Location: Winter Garden
Do Not Show Listings
6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$875,00053 Days on yellowkey MLS ID: O6412033
REDUCED by $75,000 (7.9%) on 07/20/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3777 Built: 2016Monthly Fee: $195 Tax: $11,678 (2025)Community: Signature Lakes Ph 3B-4 3B-5 & 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,678
Elementary School: Independence Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Virtually Staged. HUGE CORNER LOT featuring 5 bedrooms, 3 full bathrooms and a 3 car garage with Epoxy flooring in a highly desirable neighborhood! With new fresh paint throughout, this move-in-ready home offers space, comfort, and versatility. The oversized backyard offers endless possibilities for customization, outdoor entertaining, and recreation. The spacious owner's suite is complete with two walk-in closets and a private en-suite bathroom. Upstairs, the expansive bonus room offers endless possibilities as a home theater, game room, in-law suite, or large bedroom. In addition to the owner's suite and bonus room, you'll find three generously sized secondary bedrooms upstairs that provide ample space and flexibility. Downstairs features another room with a closet and it has a connecting full bathroom, making it ideal for an office or additional guest room. The beautifully upgraded kitchen is the heart of the home, offering the perfect space for cooking, dining, and creating lasting memories. Featuring two expansive living rooms on the main level plus a formal dining room, this home is ideal for both entertaining guests and enjoying quality time together. With a versatile floor plan, generous living spaces, and endless possibilities, come experience everything this remarkable property has to offer. This is more than a house, it's a place to call home. Some photos have been virtually staged to illustrate potential furniture placement, room functionality, and design possibilities, helping buyers envision the home's full potential.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Crystal Taylor (407-607-6585)
16044 CITRUS KNOLL DR, WINTER GARDEN, FL 34787
$1,100,00022 Days on yellowkey MLS ID: O6419284
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 3617 Built: 2016Monthly Fee: $235 Tax: $13,692 (2025)Community: Hickory Hammock Ph 1DSingle Family
Taxes:$13,692
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: Hamlin Middle
Remarks: Welcome to this exceptional pool home in the highly sought-after gated community of Hickory Hammock in Winter Garden. Offering more than 3,600 square feet beautifully designed living space, this impressive five bedroom, four bathroom, 4 car garage residence blends timeless elegance with everyday functionality. From the moment you step inside, you'll be captivated by soaring ceilings, georgous formal dining space, elegant coffered and wainscoting details, custom built-ins, and an abundance of natural light. The open concept floor plan creates an effortless flow, making the home ideal for both intimate gatherings and grand entertaining. At the heart of the home, the gourmet kitchen overlooks the expansive living and dining areas, it features quartz counter tops, abundant cabinetry, generous prep space, and a layout designed for both entertaining and everyday living. A downstairs private home office offers a refined work from home setting, while the expansive upstairs loft is an entertainer's dream, complete with a projector and oversized movie screen, creating the perfect setting for cinematic experiences, game days, or a stylish media lounge. The luxurious primary suite serves as a peaceful retreat with a spacious walk-in closet and spa-inspired ensuite bath. Thoughtfully designed secondary bedrooms and bathrooms provide comfort and privacy for family and guests. Step outside to your own private outdoor oasis where a screened resort-style pool and covered lanai create the ultimate setting for year-round Florida living. Whether hosting guests or enjoying a quiet evening at home, this backyard is designed for relaxation and entertaining. Recent enhancements that showcase true pride of ownership, including a freshly repainted interior, whole home pressure washing, new landscape, and a professionally serviced and cleaned air conditioning system. Residents of the gated community of Hickory Hammock enjoy an exceptional lifestyle with resort-style amenities including a clubhouse, fitness center, community pool, playgrounds, dog park, scenic walking trails, fishing pier, and boat ramp access to the beauty of Johns Lake. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, top rated schools, shopping, dining, SR 429, Walt Disney World, and Orlando's world class attractions, this remarkable home offers the perfect balance of luxury, lifestyle, and convenience. Schedule your showing today!
