Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Living Area Square Feet: 2500 to 2999
Do Not Show Listings
Winter Garden - 130 properties found
6177 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$729,3859 Days on yellowkey MLS ID: G5111566
0 Days Off yellowkey (back on 4/25/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2688 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$0
Elementary School: Hamlin Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Under Construction. The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering FOUR bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provide ample space for family members or guests. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787
$680,000324 Days on yellowkey MLS ID: S5129072
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2868 Built: 2015Monthly Fee: $172 Tax: $10,554 (2024)Community: Orchard Hills Ph 2Single Family
Taxes:$10,554
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2024
Middle School: Bridgewater Middle
Remarks: Located in the highly sought-after community of Orchard Hills, this stunning home offers the epitome of Central Florida living. Orchard Hills is a community that attracts buyers from all walks of life, making it an ideal investment. This spacious, single-story residence boasts 5 bedrooms, 3 full bathrooms, and one half-bath, ready for you to move in. From the moment you step inside, you'll be captivated by the expansive open spaces that flow seamlessly, creating a welcoming and bright ambiance. The well-thought-out design ensures that every corner of the home feels expansive and filled with natural light. The heart of this home is, without a doubt, its gourmet kitchen. Equipped with modern stainless steel appliances, gleaming granite countertops, and a generous center island, this kitchen is a chef's dream. Whether you're preparing a quick meal or hosting a large gathering, you'll have all the space and amenities you need. Adjacent to the kitchen, the ample living area provides the ideal space to relax and enjoy moments with your loved ones. Washer & Dryer do NOT convey. Click Virtual Tour 1 to visit the Property. Carpets removed, New Laminated Floors refresh up the living space.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Carlos Hernandez Franquet (786-816-7138)
9409 EMERALD BERRY DR, WINTER GARDEN, FL 34787
$875,00062 Days on yellowkey MLS ID: S5144953
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2923 Built: 2024Monthly Fee: $85Community: Summerlake ReserveSpa: NoSingle Family
Elementary School: Panther Lake Elementary
Remarks: Under contract-accepting backup offers. Nestled on a premium homesite with no rear neighbors in the exclusive Summerlake Reserve enclave, this beautifully designed home blends comfort, functionality, and thoughtful upgrades throughout. The home offers 4 bedrooms, 3.5 bathrooms, a private office with barn doors, a spacious loft, and an extended covered lanai ideal for indoor-outdoor living. The gourmet kitchen is both elegant and functional, featuring quartz countertops, 42” upper cabinets, soft-close cabinetry, built-in oven and microwave, a smooth cooktop with vent hood, a contrasting island with pendant lighting, and a generous butler’s pantry. Interior highlights include an open baluster staircase, tray ceiling in the owner’s suite, and a freestanding soaking tub in the primary bath. Additional enhancements such as crown molding and decorative millwork, custom window treatments and blinds, travertine tile on the front porch and extended rear lanai, a luxury electric bidet toilet in the primary bath, a whole-home water filtration system, and an attic access ladder for convenient storage. Located in the intimate Summerlake Reserve community of just 41 homesites, this property is minutes from Horizon West’s top-rated schools, shopping, dining, and entertainment.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Manuella Espinosa (407-433-5352)
7580 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$693,23010 Days on yellowkey MLS ID: G5111519
0 Days Off yellowkey (back on 4/24/2026)
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.
