Location: Winter Garden, 34787
Do Not Show Listings
14591 BLACK QUILL DR, WINTER GARDEN, FL 34787
$1,335,00011 Days on yellowkey MLS ID: O6420836
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4057 Built: 2016Monthly Fee: $215 Tax: $8,212 (2025)Community: West Lake Hancock EstatesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,212
Elementary School: Independence Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Welcome to this beautifully upgraded luxury home in Hamlin, offering 4 bedrooms, a dedicated theater room, bonus room, resort-style pool and spa, summer kitchen, and putting green. Built in 2016 and meticulously maintained, this exceptional residence sits on one of Overlook at Hamlin’s most desirable homesites, featuring rare elevated conservation and water views that provide privacy and a setting unlike the typical flat Florida lot. Inside, soaring ceilings, abundant natural light, and an open-concept layout create the perfect balance of comfort and sophistication. The fully remodeled chef’s kitchen features quartz countertops, brand-new appliances, an oversized island, built-in microwave, wine refrigerator, and a stunning custom Venetian plaster hood. The spacious primary suite offers custom walk-in closets and a spa-inspired bath with luxury designer touches. Additional highlights include a dedicated movie theater with tiered seating, a large bonus room, custom laundry room, camera security system, designer lighting, and premium finishes throughout. Step outside to your own private backyard retreat featuring a screened-in pool and spa, summer kitchen with fire feature, covered outdoor living space, putting green, and breathtaking conservation views. Living in Overlook at Hamlin means enjoying some of the best amenities in the area, including a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and private lake access. Just minutes from Hamlin Town Center, you’re surrounded by great restaurants, shopping, and entertainment. With amazing sunsets and a prime location in the heart of Horizon West, this is a rare opportunity to own a luxury pool home in one of Winter Garden’s most sought-after communities.
Listing is courtesy of: TOP TIER RESORT REALTY (407-375-4566)
Listing Agent: Seth Flaugher (407-375-4566)
9605 LOST CREEK DR, WINTER GARDEN, FL 34787
$699,000301 Days on yellowkey MLS ID: V4944858
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2117 Built: 2021Monthly Fee: $261 Tax: $614 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$614
Elementary School: Water Spring Elementary
Tax Year: 2024
Middle School: Water Spring Middle
Remarks: Short Sale. ***SHORT SALE. ***ALL OFFERS MUST GO THROUGH SHORT SALE PROCESS WITH SELLERS LENDER FOR APPROVAL/DENIAL.** The Bellmore in Waterleigh! This elegant single-story four-bedroom, two-bath residence offers 2,984 total square feet of refined living on a premier corner lot with wooded privacy and pond access. Blending timeless design with modern upgrades, this home showcases luxury finishes inside and out. The gourmet kitchen is a centerpiece, featuring stainless steel appliances, a walk-in pantry, and an oversized island with abundant prep and seating space. It opens seamlessly to the spacious family room, creating a setting for gatherings. Designer touches include recessed wood-insert ceilings in the foyer and primary suite, a dramatic brick accent wall in the living room, upgraded lighting throughout and a striking chandelier in the foyer. The primary suite offers a custom closet organization system, while ceiling fans are thoughtfully placed in almost every room. Outdoor living rivals a private resort with a screened, heated saltwater pool and cascading waterfalls, surrounded by lush tropical landscaping. The covered lanai features a 10-foot drop-down projection screen for outdoor cinema nights, while brick pavers enhance the driveway, walkways, and patio. A 13.67-kilowatt solar system with net metering ensures energy efficiency. From the backyard, enjoy nightly views of the spectacular Disney fireworks—an unforgettable backdrop unique to Central Florida living. Optional luxury additions for additional purchase include a four-seat electric golf cart with charger, professional-grade garage storage racks and a complete home gym with free weights. Waterleigh is Winter Garden’s flagship planned community, offering two expansive clubhouses with resort-style pools, state-of-the-art fitness centers, tennis courts, miniature golf, walking trails, dog parks, community gardens and scenic lakes with fishing piers. Ideally near Disney, major highways, shopping and dining, Waterleigh combines convenience with unmatched amenities. Ranked as one of the top communities in the United States, Winter Garden is celebrated for its vibrant downtown, lifestyle amenities and exceptional quality of life—making this home a rare opportunity to own in one of the nation’s desirable areas. This one is a must-see. By appointment only. BUYER MUST ASSUME 50K SOLAR PANEL LOAN- BANK WILL NOT CONSIDER ANY OFFERS ASKING FOR BANK TO PAY OFF SOLAR PANELS. OCCUPIED- BY APPOINTMENT ONLY.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (386-761-2172)
