Location: Winter Garden
Do Not Show Listings
16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787
$560,00065 Days on yellowkey MLS ID: O6404448
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2487 Built: 2018Monthly Fee: $257 Tax: $9,371 (2025)Community: Waterleigh Ph 2ASingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,371
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Move in ready home in Waterleigh one of Winter Garden’s most desirable places to live! Ideally positioned within the community for quick and convenient access, this home also sits directly across from a playground and green space perfect for families and outdoor fun. Freshly updated with new interior paint and brand new carpet throughout the bedrooms and upstairs, this home is truly turnkey. Featuring 4 bedrooms and 3.5 baths, the open concept layout offers a spacious kitchen with granite countertops, stainless steel appliances, large island, and walk in pantry overlooking the living and dining areas. Sliding doors lead to a covered lanai for easy indoor-outdoor living. The first floor includes a bedroom with ensuite bath and a powder room. Upstairs offers a versatile loft, a spacious primary suite with walk-in closet and dual vanities, two additional bedrooms, a full bath, and a convenient laundry room. Enjoy resort-style living in Waterleigh with pools, clubhouse, fitness center, parks, trails, and more all designed for a true Florida lifestyle.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Phil Mariani (407-257-3609)
15149 CANOE PL, WINTER GARDEN, FL 34787
$798,89135 Days on yellowkey MLS ID: O6412776
REDUCED by $1 (0.0%) on 06/23/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3081 Built: 2019Monthly Fee: $385 Tax: $9,388 (2025)Community: Lakeshore Preserve Ph 2Single Family
Taxes:$9,388
Elementary School: None
High School: None
Middle School: None
Remarks: Imagine coming home to space, style, and ease—where every detail is already done. This move-in-ready Toll Brothers home offers 4 bedrooms, 3.5 baths, and 3,304 sq. ft. in one of Horizon West’s most desirable communities. From the Tuscan-inspired curb appeal and welcoming front porch to the bright, open living spaces, this home was designed for comfort, flexibility, and effortless entertaining. The chef’s kitchen features a large island and flows seamlessly into the family room and covered lanai. With two primary suites, including one on the main level, the floor plan is ideal for guests, multigenerational living, or a private owner’s retreat. The oversized backyard offers room to create your dream outdoor oasis, including space for a future pool. Enjoy resort-style amenities with lawn care included, a clubhouse, fitness center, parks, playgrounds, and a lakeside pool overlooking Panther Lake. Located minutes from top-rated schools, Hamlin Town Center, Disney, and everything Horizon West has to offer. Luxury without waiting. Space without compromise. This is where your next chapter begins.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: William Grim, Iii (407-314-9784)
8124 RED CROSSBILL ST, WINTER GARDEN, FL 34787
$830,000292 Days on yellowkey MLS ID: O6345400
0 Days Off yellowkey (back on 7/3/2026)
REDUCED by $10,000 (1.2%) on 06/16/2026
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3708 Built: 2013Monthly Fee: $246 Tax: $7,515 (2024)Community: Summerlake Pd Ph 1ASingle Family
Taxes:$7,515
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Virtually Staged. Buyers Financing Failed... Now available, this Premium 6-bedroom, 4-bath executive home sits on one of the largest lots in the community at .29 acres and features a heated saltwater pool with screened enclosure, cascading waterfall feature, travertine deck, and outdoor speakers for the ultimate Florida lifestyle. From the curb, you’ll be impressed by the oversized paver driveway, side-loading garage, and charming front rocker porch. Inside, the home welcomes you with formal living and dining areas, leading into the spacious family room, dinette, and a chef-inspired kitchen with natural gas cooking, stainless steel appliances, abundant counter space, and plentiful storage. The downstairs also includes a guest bedroom, private laundry room, and a flexible nook ideal for a reading area or office. Upstairs, you’ll find the remaining bedrooms, a versatile loft space, and an expansive primary suite featuring a spa-like bath with a soaking tub, walk-in shower, dual vanities, and a makeup prep station. Recent updates include a freshly painted exterior, updated water heater, and a 2025 HVAC system. The shining star of this home is the private backyard retreat with its heated saltwater pool and expansive lot, perfect for entertaining or relaxing in style. The Summerlake community adds to the appeal, offering residents a fitness center, playground, dog park, tennis courts, and community pool, all with the convenience of Harmony just minutes down the road. Truly a must-see to appreciate!
