Location: Winter Garden
Do Not Show Listings
931 KYLEE ALY, WINTER GARDEN, FL 34787
$849,00058 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,637
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
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)
15312 GILLIGAN CT, WINTER GARDEN, FL 34787
$1,150,000100 Days on yellowkey MLS ID: O6372954
0 Days Off yellowkey (back on 4/14/2026)
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
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2024
Middle School: Water Spring Middle
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
$606,44045 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
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 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.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787
$1,390,00086 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
$617,50019 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)
16563 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787
$414,99064 Days on yellowkey MLS ID: O6386283
2 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1567 Built: 2025Monthly Fee: $205 Tax: $1,424 (2025)Community: WaterleighSpa: NoTownhouse
Taxes:$1,424
Elementary School: None
High School: None
Middle School: None
Remarks: Under Construction. Charming townhome in Waterleigh with 3 bedrooms, 2.5 baths, smart home technology, and a gourmet kitchen. Features an open living area, spacious bedrooms, and a versatile loft space. Offers modern living with creative and personalized options. It’s also located in a desirable community for tranquility and convenience. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
14006 FRASIER STREET, WINTER GARDEN, FL 34787
$659,00019 Days on yellowkey MLS ID: O6398760
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2098 Built: 2023Monthly Fee: $100 Tax: $8,274 (2025)Community: Highland RidgeSingle Family
Taxes:$8,274
Remarks: Stunning Corner Lot Home Welcome to this beautifully designed, home situated on a desirable corner lot in the sought-after Highland Ridge community in Winter Garden, FL. Built by Meritage Homes, this residence offers the perfect blend of modern style, comfort, and energy efficiency. The open-concept first floor features a spacious great room and dining area that flow seamlessly together, creating an ideal space for entertaining and everyday living. The gourmet kitchen is the heart of the home, complete with a large island overlooking the main living areas and patio—perfect for gatherings with family and friends. Upstairs, the private primary suite offers a relaxing retreat with an oversized walk-in closet, dual vanities, and a sleek walk-in shower. Thoughtfully designed throughout, the home showcases professionally curated finishes, including elegant granite or quartz countertops and stylish tile flooring. Additional highlights include a detached two-car garage, ample natural light, and smart, energy-efficient features designed to provide long-term savings, improved comfort, and healthier living. Located in a vibrant community with top-rated schools and convenient access to major employment centers, shopping, and dining, this home truly offers the best of modern Florida living. Furnishings may be negotiable, offering a convenient, move-in-ready opportunity for buyers.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Vinny Apolinario (407-371-2227)
15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787
$609,85042 Days on yellowkey MLS ID: S5146095
REDUCED by $3,050 (0.5%) on 04/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2420 Built: 2024Monthly Fee: $95 Tax: $8,065 (2025)Community: Osprey Ranch Ph ISingle Family
Taxes:$8,065
Remarks: Welcome to this stunning corner-lot residence located within the exclusive Osprey Ranch community in Winter Garden, just minutes from Walt Disney World and surrounded by fine dining, premium shopping, upscale hotels, and top-rated schools. This beautifully appointed home offers 2,420 sqft of refined living space, featuring 4 spacious bedrooms and 3 full bathrooms, thoughtfully curated to deliver both comfort and sophistication. A standout feature of this residence is the first-floor bedroom with a full bathroom, ideal for multigenerational living, guests seeking privacy, or a flexible office space. Designed for a seamless indoor-outdoor lifestyle, this home showcases: • A fully private fenced backyard, offering both security and tranquility • Custom-designed window treatments, adding a refined designer touch • Expansive bedrooms filled with natural light and generous proportions • A charming private courtyard, perfect for outdoor dining, BBQs, and entertaining Positioned on a premium corner lot, this residence offers enhanced privacy, abundant natural light, and a distinguished presence within the community. Located within a top-rated school district and in one of Central Florida’s most desirable growth corridors, this property seamlessly blends luxury, functionality, and long-term value. An exceptional residence that blends sophistication, comfort, and an elevated way of living.