Listing is courtesy of: HOGAN REALTY GROUP INC (321-474-2004)
Listing Agent: Kaitlin Sidders (407-797-2985)
14511 ISLEVIEW DR, WINTER GARDEN, FL 34787
$3,330,00086 Days on yellowkey MLS ID: O6403188
3 Days Off yellowkey (back on 7/20/2026)
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5290 Built: 2001Monthly Fee: $300 Tax: $32,571 (2025)Community: Isles Lake HancockSingle Family
Taxes:$32,571
Elementary School: Summerlake Elementary
High School: Horizon High School
Remarks: Under contract-accepting backup offers. Get ready to be impressed by this exceptional lakefront residence at 14511 Isleview Dr in Winter Garden, fully renovated by the renowned Davila Homes. Set directly on the pristine shores of Lake Hancock, this luxury property offers breathtaking water views and a private dock, perfect for boating, sunset lounging, or embracing the ultimate Florida lifestyle. This thoughtfully designed home features 5 spacious bedrooms, including a private mother-in-law suite ideal for multigenerational living or guests. A dedicated home office provides the perfect space for remote work or quiet study, while a fully equipped home gym adds to the home’s functional appeal. At the heart of the home is a stunning chef’s kitchen, complete with top-of-the-line appliances, custom cabinetry, and premium finishes—designed to impress both everyday cooks and seasoned entertainers alike. With refined modern design, high-end finishes, and meticulous attention to detail throughout, this residence offers an unmatched blend of luxury, comfort, and lakefront living in one of Winter Garden’s most desirable locations.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Fernanda Negromonte (407-592-1744)
13092 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787
$850,00036 Days on yellowkey MLS ID: O6417386
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2993 Built: 2024Monthly Fee: $140 Tax: $9,934 (2025)Community: Harvest/OvationSpa: NoSingle Family
Taxes:$9,934
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Prepare to be impressed by this exceptional pool home in the highly sought-after Harvest at Ovation! Offering 4 bedrooms, with a 5th bedroom/office option, 3.5 bathrooms, and nearly 3,000 square feet of thoughtfully designed living space, this stunning two-story residence combines luxurious finishes with incredible indoor and outdoor living. Situated on a corner lot, the home immediately captivates with its beautiful exterior, split two-car garage, and charming front porch, along with a dedicated electric vehicle charger conveniently located in the garage. Inside, you’ll immediately notice the designer touches and high-end finishes throughout. The open-concept layout effortlessly connects the living room, dining area, and kitchen, creating a space that is equally suited for entertaining and everyday living. At the heart of the home, the gourmet kitchen features Samsung appliances, including a Smart Technology refrigerator, gas cooktop, range hood, and a modern tile backsplash. The inviting living room is enhanced by a custom accent wall and expansive three-panel sliding glass doors that fill the space with natural light. The first-floor primary suite is a true retreat, featuring a spa-inspired bathroom with dual vanities, a soaking tub, separate walk-in shower, and a custom walk-in closet. Upstairs features a spacious loft with a built-in desk and shelving, offering versatile additional living space. Two secondary bedrooms are also located on this level, including one with a private en suite bath. The backyard is nothing short of spectacular. A screened lanai overlooks the brand-new inground pool, paver patio, and fenced backyard, creating your own private oasis. Residents enjoy access to community amenities, including a pool and playground. Ideally located near shopping, dining, major highways, Downtown Orlando, Orlando International Airport, and just minutes from Walt Disney World, this remarkable home truly has it all.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: David Bollet (407-927-4595)
9606 WOODCRANE DR, WINTER GARDEN, FL 34787
$525,00063 Days on yellowkey MLS ID: O6410113
2 Days Off yellowkey (back on 7/20/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2101 Built: 2017Monthly Fee: $164 Tax: $5,079 (2025)Community: Watermark Ph 2BSingle Family
Taxes:$5,079
Elementary School: Panther Lake Elementary
Remarks: Under contract-accepting backup offers. Prime corner lot home in the highly sought-after Horizon West community of Watermark in Winter Garden with no front neighbors and peaceful water views. Ideally located just a short walk to the community amenity center and The Mark shopping center featuring Starbucks, New York Beer Project, 7-Eleven, Walgreens, dining, entertainment, and more. Enjoy nightly Disney fireworks views right from the front porch, living room or loft sofa. Conveniently located near State Road 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center, and Walt Disney World. This home offers the perfect blend of lifestyle, convenience, and location in the heart of Horizon West.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
46 W VINING ST, WINTER GARDEN, FL 34787
$544,90067 Days on yellowkey MLS ID: O6408720
REDUCED by $5,000 (0.9%) on 07/20/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1273 Built: 1938 Tax: $6,287 (2025)Community: Ellman ParkSingle Family
Taxes:$6,287
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)
Listing Agent: Michael Mitchell, Jr (352-768-1712)
17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$485,00053 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
Taxes:$3,704
Elementary School: None
High School: None
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 Agent: Heidi Pfeffer-Morgan (407-408-6101)
729 MEADOW GLADE DR, WINTER GARDEN, FL 34787
$525,00071 Days on yellowkey MLS ID: O6407943
REDUCED by $4,000 (0.8%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2070 Built: 2011Monthly Fee: $72 Tax: $3,138 (2025)Community: Covington Park A B D E F G & JSingle Family
