Location: Winter Garden
Keyword(s): Lakeview Middle
Keyword(s) Middle School: Lakeview Middle
Do Not Show Listings
1674 VICTORIA WAY, WINTER GARDEN, FL 34787
$669,990182 Days on yellowkey MLS ID: O6357191
REDUCED by $5,000 (0.7%) on 04/28/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2239 Built: 1992Monthly Fee: $29 Tax: $6,345 (2024)Community: TuscanySpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,345
Elementary School: Maxey Elem
High School: Ocoee High
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: Beautifully updated POOL home in the desirable Tuscany community! Major updates include a new water heater (2020), whole house re-plumed (2021), new saltwater pool/spa with panoramic screen (2022), and new HVAC (2024). Pool features include Heat pump/chiller combo, iAquaLink (an intelligent pool control-turn on filter, lights, spa through app), auto fill/auto drain, bubbler, and Eco pool feature (circulation). Kitchen features quartz counters, 42” cabinets, stone backsplash, and stainless appliances, opening to a cozy family room with fireplace and French doors to the pool. Enjoy a private primary suite with pool access and a luxurious bath. Additional highlights include crown molding, 10-ft ceilings, bamboo/slate/travertine flooring, smart thermostat, and a fully fenced backyard. Excellent location near the West Orange Trail, downtown Winter Garden, and SR 429. This home truly shines!
Listing is courtesy of: RE/MAX DOWNTOWN (407-770-2050)
Listing Agent: Marlon Vega (407-791-0572)
1419 HUNTERMAN LN, WINTER GARDEN, FL 34787
$479,90051 Days on yellowkey MLS ID: O6390064
1 Days Off yellowkey (back on 3/20/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2840 Built: 2005Monthly Fee: $42 Tax: $7,786 (2025)Community: Chapin Station ASingle Family
Taxes:$7,786
Tax Year: 2025
Remarks: Under contract-accepting backup offers. This impressive 5-bedroom, 3.5-bathroom residence is situated on a sprawling large corner lot, offering both privacy and abundant outdoor space. The interior is defined by high ceilings and an array of large windows that flood the home with natural light, creating an airy and ambiance. Designed for maximum comfort and privacy, the layout features a primary master suite along with two additional bedrooms boasting their own en suite bathrooms, making it an ideal floor plan for multi-generational living or hosting guests. With its generous proportions and premium lot positioning, this home represents a rare opportunity for those seeking space, light, and a versatile, high-end configuration.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
312 SILVERDALE AVE, WINTER GARDEN, FL 34787
$559,90026 Days on yellowkey MLS ID: O6396680
0 Days Off yellowkey (back on 4/27/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 2007Monthly Fee: $72 Tax: $2,473 (2025)Community: Covington Park A B D E F G & JSingle Family
Taxes:$2,473
Elementary School: Dillard Street Elem
Remarks: Located in the golf cart district just minutes from the charm of Downtown Winter Garden, this beautifully maintained 3-bedroom single-family home in the highly desirable Covington Chase community offers the perfect blend of comfort, functionality, and lifestyle. Inside, you'll find a flexible and spacious open-concept layout, featuring a front living area and formal dining space, seamlessly connected by an open kitchen and main living area. The kitchen is well-appointed with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, along with a breakfast bar and space for a casual dining table. The primary suite is privately situated off the living room and features a walk-in closet and an ensuite bathroom complete with dual vanities, a soaking tub, and a separate walk-in shower. Two additional generously sized bedrooms and a full family bathroom are thoughtfully positioned, along with a dedicated laundry room that provides direct access to the two-car garage. Sliding glass doors from the living area lead to a screened rear patio, opening out to a spacious, fully fenced backyard, with vinyl panels to the back and aluminum fencing to the sides. Residents of Covington Chase enjoy access to a community pool and playground, while the home’s location along the West Orange Trail makes it easy to enjoy an active, outdoor lifestyle. With close proximity to local restaurants, cafés, shops, and everyday conveniences, as well as easy access to major roadways, this home truly offers the best of Winter Garden living.
