enjoy. A short block away has a fenced dog park and a walking trail around a long pond with Activities such as Corn hole, Bocce Ball courts, and picnic tables. Further inside the community has more open park areas with trails by scenic ponds currently under construction along with the back park which the playground should soon be built. Just a few miles off the major interchange of 429 and Western, just outside Disney West provides fast and easy access anywhere. Hospitals, restaurants and shopping are all close and many more are being built nearby. The builder states; Water Spring Elementary, Bridgewater Middle, and Windermere Highschool.
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Chun Cai (951-699-4983)
15312 GILLIGAN CT, WINTER GARDEN, FL 34787
$1,150,00091 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
$606,44036 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
$1,390,00077 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)
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