Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
Do Not Show Listings
1125 LINCOLN TER, WINTER GARDEN, FL 34787
$242,400234 Days on yellowkey MLS ID: O6345921
0 Days Off yellowkey (back on 4/28/2026)
REDUCED by $2,500 (1.0%) on 04/09/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 814 Built: 1961 Tax: $2,026 (2024)Community: Bay St ParkSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,026
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. **NOW FHA AVAILABLE** DISCOVER THE SERENE BEAUTY OF THIS STUNNING HOME! GORGEOUS 3-BEDROOM, 1-BATHROOM, 1-CARPORT HOME boasting a SPACIOUS FLOOR PLAN that effortlessly blends functionality with modern style. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook like a pro in the NEWER KITCHEN featuring NEW QUARTZ COUNTERTOPS and SLEEK STAINLESS STEEL APPLIANCES—perfect for culinary enthusiasts. This home is LOADED WITH UPGRADES, including: New Roof with 30-Year Shingles, New HVAC System, New Laminate Flooring Throughout, Renovated Bathrooms, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Interior Doors, and Closet Doors. CONVENIENTLY LOCATED near all major highways, shopping, restaurants, and entertainment—this move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer for accuracy. Virtual Staging was added to some of the pictures.
Listing is courtesy of: IHOME REALTY FL LLC (407-730-9971)
Listing Agent: Karen Sweat (407-730-9971)
17608 DEER ISLE CIR, WINTER GARDEN, FL 34787
$1,025,000218 Days on yellowkey MLS ID: O6350825
1 Days Off yellowkey (back on 4/27/2026)
REDUCED by $25,000 (2.4%) on 04/20/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3144 Built: 1997Monthly Fee: $207 Tax: $6,334 (2024)Community: Deer Island Ph 02Spa: YesSingle Family
Taxes:$6,334
Elementary School: Tildenville Elem
Remarks: Under contract-accepting backup offers. Bring your ideas to a truly exceptional custom home, perfectly situated in a private, gated community on the shores of breathtaking John’s Lake. Set on over an acre of a beautifully updated landscaped property with panoramic water views throughout the island, this 4-bedroom estate offers the ultimate Florida lifestyle — complete with resort-style amenities and convenient access to Historic Downtown Winter Garden, as well as Downtown Orlando and major attractions just 30 minutes or less away. Your ideas await as charm and craftsmanship are evident in every detail. Step through the front door into an inviting floor plan that seamlessly blends elegance with functionality. The spacious living room is anchored by a cozy wood-burning fireplace, enhanced by warm canned lighting and plantation shutters that frame every window. Wood flooring flows throughout the main living areas, setting a tone of timeless sophistication. The kitchen features granite countertops, KraftMaid cabinetry, Sub-Zero refrigerator, cooktop, double ovens, and a large pantry. The open design keeps the heart of the home connected to the main living space — ideal for entertaining and family gatherings but separate enough to hide the meal prep! The primary suite is a peaceful retreat, with serene views of the pool, dual walk-in closets, garden tub, separate shower, and a cleverly designed storage area. The home's split-bedroom layout ensures privacy for guests and family alike and are all thoughtfully located on the first floor. Upstairs, two large bonus rooms offer endless possibilities — from a playroom to a home theater — and includes a hidden safe room / office with skylights and easy attic access for extra security and utility. The 3 car garage features extra width for additional storage and Gladiator garage organizational wall units. Step outside into your private backyard paradise, where a sparkling saltwater pool and attached hot tub await, surrounded by pavers and an outdoor grilling station. Whether hosting a summer barbecue or enjoying a quiet evening under the stars, this backyard fenced-in space delivers year-round relaxation. Eight outdoor security cameras offer peace of mind, while a three-car garage and spacious driveway provide ample storage and parking. An in-wall pest control system, central vacuum, built-in wine bar, hidden storage and closet organization are examples of many upgrades throughout the home. This home also boasts a well water system with a full purification setup, and a laundry room inside with washer, dryer and utility sink included. Beyond the home itself and its many additional upgrades, the Deer Island community offers unparalleled amenities, including a community boat ramp for direct access to John’s Lake — perfect for boating, fishing, and water sports — as well as two catch and release fishponds, basketball courts, tennis courts, pickleball facilities and easy access to the West Orange bike trails. With stunning lake views, lush surroundings, and a true sense of privacy, this is a place where families grow, memories are made, and every day feels like a getaway. Don’t miss the opportunity to own this fabulous home, where elegance meets comfort and lifestyle meets location.