Homes for Sale Near West Orange High in Winter Garden - 84 homes

Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

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

Listing Agent: Erica Diaz (407-897-5400)

Remarks: One or more photo(s) has been virtually staged. Welcome to 940 Marsh Reed Drive, a beautifully upgraded 5 bedroom, 3 bathroom, SOLAR HEATED POOL HOME offering just under 3,500 square feet of well-designed living space in the highly sought-after Johns Lake Pointe community! Additional OFFICE and LOFT / BONUS ROOM. Solar panels are paid off! From the moment you arrive, the home makes a strong impression with its tile roof, enhanced landscaping, and well manicured appearance, setting the tone for what’s inside. The interior opens to a bright, expansive layout with high ceilings, neutral finishes, and multiple living and dining areas designed for both everyday comfort and entertaining. The heart of the home is the open-concept kitchen, featuring abundant cabinetry, walk-in pantry, granite countertops, stainless steel appliances, extended butler's pantry style prep area, and a large center island that flows seamlessly into the main living area. Natural light fills the space, creating an inviting atmosphere that connects effortlessly to the indoor and outdoor living areas. The first floor dedicated office provides the ideal work-from-home setup or can easily function as a flex space to suit your needs. Upstairs, a spacious loft/bonus area offers additional versatility—perfect for a media room, playroom, or secondary living space. The primary suite is generously sized and features tray ceilings, large windows, and a relaxing, private feel. The en-suite bathroom includes dual vanities, a walk-in shower, walk-in closet, and ample storage, creating a comfortable retreat at the end of the day. Step outside to your private backyard oasis, where the SCREENED-IN POOL and covered lanai deliver the ultimate Florida lifestyle. The pool is equipped with SOLAR HEATING for year-round enjoyment and a NEW POOL PUMP for efficiency. A standout feature is the $7,000 integrated smart exterior lighting system, including the pool enclosure, creating a stunning nighttime ambiance perfect for entertaining. Additional upgrades include a new gutter drainage system and overhead garage storage racks, offering both convenience and functionality. Located in Johns Lake Pointe, residents enjoy access to resort-style amenities including a community pool, fitness center, playground, and sports courts, all while being just minutes from major highways, shopping, dining, Winter Garden's Historic Plant Street, and everything Central Florida has to offer. Only a short drive to Disney! Close to HIGH-RATED SCHOOLS. This is a rare opportunity to own a move-in ready home that combines space, upgrades, and lifestyle in one exceptional package. Call now for your private showing!

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

Listing Agent: Andrew Kincaid (407-304-0454)

Remarks: One or more photo(s) has been virtually staged. Experience comfort, style, and convenience in this lovely 2 bed + 2 bath condo located just 5 minutes from popular Plant Street in Winter Garden. This bright, well-maintained unit features a wonderful split floor plan with two spacious bedrooms separated by an 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)

Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.

Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)

Listing Agent: Xiaoli Lin (561-385-7610)

Remarks: Priced below market value and packed with exceptional upgrades, this stunning home in the highly sought-after Belle Meade community is an incredible opportunity. Offering over 4,400 square feet of living space, this spacious 7-bedroom, 4-bathroom residence features oversized bedrooms and soaring ceilings on both levels, creating an open and airy feel throughout. Designed for both comfort and entertaining, the upstairs bonus room includes its own bar, while the air-conditioned sunroom provides the perfect space to relax and enjoy year-round. Step outside to a fully fenced backyard set on more than a quarter acre, complete with two mature mango trees for a true Florida touch. This home also offers outstanding peace of mind with major recent improvements, including a new roof in 2023, new windows, a whole-house water filtration system, and fully paid-off solar panels—an incredible value and long-term savings for the next owner. Families will love the top-rated school zoning for Whispering Oak Elementary, Sunridge Middle, and West Orange High, along with the added convenience of being directly across from Foundation Academy, one of Winter Garden’s premier private schools. For recreation and leisure, West Orange Country Club is just one mile away, offering golf, tennis, and more. Ideally located near Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and New Independence, this home also provides easy access to Disney, Universal, Orlando International Airport, and major highways including the 429, Turnpike, and 408. This is the perfect blend of size, upgrades, location, and value—schedule your private showing today.