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Juan Castro (407-808-5353)
13086 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787
$849,00021 Days on yellowkey MLS ID: O6415942
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2835 Built: 2025Monthly Fee: $140 Tax: $2,829 (2025)Community: Harvest/OvationSingle Family
Taxes:$2,829
Remarks: Heavily upgraded RockWell Faulkner in Harvest at Ovation with rare upstairs primary suite featuring a covered balcony and peaceful water view. East-facing front means soft morning light out front and sunset views from the balcony every evening. 5 bed, 3.5 bath, open-concept main level, gourmet kitchen, and 2-car attached garage. Zoned for top-rated Water Spring schools and Horizon High, just minutes to Disney and Horizon West dining.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Suheil Albaree (407-426-4266)
4863 LACEWING DR, WINTER GARDEN, FL 34787
$540,00089 Days on yellowkey MLS ID: O6397857
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
Elementary School: Independence Elementary
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)
2230 ROMANUM DR, WINTER GARDEN, FL 34787
$565,000117 Days on yellowkey MLS ID: O6389947
1 Days Off yellowkey (back on 5/17/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2562 Built: 2014Monthly Fee: $207 Tax: $8,425 (2025)Community: Alexander RdgSingle Family
Taxes:$8,425
Elementary School: Hamlin Elementary
High School: West Orange High
Middle School: Hamlin Middle
Remarks: Motivated seller – bring your offers! Location, Location, Location! Don't miss the opportunity to own this beautiful and cozy 4-bedroom, 4-bath home featuring thoughtfully designed living spaces that combine comfort, functionality, and inviting charm. The main floor features all four bedrooms, offering convenience and privacy for everyday living. Upstairs, you’ll find a spacious bonus room with a full bathroom, perfect for a media room, game room, home office, or additional living space. This is the only area of the home with carpet, creating a comfortable and cozy environment for relaxation or entertainment. Throughout the main living areas, the home features luxury vinyl flooring, providing durability and a modern look while enhancing the overall warmth of the home. The kitchen opens beautifully to the main living area, creating a welcoming space for gathering with family and friends. The kitchen cabinets were recently refinished and painted, giving the kitchen a refreshed and updated appearance. Step outside and enjoy the screen-enclosed patio, offering a comfortable outdoor space where you can relax and enjoy Florida living with added protection from insects. The home also features attractive landscaping and brick pavers on the driveway and entrance, creating great curb appeal and a welcoming first impression. Additionally, the property includes solar panels, contributing to improved energy efficiency. This home offers a warm and inviting atmosphere with well-distributed spaces that make it perfect for both everyday living and entertaining. Schedule your private showing today and come experience the comfort and charm this home has to offer in a perfect location!
1338 UNION CLUB DR, WINTER GARDEN, FL 34787
$890,00028 Days on yellowkey MLS ID: O6412710
REDUCED by $10,000 (1.1%) on 06/10/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2637 Built: 2014Monthly Fee: $208 Tax: $13,895 (2025)Community: Oakland ParkaSpa: YesSingle Family
Taxes:$13,895
Remarks: Virtually Staged. Imagine 1338 Union Club Dr, a residence recently updated with partial flooring replacement. Its kitchen includes all stainless steel appliances, an accent backsplash, and an island, while the primary bedroom features a walk in closet and the primary bathroom provides double sinks. Beyond, a covered patio overlooks an in ground pool within a fully fenced in backyard. This updated residence provides modern comfort and an inviting outdoor space.. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787
$595,00029 Days on yellowkey MLS ID: O6414996
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2420 Built: 2024Monthly Fee: $96 Tax: $8,683 (2025)Community: Osprey Ranch Ph 1Single Family
Taxes:$8,683