Listing is courtesy of: A & V FLORIDA REALTY GROUP LLC (786-641-7923)
Listing Agent: Edgar Brito (786-641-7923)
7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787
$658,90023 Days on yellowkey MLS ID: O6389013
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2385 Built: 2016Monthly Fee: $252 Tax: $8,915 (2025)Community: Summerlake Pd Ph 3ASingle Family
Taxes:$8,915
Elementary School: Summerlake Elementary
Remarks: Under contract-accepting backup offers. Welcome to refined Florida living in this pristine Lennar Executive Collection sprawling ranch home, ideally situated on an oversized, fully fenced home site, in the highly sought-after Summerlake community of Horizon West. Offering over 2,300 square feet of thoughtfully designed OPEN floorplan living, this four-bedroom, 2.5-bath residence with a three car garage(2 tandem with professionally installed overhead storage) has been used exclusively by the owners as their second home for vacation (never rented out) and feels nearly new, with several appliances never even used. At the heart of the home, the chef-inspired kitchen showcases a GAS RANGE, stainless steel appliances, granite countertops, a generous island with abundant seating, a walk-in pantry, and a dedicated dining area that easily accommodates both casual and formal dining. Glass sliders open to the screened lanai, extending the living space outdoors and overlooking the oversized backyard with ample room to design a resort-style pool, outdoor kitchen, and/or a private oasis tailored to your vision. The kitchen flows seamlessly into the expansive great room, creating an ideal setting for entertaining and everyday living. Privately tucked away, the Primary Suite offers a serene retreat complete with crown molding, an en-suite bathroom with dual vanities showcasing granite countertops, a soaking tub, separate oversized walk-in shower, and a custom-designed boutique-style closet that enhances both elegance and organization. The light-filled split-bedroom floor plan features tile and luxury vinyl plank flooring throughout, creating a completely carpet-free interior with a clean, modern aesthetic. Three spacious secondary bedrooms and a full bath are privately positioned toward the front of the home. There is also a laundry room with a drop zone located off the garage entry. Additional upgrades include a tankless water heater, water softener, newer A/C system, a wired security system that is also wired for outdoor cameras , crown molding throughout the primary living area, and an in-wall pest system. Low HOA’s that includes but is not limited to lawn care, bush trimming, and mulch application allows for low-maintenance living. Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse for social events, fitness center, basketball, tennis/pickleball courts, dog park, playgrounds, zip line ,walking paths, multiple ponds ,fishing dock, all conveniently located near shopping, dining, major highways and world renowned theme parks. You can enjoy Disney fireworks from the community viewing areas. Also, the golfer in you will be happy to know that you are only a short drive away from the Orange County National Golf Course. This exceptional home offers the perfect blend of comfort, elegance, and lifestyle convenience in one of Horizon West’s most desirable communities. Summerlake,Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! SEE DRONE TOUR OF INTERIOR , click on Tour#1
Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)
Listing Agent: Ann Wargo (407-616-3041)
14058 FRASIER ST, WINTER GARDEN, FL 34787
$459,00071 Days on yellowkey MLS ID: V4947394
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1996 Built: 2023Monthly Fee: $110 Tax: $7,893 (2024)Community: Highland RdgSingle Family
Taxes:$7,893