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Karen Jacobs (407-579-0062)
2217 RICKOVER PL, WINTER GARDEN, FL 34787
$1,059,00066 Days on yellowkey MLS ID: O6388647
REDUCED by $16,000 (1.5%) on 04/20/2026
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4324 Built: 2008Monthly Fee: $260 Tax: $8,547 (2025)Community: Bronsons Lndgs F & MSpa: YesSingle Family
Taxes:$8,547
Elementary School: Lake Whitney Elem
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. This stunning waterfront model home in the prestigious gated community of Bronson's Landing in Winter Garden, Florida, offers the perfect blend of luxury, comfort, and waterfront living. Step inside to an elegant foyer featuring a custom staircase and a private office, setting the tone for this thoughtfully designed 5-bedroom, 5-full-bath residence with an additional loft, theater room, and versatile flex spaces ideal for relaxation and effortless entertaining. The heart of the home is the expansive open-concept gourmet kitchen, boasting sleek stone countertops, modern hardware, premium stainless steel appliances, built-in ovens, abundant cabinetry, a walk-in pantry, and a large island bar overlooking the sparkling pool, extended lanai, and tranquil pond views. Upgraded wood flooring flows throughout, while abundant natural light floods the seamless kitchen, dining, and living areas creating an inviting space perfect for year-round gatherings. The luxurious primary suite is a true retreat, with peaceful water views, crown molding, and a spa-like en-suite bath featuring a large soaking tub, separate shower, and an extended walk-in closet with custom built-ins. Upstairs, a second master bedroom awaits, complete with its own private sitting area and full bath that’s ideal for multigenerational living or guests seeking privacy. Generously sized secondary bedrooms accommodate family or visitors comfortably, while the flexible upstairs theater/flex room with kitchenette doubles as a superb loft or secondary living space. Outside, your private outdoor oasis beckons: an extended covered lanai with sliding glass doors opens to a resort-style pool and spa, fully fenced extended backyard, and panoramic water views that make every day feel like a vacation. Additional premium features include custom window treatments, designer lighting throughout, a whole-home central vacuum system, energy-efficient double-pane windows, and a convenient 3-car attached garage. Immaculately maintained and brimming with thoughtful details, this exceptional waterfront home must be experienced in person to truly appreciate its elegance and tranquility.
Listing is courtesy of: FL PRO BROKERS LLC (407-790-7341)
Listing Agent: Michael Blank (407-595-0144)
150 WINDTREE LN #150, WINTER GARDEN, FL 34787
$195,000160 Days on yellowkey MLS ID: O6365343
REDUCED by $4,900 (2.5%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1984Monthly Fee: $300 Tax: $2,565 (2025)Community: Windree Gardens Ph 5Condo
Taxes:$2,565
Elementary School: Maxey Elem
Remarks: One or more photo(s) has been virtually staged. One of the Best Deals in Winter Garden! 5 MINUTES TO PLANT ST! Bright, well-maintained 2 Bed + 2 Bath condo with a wonderful split floor plan separated by open-concept kitchen and living room. The kitchen has quality appliances, including a new dishwasher, an inviting eat-in bar, and neutral finishes that complement any decor. The large great room fills with natural light and opens to a private patio - perfect for morning coffee, a good book, or unwinding at the end of the day. Additional conveniences include two reserved parking spaces, a huge secured storage area, and an in-unit Bosch washer and dryer. The quiet, well-kept community offers fantastic amenities such as a private pool, basketball courts, plenty of green space, and nearby walking trails. Schedule your viewing today!