Listing is courtesy of: WINTER GARDEN REAL ESTATE (407-910-1066)
Listing Agent: Anthony O'Reilly Brookes (407-910-1066)
512 GARDEN HEIGHTS DR, WINTER GARDEN, FL 34787
$577,90092 Days on yellowkey MLS ID: S5142675
REDUCED by $7,100 (1.2%) on 04/23/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1700 Built: 1974 Tax: $3,743 (2024)Community: Garden HeightsSingle Family
Taxes:$3,743
Remarks: Price Improvement! Exceptional new value. Welcome to this beautifully maintained 4-bedroom, 2-bathroom single-family home located in the highly desirable Garden Heights community of Winter Garden, offering a prime location with NO HOA. Recently improved in price, this home now presents an even stronger opportunity in today’s market, combining location, upgrades, and value in one of Winter Garden’s most sought-after areas. Thoughtfully designed with a functional split floor plan, this residence offers 1,700 sq ft of living space filled with natural light and two separate living areas that provide both comfort and flexibility. Sliding glass doors open to a brand-new screened patio (2025), creating the perfect indoor-outdoor lifestyle for relaxing or entertaining. The interior features a beautifully updated kitchen and bathrooms, luxury vinyl plank flooring throughout, and modern upgrades including a whole-house water filtration system. Set on an expansive 0.29-acre lot, the property offers city water and sewer, along with ample space to add a pool or design a custom outdoor retreat. Conveniently located just minutes from Downtown Winter Garden, Lake Apopka, the Historic Old Winter Garden Golf District, shopping, top-rated schools, and easy access to SR-429.Homes with this combination of location, updates, and improved pricing are rarely available. Don’t miss this opportunity
Listing is courtesy of: MARCILLO REAL ESTATE LLC (954-297-3636)
Listing Agent: Maria Barrios Tovar (407-600-4040)
1125 LINCOLN TER, WINTER GARDEN, FL 34787
$242,400221 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
Taxes:$2,026
High School: West Orange High
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
$1,025,000205 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)
1606 MALCOLM POINT DR, WINTER GARDEN, FL 34787
$599,900284 Days on yellowkey MLS ID: TB8409266
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2455 Built: 2003Monthly Fee: $33 Tax: $2,940 (2024)Community: Tuscany Ph 02Single Family
Taxes:$2,940
Remarks: ***Golf Cart District*** Nestled in a serene cul-de-sac in the heart of Winter Garden, Florida, this stunning 4-bedroom, 3-bathroom contemporary stucco home offers 2,455 square feet of comfort and style. Blending elegance and functionality, this residence has been meticulously updated with high-end features, making it an ideal choice for discerning buyers seeking a move-in-ready home. Gorgeous Carrera marble countertops in kitchen and bathrooms, with stylish subway tile backsplash. Step inside to discover a bright and airy floor plan, enhanced by new windows installed in 2020, rated for hurricanes up to 185 MPH, the home features a whole-house water filtration system with UV light for clean, purified water throughout. New carpet in rarely used guest bedrooms. Master bedroom closet expanded to be pass through to His and Hers Full Bathrooms, you'll love this setup! The open-concept living area flows seamlessly, offering ample space for gatherings and everyday living, a beautifully updated kitchen, featuring refinished cabinets (2020) and stainless steel appliances, including a new induction cooktop stove, microwave, and dishwasher, all installed in 2020. There is also a brand new 55 Gallon hot water heater installed less than 2 years ago. The exterior is stucco complemented by a new roof installed in 2020, ensuring durability. The front of the home is adorned with permanent trim lights, controllable via an app to change colors and patterns. The fenced backyard provides privacy, professionally designed 32 x 15 paver patio with a sitting wall, fans with Aeromist misting system, Patio lights and a retractable awning creates a shaded outdoor oasis. A large 10 x 12 permitted site-built shed offers ample storage or workshop space and the irrigation system keeps the lush landscaping vibrant and low-maintenance. This home is designed for effortless living. Located in vibrant Winter Garden, in the highly desirable Tuscany neighborhood, this home offers easy access to charming downtown shops, restaurants, golf cart district and the scenic West Orange Trail. Prepare to be impressed!