Listing is courtesy of: COMPLETE FLORIDA REALTY LLC (407-222-7281)

Listing Agent: Brandt Myers (407-758-7166)

Remarks: One or more photo(s) has been virtually staged. Welcome home to a lifestyle of space, comfort, and effortless entertaining in this beautifully designed two-story residence with charming exterior stone accents, set on an almost ¼-acre lot in a gated community. From the moment you step inside, you’ll appreciate the open, airy layout, high ceilings, and bamboo flooring throughout — no carpet anywhere for a clean, modern feel. At the heart of the home, the gourmet kitchen shines with stainless steel appliances and a stylish tile backsplash, perfectly positioned to flow into the main living areas for gatherings both big and small. Step outside to the huge screened lanai and screened-in porch, ideal for morning coffee, weekend barbecues, or relaxing evenings enjoying the Florida breeze. The primary suite on the main level offers a true retreat, featuring dual walk-in closets that connect directly to a spa-inspired bathroom with split vanities, a center garden tub, and an extra-long walk-in shower with dual shower heads. A dedicated office or den on the first floor makes working from home easy, while a convenient guest half bath, laundry room, and generous storage add everyday practicality. Upstairs, three additional bedrooms with ceiling fans provide comfortable private spaces, while the expansive game room creates the perfect hub for movie nights, playtime, or hosting friends. A 3-car garage completes the package, offering room for vehicles, hobbies, and storage. Designed for both everyday living and memorable entertaining, this home delivers the space, flexibility, and lifestyle today’s buyers are looking for — indoors and out.

Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)

Listing Agent: Kristi Matthew (407-325-6107)

Remarks: Seller Will Contribute 5K Towards Closing Costs!! Don't Miss This Rare End Unit Opportunity in Sought After Daniels Landing! This spacious Bermuda Model Townhome, is the largest 2-bedroom floor plan in the highly desirable gated community of Daniels Landing. This unit is directly located across from the clubhouse and recreation building. It is a beautifully updated end unit that offers abundant natural light thanks to additional windows and features updated luxury vinyl flooring throughout all levels, creating a bright and modern living space. The spacious kitchen includes all new appliances, 42" cabinets and Silestone counters. The kitchen features a cozy breakfast nook that opens to a lovely private fenced brick paver courtyard perfect for relaxing or entertaining. Just beyond the courtyard is a detached oversized 1.5 car garage with automatic opener, attic storage, rear alley access, and additional guest parking. Upstairs, the primary suite features a private en-suite bath and two closets, including a large walk-in, while the second bedroom and full bath provide comfortable space for guests, family, or a home office. Additional highlights include a downstairs laundry room with washer and dryer, beautifully updated powder room, updated lighting, new roof (2025), fresh interior and exterior paint. Enjoy low HOA fees that cover exterior maintenance, roof replacement, landscaping, basic cable, high speed internet, and security monitoring - making this an excellent option for low maintenance primary living or investment potential. Residents of Daniels Landing enjoy resort style amenities, including gated entry, a sparkling community pool, clubhouse with fitness center, recreation facility, walking trails, and playground. Ideally located just minutes from Winter Garden Village, AdventHealth, and Downtown Winter Garden’s shops and restaurants, with quick access to SR-429, SR-408, and I-4. Plus, you’re conveniently close to Disney’s back gate, making this an ideal location for cast members and area professionals. Don’t Miss This Exceptional Opportunity - Schedule Your Private Showing Today! Won't Last Long - A Must See.

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

Listing Agent: Gabriel Arroyo (516-661-0075)

Remarks: Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. Thoughtfully updated, the property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Juli Onorata (407-864-7701)

Remarks: Expansive and Inviting! Welcome home to 14790 Tullamore Loop. Location says it all! Convenient to restaurants, shopping, highways, theme parks, and more, this gated community remains one of the most popular communities in the area. This family-oriented neighborhood with a community pool is sure to please. With an oversized lot and plenty of room to roam, the open floor plan of this 4-bedroom / 2.5-bath home awaits to impress. Large formal living and formal dining rooms are the perfect venue for family gatherings. An elegant, open kitchen, overlooking the dinette into the family room, offers granite counters, 42” cabinets, double built-in ovens, a large breakfast bar, and a huge walk-in pantry allowing space for everyone to help the cook. When the day is done, retire to the oversized second-floor primary suite, which offers a spacious bath with a double-sink vanity, shower, garden tub, and a walk-in closet, completing this special and intimate space. Anchoring 3 large secondary bedrooms, this home beckons to an active family, offering the space you need. Enjoy your morning coffee or an evening barbecue, while enjoying the peace of your private pool, a HUGE private backyard! Complete with fruit trees (recovering from the freeze), including mango, sugar apple, sapodilla, guava, loquat, pear, jackfruit, fig, lemon, orange, neem, and banana, gives an instant farm-to-table experience. While certainly offering plenty of space for everyone to claim their own piece of paradise, you’ll find peace of mind that your investment is in a location that can’t be beat! Highlights include: Roof replaced in 2020. AC replaced in 2018. Appliances replaced in 2022. All blinds replaced 2022. Whole Home water filtration and softener system. Be sure to click the link for an interactive 3D Virtual Tour and floor plan!

