Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Living Area Square Feet: 1500 to 1999
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Winter Garden - 76 properties found
420 E CYPRESS ST, WINTER GARDEN, FL 34787
$420,00022 Days on yellowkey MLS ID: O6412414
REDUCED by $5,000 (1.2%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1616 Built: 1950 Tax: $5,517 (2025)Community: Overstreet CrateSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,517
Elementary School: Maxey Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Trevor Zwick (863-303-6114)
14788 FIELD DAISY DR, WINTER GARDEN, FL 34787
$579,99971 Days on yellowkey MLS ID: O6398754
REDUCED by $37,501 (6.1%) on 06/16/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1992 Built: 2026Monthly Fee: $229Community: Harvest At OvationSingle Family
Taxes:$0
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Under Construction. What's Special: Game Room | Dedicated Study | Covered Lanai | North Facing Lot. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Ashwood at 14788 Field Daisy Drive in Harvest at Ovation! This welcoming new home blends spacious living with thoughtful design, featuring a bright great room that flows seamlessly into a beautifully appointed kitchen with quartz countertops and designer kitchen cabinets. Luxury vinyl plank flooring runs throughout the main living area, creating a warm and cohesive feel that is easy to enjoy every day. Just off the kitchen, the lanai extends your living space outdoors, while a versatile flex room and convenient powder room sit near the foyer. Upstairs, the primary suite offers a comfortable retreat with an en-suite bath and a large walk-in closet, alongside two secondary bedrooms that share a full bathroom and an upstairs laundry room. The rear two-car detached garage includes stairs leading to a spacious game room complete with a wet bar, full bathroom, and walk-in closet, giving you even more room to live and entertain. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Bedroom in place of loft, game room, wet bar at game room, full bathroom at game room, 8' interior doors, oak treads and painted risers. Photos are for representative purposes only. MLS#O6398754
Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)
Listing Agent: Michelle Campbell (407-756-5025)
17806 SEDONA ST, WINTER GARDEN, FL 34787
$672,50913 Days on yellowkey MLS ID: O6415594
INCREASED by $34,300 (5.4%) on 06/15/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1843 Built: 2026Monthly Fee: $140Community: Esplanade At Mckinnon GrovesSingle Family
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: Under Construction. What's Special: Dedicated Study | Gourmet Kitchen | Appliances Included | Flat Lot | East Facing Lot. New Construction - November Completion! Built by America's Most Trusted Home Builder. Welcome to the Monte at 17806 Sedona Street in Esplanade at McKinnon Groves! Step inside from the welcoming porch into a bright foyer that flows into a private study, creating a flexible space for work or quiet moments. The open great room sits at the heart of the home and connects seamlessly to a spacious lanai, filling the living areas with natural light and easy indoor-outdoor flow. The gourmet kitchen features quartz countertops, a large island, and a walk-in pantry, all perfectly positioned beside the dining area for effortless entertaining. The primary suite offers a peaceful retreat with a well-appointed bath, generous walk in closet, and convenient access to the laundry area. A secondary bedroom and full bath provide comfortable accommodations for guests or everyday living. Thoughtful design and open sightlines create a warm, inviting layout that feels both stylish and functional. Additional Highlights Include: whole house blinds, 8' interior doors, appliances included, and laundry cabinets. Photos are for representative purposes only. MLS#O6415594 Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!