Remarks: Welcome to 15143 Blue Peacock Lane in Winter Garden’s Osprey Ranch, a beautifully finished two-story home offering a bright open concept layout, updated finishes, and easy indoor-outdoor living. The main level features light wood-look flooring, recessed lighting, and a spacious living and dining area that flows seamlessly into the chef’s kitchen. Designed with both everyday function and entertaining in mind, the kitchen showcases white cabinetry, stone counters, a large center island, tile backsplash, stainless steel appliances, a gas cooktop, wall oven, and modern pendant lighting. Sliding glass doors open to a covered rear patio and fenced backyard, creating a comfortable extension of the living space. Upstairs, the primary suite offers soft carpet, a tray ceiling, ceiling fan, walk-in closet, and a spa-inspired en suite bath with dual sinks, a large glass-enclosed shower, private water closet, and modern finishes. Additional bedrooms feature carpet and natural light, while the upstairs bonus/flex area provides useful extra space for work, play, or relaxation. Osprey Ranch offers attractive community amenities, including a resort-style pool, clubhouse area, playground, open green space, and walking areas, all in a convenient Winter Garden location near shopping, dining, and everyday conveniences.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Jorge Martinez, Jr (407-513-2366)
914 TROWMAN ALY, WINTER GARDEN, FL 34787
$649,00042 Days on yellowkey MLS ID: O6410871
REDUCED by $26,000 (3.9%) on 06/02/2026
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
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: Virtually Staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled with natural light, spacious bedrooms, and a layout designed for modern living and entertaining. Pride of ownership shines in every detail, making this home truly stand out. Located in a charming golf cart community with resort-style amenities, residents enjoy access to parks, schools, walking trails, and more. Just minutes from vibrant Downtown Winter Garden, you'll love being close to the award-winning farmers market, lively festivals, boutique shopping, dining, and entertainment. This is your opportunity to own a well-maintained, upgraded home in one of Winter Garden's most desirable communities!
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
15353 OAK APPLE CT, WINTER GARDEN, FL 34787
$347,500104 Days on yellowkey MLS ID: O6393663
REDUCED by $2,500 (0.7%) on 05/27/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1699 Built: 2008Monthly Fee: $283 Tax: $1,863 (2025)Community: Tucker Oaks Bldg 5Townhouse
Taxes:$1,863
Remarks: Welcome to this spacious 3 bedroom 2.5 bath home situated on a quiet cul-de-sac with no rear neighbors and low HOA in the highly desirable Winter Garden area! This well maintained property features an open and functional floor plan with generous living spaces and abundant natural light, ideal for both everyday living and entertaining. The kitchen offers ample cabinet and counter space, flowing seamlessly into the main living areas. The primary suite provides a comfortable retreat with a private bath, while two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy a private screened patio perfect for relaxing or hosting gatherings. Prime location, just minutes from everything Winter Garden has to offer! Conveniently located near shopping, dining, and entertainment with easy access to Highway 50 and the Florida Turnpike. Don’t miss this opportunity, schedule your private showing today!
Listing is courtesy of: EPIC REAL ESTATE ADVISORS LLC (407-495-3672)
Listing Agent: Julian Torres, Jr (407-361-7546)
2006 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$750,0007 Days on yellowkey MLS ID: O6420951
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3011 Built: 1999Monthly Fee: $90 Tax: $5,441 (2025)Community: Wintermere PointeSpa: NoSingle Family
Taxes:$5,441
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Virtually Staged. Tucked away on a cul-de-sac within the gated community of Wintermere Pointe, this spacious 5-bedroom, 4-bath pool home is situated on an oversized homesite of more than 1/4 acre with a beautiful wooded backdrop. The private backyard provides an inviting setting for outdoor living, featuring a screened pool and patio that create the perfect space for entertaining or simply enjoying the natural surroundings. Designed with one of the community’s most sought-after floor plans, this home offers exceptional flexibility with generous living spaces throughout. The formal living and dining rooms are sized to accommodate large furniture, while the centrally located family room flows seamlessly into the kitchen and outdoor living areas. The home office is thoughtfully positioned adjacent to the primary suite, making it equally suitable as a fifth bedroom, nursery, den, or private workspace. