Location: Winter Garden
Do Not Show Listings
17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$485,00056 Days on yellowkey MLS ID: O6411409
REDUCED by $14,999 (3.0%) on 07/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1692 Built: 2017Monthly Fee: $215 Tax: $3,704 (2025)Community: Waterside/Johns Lake Ph 2ASingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,704
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Motivated sellers! Welcome to this highly sought-after home in the infamous Waterside Johns Lake. This adorable 3-bedroom, 2-bath home is truly a gem! This freshly painted home has delightful curb appeal, featuring an oasis of flowers and shrubs and a charming porch, perfect for sitting out and savoring life as it passes. This open floor plan is enhanced by modern high-end finishes throughout. The kitchen boasts of like-new cabinets, quartz countertops, stainless steel appliances, a walk-in pantry, and an oversized kitchen island that overlooks the family room, with the dining area conveniently located just off the kitchen, great for entertaining! The ceramic tile runs throughout with luxury Vinal plank fitted floors in two of the bedrooms. The living areas flow seamlessly together, creating an inviting space for everyday use. The primary suite offers both comfort and convenience, complete with a generous walk-in closet, dual vanities, quartz counters, and a walk-in shower. The laundry room is spacious and comes with a separate washer and dryer. The garage is located next to the laundry room, providing direct access into your home. Sliding doors open onto your own screened-in patio, perfect for enjoying the evenings or grilling out. This home has a newer roof 2025, a new tankless water heater 2026. Waterside at Johns Lake offers resort-style amenities, including a fully equipped gym, large well maintained swimming pool and a club house, this is all located just over the street for your convenience. There is easy access to all major highways including 429 and Florida's Turnpike for seamless access to downtown Orlando, area theme parks, and Orlando International Airport. Schedule your showing today! This won't last long.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Heidi Pfeffer-Morgan (407-408-6101)
5973 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$734,90057 Days on yellowkey MLS ID: O6412179
REDUCED by $5,100 (0.7%) on 07/21/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3532 Built: 2017Monthly Fee: $195 Tax: $9,630 (2025)Community: IndependneceSingle Family
Taxes:$9,630
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome to 5973 Cypress Hill Road, an exceptional 5-bedroom, 3.5-bathroom home offering nearly 3,500 square feet of thoughtfully designed living space in the highly sought-after Independence community of Winter Garden. Located in the heart of Horizon West, one of Central Florida's fastest-growing and most desirable areas, this move-in-ready home combines spacious living, resort-style amenities, top-rated schools, and unbeatable convenience. Seller is willing to help with buyers closing costs Step inside and discover a versatile floor plan designed for today's lifestyle. Multiple living spaces, including a formal living room, family room, and great room, provide the flexibility needed for entertaining, working from home, multigenerational living, or simply enjoying time with family. The spacious first-floor primary suite offers a private retreat away from the secondary bedrooms, while each of the five bedrooms features its own walk-in closet, abundant natural light, and comfortable carpeting. With room for everyone and everything, this home delivers the space buyers are searching for. At the heart of the home, the kitchen features stainless steel appliances, ample cabinetry, tile flooring, and generous workspace for meal preparation and entertaining. The washer, dryer, and all kitchen appliances convey with the sale, making your transition seamless. Step outside to the screened lanai and enjoy Florida living year-round. Whether you're enjoying your morning coffee, hosting weekend barbecues, or unwinding after a long day, this outdoor living space provides the perfect setting. Additional highlights include a newer HVAC system, a