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8199 Gray Kingbird Drive, Winter Garden
$715,000
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 4b SubDv. ⋅ 34787 Zip Code
Welcome to a spacious and energy-conscious home offering flexible living spaces, exceptional storage and a convenient location just minutes from Hamlin. The open-concept main living area connects the kitchen, dining space and family room—perfect for both everyday living and entertaining. The kitchen features granite countertops, abundant cabinetry, stainless steel appliances, a gas range and a generous island with seating. The first-floor primary suite offers a comfortable retreat with an en-suite bath and two walk-in closets. Upstairs, you’ll find three spacious bedrooms and an oversized bonus room—currently used as a home gym and equally suited for a second living room, media room, playroom or home office. Plentiful closets provide storage throughout the home. Outside, the large fenced backyard offers plenty of room for pets, play and outdoor living. Additional highlights include a tankless gas water heater and fully paid solar panels. The seller reports average electric bills of approximately $50 per month; usage may vary. Enjoy easy access to Hamlin’s growing collection of restaurants, shopping, entertainment and community events.

8199 Gray Kingbird Drive, Winter Garden

194 & 196 Mary Street, Winter Garden
$299,000
2 Beds ⋅ 2 Baths ⋅ Mary Jean Sub SubDv. ⋅ 34787 Zip Code
Welcome to 194 & 196 Mary Street, a beautifully refreshed duplex in the heart of charming Winter Garden! This solid block home offers 960 square feet of heated living space split into two units, each with one bedroom, so it’s an easy fit for investors, house hackers, or anyone looking to live in one side and let the other help pay the mortgage. Please note: the county tax records list the property as 194 Mary Street, but the units are addressed as 194 and 196 Mary Street, and that’s how they’re set up with the water and electric utilities. Step inside and you’ll find bright, freshly updated interiors with durable, water-resistant luxury vinyl plank flooring throughout, crisp white walls, and stylish modern lighting. The kitchens feature clean white cabinetry and sleek finishes, while the bathrooms impress with floor-to-ceiling marble-look tile and contemporary fixtures. Each unit also offers convenient in-unit washer and dryer hookups, a big plus for tenants and owners alike! Ductless mini-split A/C keeps every room comfortable all year long. Just minutes from downtown Winter Garden’s shops, restaurants, farmers market, and the West Orange Trail, this is a turnkey opportunity you won’t want to miss. Schedule your showing toda

194 & 196 Mary Street, Winter Garden

421 Eron Way Unit 36, Winter Garden
$210,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Virtually Staged. Live the Winter Garden lifestyle in this updated 2-bedroom, 2-bath condo located in the highly desirable Downtown Winter Garden Golf Cart District! Enjoy the convenience of golf cart access to Historic Downtown Winter Garden, where you can spend your weekends exploring Plant Street, local restaurants and shops, the popular Saturday Farmers Market, community events and the West Orange Trail. Inside, this home offers vaulted ceilings, a new skylight, no popcorn ceilings and thoughtful updates throughout. The kitchen features new countertops and all new appliances, including the refrigerator, dishwasher, range and microwave. Both bathrooms have been refreshed, with the primary suite featuring an oversized walk-in shower. The guest bathroom has been reglazed in a crisp white finish and updated with a new shower head, light fixture and mirror. Step outside to the screened porch with no rear neighbors, creating a private space to relax and enjoy the Florida weather. Vinyl window panels provide additional protection and versatility for the porch. Additional features include a new roof, extra attic access with pull-down stairs, additional concrete near the A/C area and a heat pump system. Whether you're searching for a primary residence, seasonal Florida home or a low-maintenance property close to all that Downtown Winter Garden has to offer, this one is worth seeing. Bring your golf cart and start enjoying one of Central Florida's most loved downtown communities!