Listing is courtesy of: ROMAN REALTY GROUP, LLC (407-876-1990)
Listing Agent: Brian Lemay (321-314-5412)
15684 ORANGE HARVEST LOOP, WINTER GARDEN, FL 34787
$469,90019 Days on yellowkey MLS ID: W7885221
INCREASED by $100,000 (27.0%) on 04/26/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2012 Built: 2016Monthly Fee: $366 Tax: $5,348 (2025)Community: Hickory HammockSpa: NoTownhouse
Taxes:$5,348
Elementary School: Whispering Oak Elem
Middle School: Hamlin Middle
Remarks: Welcome to 15684 Orange Harvest Loop, a 3-bedroom, 2.5-bath townhouse with a loft, located in the highly desirable Hickory Hammock neighborhood of Winter Garden, Florida. Known for its charming architecture and resort-style amenities, Hickory Hammock offers an exceptional lifestyle in one of Winter Garden's most sought-after communities. This inviting townhouse features a bright, open floor plan designed for both everyday living and entertaining. The main living areas create a warm and welcoming atmosphere that flows seamlessly into the kitchen, which offers ample cabinet and counter space for cooking, hosting, and gathering with family and friends. Upstairs, the spacious loft provides flexible living space ideal for a home office, media room, play area, or additional lounge. All three bedrooms are well sized, offering comfort and privacy. The primary suite serves as a relaxing retreat with an en-suite bathroom with dual vanities, while the additional bedrooms share a conveniently located full bath with a double sink vanity. A half bath on the main level adds extra convenience for guests. Residents of Hickory Hammock enjoy a wide array of resort-style amenities including a community pool, clubhouse, fitness center, playgrounds, walking trails, tennis courts, a dog park, scenic parks, and a fishing pier. Ideally located near Disney World, downtown Winter Garden, top-rated schools, shopping, dining, and major roadways such as SR 429, this home offers both convenience and an active, community-focused lifestyle. Schedule your private showing today and experience everything this wonderful townhouse has to offer.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Mary Sue Piesik (352-232-6873)
13212 SOCIAL LN, WINTER GARDEN, FL 34787
$595,00029 Days on yellowkey MLS ID: O6398708
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2005Monthly Fee: $100 Tax: $4,474 (2025)Community: Regency Oaks FSpa: NoSingle Family
Taxes:$4,474
Elementary School: SunRidge Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the highly sought-after Regency Oaks community. Thoughtfully upgraded for long-term peace of mind, this residence features a newly replaced roof, a 2023 HVAC system (both indoor and outdoor units), and a 2023 water heater—major improvements that add exceptional value and confidence for the next owner. Step inside to discover a bright, open floor plan with luxury vinyl flooring throughout, offering durability, modern style, and easy maintenance. The remodeled kitchen showcases sleek modern cabinetry and quartz countertops, creating a fresh, contemporary space perfect for everyday living and entertaining. The spacious primary suite provides a comfortable retreat, complemented by three additional bedrooms ideal for family, guests, or a home office. With two full bathrooms and a convenient half bath, the layout is designed for both functionality and comfort. Enjoy Florida living at its best with a screen-enclosed patio and a fully paved backyard, offering a low-maintenance outdoor oasis perfect for gatherings, grilling, or quiet relaxation. Located just 15 minutes from Universal Studios and Disney Parks and less than a 2-minute walk to AdventHealth, this home is perfectly positioned for both families and professionals. Regency Oaks offers resort-style amenities including a sparkling pool, clubhouse, tennis courts, playground, and a scenic park—enhancing the lifestyle experience beyond your front door. This move-in-ready home combines modern upgrades, unbeatable convenience, and exceptional community features—an outstanding opportunity to enjoy the best of Winter Garden and Orlando living. Some photos have been virtually staged for visualization purposes.