Remarks: Welcome to 14058 Frasier Street in the heart of Winter Garden, Florida—where modern comfort meets small-town charm! Located in one of Central Florida’s most sought-after communities, this beautifully maintained home offers the perfect blend of style, space, and convenience. Step inside to discover an inviting open-concept floor plan filled with natural light, high ceilings, and thoughtfully designed living spaces ideal for both everyday living and entertaining. The spacious kitchen serves as the centerpiece of the home, featuring ample cabinetry, generous counter space, and a seamless flow into the dining and living areas—perfect for hosting family and friends. The primary suite provides a private retreat with a well-appointed en-suite bath and generous closet space. Additional bedrooms are comfortably sized and versatile, ideal for guests, a home office, or a growing family. Every detail has been carefully maintained to create a move-in-ready opportunity. Enjoy Florida living year-round with a private backyard space perfect for relaxing evenings, weekend barbecues, or creating your own outdoor oasis. Whether you envision a garden, play area, or custom patio retreat, the possibilities are endless. If you’re looking for a home that offers comfort, location, and lifestyle all in one—14058 Frasier Street is ready to welcome you home. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ali Partovi (386-295-5115)
15324 GILLIGAN CT, WINTER GARDEN, FL 34787
$950,00037 Days on yellowkey MLS ID: O6393498
0 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2794 Built: 2020Monthly Fee: $102 Tax: $641 (2025)Community: Winding Bay Ph 1BSingle Family
Taxes:$641
Remarks: Under contract-accepting backup offers. Winter Garden’s finest — a spacious 4-bedroom, 3.5-bathroom home with a 3-car garage, pool, outdoor kitchen, and breathtaking pond views. This exceptional home is filled with custom upgrades throughout, including custom beams, a striking stone entry wall, built-in dining seating, an expanded drop zone with additional cabinetry, and a custom bar area complete with a wine refrigerator. The gourmet kitchen features 42-inch white cabinets, stainless steel appliances, a large farmhouse sink, and an oversized pantry/storage area. A first-floor den/office offers the perfect flex space for work or relaxation. Upstairs, the primary suite is a true retreat with a custom-designed bath, wood-trimmed tray ceiling, private balcony overlooking the pond, and custom built-ins in the walk-in closet. The adjacent bedroom has been transformed into a dream walk-in closet with shoe storage and a lighted vanity, but can easily be converted back into a bedroom upon request. Two additional bedrooms complete the second floor, including one with its own private ensuite, while the open loft with custom beams creates the perfect setting for a cozy movie night. A second-floor laundry room adds everyday convenience. Step outside into your private resort-style oasis, featuring stunning pond views, a tongue-and-groove stained ceiling, built-in seating, and a fully equipped outdoor kitchen with sink, grill, pizza oven, refrigerator, and stainless hood. The heated UV-filtered pool, connected to the home’s water softener system, is enhanced by a beautiful stone waterfall. A sauna and cold plunge complete this extraordinary outdoor retreat — truly an at-home resort experience. Lush landscaping surrounds the patio and pool area, creating a tropical and private escape, complemented by thoughtfully added rock garden beds and light paver stone walkways along the side of the home that enhance both beauty and functionality. Beyond the pond, a wooded area owned by Disney provides a protected natural backdrop that will never be developed, preserving both privacy and tranquility. The 3-car garage is equally impressive with custom built-ins, overhead storage racks, and a metallic epoxy floor. New exterior painting is currently in progress. Life here extends beyond the home. Morning walks along tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style community amenities create a rhythm that feels both relaxed and vibrant. Residents enjoy access to a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and two dog parks. Located in an area known for top-rated schools, with convenient access to shopping and dining, and just minutes from Walt Disney World Resort, this home perfectly blends Central Florida convenience with the feeling of being tucked into something truly special. More than a house — this is a place to settle in, build memories, and truly feel at home in Winter Garden.
15508 BLACKBEAD ST, WINTER GARDEN, FL 34787
$430,000115 Days on yellowkey MLS ID: O6371455
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1754 Built: 2017Monthly Fee: $313 Tax: $6,652 (2025)Community: Summerlake Pd Ph 2C-2ETownhouse
Taxes:$6,652
Middle School: Horizon West Middle School