Taxes:$3,138
Remarks: Virtually Staged. New Interior Paint!! New Roof being Installed!! Don't Wait!! Welcome to the highly sought after GOLF CART DISTRICT of downtown Winter Garden! Located in Covington Chase, this beautifully maintained home offers functionality, charm, and the unbeatable lifestyle that makes Winter Garden one of Central Florida’s most loved communities. Situated on a desirable corner lot, the curb appeal immediately stands out with mature landscaping, lush lawn space, and a welcoming exterior that makes a lasting first impression. Step inside and you will find a spacious open floor plan designed for both comfortable everyday living and entertaining guests. Natural light fills the home and creates a warm and inviting atmosphere throughout. The kitchen is truly the heart of the home featuring granite countertops, beautiful cherry cabinetry, closet pantry, breakfast bar seating, and plenty of prep space for cooking and hosting. The open concept layout allows full views into the family room so you never miss a moment while entertaining or spending time with family and friends. Sliding glass doors lead directly out to the screened lanai creating seamless indoor and outdoor living. The partially vinyl fenced backyard offers both privacy and flexibility with plenty of room to design the pool of your dreams, create an outdoor kitchen, garden space, or simply enjoy the Florida sunshine. Whether hosting weekend barbecues or relaxing after a long day, this outdoor space provides endless possibilities. The split bedroom floor plan offers privacy and convenience for everyone. The spacious secondary bedrooms are thoughtfully positioned with access to a guest bathroom that could easily function as a future pool bath. The primary suite offers a relaxing retreat with generous space and functionality. Inside laundry adds even more convenience to daily living. What truly makes this home special is the incredible Winter Garden lifestyle. Hop on your golf cart and head into historic downtown Winter Garden where you can spend your evenings enjoying local restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals, and community events year round. Cool off at the splash pad, bike or walk the scenic West Orange Trail, and experience the award-winning Winter Garden Farmers Market every Saturday morning which has become one of the most beloved attractions in Central Florida. Residents of Covington Chase also enjoy access to community amenities including a pool, playground, parks, and walking areas, all while being conveniently located near major highways, shopping, dining, and top rated schools. The location offers the perfect blend of peaceful neighborhood living with easy access to everything Winter Garden and Orlando have to offer. This is more than just a home. It is a lifestyle that so many are searching for and very few neighborhoods can truly offer. Come experience the charm, convenience, and golf cart lifestyle of downtown Winter Garden for yourself. Schedule your private showing today!
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
15187 HARROWGATE WAY, WINTER GARDEN, FL 34787
$425,00099 Days on yellowkey MLS ID: TB8497081
REDUCED by $10,000 (2.3%) on 07/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1296 Built: 2003Monthly Fee: $46 Tax: $5,808 (2025)Community: Stone CrkSingle Family
Taxes:$5,808
Middle School: SunRidge Middle
Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Maria Howard (410-422-3518)
9611 LOST CREEK DR, WINTER GARDEN, FL 34787
$745,000191 Days on yellowkey MLS ID: O6373845
REDUCED by $20,000 (2.6%) on 07/20/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2909 Built: 2021Monthly Fee: $260 Tax: $11,300 (2025)Community: WaterleighSingle Family
Taxes:$11,300
Remarks: No rear neighbors! Situated on a premium conservation lot with lake views, this fully furnished 4-bedroom, 3-bathroom two-story home in the desirable Waterleigh community offers privacy, upgrades, and true move-in-ready convenience. Exceptional curb appeal features a brick paver driveway and welcoming front porch. Inside, enjoy wood-look tile throughout the main living areas, a flexible formal sitting room ideal for entertaining or home office, and an open-concept layout filled with natural light. The upgraded kitchen showcases custom gray cabinetry, stainless steel appliances, designer backsplash, pendant lighting, and generous counter space, flowing seamlessly into the dining and family room. Large windows frame tranquil views of the conservation area and lake, creating a peaceful backdrop for everyday living and entertaining. A first-floor bedroom with full bathroom provides an ideal guest or multigenerational suite. Upstairs, the spacious primary retreat features a tray ceiling and spa-style bath with dual sinks, soaking tub, and separate shower. A large loft offers flexible space for media, office, or play area, also with serene backyard and water views. Two additional bedrooms and a full bath complete the upper level. Step outside to your private outdoor oasis featuring a covered brick-paver lanai with summer kitchen, perfect for entertaining, plus a fully fenced backyard with room to add a pool — all while enjoying the privacy of no rear neighbors and protected conservation behind the home. Waterleigh residents enjoy 3 resort-style pools, 2 clubhouses with fitness centers, walking trails, sand volleyball, dog park, fishing and observation pier, tennis courts, pickleball, playgrounds, and lawn maintenance included in HOA. Zoned for Water Spring Elementary, Water Spring Middle School, and Horizon High School. Prime location near Disney, shopping, dining, SR-429, I-4, SR-417, and Publix. With furniture, golf cart, seller credit, premium lot, outdoor kitchen, and EV-ready garage all included, this home offers outstanding value and an effortless move-in experience.Schedule your private showing today.