Listing Agent: Jennifer Matacale (386-212-9277)
15607 SYLVESTER PALM DR, WINTER GARDEN, FL 34787
$729,00047 Days on yellowkey MLS ID: O6410558
REDUCED by $20,000 (2.7%) on 07/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2092 Built: 2017Monthly Fee: $281 Tax: $10,040 (2025)Community: Lakeshore Preserve Ph 1Single Family
Taxes:$10,040
Remarks: Welcome to this stunning modern single-story home featuring a full CRESTRON Whole-Home Smart System, located in the highly sought-after Lakeshore Preserve community in Winter Garden. Built in 2017, this beautifully maintained residence offers approximately 2,092 square feet of living space situated on a 7,719 square foot lot. Inside, you’ll find 3 spacious bedrooms, 2 full bathrooms, and an open-concept layout that seamlessly connects the living, dining, and kitchen areas — creating the perfect space for both everyday living and entertaining. The stylish kitchen is equipped with modern appliances, including a built-in oven, cooktop, dishwasher, and disposal, along with solid surface countertops designed for both function and style. Additional upgrades and features include central heating and air conditioning, a tankless water heater, and an attached two-car garage. Residents of Lakeshore Preserve enjoy access to exceptional community amenities such as a clubhouse, resort-style pool, and recreational facilities. Offering a move-in ready lifestyle in one of Winter Garden’s most desirable communities, 15607 Sylvester Palm Drive combines modern comfort, smart-home convenience, and the ease of single-level living.
Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)
Listing Agent: Corey Smith (407-927-0599)
20 W CREST AVE, WINTER GARDEN, FL 34787
$2,349,00022 Days on yellowkey MLS ID: O6417710
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4668 Built: 2020 Tax: $13,263 (2026)Community: Boyd-Lutz SubSpa: YesSingle Family
Taxes:$13,263
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2026
Middle School: Lakeview Middle
Remarks: Virtually Staged. Step into a home designed for the way you truly want to live. From its elevated concrete construction to its hurricane-rated engineering, this residence offers the rare combination of luxury, security, and effortless comfort. Natural light fills the interior, where level-5 walls, rich wood flooring, crown molding, and custom shutters create a warm, refined atmosphere. The heart of the home is the open living and kitchen area—perfect for gathering, cooking, and connecting. A gas range, pot filler, and handcrafted cabinetry make everyday meals feel elevated. Slide open the dramatic retractable pocket door and the entire space transforms into an indoor-outdoor retreat. The back porch is built for hosting: pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, 1/2 bath, and room for everyone to unwind. The primary suite is a sanctuary of its own, offering a spa-inspired bath with dual shower heads, soaking tub, and digital controls. A custom closet and private concrete safe room add both convenience and peace of mind. With a butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring, this home is designed for modern living at its finest—where every detail supports a lifestyle of ease, elegance, and connection. Upstairs, the bonus/game room and oversized balcony access create the perfect hangout zone. You won't complain about storage or closet space as most rooms have walk-in closets and the additional closets are oversized as well. Let your imagination run wild because the possibilities are endless with the finished two-story garage loft that is pre-plumbed and air conditioned! Mother-in-law suite, man cave with a golf simulator or a gym, home office or game room. Outside, the home is framed by curated Florida landscaping, gas lanterns, an architectural driveway, and a built-in heated concrete hot tub with Wi-Fi controls—ideal for quiet evenings or weekend entertaining. Fiber-cement siding, Ipe hardwood porch, impact windows, and full foam insulation ensure long-lasting beauty and efficiency. Prime location near Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, award-winning Farmers Market, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre — a truly elevated lifestyle.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Lora King (407-947-7653)
14776 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787