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Rita Phillips (407-928-0573)

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)

Remarks: Welcome to this fully renovated 3-bedroom, 2-bath home on an oversized 0.20-acre lot in one of Winter Garden’s growing corridors. This move-in ready property offers immediate livability with long-term upside. Recent upgrades include a new AC system and water heater (2026) and a roof replaced in 2019, minimizing near-term capital expenses. The home features updated interiors and a functional layout suited for both owner-occupants and investors. The large lot provides flexibility for outdoor use and potential future enhancements. Zoned R-4, the property may provide additional possibilities for expansion or income-producing use. Buyer to verify all zoning and development options with the city. Located just minutes from major highways, shopping, and ongoing development, this property is well-positioned for both convenience and future growth.

Listing is courtesy of: LIVE MVRK LLC (407-756-4563)

Listing Agent: Gabriel Flete (407-341-9663)

Remarks: A home designed for the way you live today, where walls of glass open completely, blending indoor and outdoor spaces into one seamless experience. Located in the gated community of Canopy Oaks, this A.R. Bailey Homes LLC Delray model offers elevated design, flexibility, and everyday convenience. Well-maintained and only eight years young, this residence is set within an intimate enclave of just 49 homesites, offering a rare sense of privacy while remaining ideally positioned on Roper Road between Winter Garden’s historic downtown district and the Winter Garden Village shopping complex. The location further enhances its appeal with walkability to West Orange High School. From the moment you arrive, the home makes a lasting impression with high-end driveway pavers, a durable concrete tile roof, woodgrain garage doors, stone facade accents and grand 8-foot solid wood arched double entry doors. Inside, the layout unfolds with intention, balancing elegant design and functional living. The first-floor primary suite offers a peaceful retreat with a soaking tub, an oversized walk-in shower with dual heads and a bench, dual granite vanities and a custom closet system. A secondary first-floor, en-suite bedroom or office provides flexibility, while upstairs features a second primary suite, two additional ensuite bedrooms, a loft, a guest half bath and a covered rear balcony for added privacy and comfort. At the center of the home, the kitchen is designed to bring people together, featuring a natural gas cooktop with exterior venting, a built-in oven, upgraded KitchenAid appliances, a pot filler, 42-inch cabinetry with crown molding, a tile backsplash, under-cabinet lighting, a walk-in pantry and a large island that opens to the great room with coffered ceilings. Just beyond, a wine cellar with an iron gate adds a distinctive focal point for entertaining. The true standout is the home’s seamless indoor-outdoor connection. A full corner-opening glass wall, along with three-panel stackable sliding doors, extends both the dining and great rooms to a covered lanai with a motorized retractable screen, creating a natural flow for entertaining or everyday living. The spacious backyard, framed by a concrete stucco privacy wall, offers a blank canvas for a future pool or custom outdoor retreat. Thoughtful upgrades continue throughout, including motorized custom light filtering roller shades in the dining and great rooms, dual tankless water heaters, two AC units with zoned climate control, a mudroom, a reading nook and elegant iron stair railings. Residents of Canopy Oaks also enjoy a nature trail and a children’s play park. With proximity to downtown Winter Garden, Winter Garden Village, area hospitals, shopping, dining and major roadways including the Florida Turnpike, 429, 408 and I-4, this home presents a compelling opportunity to experience a lifestyle where design, comfort and location come together effortlessly.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Lisa Rutkowski (407-793-2416)