14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787
$450,000355 Days on yellowkey MLS ID: O6320739
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1904 Built: 2016Monthly Fee: $159 Tax: $7,554 (2024)Community: Watermark Ph 2CSingle Family
Taxes:$7,554
Elementary School: Panther Lake Elementary
Tax Year: 2024
Middle School: Hamlin Middle
Remarks: Short Sale. BACK ON THE MARKET — THROUGH NO FAULT OF THE SELLER! Buyer financing fell through. Welcome Home! 14536 Golden Harbor – a beautifully designed 3-bedroom, 2.5-bathroom home offering 1,904 square feet of thoughtfully laid-out living space. Nestled on the desirable Watermark community on the Disney side of Winter Garden, this Meritage Angelou II model combines modern efficiency with everyday comfort. The home comes equipped with fully PAID OFF solar panels, already wired and ready for connection—making this an energy-smart choice for eco-conscious buyers. As you walk in you are greeted with open-concept living/ dining room area that is ideal for entertaining, with a spacious kitchen located at the rear of the home. Enjoy stainless steel appliances, crown-topped cabinetry, a walk-in pantry, and a generous granite island that flows seamlessly into the living and dining areas. You’ll also find a built-in office nook and a convenient half-bath on this level. Upstairs, a spacious loft adds flexibility—perfect as a second living area, playroom, or home office. The laundry area is thoughtfully tucked away, and the split-bedroom design offers added privacy. The primary suite includes a walk-in closet, dual vanity, and a walk-in shower. Two additional bedrooms are located toward the front of the home and extend access to a private, covered balcony—an ideal spot to catch Disney’s nightly fireworks with a glass of wine and a great book. Whether you're unwinding on the front porch, enjoying balcony views, or taking advantage of community amenities—including a resort-style pool, playground, fitness center, basketball court, and more—you’ll find the lifestyle here hard to beat. You are just walking distance to The Mark, a versatile retail neighborhood center, with stores, restaurants, gas station, and more! Best of all, you’re just minutes from Walt Disney World, Magic Kingdom, Epcot, and Hollywood Studios—each less than 20 minutes away.
Listing is courtesy of: PIXEL REALTY (352-678-9405)
Listing Agent: Nurit Bland (407-529-8710)
1968 PANTHEON DR, WINTER GARDEN, FL 34787
$529,90047 Days on yellowkey MLS ID: O6404386
0 Days Off yellowkey (back on 6/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1971 Built: 2015Monthly Fee: $211 Tax: $3,832 (2025)Community: Alexander RdgSingle Family
Taxes:$3,832
Elementary School: Hamlin Elementary
Remarks: Beautifully maintained home in the Heart of Winter Garden! Located in the highly sought-after neighborhood of Alexander Ridge, this single story Craftsman-style home embodies the feeling of a peaceful family community, with its stone-covered columns and a welcoming front porch. Continuing through the wide foyer you'll find a den/flex room, well-suited for a home office or playroom. The upgraded kitchen with thick quartz countertops, 42” solid wood cabinets, and a large island, is open to the dining and family rooms, making it ideal for entertaining. At the end of the day, the expansive owners' suite is a true retreat, featuring a massive walk-in closet, dual vanities, a soaking tub, and a large upgraded walk-in shower. Set apart from the Owners' suite, you'll find the two additional bedrooms, a tasteful guest bath, and the spacious laundry room. Step outside to the relaxing covered and screened lanai, perfect for enjoying the evening breezes in privacy. Situated in a fantastic community with a neighborhood park, gazebo, miles of trails, and a refreshing pool, you'll be just minutes from the best of Hamlin and Winter Garden—shopping, dining, and top-rated schools. Although the serenity feels like its own little world, you're only a short drive to Disney World®, Universal Studios® and all the attractions Central Florida has to offer. Don’t miss this incredible opportunity—schedule your showing today!