$880,00025 Days on yellowkey MLS ID: O6416354
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2876 Built: 2017Monthly Fee: $187 Tax: $11,232 (2025)Community: Orchard Hills Ph 3Spa: NoSingle Family
Taxes:$11,232
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Remarks: Discover Your Dream Home in the Exclusive Orchard Hills Community! This stunning residence perfectly blends elegance, comfort, and functionality in one of Winter Garden's most sought-after neighborhoods. Featuring 4 spacious bedrooms, 3 full bathrooms, and 1 half bath, this home offers thoughtfully designed living spaces ideal for both everyday living and entertaining. At the heart of the home is a beautifully appointed gourmet kitchen, complete with a large center island, elegant granite countertops, and ample cabinetry. The kitchen seamlessly flows into the expansive open-concept living and dining areas, creating the perfect setting for gatherings with family and friends. A charming front porch welcomes you and provides the perfect place to relax and enjoy Florida’s beautiful weather. Step through the sliding glass doors and discover your own private outdoor retreat. The backyard features a spectacular covered gourmet outdoor living area and a beautiful private pool, offering the ideal space for entertaining, relaxing, and enjoying year-round outdoor living. Living in Orchard Hills means enjoying an exceptional lifestyle with resort-style amenities, including a clubhouse, fitness center, resort-style swimming pool, dog park, playgrounds, walking trails, and community events throughout the year. Ideally located, this home is just minutes from Hamlin Town Center, Winter Garden Village, top-rated schools, shopping, dining, grocery stores, and major highways, including SR-429. You'll also enjoy convenient access to world-famous attractions such as Walt Disney World and the many entertainment options that make Central Florida such a desirable place to live. This is a rare opportunity to own a beautiful home in one of Winter Garden's premier communities. Schedule your private showing today and experience everything this exceptional home has to offer!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Erika Castellani (781-502-6199)
9567 MEADOW HUNT WAY, WINTER GARDEN, FL 34787
$965,0005 Days on yellowkey MLS ID: O6422408
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4305 Built: 2019Monthly Fee: $164 Tax: $9,084 (2025)Community: WatermarkSingle Family
Taxes:$9,084
Elementary School: Panther Lake Elementary
Middle School: Hamlin Middle
Remarks: Currently occupied by tenant. Tenant will move out Jan 2027. Welcome to this beautifully upgraded 5-bedroom, 5-bathroom floorplan, where comfort meets style in the highly sought-after Watermark community. One of the bedrooms has been thoughtfully converted into a spacious media room by the original owners in 2019, but it can easily function as a fifth bedroom if needed. From the charming front porch to the shining luxury tile floors, this home is filled with elegant touches throughout. As you step inside, you’re greeted by a custom full-length glass wall in the hallway, adding depth and openness to the floorplan. The first room on the left is a fully equipped office. Adjacent is a sophisticated formal dining room with stylish wallpaper. The soaring ceilings and oversized family room are designed for both entertaining and everyday comfort, featuring stunning window treatments, a high-resolution projector, and a built-in surround sound system—perfect for cinematic nights at home. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances, a large quartz countertop, a summer kitchen layout, and designer pendant lights, all of which can remain with the home. The first-floor master suite is a true retreat with blackout window treatments, a spa-like bath with a soaking tub, and a generous walk-in closet. Upstairs, you’ll find three additional bedrooms, a spacious loft, a study/den, and a one-of-a-kind themed game room with a hand-painted moon mural, cloud accents, twinkling ceiling lights, and a second surround sound system. Step outside to a covered patio with a heat-block screen and ambient ceiling lighting—ideal for evening gatherings. Located just a short walk from the luxury clubhouse and nearby commercial plaza, you’ll enjoy resort-style amenities including pool, a fitness center, fire pit, waterslides, tennis and basketball courts—all with a low HOA. This home offers the perfect combination of luxury, convenience, and community living. There are four lights have been removed compared to the original listing photos: • The fixture in the front study room • The one in the formal dining room • The light above the staircase• The one in the morning/breakfast area Please call for showing.
Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)
Listing Agent: Emma Yue (626-328-8535)
15063 GROVESIDE RD, WINTER GARDEN, FL 34787
$516,4305 Days on yellowkey MLS ID: O6420626
0 Days Off yellowkey (back on 7/5/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 2026Monthly Fee: $247 Tax: $1,210 (2025)Community: Parkview At HamlinTownhouse
Taxes:$1,210
Elementary School: Hamlin Elementary
Remarks: Under Construction. Ready in August 2026! 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 by 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)
13230 SERENE GLADE RD, WINTER GARDEN, FL 34787
$456,4966 Days on yellowkey MLS ID: G5114659
0 Days Off yellowkey (back on 7/4/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2026Monthly Fee: $216Community: Serenade At OvationTownhouse
Taxes:$0
Remarks: Virtually Staged. Under Construction. Sample Images Harbor Town Home – offering 1,644 sq. ft. of thoughtfully designed living space, featuring three bedrooms, two and a half baths, and a spacious two-car garage with a charming paver driveway. Step inside to impressive tall ceilings, enhancing the natural light and creating a bright, open, and airy atmosphere throughout. Elegant linen cabinets and sleek quartz countertops, perfectly paired with durable, designer-inspired RevWood laminate flooring that flows seamlessly across the first floor. A perfect blend of style, functionality, and modern comfort—ideal for everyday living and effortless entertaining.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
14095 TITLE WAY, WINTER GARDEN, FL 34787
$420,000130 Days on yellowkey MLS ID: O6382795
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1628 Built: 2020Monthly Fee: $268 Tax: $6,056 (2024)Community: Storey Grove Ph 2Townhouse
Taxes:$6,056
Remarks: Impeccably maintained townhome in the highly desirable community of Storey Grove! Built in 2020, this beautifully cared-for 3-bedroom, 2.5-bath residence offers the perfect blend of style, comfort, and prime location. The open-concept first floor is designed for modern living and effortless entertaining, featuring tile flooring throughout the entire home, creating a clean, cohesive, and low-maintenance living environment. The spacious kitchen is a true highlight, offering abundant cabinetry, solid-surface countertops, stainless steel appliances, and a large center island that provides generous prep space and seating. The open layout allows the kitchen to flow seamlessly into the dining and living areas, making it ideal for gatherings and everyday living. Step outside to your privately fenced courtyard featuring a beautiful canopy, creating a shaded and inviting outdoor retreat perfect for relaxing or entertaining year-round. Upstairs, you’ll find three generous sized bedrooms and two full bathrooms. The primary suite includes a spacious walk-in closet and an elegant en-suite bath with dual vanities, offering both comfort and privacy. Ideally located just minutes from Walt Disney World, Disney Springs, Flamingo Crossings, major highways, shopping centers, restaurants, hospitals, and top-rated schools, this home delivers exceptional convenience in one of the most desirable areas near Orlando’s attractions. Whether you're searching for a primary residence or an investment opportunity, this property is must-see.
Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)
Listing Agent: Leidy Sanquiz (407-451-7197)
13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787
$599,000179 Days on yellowkey MLS ID: O6367311
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1906 Built: 2024Monthly Fee: $96 Tax: $2,239 (2024)Community: Westhaven At OvationSingle Family
Taxes:$2,239
Elementary School: None
Middle School: None
Remarks: Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to offer. Community amenities are conveniently located just across the way, making it effortless to enjoy the Florida lifestyle. Inside, the open floor plan is enhanced by beautiful LVP flooring throughout the main living areas on the first floor and in the primary bedroom upstairs, while the additional bedrooms feature comfortable carpet. The kitchen is a standout with crisp white cabinetry, a spacious island accented by three pendant lights, and a stylish backsplash that adds a pop of energy to the inviting neutral palette. Outdoor living is just as impressive, with a screened-in lanai plus additional uncovered outdoor space that connects to the two-car detached garage—one of the few bungalow designs with a detached garage concept, offering even more ways to enjoy Florida’s beautiful weather. WELCOME HOME!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Amy Kidwell Pa (407-848-8042)
1349 CASTLEPORT RD, WINTER GARDEN, FL 34787
$720,000129 Days on yellowkey MLS ID: O6377923
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3673 Built: 2001Monthly Fee: $250 Tax: $9,122 (2024)Community: Stoneybrook West 44/134Single Family
Taxes:$9,122
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: This beautiful renovated 5-bedroom home located in the guard-gated golf community of Stoneybrook West, in Winter Garden, offers two primary suites, three additional bedrooms, and a large loft/flex space, ideal for multi-generational living or a home office. New stair and loft railings have been installed to enhance safety and functionality. The open-concept floor plan features abundant natural light and a seamless layout for entertaining. Enjoy a spacious fenced backyard with room for a pool or outdoor living area. Stoneybrook West offers a boat ramp, fishing areas, and lake access for water enthusiasts, a clubhouse, fitness center, and a large resort-style community pool. Residents can enjoy tennis courts, a golf course, basketball court, a playground, and feel at ease with a 24-hour guard-gated entrance ensuring a secure and peaceful living environment with scenic walking and biking trails. Conveniently located near shopping, dining, top-rated schools, and major roadways with easy access to Orlando and area attractions. Resort-style living in a prime Winter Garden location.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787
$579,90086 Days on yellowkey MLS ID: O6396640
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2626 Built: 2013Monthly Fee: $128 Tax: $6,746 (2025)Community: Johns Lake Pointe A & SSingle Family
Taxes:$6,746
High School: None
Remarks: Back on Market due to buyer unable to secure funding. Their loss, your opportunity. Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjacent to the John Lake Conservation Area, you'll also enjoy easy walking and biking access to Tucker Ranch, the future site of a holistic wellness center, teaching farm, playground and family activity hub. Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe community! This expansive 2,626 sq. ft. home sits on a generous 0.25-acre corner lot. Enjoy the comfort of a newer A/C unit and handler installed in January 2025 and freshly painted interiors (2022) that create a crisp, modern ambiance. The spacious eat-in kitchen features a large island with seating for four, ample cabinetry, a custom pantry, and extensive counter space—perfect for gatherings or morning routines. The first floor features a flexible private bonus room that can easily serve as a home office, study, or a welcoming fifth bedroom for overnight guests. The primary suite includes a beautifully crafted walk-in closet, while the custom laundry room offers built-in cabinetry and a convenient hanging bar for added functionality. Just beyond the living space, the screened-in lanai invites you to relax and unwind. Situated on a prime corner lot, the property also boasts a generously sized yard with endless potential for outdoor enjoyment. The epoxy-coated two-car garage is both functional and stylish, freshly painted and equipped with motion-sensor lighting for your convenience. This Meritage home is solid construction with 6 panel doors throughout and spray foam insulation in the attic. Community amenities include a pool, clubhouse, fitness center, yoga studio, pickleball and tennis courts—everything you need for a vibrant, active lifestyle. With its thoughtful design, abundant amenities, and unbeatable location, this home offers the perfect blend of comfort, convenience, and community.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lauren Marason (610-223-7086)
12475 CLEAR SAPPHIRE DR, WINTER GARDEN, FL 34787
$644,99044 Days on yellowkey MLS ID: O6411217
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2500 Built: 2026Monthly Fee: $96 Tax: $5,390 (2026)Community: Osprey RanchSingle Family
Taxes:$5,390
Remarks: Under contract-accepting backup offers. Under Construction. .