Listing is courtesy of: M2M REALTY (407-401-2275)
Listing Agent: Patricia Mendonca Garcia Cunha (321-333-1946)
15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787
$765,00021 Days on yellowkey MLS ID: S5152807
0 Days Off yellowkey (back on 7/10/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3902 Built: 2005Monthly Fee: $243 Tax: $8,428 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,428
Remarks: Finding nearly 4,000 sqft of beautifully UPDATED living space on an oversized CORNER LOT is increasingly rare. Add a full-width BALCONY overlooking the GOLF course, extensive RENOVATIONS throughout, and a backyard that extends well beyond the existing fence line, and this home immediately stands out. From the moment you step inside, you'll notice how effortlessly this unfurnished home flows. Whether you're looking for multiple living areas, a dedicated home office, fitness space, media room, or simply room to spread out, this flexible layout adapts to the way you live. At the heart of the home is the beautifully REMODELED KITCHEN, redesigned in 2022 with quartz countertops, an oversized island, abundant cabinetry, and a Samsung Bespoke appliance suite installed in 2024. It creates a natural gathering space before flowing seamlessly into the family room, where the fireplace provides a warm focal point for everyday living and entertaining. Luxury vinyl plank flooring runs throughout the home, while EVERY BATHROOM has been tastefully RENOVATED and FRESH interior PAINT gives the home a bright, contemporary, move-in-ready feel. Upstairs, the expansive LOFT has already been transformed into an impressive HOME CINEMA, complete with in-ceiling surround sound, dedicated audio equipment, a high-performance subwoofer, and discreet in-wall cable management. It also offers exceptional flexibility as an additional living area, games room, or creative workspace. One of the home's most distinctive features is the impressive full-width balcony spanning the rear of the property. Accessible from both the primary suite and the adjoining bedroom or office, it's the kind of OUTDOOR SPACE you'll genuinely use, whether that's enjoying your morning coffee overlooking the golf course, catching the evening breeze, or simply taking a quiet moment at the end of the day. Outside, the sense of space continues. The backyard feels like an extension of the home's living space, with a PRIVATE PUTTING GREEN, artificial turf, upgraded deck, patio lighting, and refreshed landscaping creating an inviting setting for relaxing or entertaining outdoors. The FENCED YARD provides a wonderful private outdoor space, but what many buyers won't immediately realise is that the property extends significantly beyond the current fence line, giving you even more usable land than first meets the eye. Combined with the generous side yard afforded by this oversized corner homesite, the amount of outdoor space is truly impressive. Equally valuable are the updates you may not immediately notice. Major improvements include a NEW ROOF (2022), high-efficiency HVAC system (2022), whole-home SOLAR system (2022), whole-home WATER SOFTENER and filtration system (2025), automatic irrigation system with timer, Alexa-compatible smart home features and an electric vehicle charging station. Set within the GUARD-GATED community of Stoneybrook West, residents enjoy championship golf, a WATERFRONT CLUBHOUSE overlooking Lake, resort-style pool, FITNESS center, TENNIS and BASKETBALL courts, playgrounds, PRIVATE BOAT RAMP with lake access, community boat storage, and 24-hour guarded security. Conveniently positioned near one of the community entrances, the home offers quick access to Winter Garden Village, shopping, dining, schools, and major roadways, combining exceptional convenience with one of Winter Garden's most sought-after lifestyles.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Zoe Attwood (407-516-9009)
15403 MURCOTT HARVEST LOOP, WINTER GARDEN, FL 34787
$649,000142 Days on yellowkey MLS ID: O6386748
REDUCED by $10,000 (1.5%) on 07/07/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2834 Built: 2018Monthly Fee: $90 Tax: $6,526 (2025)Community: Summerlake GrvsSingle Family
Taxes:$6,526