two-car garage, ceramic tile flooring in the main living areas, and abundant storage throughout the home. Residents of Independence enjoy access to an impressive collection of community amenities, including resort-style swimming pools, a fitness center, parks, playgrounds, walking trails, sports courts, and year-round community events. The location places you just minutes from Hamlin Town Center, downtown Winter Garden, shopping, dining, entertainment, major highways, and world-renowned attractions including Walt Disney World. Families will appreciate the home's location within the highly regarded school zones for Independence Elementary, Bridgewater Middle School, and Windermere High School. If you've been searching for a spacious Winter Garden home for sale with a downstairs primary suite, walk-in closets in every bedroom, resort-style community amenities, and convenient access to everything Central Florida has to offer, 5973 Cypress Hill Road deserves a spot at the top of your list. Schedule your private showing today and experience the Independence lifestyle for yourself. All information provided is deemed reliable but not guaranteed. All buyers should verify all information provided
Listing is courtesy of: NEARBY REALTY (407-349-7533)
Listing Agent: Michael Ellingson (970-978-8101)
11031 JACKSON CV, WINTER GARDEN, FL 34787
$715,00011 Days on yellowkey MLS ID: O6425544
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2931 Built: 2023Monthly Fee: $300 Tax: $10,935 (2025)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$10,935
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Virtually Staged. Experience the highly sought-after KENTON FLOOR PLAN in the award-winning WATERLEIGH community, just MINUTES FROM DISNEY! Ideally situated on a QUIET CUL-DE-SAC with NO THROUGH TRAFFIC, this beautifully upgraded 4 BEDROOM, 3 BATHROOM home offers WOOD-LOOK TILE throughout the main living areas and LUXURY VINYL PLANK upstairs. Enjoy the unique opportunity to WATCH ROCKET LAUNCHES from your own backyard. A welcoming foyer with TRAY CEILING opens to a versatile FLEX ROOM, perfect for a home office or formal dining room. The OPEN-CONCEPT design centers around a stunning GOURMET KITCHEN featuring 42" UPGRADED SHAKER CABINETS WITH CROWN MOLDING, QUARTZ COUNTERTOPS, UPGRADED TILE BACKSPLASH, 7' ISLAND, STAINLESS STEEL APPLIANCES, VENT HOOD, WALL OVEN & MICROWAVE COMBO, 5-BURNER COOKTOP, OVERSIZED SINGLE-BASIN SINK, WALK-IN PANTRY, plus a built-in COFFEE BAR/DROP ZONE. The spacious family room overlooks the covered lanai and backyard. A FIRST-FLOOR BEDROOM & FULL BATH provide the perfect guest or multigenerational suite. Upstairs, the PRIMARY SUITE features a TRAY CEILING, spa-inspired bath with GARDEN TUB, GLASS-ENCLOSED SHOWER, DUAL QUARTZ VANITIES, and an OVERSIZED WALK-IN CLOSET. A large LOFT offers the perfect space for a media room or playroom. Bedrooms 3 and 4 share a bath with DOUBLE SINKS, while the oversized laundry room includes a UTILITY SINK, WASHER & DRYER. Additional upgrades include BLOCK-ON-BLOCK CONSTRUCTION, WHOLE-HOUSE WATER FILTRATION, REVERSE OSMOSIS SYSTEM, UPGRADED LIGHTING & FANS, VIDEO DOORBELL, LOW-E DOUBLE-PANE WINDOWS, R-30 INSULATION, and RECLAIMED WATER IRRIGATION for outstanding energy efficiency. Enjoy MAINTENANCE-FREE LIVING with lawn care included and access to 4 RESORT-STYLE POOLS, 3 CLUBHOUSES, FITNESS CENTERS, TENNIS COURTS, FISHING PIER, PLAYGROUNDS, PARKS, WALKING TRAILS, and more. WATER SPRING ELEMENTARY and WATER SPRING MIDDLE SCHOOL are just a SHORT WALK AWAY, making everyday routines incredibly convenient. Zoned for HORIZON HIGH SCHOOL and ideally located near shopping, dining, Disney, and with easy access to 429, 417 & 408, this home offers the perfect blend of luxury, convenience, and lifestyle.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Sabrina Freeman (407-446-5541)
5079 PALMETTO PARK DR, WINTER GARDEN, FL 34787
$930,00017 Days on yellowkey MLS ID: G5114492
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3866 Built: 2017Monthly Fee: $190 Tax: $6,877 (2026)Community: Orchard Hills Ph 3Single Family
Taxes:$6,877
Elementary School: Keene Crossing Elementary
Tax Year: 2026
Remarks: Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.