Remarks: This pristine Taylor Morrison Abbott floor plan, offered for sale for the very first time, sits on an oversized corner lot behind the gated entrance of The Reserve at Carriage Pointe in Winter Garden. Impeccably maintained and lovingly cared for since new, this home delivers everything on your must-have list with thoughtful upgrades and timeless appeal. As you arrive, the upgraded stone facade and side-entry garage make a striking first impression. Inside, soaring ceilings welcome you into a cavernous great room flooded with natural Florida light. A fully paid-off 12.8 KW solar system conveys with the sale, significantly reducing your monthly electric bills and enhancing long-term energy efficiency. The Abbott plan offers a versatile layout with four bedrooms, three-and-a-half baths, two bonus rooms, a dedicated home office, and a formal dining room. The kitchen impresses with 42-inch espresso cabinets featuring ornate trim, a natural gas cooktop, double convection ovens, and abundant counter space perfect for meal preparation and entertaining. The main floor primary suite serves as a private sanctuary, complete with two walk-in closets, a large shower, garden jetted tub, and a generous double vanity. Upstairs, the two bonus rooms provide excellent flexibility—one is a finished home theater (all equipment will convey) this could be an ideal gym or easily convertible to a fifth bedroom if needed. Main bonus room pool table conveys too ! Outside is where this home truly shines, the expansive corner lot features a fully fenced yard, an extended covered lanai, and a generous pool deck surrounding an incredible pool , creating the ultimate setting to enjoy Central Florida’s year-round sunshine. Also under the massive screen enclosure is full summer kitchen with side burner and sink. The Patio furniture is all negotiable. The Reserve at Carriage Pointe is a charming, gated enclave offering a peaceful retreat with unmatched convenience. You’re just minutes from endless shopping and dining options in every direction, including a quick 15-minute drive to historic downtown Winter Garden for its vibrant events, unique shops, and popular Saturday farmers market. Downtown Orlando and Disney’s front gates are only about 20 minutes away. Families benefit from the highly sought-after school district, with Foundation Academy nearby and Windermere Preparatory School a short drive further. Rarely does a home in this desirable area combine such generous living space, premium features, energy-saving solar, and an enviable location at this value. Once it’s gone, it’s truly gone—don’t miss this exceptional opportunity

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Ronald Ziolkowski (407-592-7653)

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 2016 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: Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Plant Street. This beautiful 3-bedroom, 2.5-bath home offers nearly 1,700 square feet of thoughtfully designed living space in an unbeatable setting. Step inside to an expansive great room featuring stylish wood-look tile and an open-concept layout that seamlessly connects the living, dining, and kitchen areas—perfect for entertaining. The kitchen is designed for both function and style, offering abundant stylish cabinetry, gorgeous backsplash, elegant gold hardware, granite countertops, gas stove and generous prep space. A screened courtyard with pavers creates a more private/secure outdoor retreat between the home and the detached 2-car garage. Whether you envision an outdoor lounge, garden oasis, or entertainment space, the possibilities are endless. Upstairs you will find upgraded- low maintenance flooring through out and your own private owner’s retreat. The spacious primary suite features a walk-in closet and an impressive ensuite bath designed to impress. Two additional bedrooms share a full bathroom, offering flexibility for guests, family, or a home office setup. A convenient half bath is located downstairs for visitors. Enjoy your summer months cooling off in the community which is located just a couple of minutes from your front door. This community is ideally positioned between the West Orange Trail Park and the Winter Garden Branch Library, and just minutes from the 429 for easy commuting. If you like to run or bike this home is the perfect place for you since it is located along the West Orange Trail. Walk—or hop on your golf cart—to downtown Winter Garden where you’ll enjoy the vibrant atmosphere of Plant Street Market, known for its local food vendors, craft brews, artisan goods, and year-round community events. Located close to the community pool and surrounded by everything that makes Winter Garden special, this home truly offers the lifestyle buyers are searching for. Lower utility bills since it's an inside unit, double pane windows and a tankless water heater. Schedule your private showing today and experience why this location is so highly sought after.

Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)

Listing Agent: Milinda Knollinger (321-624-7384)

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: 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: Under contract-accepting backup offers. *Video Tour Available!* Experience the best of Florida living in the heart of Stoneybrook West, where resort-style amenities and a true sense of community come together. Behind 24-HOUR GUARD GATED ENTRANCE, you’ll find everything you need to live like you’re on vacation year-round—an Olympic-sized swimming POOL, splash zone, FITNESS CENTER, playground, tennis, basketball and pickleball courts, a fishing pier, plus a PRIVATE BOAT RAMP on Black Lake. Even better, the quarterly HOA INCLUDES SPECTRUM INTERNET AND CABLE, making life here as convenient as it is enjoyable. Tucked away on a quiet CUL-DE-SAC STREET with no through traffic, this home offers both privacy and charm from the moment you arrive. Warm curb appeal welcomes you inside to rich WOOD FLOORS and soaring ceilings that create a light, airy Florida feel. At the front of the home, the FORMAL LIVING AND DINING ROOMS provide flexible space for entertaining or working from home, highlighted by a welcoming staircase. Designed for gathering, the OPEN FLOOR PLAN seamlessly connects the family room and eat-in kitchen. The kitchen features abundant QUARTZ COUNTERTOPS, upgraded cabinetry, and a pantry to keep everything organized. Double sliding doors from both the kitchen and family room open to a SCREENED PATIO OVERLOOKING A PEACEFUL POND—no rear neighbors, just tranquil views and evening sunsets. Upstairs, you’ll find the bedrooms along with a convenient laundry room. The primary suite is spacious with wood floors, double sinks, quartz countertops, a water closet, and WALK-IN CLOSET. The RENOVATED SECOND BATHROOM offers a beautifully tiled shower and tub with a built-in shampoo niche. Generously sized secondary bedrooms feature deep closets for all your storage needs. Additional upgrades include a NEWER ROOF (2021), NEWER WATER HEATER (2024), ceiling fans throughout the home and patio, a convenient half bath downstairs, new irrigation panel, updated faucets and shower head in the primary bath, newer microwave and refrigerator, window blinds and exceptional storage throughout. This is more than a home—it’s your opportunity to embrace the Florida lifestyle, where sunny days, waterfront adventures, and a vibrant community are all right outside your door.

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Tennille Biggers (850-628-4455)

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)

Remarks: Perfectly positioned fronting one of Oakland Park’s picturesque green spaces, this exceptional home offers a rare opportunity to enjoy PARK-SIDE living in one of Winter Garden’s most celebrated communities. Oakland Park, a PARADE of HOMES award-winning neighborhood, is admired for its timeless architecture & inviting outdoor spaces that create a true sense of community. This beautifully designed Seaside floorplan blends classic charm with modern livability, offering 4 bedrooms, 3.5 baths, a STUDY, dining area, spacious loft, oversized garage, & FENCED yard. The primary suite is conveniently located on the main level, creating a peaceful retreat complete with a generous walk-in closet, a separate linen closet, & direct access to the laundry room, which has been enhanced with custom cabinetry for optimal storage & organization. Upstairs, the loft provides a versatile secondary living area—ideal for a media room or play space—accompanied by three additional bedrooms & two full baths, including one private en-suite. At the center of the home, the expansive kitchen is designed for both everyday living & effortless entertaining, enhanced with under cabinet lighting & tile backsplash. Abundant cabinetry & extensive counter space provide exceptional functionality, while the large island offers ample seating, making it the natural gathering place for family & guests alike. The adjoining dining area is equally impressive, featuring a dedicated buffet—perfect for hosting celebrations, holidays, or casual dinners. The home showcases rich WOOD flooring throughout the main living areas, adding warmth and sophistication, while soft carpeting in the bedrooms enhances comfort & tranquility. One of the home’s most captivating features is the inviting wraparound front porch, where French doors open to sweeping views of the beautifully maintained park. The home’s outdoor living continues in the screened rear porch, thoughtfully designed with retractable screens to maximize comfort & flexibility throughout the seasons. Beyond the porch, the backyard has been carefully curated as a private entertainment retreat. A paver patio anchors the space, complemented by a cozy FIRE-PIT, additional seating areas, & an outdoor kitchen featuring a built-in grill, mini fridge, & sink. Pet lovers will appreciate the dedicated dog area finished with low-maintenance artificial turf, creating a convenient & attractive space for four-legged family members. With its prime park-front location, versatile living spaces, & thoughtfully designed indoor-outdoor lifestyle, this home offers an exceptional blend of elegance, comfort, & community. Just a short GOLF CART ride away, you’ll find the charm and 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, 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, including access to the 22 mile long WEST ORANGE TRAIL. 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!

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

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