Remarks: Virtually Staged. Live the golf course lifestyle in the highly desirable Summerlake Groves community at Orange County National Golf Center and Lodge in beautiful Winter Garden. This thoughtfully designed 2 story home offers 5 bedrooms and 3 bathrooms, with a bright open concept layout that makes everyday living and entertaining effortless. The spacious kitchen flows seamlessly into the living and dining areas, creating a welcoming space filled with natural light. One of the bedrooms has been transformed into an incredible custom style closet, offering the ultimate dream space for storage, organization, and style. Upstairs you will also find a versatile bonus room with its own private bathroom, making it ideal for a guest suite, media room, home office, or additional living space. Disney Firework visible from upstairs. Step outside to the covered lanai, the perfect place to enjoy relaxing mornings or unwind in the evening while taking in the peaceful surroundings. Located in an amenity rich neighborhood just minutes from shopping, dining, and major roadways, this home offers the perfect balance of lifestyle, convenience, and community living.
Listing is courtesy of: KRESSLER REAL ESTATE (407-864-2184)
Listing Agent: Andre Kressler (407-864-2184)
20 W CREST AVE, WINTER GARDEN, FL 34787
$2,190,00036 Days on yellowkey MLS ID: O6417710
REDUCED by $159,000 (6.8%) on 07/20/2026
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
Tax Year: 2026
Remarks: Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. A rare blend of craftsmanship, luxury, and location—now at an even more compelling price.
Listing Agent: Lora King (407-947-7653)
7773 MINUTEMEN LOOP, WINTER GARDEN, FL 34787
$875,0008 Days on yellowkey MLS ID: O6425792
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3393 Built: 2014Monthly Fee: $215 Tax: $7,123 (2025)Community: Overlook At HamlinSingle Family
Taxes:$7,123
Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bath home with a dedicated office, offering the perfect blend of elegance, comfort, and functionality in the highly desirable Overlook at Hamlin community of Winter Garden. Thoughtfully designed for today's lifestyle, this spacious floor plan features a sought-after first-floor primary suite, providing a private retreat with convenience and flexibility. From the moment you enter, you'll appreciate the pride of ownership evident throughout. Gorgeous wood flooring flows through the main living areas, complemented by brand-new carpet and fresh interior paint for a truly move-in-ready feel. The dedicated office is ideal for working from home, studying, or creating a quiet flex space. The heart of the home is the open-concept living area, where a beautiful gas fireplace creates a warm and inviting focal point. The spacious kitchen overlooks the family room and dining area, making it easy to entertain while staying connected with family and guests. Step outside to one of the home's standout features—an oversized covered lanai and an expansive screened enclosure that extends your living space outdoors. Whether you're enjoying your morning coffee, dining al fresco, or hosting gatherings, this incredible outdoor retreat is designed for year-round Florida living. Upstairs, you'll find generously sized secondary bedrooms that provide plenty of space for family and guests, while the thoughtful layout offers privacy and versatility for every stage of life. Located in the sought-after Hamlin area, residents enjoy exceptional resort-style amenities, including a private community boat ramp with access to Lake Hancock, a lakeside clubhouse, fitness center, community pool, playgrounds, parks, walking trails, and waterfront recreation. Just minutes from Hamlin Town Center, Walt Disney World, shopping, dining, entertainment, top-rated schools, and major highways, this location offers unmatched convenience and an exceptional lifestyle. With fresh interior paint, gorgeous wood floors, new carpet, a first-floor primary suite, dedicated office, gas fireplace, and an incredible screened outdoor living space, this meticulously maintained home is truly move-in ready and offers everything today's buyers are looking for.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Shelley Dawson (407-492-1900)
16149 WIND VIEW LN, WINTER GARDEN, FL 34787
$495,000133 Days on yellowkey MLS ID: O6389892
REDUCED by $3,000 (0.6%) on 05/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2036 Built: 2016Monthly Fee: $332 Tax: $4,472 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$4,472