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, abundant cabinet storage, and a full appliance package, including a 5-burner glass cooktop range with a convection oven. The adjacent dinette overlooks the pool and backyard, while replacement sliding glass doors installed in 2017 provide direct access from the living room, dinette, family room, and primary suite to the screened patio and pool. The spacious primary suite features wood flooring, coffered ceilings, double closets, and oversized sliding glass doors that open directly to the pool area. The ensuite bath features dual vanities with stone countertops, a relaxing garden tub, a separate shower, and a private water closet. The secondary bedrooms are generously sized and conveniently located for easy access to the home’s full bathrooms, each enhanced with updated vanities and mirrors. A full bath located just off the family room also serves as an ideal pool bath. Just beyond the kitchen and laundry room, a hallway provides access to the 3-car garage and a wood staircase leading to the expansive bonus room. Complete with a full bath, walk-in closet, and newer windows overlooking the oversized backyard and wooded backdrop, this versatile space is ideal as a guest suite, sixth bedroom, recreation room, media room, home gym, or private retreat. Numerous updates provide added value and peace of mind, including multiple replacement windows (2015), a new roof (2016), replacement sliding glass doors and front entry door (2017), a new paver driveway (2020), a new water heater (2020), and a new HVAC system (2025). Wintermere Pointe is a gated community offering residents a playground and tennis courts. Conveniently located with access to Lake Whitney Elementary, SunRidge Middle School, and West Orange High School, the home also provides easy access to shopping, dining, major roadways, and many of Central Florida’s most popular destinations.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: David Dorman (407-948-8295)
33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787
$535,00047 Days on yellowkey MLS ID: O6408941
REDUCED by $10,000 (1.8%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1584 Built: 2004Monthly Fee: $46 Tax: $7,326 (2025)Community: Timbercreek Pines A B C & DSingle Family
Taxes:$7,326
Elementary School: Dillard Street Elem
Remarks: Welcome to this beautifully renovated single-story gem nestled in the heart of Historic Winter Garden, one of Central Florida’s most sought-after communities. Perfectly situated just two blocks from vibrant downtown Winter Garden and iconic Plant Street, this home offers the ultimate blend of historic charm, modern luxury, and walkable convenience. Located within the highly desirable golf cart district and just moments from the renowned West Orange Trail, you’ll enjoy easy access to cobblestone streets, boutique shopping, coffee houses, award-winning restaurants, and the beloved Saturday Farmer’s Market — all right outside your door. Completely renovated from top to bottom, inside and out, this move-in ready home showcases exceptional attention to detail and thoughtful upgrades throughout. Step inside to discover a bright open floor plan enhanced by luxury vinyl plank flooring, upgraded 6-inch baseboards, updated light fixtures, neutral designer finishes, and ceiling fans in every bedroom. The stunning remodeled kitchen serves as the heart of the home, featuring crisp white cabinetry, elegant quartz countertops, modern backsplash, dark designer hardware, LED lighting, stainless appliances, and an oversized island with seating for six — perfect for entertaining family and friends. The bathrooms have been tastefully updated to blend timeless character with modern functionality, while the inside laundry room and abundant storage, including two hallway closets near the secondary bedrooms, add everyday convenience. Outdoor living shines with a newly added tiled screened lanai complete with new sliding doors and windows that create seamless indoor-outdoor flow. The expansive fenced backyard is a private oasis featuring fresh landscaping, a Magnolia tree, Orange tree, and Avocado tree — the perfect setting to relax and enjoy Florida living year-round. Additional highlights include a brand-new AC unit, anti-slip garage floor coating, and a 6-foot white vinyl privacy fence. This one-of-a-kind home perfectly captures the charm of Historic Winter Garden while offering the modern updates today’s buyers desire. WELCOME HOME.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Peyton Blanton (407-462-7891)
15340 OAK APPLE COURT CT #16B, WINTER GARDEN, FL 34787
$350,00012 Days on yellowkey MLS ID: O6419809
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008Monthly Fee: $282 Tax: $4,127 (2025)Community: Tucker Oaks Condo Ph 4Condo
Taxes:$4,127
Elementary School: SunRidge Elementary