Listing is courtesy of: K HOVNANIAN FLORIDA REALTY (321-263-2601)
Listing Agent: Richard Selikoff (201-741-7242)
9738 TOWER PINE DR, WINTER GARDEN, FL 34787
$950,00021 Days on yellowkey MLS ID: O6417627
2 Days Off yellowkey (back on 7/5/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2526 Built: 1993 Tax: $7,549 (2025)Community: Lake Avalon Rural SettlementSingle Family
Taxes:$7,549
Remarks: Under contract-accepting backup offers. Escape to your own private retreat in the highly sought-after Lake Avalon area of Winter Garden! Nestled on nearly 5 picturesque acres, this charming home offers the perfect blend of country living and modern convenience. Featuring 3 bedrooms, 2 full bathrooms, and over 2.500 square feet of living space, the home welcomes you with high ceilings, an open-concept floor plan, and an updated kitchen that flows seamlessly into the spacious living and dining areas—perfect for everyday living and entertaining. Bring your horses, recreational vehicles, and outdoor toys—there's no HOA and ample space to create the lifestyle you've been dreaming of. Enjoy the peace and privacy of acreage living while remaining just minutes from shopping, dining, Disney, Downtown Winter Garden, and convenient access to SR-429. Whether you're looking for a private homestead, hobby farm, or simply room to spread out, this rare acreage property offers endless possibilities in one of Central Florida's most desirable locations.
Listing is courtesy of: KORR REALTY CORP (407-732-6987)
Listing Agent: Jacquelyn Retherford (917-270-4699)
16570 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787
$414,99072 Days on yellowkey MLS ID: O6403257
REDUCED by $5,000 (1.2%) on 07/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1567 Built: 2025Monthly Fee: $204 Tax: $1,424 (2025)Community: WaterleighSpa: NoTownhouse
Taxes:$1,424
Remarks: Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *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)
411 MILLWOOD PL, WINTER GARDEN, FL 34787
$459,00030 Days on yellowkey MLS ID: TB8518055
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1696 Built: 2014Monthly Fee: $72 Tax: $6,471 (2025)Community: Covington Chase Ph 2ASingle Family
Taxes:$6,471
Remarks: Welcome to Covington Chase — one of Winter Garden's most sought-after communities! This charming 3BR/2BA/2-car garage home built in 2014 features an open great room layout, split bedrooms, and a 2-car garage. Enjoy community amenities including a pool, playground, and clubhouse, all just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village shopping, and SR 429. Disney World and Universal Studios are less than 20 miles away. Don't miss this gem — schedule your showing today!
Listing is courtesy of: PEOPLE'S TRUST REALTY (727-946-0904)
Listing Agent: Kimberly Watson-Johnson (727-946-6949)
6051 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$737,11027 Days on yellowkey MLS ID: G5113741
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2235 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: Virtually Staged. 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.
15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787
$1,999,94558 Days on yellowkey MLS ID: O6405850
REDUCED by $2 (0.0%) on 07/01/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3837 Built: 2016Monthly Fee: $195 Tax: $17,089 (2025)Community: Signature Lakes Ph 02 A B H I JSpa: YesSingle Family
Taxes:$17,089
Middle School: Horizon West Middle School
Remarks: .....LOCATION! LOCATION! LOCATION!.....LAKE HOME!.....PRIVATE DOCK!.....SALTWATER POOL!.....PRIMARY BEDROOM on MAIN!!!!!..... Gorgeous 5 bedroom. 4.5 bath home on Lake Hancock located in Hamlin Town Center. Upon entering, the home welcomes you with a bright, OPEN-CONCEPT design that seamlessly connects the main living areas, creating an ideal flow for entertaining and everyday living. Stunning LAKE VIEWS can be enjoyed from the gourmet kitchen, main level primary suite, additional bedroom and great room. The JUNIOR SUITE would make a wonderful mother in law suite. The UPPER LEVEL features a spacious BONUS ROOM ideal for media/game/play/home gym or secondary living area; along with FULL BATH and BEDROOM, providing flexibility and privacy away from the main living spaces. Step outside to a massive RESORT STYLE OUTDOOR LIVING AREA making it your personal oasis for both relaxation or entertaining. The expansive PAVER DECK leads to a pristine heated saltwater pool and spa. Your private dock offers the perfect