Remarks: One or more photo(s) has been virtually staged. If you’re looking for low-maintenance living without giving up space, convenience, or community, 15508 Blackbead Way is worth a closer look. This 3-bedroom, 2.5-bath townhome is located in Summerlake, a well-established Winter Garden neighborhood known for its amenities and everyday ease. The main floor features an open, fluid layout designed for both entertaining and day-to-day living, complete with a convenient half bath. The open kitchen flows naturally into the dining and living spaces, creating a connected feel that works just as well for hosting as it does for quiet nights at home. Upstairs, all bedrooms are thoughtfully positioned alongside a centrally located laundry room, keeping everything right where you need it. The generous primary suite offers comfortable separation from the secondary bedrooms and includes a large walk-in closet. One of the most unique features of this home is the oversized driveway—a rare find for a townhome and a direct result of the lot’s placement. It offers exceptional parking and flexibility, and as an added bonus, you can enjoy views of the Magic Kingdom fireworks right from the driveway—an unexpected and special touch that truly sets this home apart. Summerlake residents enjoy a resort-style pool, fitness center, walking trails, parks, playgrounds, and a true sense of community, including Food Truck Thursdays held on the third Thursday of each month. With easy access to shopping, dining, major roadways, and nearby schools, this is an opportunity to enjoy Winter Garden living with comfort, connection, and less upkeep.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Hilary Hall (407-902-9311)
8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787
$565,00022 Days on yellowkey MLS ID: TB8496196
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2019 Built: 2017Monthly Fee: $312 Tax: $5,109 (2025)Community: Waterleigh Phase 1CSpa: YesSingle Family
Taxes:$5,109
Elementary School: Panther Lake Elementary
Remarks: **New landscaping in progress with pictures to follow, expected by April month end** Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade, private backyard with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Timothy Shepard (727-204-9618)
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,00024 Days on yellowkey MLS ID: O6397340
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1005 Built: 1950 Tax: $5,389 (2025)Community: Orange Grove SubSingle Family
Taxes:$5,389
Elementary School: Dillard Street Elem
Remarks: **** HEART OF DOWTOWN WINTER GARDEN **** CAN'T GET MUCH CLOSER TO ***HISTORIC DOWNTOWN WINTER GARDEN *** THAN THIS! SERIOUSLY! FRESH OWNER REDO WITH DISCERNING DESIGN CHOICES ON THIS SOLID & ADORABLE 3 BEDROOM/2 BATH FENCED YARD (SOLID CONCRETE BLOCK) CHARMER. *** NO HOA OR FEES*** HOOOORAY! & WITHIN STEPS TO DOWNTOWN PLANT STREET, TONY'S, HARLOW GROVE RESTAURANT, CHURCHES, FARMERS MARKET, CROOKED CAN FOOD HALL, JESSIE BROCK COMMUNITY PARK, PUBLIC BOAT RAMP AT NEWTON PARK, AND ALL THAT FAST GROWING DOWNTOWN HISTORIC WINTER GARDEN HAS TO OFFER!!! AMAZING CHANGES ARE ON THE HORIZON!!!----GET IN ON YOUR OWN LOCKED IN LOCATION NOW!!!----- (LOCATED WITHIN THE ZONED GOLF CART DISTRICT). WITHIN MINUTES TO HWY 50, FOWLER GROVES/LOWES/TARGET & 429 FREEWAY ENTRANCE, AS WELL AS FLORIDA TURNPIKE AND E-W EXPRESSWAY ENTRANCES BEING MERE MINUTES AWAY ON EAST PLANT STREET; OH SO CENTRALLY LOCATED DIRECTLY IN "TOWN PROPER" JUST A FEW LOTS UP FROM PLANT STREET; & JUST A LITTLE FURTHER DOWN MAIN STREET AND YOU ARE AT THE PUBLIC BOAT RAMP, NEWTON PARK AND THE FARNSWORTH CITY POOL!!! BEYOND EXCELLENT ACCESS TO MULTIPLE GROCERIES, TAILORS & SHOPPING OPTIONS AT HWY 50, PARK AVENUE, DILLARD STREET AND NEARBY OAKLAND! ALSO, THE WEST ORANGE TRAIL RUNS PERPENDICULAR TO MAIN STREET (YOUR STREET) & IS STEPS FROM YOUR HOME-----CONCRETE BLOCK CONSTRUCTION BUILT W/TERMITE BOND/MONTHLY PEST TREATMENT-ALL WITH MASSEY SENTRICON & TRANSFERABLE BOND TO THE NEW OWNER--- HOME HAS GROOMED MATURE OAKS WITH FENCED IN BACK YARD (WOOD PLANK AND VINYL) WITH ELEVATED WOOD DECK FOR FLIPPING OPEN THE BRAND NEW DOUBLE FRENCH DOORS AND ENJOYING FOR ENTERTAINING!!! ***EXCELLENT VALUE/EXCELLENT LOCATION/GOLF CART DISTRICT/NO HOA!***--WHY RENT WHEN YOU CAN (OWN) YOUR OWN PROPERTY FOR JUST A FEW BUCKS MORE PER MONTH? -----HOME WARRANTY OPTIONS AVAILABLE. WITHIN ZILLOW RANGE PRICING! GREAT DEAL. COME SEE FOR YOURSELF...........