Listing is courtesy of: FLORIDA PLUS REALTY, LLC (352-901-9100)
Listing Agent: Claire Brooks (407-967-5829)
1808 WESTERN TRAILWAY DR, WINTER GARDEN, FL 34787
$599,00020 Days on yellowkey MLS ID: S5152973
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1860 Built: 2019Monthly Fee: $165 Tax: $8,389 (2025)Community: Hull Island/OaklandSpa: NoSingle Family
Taxes:$8,389
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,800 square feet of thoughtfully designed living space in the highly sought-after Hull Island community of Oakland. Tasteful décor and stylish finishes create a warm, inviting atmosphere, while the open-concept floor plan features a spacious kitchen with stainless steel appliances, a large center island with counter seating, and seamless flow into the living and dining areas—perfect for everyday living and entertaining. Step outside to your private backyard featuring maintenance-free turf, providing a lush, green outdoor space you can enjoy year-round without the upkeep. Residents also enjoy access to the community pool, scenic walking trails, and direct access to the West Orange Trail, with beautiful Lake Apopka just a couple of blocks away. Best of all, you’ll enjoy all these incredible amenities while benefiting from a LOW HOA FEE! Whether you’re purchasing your first home, growing your family, or right-sizing after the kids have moved out, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Hull Island is a welcoming, family-oriented community for all ages, conveniently located near charming downtown Winter Garden, shopping, dining, parks, and major roadways. Don’t miss your opportunity to make this move-in-ready home your own!
Listing is courtesy of: FLORIDA IN MOTION REALTY INC (407-947-2757)
Listing Agent: Susan Koptieff (407-334-7770)
15717 E OAKLAND AVE, WINTER GARDEN, FL 34787
$1,795,00020 Days on yellowkey MLS ID: O6419032
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3515 Built: 1997 Tax: $6,623 (2025)Community: OaklandSingle Family
Taxes:$6,623
Elementary School: Tildenville Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Welcome to this exceptional ONE-OWNER CUSTOM HOME, sitting on a ONE-ACRE HOMESITE in one of Oakland’s most sought-after locations. Offering 3,515 square feet of living space (4,890 total square feet), this thoughtfully designed 4-bedroom, 3.5-bath residence combines timeless Old Florida charm with OUTSTANDING QUALITY CONSTRUCTION, FEATURING ALL-STEEL CONSTRUCTION—INCLUDING STEEL ROOF TRUSSES—for exceptional durability and peace of mind. A circular driveway and side-entry OVERSIZED TWO-CAR GARAGE create impressive curb appeal, while double front doors welcome you into a spacious, OPEN FLOOR PLAN with 17.5' VAULTED CEILINGS in living area and 10' CEILING HEIGHT in bedrooms.This home has been designed for both everyday living and entertaining. At the heart of the home is a stunning DOUBLE-SIDED FIREPLACE with Tennessee Stone which creates a beautiful focal point between the formal living room and the inviting family room. The living areas flows seamlessly into the kitchen, separated only by a short wall between the kitchen and dining room that preserves the home’s open, airy feel. The EXPANSIVE KITCHEN is designed to bring everyone together, featuring TWO SINKS, a WRAPAROUND BREAKFAST BAR with seating for up to eight, a center ISLAND WITH COOKTOP, generous eat-in dining area, WALK-IN PANTRY with custom built-in shelving, and abundant countertop workspace. The open layout allows the kitchen, dining, and living areas to remain connected, making this home ideal for entertaining, holidays, and family gatherings. The desirable THREE-WAY SPLIT FLOOR PLAN offers both privacy and flexibility. Two secondary bedrooms and a full bath are located toward the front of the home, while a separate guest wing features an additional bedroom, full bath, oversized laundry room with storage, and a convenient half bath. Privately tucked away on the opposite side of the home, the spacious primary suite offers two walk-in closets and an ensuite bath with a walk-in shower. Double glass doors open to an expansive screened lanai that extends the living space outdoors, complete with a summer kitchen and peaceful views of the lush backyard. Additional updates include a tile roof (2015), HVAC ductwork (2020), exterior stucco upgrades and fresh paint (2021), one water heater replaced in 2018 and the second in February 2025, Connection to city water in 2019, The well was retained exclusively for lawn irrigation. Perfectly located with convenient access to the Florida Turnpike, Highway 50, shopping, dining, and area attractions. This meticulously maintained custom home offers the rare combination of quality construction, timeless design, generous living spaces, and an unbeatable Oakland location. This is Florida living at its finest.
Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)
Listing Agent: Janelle Conway (407-595-0009)
914 TROWMAN ALY, WINTER GARDEN, FL 34787
$625,00062 Days on yellowkey MLS ID: O6410871
REDUCED by $24,000 (3.7%) on 07/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1642 Built: 2022Monthly Fee: $356 Tax: $6,421 (2025)Community: Oakland ParkSingle Family
Taxes:$6,421
Remarks: Looking for a move-in ready home in Winter Garden with modern upgrades, an ideal location, and a true sense of community? Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in the highly desirable Oakland Park neighborhood. Designed for today's lifestyle, this home features a bright open-concept floor plan, abundant natural light, spacious living areas, and a functional layout that's perfect for both everyday living and entertaining. Premium upgrades include gas appliances, elegant plantation shutters, and stylish finishes throughout, offering a turnkey, low-maintenance home you can enjoy from day one. Located in one of Winter Garden's most sought-after golf cart communities, Oakland Park offers resort-style amenities, scenic trails, parks, green spaces, and top-rated schools, creating the perfect setting for an active, connected lifestyle. Just minutes from Historic Downtown Winter Garden, you'll have easy access to the nationally recognized farmers market, local restaurants, boutique shopping, coffee shops, seasonal festivals, live entertainment, and the West Orange Trail. Whether you're searching for a close knit neighborhood, a home near downtown Winter Garden, or a community with exceptional amenities, this property checks every box. Don't miss this opportunity to own a beautifully upgraded home in one of Central Florida's most desirable communities.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
16185 TALIESIN ST, WINTER GARDEN, FL 34787
$649,99074 Days on yellowkey MLS ID: O6407177
REDUCED by $10,010 (1.5%) on 06/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2372 Built: 2020Monthly Fee: $127 Tax: $6,048 (2025)Community: HawksmoorSpa: NoSingle Family
Taxes:$6,048
Elementary School: Water Spring Elementary
Remarks: Virtually Staged. Beautifully maintained 4-bedroom, 3-bathroom two-story home located in the highly desirable Winter Garden area. Featuring over $58,000 in builder upgrades and premium features, including a premium corner lot, this home offers the perfect blend of comfort, style, and functionality. Fully paid solar panels and a fully owned whole-house water filtration system add even more value and energy efficiency. From the charming front porch and landscaped entry to the thoughtfully designed interior, every detail has been carefully selected. The open-concept first floor features tile flooring throughout the main living areas and is filled with natural light, creating a bright and airy feel. The spacious living and dining areas flow seamlessly into the gourmet kitchen, complete with stainless steel appliances, elegant upgraded cabinetry, quartz countertops, designer backsplash, and generous counter space, making it ideal for everyday living and entertaining. A first-floor bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a private home office. Upstairs, a spacious loft offers a great flex space for a media room, game room, or additional living area. The expansive primary suite serves as a relaxing retreat with a tray ceiling, large walk-in closet, and private bath featuring dual sinks. Additional bedrooms provide comfortable space and ample storage. Additional upgrades include upgraded lighting fixtures, enhanced tile and carpet flooring, 8-foot first-floor doors, added laundry room cabinetry, and an attached two-car garage with epoxy flooring, custom cabinetry, and an additional refrigerator. Residents enjoy access to fantastic community amenities including a clubhouse, resort-style pool, park, playground, and sidewalks throughout the neighborhood. Conveniently located just minutes from Hamlin Town Center, shopping, dining, entertainment, Walt Disney World, and major highways with easy access to Orlando and surrounding areas. This exceptional home combines modern upgrades, energy-efficient features, functional living spaces, and an unbeatable location. Schedule your private showing today.