setting to enjoy fishing, sunsets, and nightly Disney fireworks from the comfort of home. LAKE HANCOCK is renewed for it’s exceptional recreational opportunities, making it ideal for boating enthusiasts and avid anglers alike. The lake is well known for its excellent fishing, canoeing, paddle boarding, water skiing and wake sports. The lakes size and depth also accommodate seaplane activity. The COMMUNITY features multiple playgrounds, tennis courts, basketball, pools, fitness centers, arcade, clubhouse, dog parks, business center and CABLE/INTERNET included in HOA DUES.....Located in one of Central Florida's most sought after areas-HAMLIN TOWN CENTER, the vibrant heart of the HORIZON WEST community. The NEIGHBORHOOD offers sidewalks. paved WAKING/BIKING trails connecting to everything you need. Close walk to grocery store, dining, shopping, Cinepolis, POPSTROKE (Tiger Woods designed Putt Putt), Restaurant/Ice Cream Parlor/Playground), Urban Air Adventure & Trampoline Park. Convenient access to SR429! ***All information deemed reliable but not guaranteed and should be independently verified by the buyer***
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Tina Carroll (678-850-8036)
5754 SURPRISE LILY DR, WINTER GARDEN, FL 34787
$499,00028 Days on yellowkey MLS ID: S5151845
REDUCED by $16,000 (3.1%) on 06/24/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2128 Built: 2021Monthly Fee: $91 Tax: $8,266 (2025)Community: Hamilton Gardens Ph 2A 2BSingle Family
Taxes:$8,266
Remarks: Location, Location, Location! Welcome to this beautiful 4-bedroom home located in the highly desirable Hamilton Gardens community in Winter Garden. Just minutes from Hamlin Town Center, you’ll enjoy convenient access to shopping, restaurants, coffee shops, movie theaters, fitness centers, Publix, and everyday essentials. This spacious home features 4 bedrooms, with all bedrooms conveniently located upstairs, creating a functional layout that offers privacy and separation from the main living areas. Downstairs, you’ll find a versatile flex space that can be used as a home office, study area, playroom, or additional sitting room. The open-concept kitchen features a gas stove, perfect for those who enjoy cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and everyday living. Residents of Hamilton Gardens enjoy access to the community swimming pool and beautifully maintained neighborhood amenities. The home is also conveniently located near SR-429, providing quick access to Disney, Downtown Winter Garden, Downtown Orlando, and other major destinations throughout Central Florida. Families will appreciate the excellent school district, including highly rated elementary and middle schools, making this one of the most desirable areas in Winter Garden.
Listing is courtesy of: NUMBER 1 BROKER, LLC (407-566-3400)
Listing Agent: Eric Jia (407-401-1431)
5755 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$455,00068 Days on yellowkey MLS ID: O6404161
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1797 Built: 2019Monthly Fee: $338 Tax: $4,506 (2025)Community: Orchard Hills Ph 4Townhouse
Taxes:$4,506
Remarks: Welcome to this beautifully maintained corner townhouse in the sought-after Orchard Hills community of Winter Garden, offering 3 bedrooms, 2.5 baths, a 2-car garage, and abundant natural light throughout. As you enter the home, you are welcomed into the dining area which then flows seamlessly into the spacious living room and kitchen, creating an inviting layout perfect for everyday living and entertaining. Tile flooring extends throughout the downstairs living areas, kitchen, and wet areas for style and easy maintenance. The kitchen features stunning granite countertops that contrast beautifully with the white cabinetry, along with stainless steel appliances all included. Upstairs, you’ll find all three bedrooms with comfortable carpet flooring, as well as a convenient laundry room complete with washer and dryer. The primary bedroom offers private access to a balcony where you can enjoy peaceful water views and relax in a serene outdoor setting. Residents of Orchard Hills enjoy exceptional amenities including a clubhouse, fitness center, picnic area with grills, dog park, playground, and a vibrant community atmosphere with events and social clubs designed to build lasting relationships.
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)
Listing Agent: Francisco Nieves-Taranto (321-248-4149)
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