8807 SONOMA COAST, WINTER GARDEN, FL 34787
$799,90053 Days on yellowkey MLS ID: O6388886
REDUCED by $19,100 (2.3%) on 04/24/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2840 Built: 2022Monthly Fee: $261 Tax: $9,520 (2025)Community: Waterleigh Ph 3B 3C & 3DSpa: NoSingle Family
Taxes:$9,520
Elementary School: None
Middle School: Water Spring Middle
Remarks: Welcome to the beautiful community of Waterleigh in Winter Garden! This meticulously maintained home features 5 bedrooms, 4 bathrooms, and a second floor laundry and bonus/game room. This thoughtfully designed open-concept home offers functionality and space for all. The spacious foyer invites you into the great room filled with natural light and overlooks the pond. The kitchen features stainless steel appliances, quartz countertops, and a large island that overlooks the dining and living areas. There is also a bedroom on the first floor that can also be used as a private office. The staircase with iron railing leads you to the second floor which houses the primary suite that provides a relaxing retreat with a spa-like bathroom and generous walk-in closet and pond view, and three additional bedrooms and two baths (one of the bedrooms is an en-suite). The serene backyard with covered patio and view of the pond offers space for a future pool, and is perfect for outdoor dining, family gatherings, or simply enjoying Florida’s sunshine. This home boasts wood-look tile on the first floor, upgraded lighting and ceiling fans, decorator touches and wainscoting, and lots of storage. Residents of Waterleigh enjoy resort-style amenities, including two clubhouses, pools, fitness centers, tennis and volleyball courts, playgrounds, walking trails, dog parks, and even a community beach with lake access. Lawn care is included in the HOA for true low-maintenance living. Conveniently located near Disney, Horizon West shopping and dining, top-rated schools, and major highways, this home offers the perfect balance of luxury and practicality in one of Winter Garden’s most sought-after neighborhoods.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
9062 SONOMA COAST DR, WINTER GARDEN, FL 34787
$785,000201 Days on yellowkey MLS ID: O6352763
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2909 Built: 2021Monthly Fee: $261 Tax: $10,736 (2024)Community: Waterleigh Ph 3B 3C & 3DSingle Family
Taxes:$10,736
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Special Financing Available — Ask for Details! Experience resort-style living in the highly desirable Waterleigh community of Winter Garden. This one-of-a-kind home sits on a rare, oversized lot with no rear neighbors, offering ultimate privacy and tranquility — perfect for families or anyone seeking a private retreat in one of Central Florida’s most sought-after neighborhoods. Step inside and fall in love with the bright open-concept layout, filled with natural light and elegant finishes throughout. The gourmet kitchen features stainless steel appliances, quartz countertops, and a large island that connects seamlessly to the dining and living areas — ideal for family gatherings and entertaining. The primary suite provides a private retreat with a spa-inspired bathroom and a generous walk-in closet. Enjoy peaceful mornings, weekend barbecues, or evening relaxation in your spacious backyard, with plenty of room for outdoor activities. Live your best life at Waterleigh — a community known for its resort-style amenities, including two clubhouses, sparkling pools, fitness centers, tennis courts, playgrounds, walking trails, dog parks, and even a community beach with lake access. HOA includes lawn care for true low-maintenance living. Located near Disney, Horizon West shopping and dining, top-rated schools, and major highways, this home offers both luxury and convenience in one of Winter Garden’s premier neighborhoods. Special Incentive: Through the seller’s preferred lender, qualified buyers can access temporary rate buydowns and forgivable down payment assistance, designed to lower monthly payments and increase affordability. (No obligation to use preferred lender. Programs subject to qualification and market conditions.) Please note: Photos #2–17 have been virtually staged for marketing purposes only.
Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)
Listing Agent: Asher Chen (407-717-5232)
7526 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$676,24511 Days on yellowkey MLS ID: G5111448
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2680 Built: 2026Monthly Fee: $150Community: 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.