4620 GLIDING WAVE ST, WINTER GARDEN, FL 34787
$539,000185 Days on yellowkey MLS ID: O6370772
REDUCED by $36,000 (6.3%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2184 Built: 2021Monthly Fee: $136 Tax: $8,224 (2025)Community: Lakeview Preserve Ph 2Single Family
Taxes:$8,224
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: A STUNNING, ENERGY-EFFICIENT HOME LOCATED IN ONE OF WINTER GARDEN’S MOST DESIRABLE GATED COMMUNITIES. Located at the highly desirable gated community of Lakeview Preserve, this 2021-built residence offers a rare combination of modern design, comfort, and quality of life in one of Central Florida’s fastest-growing and most appreciated areas. The home features 3 bedrooms and 2 bathrooms with a fully open and integrated floor plan that creates spacious, functional living areas filled with natural light, ideal for both everyday living and entertaining. A key highlight of this property is the installed solar panel system, providing meaningful energy savings, increased efficiency, and lower monthly utility costs, adding immediate value while aligning comfort with sustainability. Lakeview Preserve is a distinctive community surrounded by nature and thoughtfully designed to deliver leisure, security, and well-being. In addition to being a gated and well-maintained neighborhood, the community offers a full range of amenities, including a swimming pool, fitness center, clubhouse for various activities and events, a splash pad, lake access with designated kayaking areas, and inviting outdoor spaces that promote a relaxed and family-friendly atmosphere. The location is strategic, with convenient access to major roadways, highly rated schools, shopping, dining, and all that Winter Garden has to provide, making this property an excellent choice for both homeowners and investors seeking long-term value, strong demand, and consistent appreciation.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Simone De Souza Nunes Silva (689-837-5076)
769 HOME GROVE DR, WINTER GARDEN, FL 34787
$524,50018 Days on yellowkey MLS ID: O6420766
0 Days Off yellowkey (back on 7/25/2026)
REDUCED by $5,500 (1.0%) on 07/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2305 Built: 2005Monthly Fee: $99 Tax: $4,372 (2025)Community: Regency Oaks Ph 02 A-CSingle Family
Taxes:$4,372
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Price Improvement! Seller says Sell it! Offering $5,000 Buyers Incentive at closing. Welcome to established Regency Oaks subdivision in Stonecrest, in the heart of Winter Garden! Situated on a desirable corner lot, this screened-in POOL home offers an incredibly flexible floor plan designed to fit today's lifestyle. Listed as a 3-bedroom home, it also features a spacious flex room overlooking the pool and backyard, along with a separate oversized bonus room that can easily serve as an additional bedroom, home office, media room, playroom, fitness studio, guest retreat, or additional living space. The split-bedroom layout provides privacy, while the primary suite features a walk-in closet, garden tub, and separate shower. Fresh interior paint and updated laminate flooring enhance the home's inviting feel. Step outside to your private backyard oasis complete with a sparkling pool, mature shade trees, a side yard for gardening and a pool safety fence—creating the perfect setting for entertaining or relaxing while enjoying Florida's indoor-outdoor lifestyle. Recent improvements include a new roof (2023), 2017 air handler, 2018 A/C condenser, and a recently serviced irrigation system for added peace of mind. Residents of Regency Oaks enjoy low monthly HOA fees and outstanding community amenities including scenic walking trails around a picturesque pond with benches, a clubhouse, community pool, and two neighborhood parks/playgrounds. Ideally located walking distance of Winter Garden Village at The Grove and just minutes from Historic Downtown Winter Garden, the West Orange Trail, major highways, shopping, dining, entertainment, top rated schools and Central Florida's world-famous attractions. Orlando International Airport and Florida's east coast beaches are both approximately an hour away.
