Homes for Sale Near Lakeview Middle in Winter Garden - 41 homes

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)

Remarks: 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)

Remarks: Golf cart district * Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden.It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!

Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)

Listing Agent: Mingke Li (352-973-2303)

Remarks: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Rick Evans, Ii (407-538-9295)

Remarks: 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)

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 is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

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)

Remarks: Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 of an acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. At the heart of the home, the chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, community connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)

Remarks: 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)

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!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. Live the downtown Winter Garden lifestyle in this beautifully upgraded CORNER UNIT townhome in the sought-after community of Heritage at Plant Street—perfectly located in the GOLF CART DISTRICT with direct access to the renowned WEST ORANGE TRAIL. Built in 2018 by M/I Homes and meticulously maintained by its original owners, this 2-story, 3 bedroom, 2.5 bath townhome with a 2-car garage offers the ideal combination of low-maintenance living, thoughtful upgrades, and a prime corner location. With HOA-covered exterior maintenance—including the roof and grounds—you’ll spend less time on upkeep and more time enjoying everything downtown living has to offer. The coveted corner placement provides extra privacy, abundant natural light, and a common area GRASSY SIDE YARD perfect for pets or play, while a large guest parking lot sits conveniently just steps from the front door. Inside, the Windham II floor plan features soaring ceilings and a bright, open layout. A light-filled den off the foyer with three large windows offers flexibility as a home office, playroom, or second living space. The heart of the home is the DESIGNER KITCHEN, showcasing slate GE Profile appliances, a NATURAL GAS COOKTOP AND CUSTOM RANGE HOOD, stacked convection wall oven and microwave, and 42" dark shaker cabinetry with hardware. SILESTONE countertops, tiled backsplash, under-cabinet LED lighting, and stylish pendant lights complete the space. The large island with breakfast bar and included barstools opens seamlessly to the dining area and great room, creating the perfect setup for entertaining. Corner-unit placement provides windows on two sides of the great room and dining area, creating a bright, naturally lit living space. The entire first floor features durable large format ceramic tile flooring, while the staircase has been upgraded with dark engineered wood for a polished, low-maintenance look. A spacious laundry room with full-size washer and gas dryer, upper cabinets, and an oversized under-stair storage nook adds everyday convenience. Upstairs, the private primary suite offers a large walk-in closet and an elegant en-suite bath with raised-height dark shaker cabinetry, Silestone double vanity, and a tiled walk-in shower with seamless glass enclosure. Two additional bedrooms share a well-appointed bathroom with matching finishes and a tiled tub/shower combination. Step outside through the French door with built-in blinds to your private, screened brick-paver courtyard, offering both covered and open seating areas—perfect for relaxing or entertaining while overlooking the grassy side yard. The adjoining two car garage with alley access includes screened sliders for a cross breeze into the patio area. Energy-efficient features include ENERGY STAR double-pane Low-E windows, HVAC, insulation, and appliances. The ROOF, HVAC, and INSTANT HOT GAS WATER HEATER were installed in 2018 and have been regularly serviced. The home also features modern high end, noise free ceiling fans with remotes in all bedrooms and living areas, faux wood blinds throughout, and a NEUTRAL INTERIOR PALETTE ready for your personal style. Residents enjoy neighborhood amenities including a POOL and DOG PARK, all just minutes from the shops, dining, and vibrant atmosphere of historic downtown Winter Garden. Spring into the season of easy living—this rare corner-unit opportunity is your key to enjoy everything downtown Winter Garden is famous for.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Kim Blaylock (407-497-9321)

Remarks: SELLER IS OFFERING $5,000 TOWARDS BUYER CLOSING COSTS. METICULOUSLY MAINTAINED 3-bedroom, 2-bath home offering 1,699 square feet of well designed living space, featuring updates including the ROOF and A/C installed in 2020 giving you peace of mind. Situated on a spacious QUARTER ACRE, FENCED BACKYARD in the desirable Spring Ridge area of Winter Garden, this property showcases exceptional curb appeal and a beautifully landscaped, meticulously maintained yard, perfect for outdoor living and entertaining. Inside, the home offers a warm and inviting layout filled with NATURAL LIGHT and comfortable living areas ideal for both everyday living and hosting guests. The living space is highlighted by a charming MASONRY FIREPLACE, creating a cozy focal point for relaxing evenings. The primary bedroom suite features a WALK-IN CLOSET and a private ENSUITE BATH with a tub, providing a peaceful retreat. Additional bedrooms are generously sized and versatile for family, guests, or a home office. The expansive backyard offers endless possibilities, including room for a pool or garden while the fenced back yard provides privacy. Conveniently located near top rated schools, shopping, dining, parks, and major roadways, this move in ready home is a rare opportunity in a highly sought-after location. Welcome to your new home in Winter Garden!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Matthew Blanco (305-484-4081)