Remarks: Welcome home to one of the most popular DR Horton floor plans- the Cordale! With a first floor primary suite, spacious open floor plan downstairs, and additional living space upstairs, it is easy to see how the functionality of this home will make it a great fit for you. This home has had 1 owner who has meticulously cared for the home as will be evident immediately upon entering. The open concept living space greets you with the kitchen, dining space, and living room. Lined with windows and recessed lighting, this space feels bright and welcoming. Stainless steel appliances, granite countertops, and ample counterspace equip the kitchen. The downstairs laundry room is tucked away in the front of the home to keep tending to that chore quiet. The primary suite is nestled in the back of the home for privacy and features and en suite bathroom. A walk-in shower, dual vanity, and walk-in closet make this room fit for luxury and comfort. An elongated drop zone leads you to the 2-car garage and has granite countertops and cabinetry in the same colors as in the kitchen for continuity of the downstairs space. The remaining 2 bedrooms are located upstairs where a loft also provides these rooms with another living space. They also share a bathroom with a shower/bathtub combination. The fun continues out back where you'll find a covered brick-paved patio. Relish in the view of not having any rear neighbors, admire the rarity of having a corner lot, and indulge in the unique green space view out of the front of the home. The Waterleigh community is known for its vast array of resort-style amenities include community pools, playgrounds, fitness centers, sports courts, walking trails, dog parks, and more! Primely located in Horizon West, this home is ready for its new owners to make memories here for years to come. Inquire today to make this gem your own! ***NEW HVAC INDOOR BLOWER UNIT, NEW HVAC OUTDOOR CAPACITOR UNIT***
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jacquelyn Voigt (941-356-3956)
15591 PANTHER LAKE DR, WINTER GARDEN, FL 34787
$1,299,00036 Days on yellowkey MLS ID: O6416459
REDUCED by $96,000 (6.9%) on 07/10/2026
Bed: 5 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3932 Built: 2017Monthly Fee: $431 Tax: $11,631 (2025)Community: Lakeshore Preserve Ph 1Single Family
Taxes:$11,631
Remarks: Welcome to 15591 Panther Lake Drive, a stunning 5-bedroom, 3.5-bath Mediterranean-inspired waterfront residence in the highly sought-after Lakeshore Preserve community of Winter Garden. Showcasing exceptional craftsmanship and timeless architectural elegance, this home offers the perfect blend of luxury, comfort, and Florida lifestyle living. Outstanding curb appeal features a bright stucco exterior, terracotta tile roof, rich wood garage doors, decorative arches, tropical landscaping, and a paver driveway. Additional highlights include two 2-car garages, dual HVAC systems (2024), and a tankless water heater. Inside, a grand two-story foyer and dramatic staircase welcome guests with soaring ceilings, elegant finishes, abundant natural light, and beautiful water views. Rich wood-look tile flooring flows throughout the main living areas. The chef-inspired kitchen features custom cabinetry, granite countertops, apron-front sink, under-cabinet lighting, premium stainless steel appliances, gas cooking, an oversized center island, and an expansive walk-in pantry with floor-to-ceiling shelving. A convenient mudroom connects to the laundry room. The spacious family room showcases a tray ceiling with stained wood accents, a gas fireplace, and large sliding glass doors that seamlessly connect indoor and outdoor living spaces. The first-floor primary suite offers tray ceilings, large walk-in closets, and a spa-inspired bath. A dedicated first-floor office provides an ideal work-from-home space. Upstairs, the expansive loft and oversized bonus room offer endless flexibility for a media room, game room, fitness area, home theater, or additional living space. Secondary bedrooms are generously sized, including a private guest suite with an ensuite bath featuring a granite vanity and tiled walk-in shower. Enjoy Florida living from the oversized screened lanai overlooking tranquil water views and green space. Brick pavers, multiple ceiling fans, and generous covered seating areas create the perfect outdoor retreat. The backyard offers ample room for a future custom pool, spa, and summer kitchen. Lakeshore Preserve residents enjoy resort-style amenities including a waterfront community pool, sun shelf, cabanas, walking trails, weekly lawn maintenance, and access to Lake Panther via a community launch for canoes, kayaks, and other non-motorized watercraft. Conveniently located near SR-429, Walt Disney World, Hamlin Town Center, and historic Downtown Winter Garden, this exceptional home delivers luxury living in one of Central Florida's premier communities.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Todd Schroth, Pa (407-641-2808)