Listing is courtesy of: METRO CITY REALTY (407-237-3331)
Listing Agent: Beatrice Miranda (407-592-4448)
14378 BLACK LAKE PRESERVE ST, WINTER GARDEN, FL 34787
$764,90052 Days on yellowkey MLS ID: O6414181
0 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3167 Built: 2015Monthly Fee: $140 Tax: $6,855 (2025)Community: Black Lake PreserveSpa: NoSingle Family
Taxes:$6,855
Remarks: Under contract-accepting backup offers. Luxury At its Finest. This Beautiful Immaculate Open Concept 4 bedrooms, 4 baths residence featuring a spacious loft with a full bath. Loft on 2 nd Floor can potentially be used as a 5th bedroom. Ideal for guests retreat, home office, media lounge, media room or additional entertainment for the entire family. The Amazing Gourmet Chefs kitchen with under cabinet lighting Gas stove, double oven showcases an extra large extended island perfect for entertaining. Complemented by elegant finishes. Open concept living spaces and exceptional comfort throughout the home in its entirety. French Doors gives access to the resort style pool with 4 therapy jets, bubblers on the sun shelf, custom hand rail with multi led lights with a Wet Edge Pool Interior. Elegant Pavers. The Pool is 3 ft on the shallow end and 6 ft on the deep end and measures 15 x 31. This home is taken care with lots of Pride and Tender Loving care. This home sits on a corner Lot with lots of privacy for all entertainment and relaxation. Garage has overhead racks for extra storage. This is a very small community that is peaceful and tranquil for great evening walks. By Appointment Only. Thank You.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Tracy Hampstead (407-803-3137)
15587 HAMLIN BLOSSOM AVE, WINTER GARDEN, FL 34787
$619,90032 Days on yellowkey MLS ID: O6418163
1 Days Off yellowkey (back on 7/25/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1860 Built: 2015Monthly Fee: $235 Tax: $7,423 (2025)Community: Hickory Hammock Ph 2ASingle Family
Taxes:$7,423
Elementary School: Whispering Oak Elem
Middle School: Hamlin Middle
Remarks: Under contract-accepting backup offers. SHOW STOPPER! Welcome to 15587 Hamlin Blossom - in the highly sought-after gated community of HICKORY HAMMOCK. A rare find, this Ashford model by M/I Homes is one of only six Ashford floor plans built in the community. Every detail of the 1860 sq. ft has been thoughtfully designed and meticulously cared-for, creating a TURNKEY experience unlike any other. Start off on your paver driveway and enjoy the handpicked lush new landscaping and welcoming porch-sitting area where you can immediately enjoy the outdoor Florida lifestyle. NEW EXTERIOR PAINT. Once inside you are greeted with perfection. NEW luxury vinyl flooring in each bedroom. NO CARPETS throughout the entire SINGLE STORY home. A foyer that immediately impresses with crafted lighting fixtures and perfectly placed decor. SPLIT FLOOR PLAN creates privacy for the two bedrooms and bath in the front of the home. Double vanity with UPGRADED lighting and hardware to elevate the bathroom space. The OPEN FLOORPLAN and dining room/living room combo is perfect for entertaining guests. Create the ideal ambiance with your ALEXA-enabled recessed lighting. A chef’s dream kitchen with BRAND NEW refrigerator, NEW dishwasher, and NEW garbage disposal. The primary suite is perfectly appointed with classic upgrades and reading nook. The HIGHLIGHT of the home is the wraparound paver patio with outdoor living/dining room space and OUTDOOR KITCHEN all under a screen enclosure overlooking a fully fenced, newly landscaped outdoor and garden area. Other upgrades include NEW washer/dryer, NEW HVAC components, NEW TESLA charging station. Hickory Hammock is a special enclave of Winter Garden that overlooks John’s Lake. Residents enjoy water views, private fishing pier, tennis courts, beach volleyball courts, nature trails, resort-sized swimming pool, fitness center, clubhouse, and nature trails. Located in the heart of Winter Garden and Horizon West, this home is approximately 5 minutes from SR 429, 10 minutes from Hamlin Town Center, 10 minutes from Downtown Winter Garden, and approximately 25 minutes from Walt Disney World. Residents enjoy convenient access to shopping, dining, entertainment, top-rated schools, major employment centers, and everything that makes Winter Garden one of Central Florida's most desirable places to live. Contact list agent for full list of upgrades AND seller’s complete maintenance schedule/records. Homes this well cared for do not come on the market often. See it for yourself today!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Michelle Zimmerman (732-616-6019)
6323 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787
$560,00047 Days on yellowkey MLS ID: O6415343
REDUCED by $10,000 (1.8%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2177 Built: 2018Monthly Fee: $425 Tax: $8,526 (2025)Community: Hamlin ReserveSingle Family
Taxes:$8,526
Remarks: Looking for a move-in ready home near Hamlin in Winter Garden with a private backyard and low-maintenance interior? This 3-bedroom, 2.5-bath residence in Hamlin Reserve offers exactly that. A covered brick paver patio overlooks an expansive, fenced backyard, offering rare outdoor space for relaxing, entertaining, or simply enjoying more privacy. Inside, wood-look tile and luxury vinyl flooring run throughout, with no carpet anywhere in the home. The kitchen features black cabinetry, quartz countertops, and stainless steel appliances, opening into a flexible living and dining layout with strong natural light. Upstairs, the primary suite includes a walk-in closet and private bath, with additional bedrooms suited for family, guests, or a home office. Hamlin Reserve is one of Winter Garden's most convenient communities, with a pool, park, playground, and dog park, minutes from Hamlin, SR 429, shopping, dining, and medical facilities. The property is zoned for Independence Elementary, Bridgewater Middle, and Horizon High School. Schedule your showing to see the layout, storage, and outdoor space in person.