Listing is courtesy of: PMI PRIME HOME (407-218-7598)
Listing Agent: Jianlin Shi (407-988-5057)
1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787
$929,00047 Days on yellowkey MLS ID: O6394506
REDUCED by $20,900 (2.2%) on 04/20/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3841 Built: 2017Monthly Fee: $184 Tax: $12,543 (2025)Community: TwinwatersSingle Family
Taxes:$12,543
Elementary School: Hamlin Elementary
Remarks: Welcome to 1646 Holcomb Creek Street. Your beautifully appointed four bedroom, 4.5-bath Meritage home offers 3,824 sq ft of thoughtfully designed living space in one of Winter Garden’s most desirable communities. Built in 2017, this energy-efficient floorplan features spray foam insulation, whole house water filtration system, a spacious open layout, high-end finishes, and multiple flexible living areas. The gourmet kitchen impresses with 42" cabinetry, quartz countertops, stainless steel appliances, extended storage, walk in pantry and a large eat-in dining area. The family room includes an electric fireplace with a floor-to-ceiling stone accent wall and triple sliding glass doors leading to the screened lanai and fenced backyard. The first-floor primary suite offers a tray ceiling and a spa-inspired bath with direct access to the laundry room. A guest suite with private bath, third bedroom with an additional private bath, powder room, and a convenient pocket office completes the main level. Upstairs, a large bonus/game room, additional bedroom, full bath, and a flexible pass-through space provides endless possibilities for a media room, playroom, office or optional 5th bedroom. Your garage offers overhead storage and a Tesla-E/V charger. Exterior features include a tile roof, stone accents, extended front porch, in ground irrigation and lush landscaping. Located minutes from top-rated schools, shopping, dining, major highways and attractions. This exceptional home offers the perfect blend of luxury, comfort, and efficiency—move-in ready and meticulously maintained.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)
Listing Agent: Jennifer Grimes (352-223-9588)
2230 ROMANUM DR, WINTER GARDEN, FL 34787
$565,00064 Days on yellowkey MLS ID: O6389947
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
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!
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcelle Da Silva Sampaio (407-369-3621)
17549 SEIDNER RD, WINTER GARDEN, FL 34787
$950,00048 Days on yellowkey MLS ID: O6392430
1 Days Off yellowkey (back on 4/18/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2130 Built: 1985Monthly Fee: $3 Tax: $3,947 (2025)Community: Lake Avalon HeightsSingle Family
Taxes:$3,947
Remarks: Under contract-accepting backup offers. Welcome to 17549 Seidner, a remarkable lakefront property that invites you to experience the enchanting lifestyle of Winter Garden, Florida. Set against a backdrop of majestic oak trees, this sprawling 3-acre haven rests on the stunning south shore of the pristine Lake Avalon. Here, the beauty of nature thrives, offering a tranquil escape where the gentle sounds of water lapping against the shore harmonize with the vibrant chorus of local wildlife. Lake Avalon, a private 184-acre freshwater lake, is celebrated as one of Central Florida's top ten lakes, perfect for fishing, water sports, and leisurely summers spent soaking in the sun. Nestled within the esteemed Avalon Rural Settlement, this property ensures that its serene, rural character remains preserved for generations to come. The existing 2,130-square-foot home provides a cozy yet spacious retreat, featuring three bedrooms and two and a half bathrooms. The thoughtfully designed split floor plan places the primary ensuite on one side of the home, complete with an inviting sitting area that grants stunning views of the lake. The kitchen, with its charming eat-in area, offers a picturesque glimpse of the expansive oaks that surround you. Step outside onto the oversized back porch to witness the breathtaking sunsets and beautiful lakefront view. On chilly nights, retreat into the lake-facing living room, where a cozy fire awaits to warm your soul. The property also boasts a large workshop equipped with electricity and water, perfect for a boat house, workshop, or extra garage space. You have the option to renovate this lake life retreat or build your dream lake front home. Immerse yourself in the exquisite flora and fauna that adorn this outdoor oasis, where sandhill cranes, wild rabbits, and a plethora of birds call home. With lovingly cultivated native plants and a cherished pond in the backyard, every day feels like a retreat into nature's embrace. This is not just a home; it’s an opportunity to live the lake life you’ve always dreamed of.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Brenda Feliciani (407-405-0931)
14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787
$1,099,00060 Days on yellowkey MLS ID: O6390518
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4661 Built: 2018Monthly Fee: $210 Tax: $14,115 (2025)Community: Oxford ChaseSpa: YesSingle Family
Taxes:$14,115