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787
$815,0008 Days on yellowkey MLS ID: O6402075
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3580 Built: 2008Monthly Fee: $72 Tax: $4,880 (2025)Community: Covington ParkSpa: NoSingle Family
Taxes:$4,880
Remarks: One or more photo(s) has been virtually staged. Welcome to Covington Chase, one of the most sought-after communities in Winter Garden, just minutes from the charm and energy of historic downtown. Situated on an oversized 0.38-acre lot, this 4-bedroom, 4 full bathroom home offers a rare combination of space, functionality, and flexibility. The fully fenced backyard provides plenty of room to relax, entertain, or create your own outdoor retreat, while the long driveway and 3-car garage give you ample parking and storage, including space for a golf cart so you can fully enjoy this golf cart district lifestyle. The floor plan is thoughtfully designed for both everyday living and long-term versatility. The primary suite is located downstairs, creating a private retreat with two walk-in closets and a large bathroom that offers both space and comfort. Also on the first floor is a dedicated office, perfect for working from home or creating a quiet, separate space for productivity. In addition, the first floor features a Jack and Jill bedroom and bathroom setup, ideal for guests, kids, or multigenerational living. This layout allows for privacy while still maintaining a connected and functional flow throughout the home. Upstairs, you will find a spacious loft that can be used as a second living area, media room, or play space, along with a full bedroom and full bathroom. This upstairs setup is perfect for guests, older children, or anyone who would benefit from having their own private area within the home. The overall layout gives you multiple living zones and flexibility, making it easy to adapt the home to your lifestyle, whether that means working from home, hosting guests, or simply enjoying extra space. The roof was replaced just a few years ago, offering added peace of mind and reducing one of the major future expenses for a new owner. Beyond the home itself, the lifestyle here is what truly stands out. You are just minutes from the Downtown Winter Garden Historic District, known for its brick-lined streets, locally owned restaurants, coffee shops, boutiques, and the popular weekly farmers market. Living in the golf cart district means you can easily head downtown for dinner, events, or a casual night out without needing to get in your car. You are also close to the West Orange Trail, a 22-mile scenic trail perfect for biking, walking, and enjoying the outdoors. Homes with this kind of lot size, a flexible floor plan with a downstairs primary suite, office, additional bedroom, plus an upstairs loft and private guest space, and a 3-car garage are hard to find this close to downtown. This is a unique opportunity to own a home that offers both the space you need and the lifestyle you want.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
150 WINDTREE LN #150, WINTER GARDEN, FL 34787
$195,000147 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
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)
408 S BOYD ST, WINTER GARDEN, FL 34787
$815,00032 Days on yellowkey MLS ID: O6394810
REDUCED by $20,000 (2.4%) on 04/15/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2295 Built: 1939 Tax: $2,572 (2025)Community: G T Smith Sub 3Spa: NoSingle Family
Taxes:$2,572
Remarks: Charming home located just blocks from Winter Garden's historical downtown in the highly sought-after GOLF CART DISTRICT! This 3 bedroom, 3 Bath house blends timeless character with modern living, featuring hardwood floors, vintage tiled bathroom, built-ins, and a traditional layout with separate dining room. The kitchen opens to a comfortable family room, ideal for everyday living. The primary suite offers a spacious, spa-like bath with freestanding tub, walk-in shower, and custom vanity. A recent addition includes an oversized two-car garage , HVAC , large pantry, and bathroom to the third bedroom, creating a private en-suite with separate exterior entrance, ideal for guests or flexible living. Situated on a fenced, .41-acre corner lot, enjoy the screened-in back porch, expansive yard with mature landscaping, and the pavered pool area-perfectly designed for entertaining. Live the Historical Downtown Winter Garden Life-Style with convenient access to dining, shopping, farmer's market, Lake Apopka sunsets, and more.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,00015 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
$1,200,000149 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.