Listing Agent: Jessica Souza Meuli (305-527-9574)
17631 LAKE STAR RD, WINTER GARDEN, FL 34787
$830,1863 Days on yellowkey MLS ID: TB8532670
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3004 Built: 2026Monthly Fee: $84 Tax: $11,000 (2025)Community: Northlake At OvationSingle Family
Taxes:$11,000
Remarks: Under Construction. Welcome to Northlake at Ovation! This gorgeous new construction home is located in the highly desirable Horizon West area of Winter Garden. This beautiful two story home features 3 bedrooms, 3 baths and flexible loft space. The open kitchen boasts plenty of upgrades from the AW Collection Milan such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings that is open to the family room with soaring two story ceiling with plenty of windows bringing in natural light throughout. Main living space features wood look tile flooring and bedrooms with upgraded carpet for comfort, plus 8' interior and exterior doors throughout the home. Enjoy the amenities with a swim in the community pool, clubhouse, shaded playground, and dog park. This home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
6274 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$1,016,0603 Days on yellowkey MLS ID: G5115512
0 Days Off yellowkey (back on 7/24/2026)
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4236 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Remarks: Virtually Staged. Pre-Construction. To be built. Welcome to the Arlington with Bonus! This stunning 4236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
637 GRASSY STONE DR, WINTER GARDEN, FL 34787
$850,0003 Days on yellowkey MLS ID: O6427944
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3241 Built: 2013Monthly Fee: $72 Tax: $9,999 (2025)Community: Covington Chase Ph 2BSpa: YesSingle Family
Taxes:$9,999
Elementary School: Dillard Street Elem
High School: Ocoee High
Remarks: Virtually Staged. Beautiful five-bedroom, three-bath pool home located in the highly sought-after Golf Cart District of Downtown Winter Garden. Situated on a spacious, fully fenced corner lot, this home offers a versatile floor plan with room to live, work, and entertain. Upon entry, a flex room is located to the right and may be used as an office, playroom, sitting room, or study. A formal dining room is located to the left. The main living area features an open-concept kitchen, living room, and dinette area. A downstairs bedroom and full bath provide a convenient option for guests or multigenerational living. Upstairs, the primary suite includes two walk-in closets. Three additional bedrooms, a full bath, and the laundry room are also located upstairs. The large media room offers flexible use as a theater room, home office, game room, or bonus space. Enjoy the private outdoor area with a covered porch, fully fenced yard, and saltwater pool and spa. Upgrades include freshly painted interior and exterior, and new carpet installed on 7/23/26. The AC unit is one year old. The seller will pay off the solar system at closing, providing added energy-efficiency benefits for the next owner. Conveniently located near the West Orange Trail, Plant Street Market, local shopping, dining, parks, and Downtown Winter Garden. Golf cart is available for purchase separately and is not included in the sale of the home.