15327 GILLIGAN CT, WINTER GARDEN, FL 34787
$664,80018 Days on yellowkey MLS ID: O6398756
2 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2506 Built: 2021Monthly Fee: $103 Tax: $7,266 (2025)Community: Winding Bay Ph 1BSingle Family
Taxes:$7,266
Elementary School: Water Spring Elementary
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained multi-generational home nestled on a quiet cul-de-sac in the highly desirable Winding Bay community of Horizon West in Winter Garden. This thoughtfully designed 4-bedroom, 3-bath residence features a private 1-bedroom suite, perfect for in-laws, aging parents, or guests. The suite offers its own laundry closet, kitchenette, and a well-appointed bathroom with a walk-in shower and granite vanity, providing both comfort and independence. Inside the main home, you’ll find a bright and spacious open-concept split floor plan that blends functionality with modern style. Elegant plantation shutters are featured throughout the home, adding both charm and privacy, while tile flooring spans the main living areas for durability and easy maintenance. A versatile flex space is ideal for a home office, art studio, or den. The chef-inspired gourmet kitchen is the heart of the home, showcasing a large island, abundant cabinetry, granite countertop and built-in stainless-steel appliances, including a new cooktop. It flows seamlessly into the expansive family room, complete with built-in surround sound, perfect for entertaining or relaxing movie nights. The primary owner’s suite is a private retreat featuring a tray ceiling, walk-in closet, and a spa-like ensuite bathroom with dual sink vanity with granite countertop and an impressive walk-in shower with multiple shower heads, including a rain feature. Step outside to enjoy the wide, screened-in covered lanai overlooking a fully fenced backyard, ideal for entertaining or unwinding in a peaceful setting. The 2-car garage offers additional storage space to meet your needs. Residents of Winding Bay enjoy access to resort-style amenities, including a community pool and playground, all just minutes from Walt Disney World, Hamlin Town Center, top-rated dining, shopping, placing you close to the best of Winter Garden and the greater Central Florida area. Convenient access to Highway 429 makes commuting a breeze. Don’t miss the opportunity to own this exceptional home. Schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Giovanni Sanginesi (407-276-0025)
13386 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787
$799,99066 Days on yellowkey MLS ID: S5144786
5 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2856 Built: 2026Monthly Fee: $125 Tax: $500 (2025)Community: Serenade At OvationSingle Family
Taxes:$500
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Step into modern elegance with this stunning new construction home that perfectly blends style, comfort, and MULTI-GENERATIONAL LIVING. Nestled on a premium lot that backs directly to serene conservation land, this home offers the ultimate in privacy and picturesque views. As you enter the home, one is greeted by 8 foot doors, Mohawk nimbus oak luxury vinyl flooring and 5 inch baseboards throughout. The open-concept living space is an entertainer’s dream, with a chef-inspired kitchen boasting Barnett Linen color cabinets with light rail and 6" bow pull hardware, Carrara Breve eased edge quartz countertops, polished chrome Sterling Traverse pulldown faucet, stainless steel single basin undermount sink and Passion Blanco gloss 3x8 backsplash tile to the ceiling. The sleek finishes, ample cabinetry, and large island overlooking the sunlit dining and living areas provide the perfect entertaining space. The thoughtfully designed layout features a first-floor master suite, providing a private retreat with spa-like amenities such as 12x24" Emser Porto Ivory Matte colored floor tile, Barnett Linen colored gentlemen's height vanity with Carrara Breve Quartz countertops, oval undermount sinks, Sterling Valton 4" Centerset Lavatory Faucet and glass shower enclosure with chrome handle finish and 12x24" inch tile walls to the ceiling. Back through the living area, a first-floor guest wing adds convenience and flexibility, making hosting visitors or multi-gen living a breeze. Upstairs, a spacious loft/game room offers endless possibilities - home theater, playroom, or even a stylish home office. The second floor also consists of 3 beds and 2 baths, one with full ensuite, the other Jack and Jill style. Outside, enjoy the best of Florida living with an oversized porch for al fresco dining and a backyard that feels like your own private oasis, bordered by lush, untouched conservation land. Whether you’re sipping your morning coffee on the patio or gathering for an evening barbecue, the setting is sure to impress. Only 20 minutes to Magic Kingdom (NO highway driving needed for access!), less than 3 miles to Flamingo Crossing Shopping area, less than 10 miles to Hamlin Town Center, and 30 minutes to Millenia and the Outlet Malls, this home provides all that Orlando Living has to offer.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Marissa Crawford (407-361-7400)