Listing is courtesy of: KUNKLE REALTY GROUP (844-978-7750)
Listing Agent: Greer Kunkle (321-250-0106)
11117 BOSTWICK ALY, WINTER GARDEN, FL 34787
$507,00040 Days on yellowkey MLS ID: O6407552
REDUCED by $13,000 (2.5%) on 06/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1685 Built: 2022Monthly Fee: $291 Tax: $6,722 (2025)Community: Waterleigh Ph 4ASingle Family
Taxes:$6,722
Elementary School: None
Remarks: This open-concept home offers a functional layout with modern kitchen, stainless steel appliances, and a large island overlooking the main living area. The home also includes a whole-house water filtration system and a screened lanai. Prime location directly across from Atwater Bay Elementary and community green space, offering added privacy and convenient access for families. Enjoy resort-style amenities including pools, fitness centers, clubhouse, playgrounds, and walking trails. Conveniently located near Disney, Hamlin Town Center, shopping, dining, and major highways.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Fernanda Bover (407-520-0127)
7558 BISHOP SQUARE DR, WINTER GARDEN, FL 34787
$554,9007 Days on yellowkey MLS ID: O6417556
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1952 Built: 2017Monthly Fee: $214 Tax: $7,627 (2024)Community: West Lake Hancock EstatesSingle Family
Taxes:$7,627
Middle School: Bridgewater Middle
Remarks: Virtually Staged. Move-in-ready 4-bedroom-plus-office home with a rare, unobstructed fountain-pond view in West Lake Hancock Estates at Overlook at Hamlin! Built in 2017 and refreshed top to bottom, this 1,952 sq ft single-story lives larger than its footprint. Open great room with luxury vinyl plank floors, a granite kitchen with large island, tiled baths, and a separate office. The big-ticket items are done: all-new 2025 appliances incl. washer/dryer, a new 2025 Goodman A/C, RainSoft whole-home water filtration with RO drinking water, and fresh paint throughout. Screened lanai over a fully fenced yard. Walk 2 minutes to the resort-style clubhouse - pool, splash pad, fitness center, dog park, and miles of trails - plus a community private boat ramp on 467-acre Lake Hancock and lakefront playgrounds. Hamlin Town Center and the new Horizon West Regional Park are minutes away, with Disney ~15 minutes away. Zoned for top-rated Independence Elementary, Bridgewater Middle, and Horizon High.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787
$459,90040 Days on yellowkey MLS ID: O6407798
REDUCED by $9,000 (1.9%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1689 Built: 2019Monthly Fee: $245 Tax: $7,600 (2025)Community: Waterleigh Ph 2C-1Single Family
Taxes:$7,600
Remarks: One or more photo(s) has been virtually staged. MOVE-IN READY with a gourmet kitchen and a layout built for real life. Welcome to Waterleigh living at its finest, where thoughtful design, beautiful upgrades, and everyday comfort come together in a home that feels both elevated and inviting from the moment you walk in. Situated on a rare oversized 145-foot-deep homesite, this beautifully maintained SINGLE STORY Laurel floor plan offers 3 Bedrooms, 2 Full Bathrooms, an extended paver driveway, a larger backyard, and the kind of open, easy flow that simply makes life feel good. From quiet mornings on the covered lanai to gathering with family and friends around the kitchen island, every space in this home was designed to be lived in, enjoyed, and remembered. At the heart of the home is the stunning GOURMET KITCHEN featuring a large granite island, walk-in pantry, upgraded pendant lighting, gorgeous Toscana stained glass accents, and BRAND NEW SS Appliances, including a French Door Refrigerator with in door ice and water. The kitchen opens seamlessly into the spacious dining and family room areas, creating a warm and welcoming space filled with natural light and perfect for both entertaining and everyday living. The private primary suite offers a peaceful retreat with plenty of room for a king sized bed and oversized furniture, while the spa like ensuite bath features DUAL SINKS, an Oversized walk-in shower with tiled bench, and a generous walk-in closet. The thoughtfully designed split floor plan places Bedrooms 2 and 3 along with the secondary bath toward the front of the home, offering added privacy and flexibility. The rear-entry garage creates a functional mudroom-style entry complete with a laundry room, built-in storage cabinetry, and granite countertop workspace, providing added organization and separation between the garage and main living areas. Additional features throughout the home include Extensive Tile Flooring, upgraded designer light fixtures, wood window sills, window blinds throughout, a spacious laundry room, and a convenient drop zone with extra cabinetry near the garage entry, the little details that make everyday living feel effortless. Built with energy efficiency in mind, the home also helps keep utility costs lower while maintaining year round