Remarks: Welcome to this beautifully upgraded 5 bedroom, 4 and a half bath pool and spa home located in the highly desirable, fully gated community of Oxford Chase! Zoned for top-rated schools, this home offers the perfect combination of luxury, privacy, and energy efficiency. This spacious residence features a 3-car garage, paver driveway, and impressive curb appeal. Inside, you’ll find thoughtfully designed living spaces including a formal dining room with a custom built-in bar, perfect for entertaining guests or hosting special occasions, multiple office spaces, upgraded flooring throughout, a large laundry room, private gated doggie retreat, and so much more. The primary suite is located on the first level, secluded for optimal privacy with oversized his and hers closets. Upstairs you'll find guest bedrooms, a large open air loft space, and plush movie theatre room. Step outside to your own gorgeous backyard oasis featuring a fully enclosed heated pool and spa, ideal for year-round Florida living. The backyard overlooks a peaceful green space with no rear neighbors, providing extra privacy and relaxing views. Enjoy outdoor entertaining with the fully equipped summer kitchen featuring a custom vented hood, perfect for grilling and gatherings. The home is also equipped with PAID IN FULL SOLAR PANELS offering incredible energy efficiency and the benefit of little to no electric bill. Located in a secure gated neighborhood close to top schools, shopping, dining, and major highways, this home truly has it all — privacy, premium upgrades, and resort-style outdoor living. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787
$645,900574 Days on yellowkey MLS ID: O6250356
2 Days Off yellowkey (back on 4/23/2026)
REDUCED by $3,900 (0.6%) on 04/17/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3359 Built: 2001Monthly Fee: $233 Tax: $8,538 (2023)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,538
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Popular Stoneybrook West Subdivision - A gated golf community with 2255 homes. 2 Story, 4 Bedrooms, 3 Full Baths. Master is upstairs, huge bedroom, with walk in closet and master bath. A large 27x24 Bonus room over 3 Car Garage. One bedroom with guest bath downstairs also LR, DR, FR, Kitchen and Laundry. Off the master bedroom is a 12x22 Deck overlooking the screened pool and golf course. Nice quiet street also. The seller will give an allowance for new flooring & kitchen appliances, so buyer can pick their favorite colors.
Listing is courtesy of: RE/MAX SELECT GROUP (407-352-5800)
Listing Agent: Paul Mcgarigal (407-352-5800)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,00028 Days on yellowkey MLS ID: O6396654
1 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $7 Tax: $5,354 (2025)Community: Kings BaySingle Family
Taxes:$5,354
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
205 SURPRISE DR, WINTER GARDEN, FL 34787
$1,200,000162 Days on yellowkey MLS ID: O6365188
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2171 Built: 1950 Tax: $3,406 (2024)Community: Winter Garden Shores RepSingle Family
Taxes:$3,406
Remarks: Under contract-accepting backup offers. PRICE ADJUSTED to reflect recent appraisal, this four-lot parcel presents immediate value- with two vacant lots ready for expansion, additional income potential, or future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four-lot parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. Two of the four lots are currently vacant, offering potential to subdivide, expand, or build. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
64 N PARK AVE, WINTER GARDEN, FL 34787
$1,095,00080 Days on yellowkey MLS ID: O6385285
REDUCED by $54,000 (4.7%) on 04/22/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2225 Built: 2023Monthly Fee: $325 Tax: $15,104 (2025)Community: 30 North ParkTownhouse
Taxes:$15,104
Remarks: Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
650 SETTING SUN DR, WINTER GARDEN, FL 34787
$740,00058 Days on yellowkey MLS ID: O6390644
1 Days Off yellowkey (back on 4/22/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3605 Built: 2006Monthly Fee: $123 Tax: $9,067 (2025)Community: Black Lake Park Ph 01Single Family
Taxes:$9,067
Remarks: Under contract-accepting backup offers. Invite your buyers to discover this beautiful 5-bedroom, 3-bath home offering 3,605 square feet of living space, freshly painted with a brand-new roof installed in 2025. The spacious open-concept kitchen flows seamlessly into the main living areas, creating the perfect space for everyday living and entertaining. Step outside to an oversized back porch, ideal for enjoying Florida’s year-round sunshine with family and friends. Located in the Black Lake Park community, residents enjoy a boat ramp, pool, tennis courts, pickleball courts, soccer field, and a large playground. Just minutes from charming Downtown Winter Garden, with easy access to shopping, dining, and scenic rides along the West Orange Trail.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Nicholas Leloudis (407-489-0711)
276 SUMMER PINE ST, WINTER GARDEN, FL 34787
$875,00083 Days on yellowkey MLS ID: O6384565