Remarks: Under contract-accepting backup offers. Welcome to Tucker Oaks, one of Winter Garden's most desirable gated communities! This beautifully maintained 3-bedroom, 2.5-bathroom townhome-style condo offers 1,544 square feet of comfortable living space, an attached two-car garage providing secure parking and additional storage, and a prime location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright and inviting interior featuring laminate flooring installed throughout the living areas and bedrooms, complemented by ceramic tile in the kitchen and bathrooms. Fresh interior paint creates a clean, modern feel, while crown molding adds an elegant touch to the main living area. The well-appointed kitchen is designed for both style and function, featuring granite countertops, 42-inch cabinetry, updated countertops, a new kitchen sink, decorative backsplash, and an abundance of workspace. A huge under-stair storage area provides valuable extra storage rarely found in similar homes. Upstairs, all three bedrooms are thoughtfully positioned for privacy. The spacious primary suite features crown molding, an en-suite bath and ample closet space, while two additional bedrooms offer flexibility for family, guests, or a home office. Additional upgrades and features include a recently replaced A/C system (2021), washer and dryer (2024).Residents of Tucker Oaks enjoy access to a community pool and low-maintenance living in a peaceful setting. Ideally located just 1.4 miles from Historic Downtown Winter Garden and the popular Plant Street Market, you'll enjoy easy access to boutique shopping, dining, entertainment, farmers markets, and year-round community events. Outdoor enthusiasts will appreciate the nearby West Orange Trail, Oakland Nature Preserve, and Oakland Arts & Heritage Center. Commuters will love the quick access to Florida's Turnpike and major highways, while the new Costco in Clermont adds even more convenience.Move-in ready and meticulously cared for, this exceptional home offers the perfect combination of comfort, convenience, and location. Schedule your private showing today!
Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)
Listing Agent: Aileen Frauman (407-928-0211)
15025 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787
$490,00046 Days on yellowkey MLS ID: O6410108
REDUCED by $15,000 (3.0%) on 07/03/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2016Monthly Fee: $195 Tax: $8,019 (2025)Community: Signature Lakes Ph 3B-4 3B-5 3B-Single Family
Taxes:$8,019
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Motivated seller. New paint and new flooring throughout. This home features two primary suites — one downstairs and one upstairs. Located in an area with all A-rated schools. Close to Disney World, and you can even enjoy Disney fireworks from the front yard. The home is conveniently located near Super Walmart, Winter Garden Village shopping centers, and top-rated restaurants. The Independence Community Association offers outstanding amenities, including: 2 community pools, green spaces & park areas, tennis & basketball courts, a main clubhouse with fitness & arcade, 2nd clubhouse with fitness & billiards, community boat ramp to ski-able Lake Hancock, dog park, bike & walking paths. HoA fee covers basic TV CABLE and WIFI.
Listing is courtesy of: CENTURY 21 CARIOTI (407-354-0074)
Listing Agent: Bo Zhang (407-848-8486)
844 OAKLAND PARK BLVD, WINTER GARDEN, FL 34787
$1,225,0006 Days on yellowkey MLS ID: O6419976
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3525 Built: 2012Monthly Fee: $208 Tax: $14,087 (2025)Community: Oakland Parkb-1B ASingle Family
Taxes:$14,087
Remarks: Virtually Staged. More than a home, this is a lifestyle. Perfectly positioned in the highly sought-after Oakland Park community, this exceptional residence combines timeless design, generous living spaces, and effortless indoor-outdoor living just a golf cart ride from the heart of downtown Winter Garden. With 5 large bedrooms plus a den spread across over 3,500 square feet, the home provides ample space for everyday living and entertaining. Upon arrival, a welcoming front porch sets the tone, offering the perfect place to enjoy a quiet morning coffee or unwind with a glass of wine at sunset. Inside, elegant French doors open to a private home office, while engineered hardwood flooring flows throughout the main living areas. The open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. At the heart of the home, the spacious kitchen overlooks the living area and seamlessly connects to the expansive screened lanai through double French doors. The first-floor primary suite is a private retreat, highlighted by a tray ceiling and a spa-inspired bath featuring dual vanities, a soaking tub, a separate walk-in shower, and an oversized walk-in closet. A secondary bedroom and full bath on the main level provide ideal accommodations for guests or multigenerational living. Upstairs, a spacious loft offers endless possibilities as a media room, game room, or additional gathering space. Three generously sized secondary bedrooms—each with its own walk-in closet—along with two full bathrooms provide comfort and privacy for family and guests alike. Step outside to one of