comfort. And beyond the home itself, Waterleigh offers the kind of Florida lifestyle that blends resort-style amenities, outdoor living, and everyday convenience. Residents enjoy access to 4 resort-style pools, 3 clubhouses with fitness centers, tennis courts, pickleball, volleyball, playgrounds, parks, putt putt golf, scenic walking trails, and community events throughout the year that truly make the neighborhood feel connected and alive. Even better, the HOA handles lawn maintenance including mowing, trimming, fertilizing, and mulch, giving you more time to enjoy your home instead of maintaining it. Perfectly located near Disney, Hamlin Town Center, shopping, dining, SR-429, and I-4, this home is also zoned for highly regarded schools, including Atwater Bay Elementary, Water Spring Middle School, and Horizon High School. Beautifully upgraded, thoughtfully designed, and move in ready, this is more than just a house, it’s the kind of home that makes everyday life feel a little more beautiful in so many ways.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Sabrina Freeman (407-446-5541)
6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787
$546,49025 Days on yellowkey MLS ID: O6412141
2 Days Off yellowkey (back on 6/14/2026)
REDUCED by $15,500 (2.8%) on 06/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1913 Built: 2026Monthly Fee: $152 Tax: $1,372 (2024)Community: Silverleaf OaksSpa: NoSingle Family
Taxes:$1,372
Remarks: Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort. This home includes 3 spacious bedrooms, 2 full bathrooms, a powder room, a loft, a covered lanai, and a 2-car rear-load detached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. The kitchen boasts a large center island, a convenient storage pantry, and Whirlpool stainless steel appliances—including a vented microwave. Elkins white cabinetry, a decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite and en suite bathroom, two spare bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor, bathrooms, and laundry room enjoy the beauty and convenience of ceramic tile. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and LED downlights—ensuring your home is as connected as it is stunning. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$597,99643 Days on yellowkey MLS ID: G5112227
INCREASED by $40,873 (7.3%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1772 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: Virtually Staged. Under Construction. Welcome to this beautifully designed newer-construction, the Amelia, a charming single-story bungalow in the highly sought-after Avalon Woods community of Winter Garden! Built in 2026, this spacious residence offers modern finishes, an open-concept layout, and a prime location just minutes from Hamlin Town Center, shopping, dining, top-rated schools, and major highways. Inside, you’ll find a bright and inviting floor plan featuring a large kitchen with upgraded cabinetry, stainless steel appliances, stone countertops, and an oversized island overlooking the main living and dining areas — perfect for entertaining. The spacious primary suite offers a private retreat with a walk-in closet and a well-appointed bathroom with dual vanities and a large walk-in shower.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
15073 VALVERSE ALY, WINTER GARDEN, FL 34787
$515,00012 Days on yellowkey MLS ID: O6416182
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1892 Built: 2017Monthly Fee: $339 Tax: $4,172 (2025)Community: Overlook 2/Hamlin Ph 2 & 5Single Family
Taxes:$4,172
Elementary School: Independence Elementary
Remarks: Beautiful home in The Cove at Hamlin Now Available. This is part of the highly desirable Overlook at Hamlin community in Winter Garden. This home has been Well Maintained, and Tastefully Upgraded by the Original Owner. Amenities and Upgrades include: Gourmet Kitchen (with 42" Cabinetry, Gas Range, Farmer's Sink, Large Center Island), Hardwood Flooring, Plantation Shutters throughout, Shiplap Accent Walls, Custom Wine Room, and more. Improvements continued to the Outdoors as well with a Large Screened Paver Patio Outdoor Living Area, Summer Kitchen complete with TV mount, and Fenced Yard (wrought iron). Relax on the front porch overlooking the community park, or take advantage of the resort-style amenities including a clubhouse, fitness center, pool, splash pad, pavilion, event space, sports lawn, amphitheater, fire pit, canoes, private boat ramp and playground. Landscaping is maintained by the community. Located just minutes from SR 429, Florida’s Turnpike, shopping, dining, medical facilities, and the major theme parks, this home combines modern comfort with unbeatable convenience in one of Winter Garden’s most sought-after neighborhoods. Don't miss your opportunity to own this amazing home. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Mike Long (407-325-4104)
12103 EASTMOOR DR, WINTER GARDEN, FL 34787