13852 JOMATT LOOP, WINTER GARDEN, FL 34787
$1,030,0003 Days on yellowkey MLS ID: O6427925
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4000 Built: 2016Monthly Fee: $75 Tax: $7,387 (2025)Community: Cypress Reserve Ph 1Spa: YesSingle Family
Taxes:$7,387
Remarks: Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
16130 WIND VIEW LN, WINTER GARDEN, FL 34787
$550,0003 Days on yellowkey MLS ID: O6412051
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 2016Monthly Fee: $344 Tax: $9,012 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$9,012
Elementary School: Panther Lake Elementary
Remarks: Welcome to your beautiful water-view home in the highly sought-after Waterleigh community! This stunning property offers the convenience of single-story living with 4 bedrooms, 3 full bathrooms and picturesque water views. Perfectly positioned with a large green space in front and stunning pond and lake views in the back, this home features a gated backyard offering added privacy and convenient outdoor access. End your evenings by enjoying a glimpse of Disney's nightly fireworks right from your own backyard. Inside, you'll find numerous recent updates, including a new HVAC system, brand-new carpet, a new refrigerator, new dishwasher, new garbage disposal, and a new washer and dryer, making this home truly move-in ready! One of the many perks of living in Waterleigh is that lawn care is included in the HOA, allowing you to spend more time enjoying the exceptional resort-style amenities. Residents have access to resort-style pools, state-of-the-art fitness centers, beautiful clubhouses, mini golf, a dog park, expansive sports fields, multiple playgrounds, beach volleyball, tennis courts, a community dock, and scenic walking trails and picnic areas, creating the perfect setting for an active and relaxing lifestyle. Ideally located in the heart of Horizon West, just minutes from Walt Disney World with quick access to SR-429, this home offers easy commuting throughout Central Florida while being zoned for highly rated schools. This is a rare opportunity to own a beautifully updated home with exceptional views in one of Horizon West's most desirable communities. Schedule your private showing today!
Listing Agent: Erica Jefferson (414-248-9118)
9718 QUIET LN, WINTER GARDEN, FL 34787
$1,300,0005 Days on yellowkey MLS ID: O6427038
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2738 Built: 2001Monthly Fee: $17 Tax: $5,389 (2025)Community: Valley ViewSpa: YesSingle Family
Taxes:$5,389
Remarks: Under contract-accepting backup offers. Tucked away on a quiet country lane, hidden behind lush mature landscaping and embraced by five private acres, this exceptional Konkol Custom Homes estate at 9718 Quiet Lane is more than a home. It is a sanctuary. A place where mornings begin with birdsong, afternoons are spent watching butterflies drift through the wildflower garden, and evenings end around the fire pit beneath a canopy of stars. Designed for both everyday living and effortless entertaining, this beautifully maintained residence offers a desirable three-way split floor plan with four bedrooms on the main level. Thoughtfully designed desk areas in each of the secondary bedrooms provide dedicated spaces for studying, working from home, or creative pursuits, making the home as functional as it is beautiful. The owner's retreat serves as a peaceful haven, complete with a private office, gym, or nursery, an expansive walk-in closet, and a beautifully updated spa-inspired bath. At the heart of the home, the thoughtfully renovated kitchen overlooks the inviting family room and fireplace, showcasing stunning leathered quartzite countertops, adding warmth, texture, and timeless sophistication throughout the living spaces. The renovated secondary bath with polished quartzite offers both style and convenience for family and guests alike. Upstairs, a generous bonus room with a full bath offers endless possibilities as a fifth bedroom, home theater, game room, craft studio, or private guest suite. An oversized walk-in floored attic provides exceptional storage today while offering exciting potential for future expansion. Step outside and discover where this property truly comes alive. The screened saltwater pool and heated spa create a private resort overlooking the peaceful acreage beyond. Wander through vibrant wildflower gardens, gather around the fire pit with family and friends, or simply unwind while birds, butterflies, and bunny rabbits make their daily appearances. Every inch of the grounds has been thoughtfully cultivated to create a setting that feels worlds away from the pace of everyday life. Additional features include a circular driveway, side-entry garage, storage shed, and complete privacy from the street. Yet despite its secluded ambiance, this remarkable estate enjoys one of Winter Garden's most sought-after locations, perfectly situated between Historic Downtown Winter Garden and Hamlin with convenient access to State Road 429 and everything Central Florida has to offer. If you've been searching for a place to escape the hustle and bustle without sacrificing convenience, welcome home to your own private refuge.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787
$885,00052 Days on yellowkey MLS ID: O6413972
REDUCED by $10,000 (1.1%) on 07/24/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4010 Built: 2005Monthly Fee: $182 Tax: $11,924 (2025)Community: Bay Isle 48 17Spa: YesSingle Family
Taxes:$11,924
Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
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