3439 BUOY CIR, WINTER GARDEN, FL 34787
$734,99048 Days on yellowkey MLS ID: O6386482
REDUCED by $13,010 (1.7%) on 04/23/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2920 Built: 2019Monthly Fee: $152 Tax: $7,013 (2025)Community: Lakeview PreserveSingle Family
Taxes:$7,013
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: Searching for a 4-bedroom home in Winter Garden with lake views, a private office, and a 3 car garage in a gated community? Welcome to 3439 Buoy Circle, a well maintained single family residence offering approximately 2,900 square feet, 4 bedrooms, a dedicated office, and 4.5 bathrooms, thoughtfully positioned to capture peaceful water views and stunning evening sunsets. Built by Taylor Morrison, this home features a well designed layout that blends comfort, privacy, and everyday functionality. Located within the gated Lakeside Preserve community on Johns Lake, this home offers a quiet residential setting with a scenic entrance that creates a sense of separation from major traffic corridors while remaining conveniently connected to daily essentials. The flexible floor plan supports modern living and includes a private office, ideal for working from home or creating a focused, dedicated space. Each bedroom features its own private full bathroom, along with an additional half bath for guests. The primary suite, bathroom, and walk-in closet span the full length of one side of the home, creating a spacious and well designed retreat with generous storage. The walk-in closet connects directly to the laundry room, adding ease and efficiency to daily routines. A standout feature is the 3 car garage, offering valuable space for vehicles, storage, recreational equipment, or hobbies. The homesite provides added privacy with only one immediate side neighbor, while the backyard is positioned to enjoy lake views and west-facing sunset exposure, creating a peaceful outdoor setting for relaxing or entertaining. Lakeside Preserve is a gated waterfront community featuring resort-style amenities, including a fitness center, pool, cabana, playground, and splash pad, along with direct access to Johns Lake with a kayak launch and dock. Natural conservation areas are thoughtfully woven throughout the neighborhood, enhancing both privacy and the overall setting. Residents enjoy close proximity to Hamlin Town Center, FL 429, AdventHealth Horizon West Hospital, Historic Downtown Winter Garden, the West Orange Trail, and the attractions of Walt Disney World, all within a short drive. This 4-bedroom home in Winter Garden offers a rare combination of lake views, ensuite bathrooms in every bedroom, a private office, and a 3 car garage within a gated waterfront community, delivering both everyday comfort and long term value in one of Central Florida’s most desirable areas. Information deemed reliable but not guaranteed. Buyer and buyer’s agent to verify all measurements, HOA information, school zoning, and property details..
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Patricia Solivan Lopez (407-218-2477)
17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$609,61177 Days on yellowkey MLS ID: G5108288
0 Days Off yellowkey (back on 4/7/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2520 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 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.
11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$819,99080 Days on yellowkey MLS ID: O6382359
REDUCED by $9,746 (1.2%) on 04/22/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2866 Built: 2025Monthly Fee: $250 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Remarks: Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 5 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a bedroom and full bathroom. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Customize the second floor of this home to create a space that meets your needs but transforming the loft area to a fifth bedroom with full bath or Guest Suite with ensuite bathroom. Like all homes in Waterleigh, the Cresswell includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *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)
16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787
$875,59598 Days on yellowkey MLS ID: G5107301
0 Days Off yellowkey (back on 1/26/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,726 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The Arlington is perfect for families of all sizes!