$445,00033 Days on yellowkey MLS ID: O6409071
REDUCED by $5,000 (1.1%) on 06/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1604 Built: 2024Monthly Fee: $225 Tax: $6,795 (2025)Community: Encore/Ovation Ph 4BSingle Family
Taxes:$6,795
Remarks: Welcome to this BEAUTIFULLY MAINTAINED 3-bedroom, 2-bath home in the highly desirable Encore at Ovation community in Winter Garden, where modern style, energy efficiency, and LOW-MAINTENANCE LIVING come together perfectly. Built in 2024, this single-story residence still FEELS BRAND NEW and currently stands out as the only home available in the neighborhood, making it a RARE OPPORTUNITY in one of Winter Garden’s most sought-after communities. From the moment you arrive, the home impresses with its beautiful landscaping, charming front porch, and EXCEPTIONAL CURB APPEAL. The HOA even includes LAWN AND LANDSCAPE MAINTENANCE, allowing you to enjoy a carefree lifestyle in this walkable community. Step through the elegant GLASS-PANELED FRONT DOOR into a bright and inviting open-concept layout where the Living Room, Dining area, and Kitchen flow seamlessly together beneath SOARING CATHEDRAL CEILINGS. Windows throughout the home fill the space with ABUNDANT NATURAL LIGHT, enhancing the airy and welcoming atmosphere while STYLISH TILE FLOORING throughout the main living areas adds both beauty and easy maintenance. The bright designer Kitchen is the heart of the home, featuring white cabinetry, quartz countertops, a FARMHOUSE SINK, stainless steel SAMSUNG APPLIANCES, a gas stove, closet pantry, and a spacious breakfast bar, creating the perfect space for entertaining or everyday living.The thoughtfully designed SPLIT-BEDROOM FLOOR PLAN offers both comfort and privacy. Tucked away at one end of the home, the Primary suite serves as a peaceful retreat, featuring a spacious walk-in closet and a BEAUTIFULLY DESIGNED EN SUITE BATH with dual sinks, a step-in shower, and a linen closet. On the opposite side of the home, two additional bedrooms each feature their own WALK-IN CLOSETS and share a full bath, making them ideal for guests, family, or a home office. Conveniently located near the primary suite, the Laundry Room comes complete with STORAGE CABINETRY, washer, and dryer for added functionality. Step outside to enjoy the COVERED SIDE PATIO with paver stone flooring, a perfect private space for morning coffee or evening relaxation. A private entrance from the patio leads directly to the REAR-FACING GARAGE with EPOXY FLOORING, preserving the home’s charming streetscape and curb appeal. Residents of Encore at Ovation enjoy OUTSTANDING AMENITIES, including a sparkling resort-style pool, clubhouse, fitness center, dog park, playground, included internet service, and LAWN AND LANDSCAPE MAINTENANCE—creating a true resort-inspired lifestyle. Located in Winter Garden, this home is JUST MINUTES from Walt Disney World Resort, making world-class entertainment, dining, and shopping incredibly convenient. You’ll also enjoy EASY ACCESS to Hamlin Town Center, featuring popular restaurants, boutiques, movie theaters, and waterfront dining, as well as NEARBY GOLF COURSES, nature trails, and MAJOR ROADWAYS for commuting throughout Central Florida. Zoned for TOP-RATED SCHOOLS and offering a perfect blend of modern design, ENERGY EFFICIENCY, and low-maintenance living, this exceptional Encore at Ovation home is an incredible opportunity to enjoy the very best of the Winter Garden lifestyle. Call and schedule your tour today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1061 PORTMOOR WAY, WINTER GARDEN, FL 34787
$535,00019 Days on yellowkey MLS ID: G5113349
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1804 Built: 2001Monthly Fee: $243 Tax: $6,801 (2025)Community: Stoneybrook West 44/134Single Family
Taxes:$6,801
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the highly desirable Stoneybrook West community—a 24-hour manned, guard-gated golf community known for its resort-style living. This home features inviting modern living spaces that flow seamlessly to a fully fenced backyard with a patio, creating the perfect setting for outdoor relaxation and entertaining. New Roof installed in 2020, water heater installed in 2022, stainless steel appliances, modernized kitchen, tiled floor in kitchen, bathrooms and laundry room. Residents of Stoneybrook West benefit from an outstanding amenity lifestyle, including 24-hour security, a clubhouse, fitness center, resort-style pool, tennis, basketball and volleyball courts, playground, fishing dock, and a boat ramp with access to Black Lake. The community is also home to Stoneybrook West Golf Club and SB Prime restaurant and bar. HOA dues include internet and Spectrum TV, offering added convenience and value. Ideally located minutes from Winter Garden Village, downtown Winter Garden, and SR-429, this home provides easy access to shopping, dining, entertainment, and everyday essentials while still offering a peaceful, gated community setting.
Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)
Listing Agent: Lisa Reed (407-509-7995)
12253 S BRACCO ST, WINTER GARDEN, FL 34787
$499,00022 Days on yellowkey MLS ID: S5150840
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1788 Built: 2024Monthly Fee: $110 Tax: $6,803 (2025)Community: Highland Rdg Ph 2Single Family
Taxes:$6,803
Remarks: BRAND NEW CONSTRUCTION – NEVER LIVED IN – MOVE-IN READY! This is a rare opportunity to own a truly brand-new home that has never been occupied since the day it closed. No previous residents, no wear and tear, no surprises. Just a fresh start in a home that feels exactly as the builder intended. Be the very first person to live here, create memories here, and even peel the protective plastic off the brand-new appliances! Located in the highly sought-after Highland Ridge community, this stunning energy-efficient home offers a spacious open-concept design perfect for today's lifestyle. The beautifully appointed kitchen features a large center island that flows seamlessly into the dining and living areas, creating the ideal space for entertaining and everyday living. Upstairs, a versatile loft provides endless possibilities: home office, media room, game room, fitness area, or additional family space. Built by Meritage Homes in 2024, this home showcases advanced energy-efficient construction designed to provide year-round comfort, healthier indoor air quality, and lower utility costs. Ideally located in the heart of Winter Garden, you'll enjoy convenient access to top-rated schools, shopping, dining, major employment centers, and world-famous Disney attractions just minutes away. Why wait months for new construction when you can move into a never-lived-in home today? Schedule your private tour and experience what "brand new" truly means!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Gil Semedo (617-860-9165)
2202 ROMANUM DR, WINTER GARDEN, FL 34787
$565,00068 Days on yellowkey MLS ID: O6398743
REDUCED by $14,900 (2.6%) on 06/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1889 Built: 2015Monthly Fee: $211 Tax: $3,839 (2025)Community: Alexander RidgeSingle Family
Taxes:$3,839
High School: None
Middle School: None
Remarks: Welcome to your next home in the heart of Winter Garden—where location, lifestyle, and upgrades come together seamlessly. This beautifully updated 3-bedroom, 2-bathroom home with an additional 135-square-foot flex space is perfectly positioned just 20 minutes from Disney, 15 minutes from Downtown Winter Garden, and only 10 minutes to Winter Garden Village, giving you easy access to everything Central Florida has to offer. Step inside to find brand-new luxury vinyl flooring, fresh exterior paint (2024), and a bright, open feel that makes the home both inviting and functional. The additional 135-square-foot living space under air conditioning, complete with elegant French doors, offers endless possibilities as a home office, playroom, fitness room, or second living area. Out back, enjoy your own private putting green—ideal for unwinding or entertaining guests. And with HOA-maintained landscaping, you can say goodbye to yard work and hello to low-maintenance living. Major updates bring peace of mind, including a new roof (2024), new AC unit (2025), and new gutters (2024). Additional features include a garage with epoxy flooring, a hybrid hot water heater, and a sleek GE Slate appliance package that adds a modern touch to the kitchen. This home checks all the boxes—location, upgrades, and lifestyle. Schedule your private showing today and experience it for yourself.