REDUCED by $5,000 (0.6%) on 04/22/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3147 Built: 2025Monthly Fee: $240 Tax: $1,914 (2024)Community: Winter GroveSpa: NoSingle Family
Taxes:$1,914
Remarks: QUICK MOVE IN!!! NEWLY BUILT Highly Desirable Community and Location!! Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from Historic Downtown Winter Garden. This Gated New Community features single-family homes on large homesites without a CDD. Step into the Coral Grand by Pulte Homes, where Luxury and Convenience seamlessly combine to create a Truly Elevated Living Experience. This Remarkable 4-Bedroom 3-Bathroom 1-Flex Room Home, Offers an Oversized Driveway and Corner Lot. The Chef-Inspired Kitchen Features Upgraded Dana White Cabinetry (Soft Close), Oversized Quarts Countertops, Undercabinet Lighting, and Whirlpool Stainless Steel Appliances with Exhaust Fan Exterior, Making Cooking a True Pleasure. The Kitchen seamlessly connects to the Café and Extended Gathering room, where a Sliding Glass Door opens to the Covered Lanai, Enhancing the flow of Indoor-Outdoor Living. The Loft area provides the perfect space to unwind, with two additional bedrooms and one bathroom complete the upper level. This Elegant Home is Equipped with a Smart Nest Thermostat, Smart Google Doorbell, ensuring your home is as connected as it is Beautiful. This home offers the perfect combination of Luxury, Convenience, and Modern Design—an ideal place to live and relax. This Split Floorplan Design of the Home and Laundry Room maximizes Privacy, Useful Space, and Peace. Residents also enjoy all the proximity to Shopping Plazas, Restaurants, Parks, and Entertainment this area is known for. Call NOW and Schedule a tour today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Raymond Tong (954-940-1628)
604 FOSTER AVE, WINTER GARDEN, FL 34787
$400,00034 Days on yellowkey MLS ID: O6389095
0 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1975 Tax: $1,633 (2024)Community: Westchester PlaceSingle Family
Taxes:$1,633
Remarks: Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart District and directly across from Veterans Memorial Park, this property offers a lifestyle that blends convenience, privacy, and outdoor living. BRAND NEW ROOF JUST INSTALLED! (April 2026, 10-yr warranty) Set on a rare double lot, the home welcomes you with mature landscaping, an orchid tree in the front yard, stylish Bermuda hurricane shutters, and a covered front porch that provides a charming place to relax and enjoy the neighborhood. Inside, the spacious layout features durable porcelain wood-grain tile flooring installed in 2017, a bright living area, and a generous kitchen designed for everyday functionality and gathering. Major updates provide peace of mind, including all new double-pane windows installed in 2021, a water heater replaced in 2020, HVAC from 2019 (installed 2021) under warranty with American Air & Heat, and upgraded WiFi. Outside is where the property truly shines. The fully fenced backyard offers exceptional privacy with mature landscaping, fruit trees including kumquat, green apple, mango, and pineapple, along with bananas, plantains, pecan, and raised herb beds featuring aloe, basil, spearmint, and Italian oregano. Entertain or unwind on the recently resealed paver patio or under the pergola, while the powered shed with custom shelving and ramp provides flexible space for hobbies or storage. Additional features include a large private driveway, gutters, double weather-stripped front doors, and a chicken coop. With extensive updates, functional living space, and a backyard designed for gardening, relaxing, and entertaining, this home offers a unique opportunity to enjoy both comfort and outdoor lifestyle.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Jackie Isham (407-917-8954)
87 WINDTREE LN #K, WINTER GARDEN, FL 34787
$205,00077 Days on yellowkey MLS ID: G5108773
REDUCED by $15,000 (6.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1984Monthly Fee: $300 Tax: $587 (2024)Community: Windtree Gardens Condo Ph 03Condo
Taxes:$587
Remarks: Large Price Improvement. Downstair location, peace and ease with this updated 2/2 FIRST FLOOR condo in Winter Garden. You will love this condo placement in the rear of the community near the pond with fountain, community pool, rentable clubhouse, basketball courts and NO STAIRS. Enjoy the private setting while sitting on your screened porch with your favorite book or beverage and the frequent visits from the neighborhood ducks. The condo has been updated to include the cabinets, counters, updated bathrooms and tile floors throughout. Move in ready so just grab your things and come on. What's Nearby? ANYTHING you could need or want. Only 1.5 miles from downtown Winter Garden, 2.5 miles to Winter Garden Village, 15 miles to Walt Disney World® and other theme parks, 24 miles to MCO Orlando's International Airport/Brightline highspeed passenger train and just over an hour to dip your toes in salty water and sand on Florida's World Famous Beach in Daytona. Downstair units with perfect location do not come around often so book your private tour today and ask your REALTOR for the video walk through link.