the home's most impressive features: an expansive screened lanai overlooking a fully fenced backyard with ample room to design the pool of your dreams. Completing the property is a coveted three-car garage, offering abundant space for vehicles, storage, and recreation. Residents of Oakland Park enjoy a picturesque, tree-lined community known for its welcoming atmosphere, resort-style amenities, seasonal community events and unmatched location. Just minutes from the award-winning shops, restaurants, farmers market, and West Orange Trail in historic downtown Winter Garden, this home offers the perfect balance of luxury, convenience, and the quintessential Central Florida lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Sophia Gordon, Llc (239-898-1841)
7467 JOHN HANCOCK DR, WINTER GARDEN, FL 34787
$1,350,0005 Days on yellowkey MLS ID: O6421848
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3964 Built: 2019Monthly Fee: $215 Tax: $16,560 (2025)Community: West Lake Hancock EstatesSpa: YesSingle Family
Taxes:$16,560
Remarks: Luxury, comfort, and an unbeatable location come together in this exceptional home in the highly sought-after Horizon West community. Perfectly positioned just minutes from Disney, shopping, dining, major highways, and top-rated schools, this move-in-ready residence offers the ideal combination of elegance, functionality, and the Florida lifestyle you’ve been looking for. Designed for both everyday living and entertaining, the home features 4 spacious bedrooms, 3 full bathrooms, a half bath, a dedicated office, a versatile bonus room, and a 3-car garage. The open-concept kitchen showcases a large center island, stainless steel appliances, and seamlessly connects to the spacious living areas. What truly sets this home apart is its stunning outdoor oasis. Since its original purchase, the owners have transformed the backyard into a private resort featuring a beautiful custom pool, an expansive covered lanai, and a fully equipped summer kitchen, creating the perfect setting for weekend barbecues, family gatherings, or simply relaxing while enjoying the peaceful pond views. Thoughtfully upgraded and impeccably maintained, this home is truly turnkey, allowing its next owners to move in and immediately enjoy one of Central Florida’s most desirable lifestyles. Whether you’re looking for your primary residence or a place where family and friends can create unforgettable memories, this property delivers the perfect blend of luxury, comfort, convenience, and quality of life.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Diogo Mac Knight (407-364-7522)
417 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787
$275,0005 Days on yellowkey MLS ID: O6421941
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1264 Built: 2005Monthly Fee: $489 Tax: $3,366 (2025)Community: Southern Pines CondoCondo
Taxes:$3,366
Remarks: NEWLY UPDATED LAMINATE FLOORING THROUGHOUT THE MAIN AREAS, BEDROOMS, AND STAIRS!!!! kITCHEN AND BATHROOMS HAVE CERAMIC TILE!!!! This amazing ready to move in 2 bed / 2 bath condo in the pristine gated community of Southern Pines with a lot of amenities. Located in the heart of charming Winter Garden and only 15 miles to Orlando. Condo Includes: 1 car GARAGE - Bonus room which is attached to living room, Walk-in closets in both bedrooms and In-unit laundry closet. Community Features Include: Water, internet, exterior & community maintenance included, amenities: Oversized Swimming pool and gazebo lounge areas - Spa / Hot Tub, Fully equipped fitness center with attached playroom, Indoor Basketball Court & Racquetball Court, Outdoor Pickleball / Tennis Court & Beach Volleyball Court, Covered Playground, Outdoor Kitchen including charcoal grills, mini fridge, sink & vending machines, Carwash station, Easy to access mailboxes at front of the community. Schedule your showing today.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Susan Young (407-408-3533)
689 BETHUNE AVE, WINTER GARDEN, FL 34787
$434,0005 Days on yellowkey MLS ID: O6421715
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1434 Built: 1950 Tax: $2,330 (2025)Community: Joe Louis Park Q162Single Family
Taxes:$2,330
Remarks: PHENOMENAL Double corner LOT NO HOA, newer updates INCLUDE: brand new AC, new roof, Re-Plumb, house/ Electrical Panel/rewired. Updated kitchen and bathrooms, Located off the Kitchen is the Dining room area which is open to the Living Room area. The master Bathrooms is completely updated features a standing shower. The Laundry is located inside. The carport/workshop is spacious to hold 2 cars and storage. Enjoy the nice-sized Backyard with a that is big enough for the whole family. You don't want to miss this opportunity to make this house your home! very nice WORKSHOP ** VALUE IS IN THE both property/land