4863 LACEWING DR, WINTER GARDEN, FL 34787
$540,00075 Days on yellowkey MLS ID: O6397857
0 Days Off yellowkey (back on 5/23/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1788 Built: 2023Monthly Fee: $171 Tax: $6,905 (2025)Community: Silverleaf Reserve BungalowsSpa: NoSingle Family
Taxes:$6,905
Middle School: Horizon West Middle School
Remarks: Located in the highly desirable Silverleaf at Hamlin in Winter Garden, this exceptional bungalow offers the perfect blend of location, lifestyle, and design. Surrounded by top-rated schools within short distance, premier dining, and a rapidly growing area with strong appreciation, this is one of the most sought-after communities in the region. This beautifully designed home features 3 bedrooms, 2/1 bathrooms, and an additional loft room, with a layout that is both functional and inviting. What truly sets this property apart is its interior. Unlike anything else currently available in the area, this home has been fully customized with high-end finishes and a cohesive, thoughtfully curated design throughout. Every element was carefully selected to create a seamless flow of elegance, comfort, and functionality. The home showcases custom-built cabinetry in every space, including closets, storage solutions, and integrated desk areas, all designed specifically for the home. The custom-made curtains were designed to fit each space perfectly, enhancing both aesthetics and comfort. Throughout the home, you’ll find LED lighting and carefully selected fixtures that complement one another, creating a warm, modern, and visually harmonious atmosphere. Custom mirrors, wood panel details, and built-in elements elevate each room, making every space feel intentional and refined. The kitchen is a true highlight a gourmet, built-in design that is highly practical, ideal for everyday living and entertaining. This is a rare opportunity to own a home that is completely move-in ready at a level rarely found, and everything has already been done with impeccable taste. Simply bring your belongings and start living. Homes like this are truly one of a kind in the area, and once you step inside, it’s impossible not to fall in love.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcelle Da Silva Sampaio (407-369-3621)
936 KYLEE ALY, WINTER GARDEN, FL 34787
$675,00089 Days on yellowkey MLS ID: O6393910
4 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1772 Built: 2022Monthly Fee: $356 Tax: $6,058 (2025)Community: Oakland ParkSingle Family
Taxes:$6,058
Elementary School: Tildenville Elem
Middle School: Legacy Middle
Remarks: Move-in ready 3-bedroom, 2.5-bathroom single-family home in the Oakland Park community of Winter Garden, Florida. Built in 2022, turnkey condition, full appliance package included, and a low-maintenance 0.05-acre homesite designed for connected daily living without the upkeep. Oakland Park is one of those Winter Garden communities people move to on purpose. Tree-lined streets, walkable sidewalks, and a thoughtfully planned layout keep daily essentials, dining, and recreation close, while the neighborhood itself still feels calm and connected. Morning coffee runs, evening walks, and simple daily rhythms all find an easy place here. Opening the door to 936 Kylee Alley, there's an immediate sense of ease. Natural light carries across the main level as the entry gives way to connected living, dining, and kitchen spaces, creating a layout that works the way life actually happens. With approximately 1,614 square feet of heated living space, this two-story single-family home is scaled for real life. Room to gather, room to retreat, and a layout that stays connected without feeling crowded. The kitchen features white shaker cabinets, quartz countertops, a kitchen island with bar seating, black pendant lighting, and stainless steel appliances including a refrigerator, range, built-in oven, microwave, and dishwasher. The open dining area sits adjacent with a sputnik-style chandelier and large windows filling the space with natural light. Hardwood-style flooring runs through the main level. Upstairs, all three bedrooms including the primary suite are grouped together, creating a quieter, more private living area away from the main floor. The primary suite includes a walk-in closet, double vanity, and a tiled shower. A shared full bathroom serves the two additional bedrooms. The upstairs laundry room with washer and dryer included keeps the daily routine on one level. Carpeted bedrooms and ceiling fans throughout add comfort. The private courtyard-style patio offers outdoor entertaining space. Scaled for morning coffee, evening drinks, or a few favorite plants without the yard work. The attached two-car garage and compact lot reinforce the low-maintenance lifestyle this Oakland Park home is designed to support. Located in Oakland Park in Winter Garden, this home provides convenient access to downtown Winter Garden, the West Orange Trail, Hamlin Town Center, SR-429, and SR-50. The Florida Turnpike, Orlando's theme parks, and the broader Central Florida corridor are all within reach. Shopping, dining, and commuter routes sit close by in a well-maintained, association-managed community. If you are looking for a move-in ready single-family home with 2022 construction, a practical two-story layout, and a connected Winter Garden lifestyle, 936 Kylee Alley in Oakland Park is best experienced in person. Winter Garden, FL 34787. Schedule your private showing today or request additional details to take the next step.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Nelson Cruz Pa (407-901-9939)