421 Eron Way Unit 36, Winter Garden

15628 Gentle Rain Drive, Winter Garden
$730,000
3 Beds ⋅ 3 Baths ⋅ Osprey Ranch-Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Spacious single-story living and a peaceful wooded backdrop come together at 15628 Gentle Rain Drive in Winter Garden’s Osprey Ranch community. Built in 2024, this 3-bedroom home offers approximately 2,614 square feet of living space, an inviting arched entry, a paver driveway, and a two-car garage. Inside, a wide entry hallway opens to an expansive great room featuring a tray ceiling, recessed lighting, and tile flooring that continues throughout the main living areas. The open layout connects the kitchen, living, and casual dining spaces, creating a comfortable setting for everyday living and entertaining. The kitchen features rich dark cabinetry, generous counter space, stainless steel appliances, a gas range, a walk-in pantry, and an oversized island with room for seating. A separate room near the entrance provides flexibility for formal dining, a home office, or an additional sitting area. The primary bedroom features a tray ceiling and a broad bank of windows overlooking the greenery behind the home. Additional highlights include a secondary bathroom with dual sinks, a guest powder room, and a dedicated laundry room. Sliding glass doors lead to a covered paver lanai overlooking the backyard and mature trees—an inviting setting for morning coffee or relaxed outdoor dining. With generous gathering spaces, neutral finishes, and the convenience of one-level living, this home offers a versatile foundation for your next chapter in Winter Garden. All information is deemed reliable but is not guaranteed. Buyers and their agents should independently verify all information material to the purchase, including, but not limited to, room dimensions, pet restrictions, rental restrictions, school district, and HOA rules and regulations.

15628 Gentle Rain Drive, Winter Garden

2004 Lake Roberts Landing Drive, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Lake Roberts Landing SubDv. ⋅ 34787 Zip Code
Welcome to 2004 Lake Roberts Landing Drive, an exclusive gated community in the heart of Winter Garden. This spacious single-story home has 4 bedrooms, 2.5 bathrooms, and a beautiful pond view. The split-bedroom floor plan gives everyone their own space. The primary suite sits apart from the secondary bedrooms for added privacy. Generous living and dining areas make it easy to entertain or relax with family. At the heart of the home, the kitchen has a breakfast bar, plenty of counter space, and a pantry. It opens to the family room, so you can cook and still be part of the conversation. The primary suite is a peaceful retreat, with a spacious bedroom, dual vanities, a garden tub, and a separate shower. Step out to the covered lanai and enjoy the views. It's an ideal spot for morning coffee, dinner outdoors, or unwinding at the end of the day. Lake Roberts Landing offers the privacy of a gated neighborhood. It's close to shopping, dining, and entertainment in Winter Garden, with easy access to SR 429. Don't miss this chance to own a lakefront home in one of Winter Garden's most desirable gated communities. Schedule your private showing today.

2004 Lake Roberts Landing Drive, Winter Garden

17385 Bal Harbour Drive, Winter Garden
$655,000
4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lk-Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful two-story home in the desirable Waterside on Johns Lake community in Winter Garden! Built in 2019, this spacious residence offers 4 bedrooms, 2.5 bathrooms, and 2,580 square feet of comfortable living space. Step inside to discover beautiful LVT (Luxury Vinyl Tile) flooring throughout the main level and staircase, complemented by comfortable carpeting upstairs. The home features a GAS STOVE, TANKLESS WATER HEATER, and OVERSIZED DOUBLE SLIDING GLASS DOORS that bring in abundant natural light and create a seamless connection between indoor and outdoor living. One of the home’s standout features is the backyard with NO REAR NEIGHBORS, providing added privacy and a peaceful outdoor setting—perfect for relaxing or entertaining. Residents enjoy resort-style community amenities, including a sparkling swimming pool, fitness center, clubhouse, scenic waterfront pier, two playgrounds, and walking paths. Conveniently located near shopping, dining, entertainment, and major highways, this home offers an exceptional combination of comfort, privacy, and convenience. Don’t miss this wonderful opportunity to own a beautiful home in Waterside on Johns Lake. Schedule your private showing today!

17385 Bal Harbour Drive, Winter Garden

6099 Flowering Cherry Bend, Winter Garden
$829,496
4 Beds ⋅ 3 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Find room to spread out in this thoughtfully configured Biscayne, Elevation B, at Avalon Woods. Four bedrooms and three full baths include a first-floor bedroom and full bath, giving you flexibility for guests or a home office. The open great room, dining area and gourmet kitchen make it easy to stay connected, with laminate flooring adding warmth to the main living spaces. The kitchen brings together an island, quartz countertops, white cabinetry, a built-in oven, electric cooktop, microwave and range hood. Upstairs, the extended primary suite offers generous walk-in storage and a spa-style shower, while a spacious bonus room gives you another place to relax, play or gather. Two additional upstairs bedrooms and an upstairs laundry room with cabinets and a sink add everyday convenience. Open the hidden sliding glass door to the covered rear lanai for a quiet morning or an easy evening outdoors. A covered front porch, stone accents and an attached two-car garage complete the picture. Discover the possibilities of this home under construction in Winter Garden.