14543 WHITTRIDGE DR, WINTER GARDEN, FL 34787
$574,90017 Days on yellowkey MLS ID: G5114561
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2224 Built: 2006Monthly Fee: $195 Tax: $8,699 (2025)Community: IndependenceSingle Family
Taxes:$8,699
Remarks: Discover refined living in this charming 3-bedroom, 2-bathroom home located in the desirable Independence community. This property offers a serene backdrop, backing directly onto a tranquil pond and conservation area. Relax on your screened-in rear porch overlooking the water, or enjoy the classic appeal of the L-shaped front porch—complete with a swing for those quiet afternoons. Inside, you will find an expansive formal dining area seamlessly connected to the living room, ideal for entertaining. The home features a recently replaced A/C system in 2025, premium tile and laminate flooring throughout, providing a clean, low-maintenance, and modern aesthetic in every room. The heart of the home is the open kitchen, featuring 42-inch cabinetry, granite countertops, a functional breakfast bar, and a cozy casual dining nook. The primary suite serves as a true retreat, boasting double-door entry, a spacious walk-in closet, and a bath equipped with a garden tub and dual vanities. Independence living offers unmatched value, with HOA fees covering your Spectrum cable and high-speed internet. Residents enjoy a premium lifestyle with access to two clubhouses, two resort-style pools, fitness centers, tennis and basketball courts, dog parks, and boat access to both Lake Speer and Lake Hancock.
Listing is courtesy of: RE/MAX TITANIUM GROUP (352-241-6363)
Listing Agent: Stephen Misciagno (352-874-6638)
14681 SETON CREEK BLVD, WINTER GARDEN, FL 34787
$815,0005 Days on yellowkey MLS ID: G5115256
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2513 Built: 2016Monthly Fee: $164 Tax: $6,379 (2025)Community: Watermark Ph 1BSpa: YesSingle Family
Taxes:$6,379
Remarks: WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!
Listing is courtesy of: SUNSHINE LIFE REALTY LLC (321-229-0627)
Listing Agent: Ariana Henderson (407-453-5106)
1608 HIGHBANKS CIR, WINTER GARDEN, FL 34787
$649,000219 Days on yellowkey MLS ID: O6367937
REDUCED by $50,000 (7.2%) on 07/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2278 Built: 2019Monthly Fee: $140 Tax: $5,152 (2024)Community: Roper ReserveSingle Family
Taxes:$5,152
Tax Year: 2024
Remarks: Roper Reserve is a cozy gated community with a low HOA and just a few minutes from the bustling Downtown Winter Garden and the Winter Garden Village, that has shops and restaurants. This stunning Delaney model by Richmond American Homes, has been beautifully upgraded and blend's location, lifestyle and comfort. With large rooms and a versatile flex room, there is plenty of room in this home for everyone. The home features a gourmet kitchen with double ovens, gas appliances, and a tankless water heater, dual laundry rooms including one in the primary suite’s custom closet, and smart upgrades like a cyber space that fits a large desk, shelves and is lined with sound dampening tiles, it also includes extra outlets! Perfect working from home and housing electronics charging hub. Enjoy the AC garage, extra-wide brick paver driveway, UV light AC treatment, and beautifully finished bedrooms—one with sound-dampening and specialty lighting. The flex room shines with moody décor and copper ceiling tiles, while outside you’ll find a private pool, screened patio, outdoor kitchen, fruiting banana trees, and no rear neighbors for ultimate privacy. Whole house water softener, automatic window wireless window blinds. The home also features security cameras at various locations outside the home. Fiber Optics internet connection has just been installed into the community, making it very convenient for those working from home or for streaming!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Rosa Aponte (407-375-9350)
1209 CASTLEPORT RD, WINTER GARDEN, FL 34787
$659,000132 Days on yellowkey MLS ID: O6390760
0 Days Off yellowkey (back on 7/19/2026)
REDUCED by $5,900 (0.9%) on 05/29/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 2001Monthly Fee: $243 Tax: $4,030 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$4,030
Remarks: Under contract-accepting backup offers. Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.
Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)
Listing Agent: Angela Magac (407-744-5557)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.