15456 GILLIGAN CT, WINTER GARDEN, FL 34787
$600,000277 Days on yellowkey MLS ID: A4660262
REDUCED by $20,000 (3.2%) on 04/21/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2571 Built: 2020Monthly Fee: $102 Tax: $8,702 (2024)Community: Winding Bay Ph 1BSingle Family
Taxes:$8,702
Remarks: A Rare Owner-Occupied Opportunity Just 3.9 Miles from Disney — Fireworks Views Included Located in the highly sought-after Winding Bay community of Winter Garden, this pristine single-story 3-bedroom, 3.5-bath residence offers a lifestyle few homes can match: proximity to Disney without the noise, crowds, or short-term rental turnover. This home is ideal for owner-occupants, Disney professionals, or second-home buyers seeking a quiet, stable community with low HOA fees and thoughtfully designed amenities. Short-term rentals are not permitted, creating a neighborhood atmosphere centered on consistency, pride of ownership, and long-term value. From the moment you arrive, the home impresses with its brick-paved driveway, stone-accented façade, and welcoming curb appeal, leading into a bright, open layout designed for modern living. Inside, you’ll find a spacious and functional floor plan featuring a dedicated built-in desk area, an oversized mudroom with adjacent laundry and custom cabinetry, and generously sized guest suites ideal for visiting family and friends. The heart of the home is the chef-inspired eat-in kitchen, showcasing: 42” soft-close cabinetry Quartz countertops and designer backsplash Vented range hood and built-in microwave Massive walk-in pantry Oversized island with seating for up to eight, perfect for entertaining The open dining and family room are flooded with natural light and flow seamlessly to the custom-designed backyard, where you can unwind and enjoy direct views of Disney fireworks from your own home — a truly rare and magical feature. Winding Bay residents enjoy: Community pool Dog park Low HOA of just $102/month Proximity to top-rated schools, dining, and shopping This home is move-in ready, meticulously maintained, and positioned for buyers who value location, lifestyle, and long-term enjoyment over transient use. This is not a short-term rental opportunity. It is a rare chance to own a refined, owner-occupied home minutes from Disney in one of Winter Garden’s most desirable communities. Private showings available by appointment.
Listing is courtesy of: NEXTHOME CASA BELLA ELITE (813-726-5646)
Listing Agent: Loren Rosenthal (813-726-5646)
14345 WABASSO LOOP, WINTER GARDEN, FL 34787
$735,00088 Days on yellowkey MLS ID: O6376609
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 2022Monthly Fee: $192 Tax: $10,615 (2025)Community: Tilden Place/Winter GardenSingle Family
Taxes:$10,615
Remarks: Located within the gated community of Tilden Place, this thoughtfully designed home offers exceptional flexibility and everyday comfort in one of Winter Garden’s most convenient locations. The main level features a private primary suite along with three additional bedrooms, including an en suite option ideal for guests, multigenerational living, or a home office. Upstairs, a spacious loft, bedroom, and full bath create a separate retreat perfect for teens, visitors, or work-from-home needs. Light-filled living and dining areas flow into the kitchen, which is well-appointed with a gas range, double ovens, generous counter space, a walk-in pantry, and breakfast bar—designed to support both everyday living and effortless entertaining. Sliding doors open to a screened porch, extending the living space outdoors for relaxed mornings and evenings. Enjoy close proximity to A-rated schools, including Keene’s Crossing, Bridgewater Middle, Windermere High, and nearby Foundation Academy. Just minutes from downtown Winter Garden, the West Orange Trail, shopping, dining, and daily conveniences, with easy access to SR 429, Orlando International Airport, and the attractions Central Florida is known for.
Listing Agent: Hilary Hall (407-902-9311)
9459 JAYWOOD RD, WINTER GARDEN, FL 34787
$755,00063 Days on yellowkey MLS ID: O6386488
REDUCED by $5,000 (0.7%) on 04/20/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2840 Built: 2020Monthly Fee: $261 Tax: $6,669 (2025)Community: Waterleigh Ph 3ASingle Family
Taxes:$6,669
Remarks: BACK ON MARKET DUE TO BUYER FINANCING FALLING THROUGH!! AS-IS sale with peace of mind! All prior repair requests have been completed, and a previous buyer’s inspection report is available for review. Back on market due to buyer financing, no fault of seller. Take advantage of a $5,000 exterior painting credit & ask about this incentive! Welcome to this stunning 5-bedroom, 4-bathroom home in the highly sought-after Waterleigh community in the heart of Horizon West, Winter Garden. This property is the perfect blend of luxury, comfort, and convenience and offers the PERFECT multi-generational home layout. Zoned for Atwater Bay Elementary School, this home is ideally positioned within a thriving and growing community. As you step through the front door, you’ll be immediately impressed by the spacious, open floor plan. To the right, you’ll find a private 5th bedroom, complete with a full walk-in shower just outside, ideal for guests or a quiet retreat. Continuing