6099 Flowering Cherry Bend, Winter Garden

15400 W Colonial Drive, Winter Garden
$4,450,000
Tucker Oaks SubDv. ⋅ 34787 Zip Code
Prime commercial development opportunity on Highway 50 (West Colonial Drive) in Winter Garden, one of the fastest-growing and most desirable areas in Greater Orlando. This 4.71-acre parcel offers excellent visibility and a strategic location with convenient access to Florida's Turnpike, SR 408, and SR 429. The property features previously approved development plans for five independent buildings totaling approximately 30,000 SF, with the flexibility to develop in phases or as a single project. Buyers may purchase the entire parcel with the existing plans or pursue their own development concept, subject to applicable approvals. An eagle nest is located at the rear corner of the property, and a permit allowing development around the nest is in place. Offered at $4,450,000, this property presents an outstanding opportunity for investors, developers, and businesses looking to establish a presence in the rapidly growing West Orlando market.

15400 W Colonial Drive, Winter Garden

13228 Tollcross Way, Winter Garden
$1,450,000
5 Beds ⋅ 5 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
Nestled in the enclave of Westhaven at Ovation, this executive two-story residence boasts over $200K in upscale upgrades, blending architectural elegance, expansive design, and transitional luxury. Offering 3,849 square feet of interior living space on an oversized 12,921-square-foot lot, this 5-bedroom, 4.5-bathroom estate delivers an unparalleled indoor-outdoor lifestyle in prestigious Winter Garden. From the moment you approach the manicured exterior highlighted by a paved driveway and elegant architectural detailing crisp contemporary lines set a grand stage. Step through the entry into a light-filled hallway featuring high-end tile flooring, crisp recessed lighting, custom wainscoting/picture-frame molding, and refined lighting fixtures. At the heart of the home lies a light-filled open-concept interior designed for grand-scale entertaining and comfortable living. With over $200,000 in premium upgrades throughout, the home features: * Elegant, wide-plank tile flooring throughout the main walk areas and hardwood stairs leading to the second level? * Detailed millwork and classic wall trim packages enhancing the main hallways? * A gourmet chef’s kitchen featuring high-end finishes, stone countertops, premium appliances, and a spacious walk-in pantry? * Expansive living space lined with windows and glass sliding doors that fill the area with natural light? * Huge TV Panel * Elegant Wall Paper * Sophisticated Window Treatment and much more. * Main Level Guest Suite: Ideal for guests or multi-generational living, offering complete privacy with an adjacent bath.? * Primary Owner’s Sanctuary: Situated upstairs for optimal seclusion, complete with double vanities, a deep soaking tub, a frameless glass shower, and oversized walk-in closets.? * Additional Bedrooms & Loft: Three additional well-appointed bedrooms offer generous closet space,centered around a versatile upper-level bonus room or loft, perfect for a private media center, game room, or home office.? Set on an expansive 0.3-acre lot with black metal perimeter fencing installed along the rear, the grounds offer privacy and space. Relax on the covered lanai or design your dream backyard oasis—with room to add a resort-style pool, outdoor kitchen, and fire pit area. * Over $200K in Upgrades: Premium custom finishes, upgraded millwork, flooring, and light fixtures.? * Spacious 2-Story Floorplan: Optimized layout featuring zoned sleeping quarters and main-floor living space.? * Oversized Lot: 12,921 sq. ft. lot with rear fencing and room for a pool.? * Prime Location: Minutes from Horizon West Town Center, golf courses, top rated Orange County public and private schools, and quick access to Walt Disney World and major Orlando highways. Schedule your private, exclusive tour today and experience sophistication firsthand!