13026 SUNSET GARDEN LN, WINTER GARDEN, FL 34787
$547,16067 Days on yellowkey MLS ID: O6400188
INCREASED by $3,000 (0.6%) on 04/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1908 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Remarks: Under Construction. Discover the Liston Coastal, a beautifully designed bungalow-style home offering 3 bedrooms, 2.5 bathrooms, and 1,908 square feet of thoughtfully crafted living space. This pre-construction opportunity features an estimated completion date in early 2027, giving buyers ample time to plan their move. As a Design Studio Ready home, buyers can personalize interior finishes and selections to create a space that reflects their unique style. Don't miss the chance to build your dream home and enjoy the quality craftsmanship and luxury living that Toll Brothers is known for.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Devahn Powell (571-234-7236)
1253 BRANDY LAKE VIEW CIR, WINTER GARDEN, FL 34787
$474,90050 Days on yellowkey MLS ID: O6404570
1 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1702 Built: 1998Monthly Fee: $89 Tax: $3,024 (2025)Community: Brandy CreekSingle Family
Taxes:$3,024
Remarks: Under contract-accepting backup offers. This stunning home is waiting just for you! Nestled in the gated community of Brandy Creek, this beautifully maintained 3 bedroom, 2 bathroom home offers a seamless blend of inviting living spaces and everyday functionality. A manicured front lawn, spacious driveway, and covered front patio set the tone for the warm welcome waiting inside. Step through the entry and you’re greeted by soaring ceilings, abundant natural light, and an open layout that effortlessly connects each living space. To one side, a formal living area offers flexibility as a home office or quiet retreat, while the formal dining room on the opposite side creates the perfect setting for hosting dinners and celebrations. At the center of the home, the kitchen shines as both a gathering place and a functional workspace. Featuring a large island with breakfast bar seating, stainless steel appliances, and generous counter space, it’s designed to handle everything from quick mornings to full-scale entertaining. Overlooking the family room, the layout ensures you’re always part of the moment. Just beyond, a cozy dinette with a partial bay window offers a peaceful spot to enjoy your morning coffee while looking out over the backyard. The split floor plan provides privacy for everyone, with the primary suite tucked away on one side of the home. This spacious retreat features a large closet, a private en suite bath with dual vanities, a garden tub, and a separate shower, plus its own direct access to the backyard. Additional bedrooms are bright, well-sized, and versatile for family, guests, or hobbies. Outside, the fenced backyard offers a private escape with a covered patio perfect for al fresco dining, weekend barbecues, or simply soaking up the Florida sunshine. It’s a space designed for both relaxation and play, with room for everyone to enjoy. Living in Brandy Creek means more than just a beautiful home, it also means you’ll also have access to a scenic lake and a dock/fishing pier for quiet moments outdoors. Just minutes away, you can explore the charm of downtown Winter Garden with its farmers markets, live music, boutique shopping, and local dining. With easy access to the Turnpike and FL-429, getting around Central Florida is simple and convenient. Don't miss out on this gorgeous home, schedule a private showing TODAY!!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Lindsay Grosshans (407-202-2954)
411 MILLWOOD PL, WINTER GARDEN, FL 34787
$459,00013 Days on yellowkey MLS ID: TB8518055
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1696 Built: 2014Monthly Fee: $72 Tax: $6,471 (2025)Community: Covington Chase Ph 2ASingle Family
Taxes:$6,471
Remarks: Welcome to Covington Chase — one of Winter Garden's most sought-after communities! This charming 3BR/2BA/2-car garage home built in 2014 features an open great room layout, split bedrooms, and a 2-car garage. Enjoy community amenities including a pool, playground, and clubhouse, all just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village shopping, and SR 429. Disney World and Universal Studios are less than 20 miles away. Don't miss this gem — schedule your showing today!
Listing is courtesy of: PEOPLE'S TRUST REALTY (727-946-0904)
Listing Agent: Kimberly Watson-Johnson (727-946-6949)
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