Listing is courtesy of: BONJORN REAL ESTATE (352-394-2112)
Listing Agent: Mendy Bacon (407-383-7213)
15350 OAK APPLE CT #17B, WINTER GARDEN, FL 34787
$329,90035 Days on yellowkey MLS ID: O6396724
0 Days Off yellowkey (back on 4/16/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008Monthly Fee: $282 Tax: $2,474 (2025)Community: Tucker OaksCondo
Taxes:$2,474
Remarks: Under contract-accepting backup offers. This beautiful 3 bedroom, 2.5 baths and 2 car garage is taken care of with Pride and Joy. Home is in Immaculate condition. Home flows from room to room with the primary en suite on the second floor. Also has lots of built in storage and overhead storage in the garage. Offers a screened in porch with no rear neighbors for relaxing and family time. Conveniently located near shopping, dining, major highways and historic downtown Winter Garden, Oakland & The West Orange Trail.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Tracy Hampstead (407-803-3137)
671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,325,00067 Days on yellowkey MLS ID: O6383438
0 Days Off yellowkey (back on 4/17/2026)
REDUCED by $25,000 (1.9%) on 04/08/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4490 Built: 2019Monthly Fee: $300 Tax: $12,519 (2024)Community: Canopy Oaks Ph 1Spa: YesSingle Family
Taxes:$12,519
Remarks: Under contract-accepting backup offers. Canopy Oaks, located in Winter Garden, Florida, is a unique blend of high-end luxury homes and suburban tranquillity. This gated enclave, developed by the distinguished home builder A.R. Bailey, features 49 classic estates. The meticulously crafted community is designed to cater to the specific needs and desires of homeowners, and includes a scenic nature trail, a children’s play park, and a community post office. From the moment you arrive at this Mediterranean POOL estate home, it makes a BOLD statement with its 8-foot Solid Wood Arched double entry doors. You are greeted with cathedral ceilings, solid wood oversized French doors to the private office, elegant hand forged custom iron railings, and a unique wine cellar with a custom hand forged iron gate. Luxury details and fine craftsmanship are inside this 5 BR/4.5 Ba/2-car garage POOL home. Open Floor plan leads pleasantly into the chef-style kitchen with the perfect layout for entertaining. The kitchen includes Bespoke Samsung stainless steel appliances, including a Family Hub Refrigerator. Gas stove top, built-in oven, and built-in convection oven. Granite counters. Completing the 1st floor, in addition to the 1st MBR, is a den/office, laundry room, generous dining area, powder bath, epoxy-coated garage floor 2-car garage, Autel Level 2 EV Charger and large lanai complete with Remote controntrolled, motorized retractable patio screens (upstairs and downstairs). The lanai and pool area are designed as additional living space, with pre-plumbing and Gas for your Summer Kitchen. Tons of architectural features throughout, upgraded light fixtures. Both Primary Suites have built in Kitchenettes. The media room includes a mini kitchenette with sink and microwave, and the theatre is wired for a 5.1 in-wall sound system. Three en-suite bedrooms and a Second Master Suite can also be found on this upper floor – perfect for multi-generational options and living privacy. The upstairs primary bathroom and closet are a dream come true. The Spa style bath has granite countertops, custom wood cabinetry, spacious dual sinks, an elegant free-standing soaking tub, seperate frameless glass wall shower with a bench. The custom-made, upgraded, solid wood oversized closet is Couture-Ready. Rainsoft whole-home water filtration/treatment/softener system. Luxury saltwater pool and spa. Privacy hedges along the side yard. Pool lighting; spa with custom tile; finished pool surface; low-maintenance turf and landscaping in the backyard. Exterior lighting, LED trim lighting. The list goes on and on. This home is a must see. An exceptional estate at an exceptional value, Canopy Oaks is located on Roper Road between Winter Garden’s downtown historic district and the Winter Garden Village shopping complex. With convenient access to major highways such as 429, 408, and the Turnpike, and its proximity to world-renowned attractions like Disney World® and Universal Studios®, this home offers an exceptional opportunity for easy commuting.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Sean Flatley (609-208-8204)
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