64 N PARK AVE, WINTER GARDEN, FL 34787
$1,095,00067 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)
604 FOSTER AVE, WINTER GARDEN, FL 34787
$400,00021 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
$205,00064 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)
156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787
$1,200,00058 Days on yellowkey MLS ID: O6384801
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3170 Built: 2018Monthly Fee: $188 Tax: $7,979 (2024)Community: Stanton EstatesSingle Family
Taxes:$7,979
Remarks: Welcome to Golf Cart Life in Historic Downtown Winter Garden! Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this stunning contemporary masterpiece is perfectly positioned in Winter Garden's coveted Golf Cart District. Built in 2018, this one-story multigenerational estate delivers 3,170 square feet of refined living on a nearly 1/3-acre lot, just a short golf cart ride from Plant Street, the Crooked Can Brewery, the weekly farmer's market, and the West Orange Trail. Inside, soaring 12-foot ceilings and abundant natural light flow through an open, flexible floor plan with four bedrooms, four full bathrooms, and a large private office. The gourmet kitchen is the heart of the home — featuring solid wood cabinetry, quartz countertops, an oversized center island, walk-in pantry, and a full suite of KitchenAid Professional appliances with a natural gas cooktop. The primary suite impresses with a recessed ceiling, expansive custom walk-in closet, and a spa-inspired oversized bath. Step outside through fully retractable sliding glass doors to a covered lanai wrapped in mature, professionally designed landscaping and privacy fencing — your own Florida retreat. Premium finishes throughout include smart home technology, motorized shades, whole-home water filtration, 8-foot solid core interior doors, colonial-style trim, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408 — this is one of Central Florida's most desirable addresses. Opportunities like this in Stanton Estates are rare. Welcome home.
Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)
Listing Agent: Joe Thomas, Jr (813-724-1922)
15350 OAK APPLE CT #17B, WINTER GARDEN, FL 34787
$329,90022 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
Elementary School: SunRidge Elementary
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)
373 ERON WAY #47, WINTER GARDEN, FL 34787
$163,999114 Days on yellowkey MLS ID: O6371713
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1989Monthly Fee: $424 Tax: $2,015 (2025)Community: Townhomes Winter GardenCondo
Taxes:$2,015
Remarks: Short Sale. MOVE-IN READY and quietly positioned within a well-established Winter Garden community, this updated 2-bedroom, 2-bath condo offers a NEW ROOF, and an easy, comfortable lifestyle in one of Central Florida’s most desirable areas. Approaching the home, you’ll appreciate the tucked-away cul-de-sac location with paved private streets and sidewalks that create a calm, residential feel. Step inside through the front entrance and you’re immediately welcomed into a bright, open living space where natural light enhances the clean layout and efficient use of square footage. The living room feels inviting and functional, offering enough space to relax, entertain, or simply enjoy a quiet evening at home. Continuing through the home, the upgraded kitchen with GRANITE counter tops, anchors the main living area with modern appliances, ample cabinetry, and practical counter space. Its open connection to the living room allows for easy conversation while cooking, hosting, or enjoying everyday routines, making the space feel connected and intentional. The primary bedroom is set apart as a comfortable retreat, featuring brand-new carpeting and a private en-suite bathroom. The bathroom has been thoughtfully renovated with updated finishes that feel fresh and clean without excess. The secondary bedroom is well-sized and flexible, ideal for guests, a home office, or additional living space, with a second fully updated bathroom conveniently nearby. Throughout the condo, the layout flows efficiently from room to room, offering smart storage, comfortable proportions, and a low-maintenance design well suited for full-time living or long-term ownership. Assigned parking adds convenience, while the community’s shared amenities—including a COMMUNITY POOL—enhance the overall lifestyle. Located just minutes from downtown Winter Garden, residents enjoy close proximity to local shops, dining, farmers markets, and the West Orange Trail. Easy access to major highways makes commuting throughout Central Florida simple, whether heading toward downtown Orlando, major employment centers, or nearby attractions. This location is ideal for buyers exploring Orlando homes for sale or those planning an Orlando relocation home in a walkable, community-oriented area. While not intended as a short-term rental investment, this Winter Garden property represents a strong opportunity within the Central Florida real estate market for buyers seeking comfort, location, and value. Contact us today for a private tour or more details on this exceptional opportunity.
Listing Agent: Simi Lakhani (407-408-7393)
441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787
$1,199,90058 Days on yellowkey MLS ID: O6385964
INCREASED by $80,900 (7.2%) on 04/02/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4001 Built: 2000Monthly Fee: $83 Tax: $5,551 (2024)Community: Courtlea OaksSpa: YesSingle Family
Taxes:$5,551
Remarks: One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Jennifer Coon (321-948-8056)
375 REGAL DOWNS CIR, WINTER GARDEN, FL 34787
$334,90066 Days on yellowkey MLS ID: O6377205
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1464 Built: 2001 Tax: $4,413 (2024)Community: Regal Pointe Ph 01 43/129Single Family
Taxes:$4,413
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!
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