13228 Tollcross Way, Winter Garden

11371 Bourbon Rose Circle, Winter Garden
$1,000,000
6 Beds ⋅ 6 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Loft | Oversized Lot | 1st Floor Primary Suite. New Construction - February Completion! Welcome to the Waikiki at 11371 Bourbon Rose Circle in Esplanade at McKinnon! This spacious two-story floor plan offers an ideal blend of comfort and flexibility. The open-concept kitchen features a large island, butler pantry, and walk-in pantry, flowing seamlessly into the casual dining area and expansive great room. A private primary suite on the first floor provides a relaxing retreat with a spacious bathroom and oversized walk-in closet, while a separate first-floor bedroom suite with a full bathroom is perfect for guests. Upstairs, a generous loft is surrounded by four additional bedrooms, including two secondary suites with private bathrooms. Enjoy outdoor living on the covered lanai, and ample storage with the three-car garage. Additional Highlights Include: tray ceiling package, whole house metal stair spindles, whole house 8' interior doors, and 80 AMP Pool/Spa Prewire. MLS#O6454960 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11371 Bourbon Rose Circle, Winter Garden

243 Zachary Wade Street, Winter Garden
$1,150,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
RARE WATERFRONT OPPORTUNITY IN WINTER GARDEN | DIRECT LAKE APOPKA ACCESS | PRIVATE BOAT DOCK Welcome to Lakeview Reserve, one of Winter Garden's desirable gated communities, where waterfront living meets the charm and convenience of Historic Downtown Winter Garden. This impressive 5-bedroom, 3.5-bathroom home offers approximately 3,097 square feet of living space and a feature that is becoming increasingly hard to find: direct access to Lake Apopka with your own covered boat dock and boat lift. Inside, the home offers spacious living areas, a beautifully appointed gourmet kitchen with upgraded cabinetry, soft-close drawers, dual sinks, a large island with prep sink, and a pot filler. The home has been freshly painted throughout, and the bathrooms have been renovated, giving the interior a fresh, updated feel. Two ensuite bedrooms upstairs provide additional comfort and flexibility for family and guests. The outdoor space is just as special. Step into your backyard and enjoy the waterfront setting, complete with a covered private dock and boat lift, making it easy to enjoy boating, fishing, and everything Lake Apopka has to offer. The backyard also features an assortment of fruit-bearing trees, including mango, avocado, star fruit, and citrus, adding a special touch to this Florida retreat. Additional features include roof replaced in 2019, recently serviced HVAC system, an oversized three-car garage, tankless water heater, and whole-house water softener and purification system. Location is another highlight, with golf cart access to Historic Downtown Winter Garden, where you can enjoy local restaurants, boutique shopping, the popular farmers market, and year-round community events. A rare opportunity to enjoy the space, privacy, and convenience of a gated community with the added luxury of direct Lake Apopka access. Come experience what makes this Winter Garden property so special!

243 Zachary Wade Street, Winter Garden

1351 & 1359 Avalon Road, Winter Garden
$265,000
34787 Zip Code
***2 PARCELS / 1 SALE – PRIME WINTER GARDEN LOCATION!*** Build your DREAM HOME OR INVESTMENT PROPERTY on this 0.46-ACRE residential property along Avalon Rd (CR 545)! Zoned R-2, these two parcels offer over 140 feet of ROAD FRONTAGE and approximately 140 feet of depth. Partially cleared with mature trees, FLOOD ZONE X, and ALL PUBLIC UTILITIES AVAILABLE NEARBY. The WETLAND DELINEATION has been COMPLETED (see survey). A previous home demolished in 2006 may qualify for impact fee credits (buyer to verify). Located in a rapidly growing area near Beazer Homes’ WINDHAM PARK community, and a SHORT WALK form the proposed COLONIAL GARDENS SHOPPING CENTER. Additional planned SR 50 retail developments and the approved OAKLAND VILLAGE shopping and dining destination are other exciting new projects nearby. Minutes from Florida’s Turnpike, Historic Downtown Winter Garden, and Winter Garden Village, these 2 parcels are a GREAT OPPORTUNITY TO BUILD OR INVEST! ~Both parcels are being sold together~

1351 & 1359 Avalon Road, Winter Garden

14501 Grove Resort Avenue Unit 3221, Winter Garden
$169,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
This stunning 2-bedroom, 2-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second bedroom and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 3221, Winter Garden