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jason Fulmer (321-303-6670)
14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787
$270,000135 Days on yellowkey MLS ID: O6368187
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1544 Built: 2018Monthly Fee: $1,103 Tax: $8,868 (2024)Community: Grove Residence & Spa Hotel Condo IiCondo
Taxes:$8,868
Remarks: Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time Residency Investor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large balcony, modern kitchen, and in-unit washer/dryer. High occupancy potential through the on-site rental program. Resort Amenities (included for guests): Surfari Water Park, surf simulator, water slides, laser river. Multiple resort-style pools, hot tubs & cabanas. Lake Austin access with fishing and water sports. Fitness center, arcade, full-service spa, on-site restaurants, bars, market, and conference center, 24/7 front desk, concierge, and gated community security. Prime Location, located in Winter Garden, FL, just minutes to Walt Disney World® and major Orlando attractions. Close to shopping, dining, and major highways. This unit is part of a condo-hotel program: no full-time residency allowed. Short-term rentals only. SHORT SALE – priced to sell fast! A great chance to secure a unit below market value in a high-demand tourist location. Ideal for investors looking for short-term rental income with professional management available on-site. Not suitable for full-time occupancy. Contact us today to schedule a showing and take advantage of this exceptional income-generating property!
Listing Agent: Nayane Seabra (407-535-7815)
17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787
$718,79930 Days on yellowkey MLS ID: TB8493597
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2224 Built: 2026Monthly Fee: $84 Tax: $2,363 (2025)Community: Northlake/Ovation Ph 1Single Family
Taxes:$2,363
Remarks: Under Construction. This stunning Plant II single-family home is located in the desirable Northlake at Ovation community. This popular one-story, open-concept layout features 4 bedrooms and 3 bathrooms, ideal for modern living. With finishes from the AW Collection Sapphire vibrant blues meet bright whites for a bold look. Enjoy a chef-inspired kitchen with 42" cabinets, quartz countertops, and large island overlooking the living and dining areas, perfect for entertaining. The home also includes luxury vinyl flooring, a private primary suite with walk-in closet, a covered lanai for outdoor living, and a spacious 2-car garage. Conveniently located in Winter Garden near shopping, dining, major roadways, and top-rated schools. Community amenities include pool, clubhouse, playground areas and dog park.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$548,00087 Days on yellowkey MLS ID: O6379918
5 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2062 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Dayene Grubert (863-521-4474)
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$795,00037 Days on yellowkey MLS ID: O6393987
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4307 Built: 2014Monthly Fee: $114 Tax: $5,670 (2025)Community: Reserve/Carriage Pointe Ph 1Single Family
Taxes:$5,670
Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.
Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)
Listing Agent: Xiaoli Lin (561-385-7610)
17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$646,09020 Days on yellowkey MLS ID: G5110934
0 Days Off yellowkey (back on 4/12/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2680 Built: 2026Monthly Fee: $140Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley model features 2,102 square feet of well-designed living space across two stories, with an above-garage Apt 576 sqft.This home includes 3 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for both daily living and entertaining. The primary suite is located on the first floor for added privacy, with a luxurious bath and walk-in closet. Upstairs, two additional bedrooms and a full bath provide flexible living options for guests or family members. The apartment is above the garage with a private entrance. This neighborhood features a variety of townhomes and single-family homes on multiple-sized homesites, with spacious floor plans designed to support a wide range of lifestyles, from growing families to move-up buyers seeking more room to live and entertain. Located just minutes from Hamlin Town Center, Winter Garden Village, and historic Downtown Winter Garden, Hamlin Meadows places shopping, dining, and entertainment close to home. Residents will also enjoy access to nearby parks, trails, and outdoor recreation, along with proximity to highly regarded Orange County schools, including Hamlin Elementary, Hamlin Middle, and Horizon High School.
17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787
$740,20520 Days on yellowkey MLS ID: G5110933
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3412 Built: 2026Monthly Fee: $140Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage
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