through the home, you'll be greeted by a seamless flow between the expansive living and dining areas. The kitchen is designed for both function and style and now features custom shelving in the pantry, providing enhanced organization and storage. Beneath the staircase, there’s a generous storage closet, and the entire home boasts brand-new carpet less than two years old, offering both comfort and style. The property is also equipped with rain gutters for added protection. Upstairs, you'll discover the luxurious primary suite, along with three additional bedrooms. The oversized loft area includes a converted den, perfect for use as an office, media space, or flex room to fit your lifestyle. The primary bathroom is a true retreat, featuring both a shower and separate soaking tub, along with a massive walk-in closet. For ultimate convenience, the laundry room is located upstairs and includes a smart leak detection system. The washer and dryer are less than three years old and practically brand new. Step outside to your screened-in lanai, ideal for outdoor entertaining, relaxing evenings, or enjoying nightly fireworks from Walt Disney World along with AMAZING views of NASA rocket launches from the Space Coast. Located just minutes from Disney, this home also provides incredible convenience within the community itself, with Publix now open, Jersey Mike’s, McDonald's, a nail salon, and more nearby. Even more exciting, a bank is coming soon, adding to the ease of everyday living. The neighborhood is golf cart-friendly and filled with abundant amenities and community events, making it easy to stay connected and entertained year-round. Don’t miss the opportunity to make this dream home YOURS! Schedule your private showing today!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787
$757,99015 Days on yellowkey MLS ID: G5111222
0 Days Off yellowkey (back on 4/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,726 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The Arlington is perfect for families of all sizes!
393 LAKE AMBERLEIGH DR, WINTER GARDEN, FL 34787
$615,000109 Days on yellowkey MLS ID: O6374079
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2684 Built: 2002Monthly Fee: $117 Tax: $2,690 (2025)Community: AmberleighSingle Family
Taxes:$2,690
Remarks: Located in a quiet, gated community within a highly rated school zone, this well-maintained home offers comfort, privacy, and thoughtful upgrades. The home features two AC systems, including a main unit with an electronic air cleaner, a high-efficiency water heater, and a whole-house reverse osmosis and water softening system, along with updated double-pane windows on the back of the home. A NEW ROOF (2024) adds long-term peace of mind. Inside, you'll find 18.5-foot ceilings in the family room, plantation shutters, custom drapes, and ceiling fans, with wood flooring and travertine tile that complement each other throughout. The kitchen is finished with granite countertops, tile backsplash, a cherry wood bar top, and quality appliances. With a private backyard that is great for cookouts you can enjoy the gated living in a home ideally located near major highways, Central Florida attractions, and Downtown Winter Garden. - Schedule your tour today!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787
$579,90019 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
Remarks: 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 Agent: Lauren Marason (610-223-7086)
18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787
$725,00067 Days on yellowkey MLS ID: O6386008
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2832 Built: 2023Monthly Fee: $281 Tax: $497 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$497
Remarks: Welcome to 18309 Oliver Twist Way, a beautifully maintained five bedroom, four bathroom home located in the highly sought after Waterleigh community in Winter Garden. Designed for both everyday comfort and effortless entertaining, this spacious home offers a thoughtful layout with flexible living spaces and modern finishes throughout. One of the standout features is the private downstairs guest ensuite, ideal for multigenerational living, visiting family, or a dedicated office space. The open concept main living area creates a warm and inviting atmosphere, seamlessly connecting the kitchen, dining, and living spaces while offering plenty of natural light. Upstairs, generously sized bedrooms provide space for everyone, while the primary suite serves as a peaceful retreat after a long day. Every detail has been carefully maintained, making this home truly move in ready.nLocated within Waterleigh, residents enjoy access to resort style amenities including multiple pools, walking trails, fitness centers, playgrounds, and community green spaces. The home is also conveniently positioned near local schools, shopping, dining, and just a short drive to Walt Disney World, offering both convenience and lifestyle. If you are looking for a home that blends space, functionality, and the vibrant community feel that Waterleigh is known for, this is one you will not want to miss.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Kerstin Crow (615-428-7046)
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