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)

Remarks: Rare opportunity in Winter Garden! This property sits on approximately one acre with no HOA, offering exceptional space, flexibility, and privacy in a highly desirable location. Conveniently located just minutes from Downtown Winter Garden), with easy access to major roadways, shopping, dining, and top-rated schools—and even the option to ride your golf cart into downtown to enjoy everything the area has. The expansive lot provides ample room for RVs, boats, recreational vehicles, and more, making it ideal for those seeking additional space and versatility. The home features generous living areas and a functional layout with great potential for customization or renovation. Outdoor amenities include a private pool, hot tub, and an extended driveway with plenty of parking space. Located approximately 2 miles from Lake Apopka and about 3 miles from Downtown Winter Garden. Properties with this amount of land and no HOA in this area are rare—schedule your showing today!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Estefania Ortega (305-905-7670)

Remarks: Under contract-accepting backup offers. $50,000+ BELOW APPRAISED VALUE (Appraisal report completed February 2026). BRAND NEW ROOF installed September 2025! Your dream pool home in the recently expanded, highly sought-after Golf Cart District in Winter Garden awaits! Set on a spacious corner lot just under a quarter acre, this stunning 5-bedroom, 4-bathroom home offers 2,994 sq ft of thoughtfully designed living space. The beautiful curb appeal, manicured lawn, and wide driveway set the welcoming tone that awaits inside. Upon entry, you'll find the formal living and dining rooms, which connect directly to the kitchen and make hosting holidays or gatherings feel effortless. The kitchen is a chefs dream, featuring stainless steel appliances, abundant counter space, crown-molded cabinetry, a breakfast bar, and generous storage. This kitchen makes meal prep of any size feels like a breeze! Just beyond, the dinette and family room create a cozy hub for everyday meals, movie nights, and time spent together. The primary suite is conveniently located on the first floor and provides a peaceful retreat with a large walk-in closet with custom shelving and an en suite bathroom complete with a soaking tub, separate shower, and dual vanities. A full laundry room with a sink and storage adds everyday ease. Upstairs, a versatile loft offers endless possibilities, whether a TV room, playroom, or home office, while additional bedrooms are bright and spacious, so everyone in the family can feel right at home. Step outside to the star of the show: a screened-in lanai and resort-style pool! Perfect for summer BBQs, refreshing dips in the pool, or relaxing evenings under the Florida sky, this lanai is waiting to be the backdrop for many memories to come. The pool was recently resurfaced in June of 2025 with a salt cell added in April 2023, providing you added peace of mind. A new A/C unit was also installed in August 2020. The fenced backyard provides a safe space for four-legged friends and little ones to roam freely, while upgraded Govee Permanent Pro Outdoor smart lighting enhances both holiday ambiance and outdoor entertaining. The location truly sets this home apart. You’re less than 10 minutes from downtown Winter Garden, where brick-lined streets, local boutiques, award-winning restaurants, and a beloved weekly farmers market create a vibrant small-town feel. Outdoor enthusiasts will love being minutes from the West Orange Trail for biking, jogging, or scenic walks, as well as close to Lake Apopka, nearby parks, and nature trails for weekend adventures. With easy access to major highways, commuting is a breeze! This home puts you just 20 minutes from Walt Disney World, plus close to top-rated schools, shopping, and everyday conveniences. This home has truly been cared for and exemplifies the best of Central Florida living. Don't miss out on this amazing property, schedule your private showing TODAY!!

Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)

Listing Agent: Grace Brazell (407-967-8608)

Remarks: Under contract-accepting backup offers. Welcome to a home that feels right the moment you arrive. Set beneath the shade of mature oak trees on a 100-foot-wide lot in Winter Garden’s golf cart district, this beautifully maintained single-story home in Island Pointe invites you to slow down, breathe a little deeper, and truly enjoy where you live. The wide, covered front porch stretches across the entire front of the home, creating the perfect place for morning coffee, evening conversations, and everything in between. Step inside and you’re greeted by soaring vaulted ceilings and natural light that pours in from every angle, giving the home an open, airy feel that lives larger than its footprint. The layout flows effortlessly with multiple living and dining spaces designed for both connection and flexibility. At the center of it all is a generously sized kitchen with abundant counter space and a center island that opens seamlessly to the family room. This is where life happens. Holidays, casual dinners, and late-night conversations all find their place here. The split floor plan offers privacy and comfort. The owner’s suite is tucked away and serves as a peaceful retreat with a walk-in closet and a spacious en-suite bath featuring dual sinks, a garden tub, and a separate shower. On the opposite side of the home, two additional bedrooms provide the ideal setup for family, guests, or a home office. This home has been lovingly cared for and offers something buyers are always searching for but rarely find: solid construction with major system updates already done, including a newer roof, updated HVAC, and a brand new water heater. The finishes reflect its original character, giving you the opportunity to modernize at your own pace and build meaningful equity along the way. But what truly sets this home apart is the lifestyle. Located in the highly sought-after Golf Cart District of historic Downtown Winter Garden, you are just minutes from everything that makes this area so special. Hop on your golf cart or bike and head to Plant Street where you’ll find charming boutiques, incredible dining, live music, festivals, and the beloved Saturday Farmers Market. Enjoy local favorites like Crooked Can Brewery and Food Hall and Scoops Ice Cream only a quick ride away. Spend your weekends exploring the West Orange Trail or relaxing at nearby Newton Park, the City Pool, playground, fishing pier, and public boat ramp. Whether it’s a morning ride, an afternoon on the water, or an evening out, everything you need is right at your fingertips. Daily convenience is just as impressive, with multiple grocery options nearby and shopping along Highway 50. You are also close to top-rated schools, Winter Garden Village, AdventHealth, and have easy access to the 429 and Florida Turnpike. All of this, paired with low HOA dues and a welcoming, established neighborhood, makes this home not just a great purchase, but a smart investment in both lifestyle and long-term value. Homes like this do not come around often. A single-story layout, a prime location, strong bones, and the chance to make it truly your own. Come see it in person. Walk the space. Feel the openness. Sit on the front porch and imagine life unfolding here.

Listing is courtesy of: UPWELL REALTY LLC (407-926-9960)

Listing Agent: Kyle Madorin Pa (407-504-9247)

Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Under contract-accepting backup offers. Welcome to your new home in the heart of Winter Garden! Featuring a brand new roof and water heater 2026! This beautifully designed home offers the perfect blend of comfort, style, and modern amenities, making it an ideal choice for families and individuals alike. Step inside to discover a spacious interior featuring an open kitchen to the living space, providing ample storage and a contemporary feel. The kitchen is equipped with whirlpool matching appliances, granite countertops, also in all bathrooms. Large windows filling the space with natural light that add a touch of elegance. Step outside to your private fenced in backyard, where you can enjoy the Florida sunshine on your patio or host barbecues with friends and family. Residents have access to community amenities such as a swimming pool, playgrounds, and walking trails. Location is key, and this home does not disappoint! Situated in walking distance to downtown Winter Garden, you’ll have easy access to charming shops, renowned restaurants, and the vibrant farmers market held weekly. Plus, you are just a short drive away from all Central Florida attractions, including the beautiful beaches and major highways. With a low monthly HOA fee of just $63, which includes access to a community pool and yard maintenance, you can enjoy a worry-free lifestyle in this fantastic neighborhood. Don’t miss your chance to own this turn key home in one of the most desirable communities. THIS PROPERTY QUALIFIES FOR A $5,000 CREDIT WHEN USING FINANCING WITH PNC BANK LENDER! CERTAIN REQUIREMENTS DO APPLY! Schedule your private showing today and make 1261 Wintergreen Way your new home.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Jason Lygren (407-756-9402)

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)

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)