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Eric Senate (407-729-6998)
6843 POINT HANCOCK DR, WINTER GARDEN, FL 34787
$435,0005 Days on yellowkey MLS ID: G5114589
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1720 Built: 2013Monthly Fee: $195 Tax: $6,895 (2025)Community: Signature Lakes Ph 2Single Family
Taxes:$6,895
Remarks: Welcome to 6843 Point Hancock Drive, a beautifully maintained 3-bedroom, 2-bathroom home offering 1,720 square feet of thoughtfully designed living space in the highly sought-after Independence community of Winter Garden. From the moment you arrive, you'll appreciate the home's inviting curb appeal and functional single-story floor plan. Inside, the open-concept design creates a bright and welcoming atmosphere, with spacious living and dining areas that flow seamlessly into the kitchen—perfect for everyday living and entertaining. The well-appointed kitchen offers ample cabinet and countertop space, making meal preparation a breeze. The spacious primary suite provides a relaxing retreat with a walk-in closet and private en-suite bathroom, while the two additional bedrooms offer flexibility for family, guests, or a home office. Every room has been designed with comfort and functionality in mind. Step outside and enjoy your private backyard, ideal for relaxing, grilling, or spending time with family and friends. Living in Independence means enjoying one of Central Florida's premier master-planned communities. Residents have access to resort-style amenities, including multiple community pools, clubhouses, fitness centers, tennis and basketball courts, playgrounds, scenic walking and biking trails, parks, and private boat ramps providing access to beautiful Lake Hancock. The HOA also includes high-speed internet and cable, adding exceptional value and convenience. Ideally located just minutes from Hamlin Town Center, Horizon West, Walt Disney World, top-rated schools, shopping, dining, and major highways, this home offers the perfect combination of comfort, convenience, and an outstanding lifestyle. Don't miss your opportunity to own this exceptional home in one of Winter Garden's most desirable communities. Schedule your private showing today!
Listing is courtesy of: FLORIDA REAL ESTATE CENTER LLC (352-241-7000)
Listing Agent: Dj Wilson, Jr. (352-241-7000)
14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787
$492,9005 Days on yellowkey MLS ID: O6421797
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2223 Built: 2012Monthly Fee: $242 Tax: $8,151 (2025)Community: Summerlake Pd Ph 01BSpa: NoSingle Family
Taxes:$8,151
Remarks: Virtually Staged. This 3-bedroom, 2-bathroom home features open concept design that connects the main spaces into one flowing layout. The primary suite is located upstairs, and a loft bonus room provides flexible space for a home office or guest retreat. The property combines practical design with convenient access to shopping, dining, and recreation throughout the Winter Garden area. The gourmet kitchen showcases stainless steel appliances and a custom tile backsplash, with solid surface countertops providing durable workspace. Luxury vinyl plank flooring runs through the formal dining area and open-concept great room, while ceramic tile anchors the foyer entryway and kitchen. The primary bedroom features carpet, as do the upstairs bedrooms, loft area, and second floor hallway. Sliding glass patio doors open the interior spaces to outdoor areas, bringing in natural light and creating visual connection to the exterior. The primary bathroom includes dual sinks for convenience, with ceramic tile flooring throughout. A laundry room with storage keeps essentials organized and accessible. The covered lanai extends outdoor enjoyment with shade and shelter, while the fenced backyard provides privacy and security. A covered front porch welcomes visitors at the entry. The architectural shingle roof protects the home, and a smart thermostat manages energy efficiency. The secluded patio offers a quiet retreat, and on clear evenings, you can catch distant Disney fireworks from the property. The community resort-style pool provides year-round recreation and social opportunities for residents. Hamlin Town Center shopping is nearby for everyday needs, while Horizon West Town Center offers expanded retail and dining options. Cinepolis Luxury Cinemas and Publix Super Market are within convenient reach. Golf enthusiasts will appreciate proximity to Orange County National Golf Center. Contact us to schedule a showing and explore this home's location and lifestyle benefits. Seller will entrain offers 5 days after list date.
Listing is courtesy of: GLORY INTL. REAL ESTATE CO (386-775-7778)
Listing Agent: Patrick D'Agostino (321-467-4555)
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