645 Autumn Oaks Loop, Winter Garden
$599,900
4 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Enjoy a spacious backyard and two covered porches at this Craftsman-style home in the Winter Oaks community of Winter Garden. This two-story home features 4 bedrooms, 2.5 bathrooms, solar panels, and a rear-entry two-car garage. The covered front porch opens to a formal living and dining area with hardwood floors and a vaulted ceiling. The eat-in kitchen features granite countertops, 42-inch cabinets, stainless steel appliances, and a pantry. The adjoining family room leads to a screened back porch overlooking the backyard. The first-floor primary suite includes a walk-in closet and a private bath with dual sinks, a soaking tub, and a separate shower. A half bath and laundry room are also on the main level. Upstairs, three additional bedrooms, a full bath with dual sinks, and an open loft offer plenty of space for a home office, playroom, or media area. Winter Oaks offers a community pool, cabana, playground, and scenic pond. Enjoy easy access to historic downtown Winter Garden, the Plant Street Market, local restaurants and shops, and the West Orange Trail. Schedule your private showing today!The seller is motivated and is offering $10,000 toward closing costs.

645 Autumn Oaks Loop, Winter Garden

15928 Citrus Knoll Drive, Winter Garden
$1,549,000
6 Beds ⋅ 6 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Virtually Staged. LUXURY LAKEFRONT LIVING AT ITS FINEST! Welcome to 15928 Citrus Knoll Drive, Winter Garden, FL 34787, an exceptional lakefront residence offering an impressive combination of elegance, space, and an extraordinary natural setting. Situated along the shores of Lake Burnett, a private conservation lake surrounded by majestic old oak trees draped in beautiful Spanish moss, this remarkable property offers a peaceful and picturesque backdrop for luxury living. Featuring 6 spacious bedrooms, and 5 1/2 bathrooms, this expansive home is thoughtfully designed for entertaining and comfortable everyday living. The interior showcases ceramic tile flooring throughout the entire first floor, elegant crown molding, and freshly painted walls in a neutral palette. The chef-inspired kitchen is sure to impress, featuring GE stainless steel appliances, a double oven, vent hood, and expansive counter space and storage, ideal for preparing meals and entertaining. Formal living and dining spaces provide an elegant setting for special occasions, while an additional butler's bar offers even more room to entertain. The luxurious primary suite offers a private retreat, complete with a screened-in balcony overlooking the majestic oak trees and serene waters of Lake Burnett. Enjoy your morning coffee or unwind in the evening while taking in the beautiful natural surroundings. The spacious primary bath features dual vanities, a large walk-in shower, and a relaxing soaking tub. The thoughtfully designed bedroom layout offers exceptional flexibility, including a convenient first-floor guest bedroom with en-suite bathroom access, ideal for visitors or multigenerational living. Two additional bedrooms feature private en-suite bathrooms and walk-in closets, providing comfort and privacy for family members and guests alike. The expansive bonus room, complete with its own bar area, creates the ultimate entertainment destination and offers endless possibilities as a game or media room. Beyond the home, enjoy an exceptional gated community lifestyle which Hickory Hammock offers, with amenities including a community fishing dock, tennis courts, clubhouse, and fitness center. The crown jewel of this property is undoubtedly its setting on Lake Burnett, where mature oak trees, graceful Spanish moss, and the peaceful conservation lake create a truly special Florida lifestyle. A rare opportunity to experience elegant lakefront living, generous entertaining spaces, and exceptional community amenities in desirable Winter Garden. This is more than a home—it's a lifestyle! (Roof 2015, A/C 2015/2025, Water Heaters 2023).

15928 Citrus Knoll Drive, Winter Garden

17152 Arrowhead Boulevard, Winter Garden
$449,000
4 Beds ⋅ 2 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code
Spectacular fully renovated Mother-in-Law suite in 2026, with lake views! 4 bedrooms, 2 bathrooms total, completely independent from each other. Full renovation: brand new walls, floors, ceilings and bathrooms. All plans completed by a certified engineer and all inspections approved by Orange County, including the final inspection, move-in ready with zero worries! The property is divided into two units: each with 2 bedrooms, 1 bathroom, its own kitchen, laundry, A/C and individual water heater. Both units feature a private entrance, independent access to the backyard and their own driveway. No HOA, no restrictions, total freedom. Park your trailer, boat or work vehicle without asking anyone for permission. Perfect for a large or extended family, multi-generational living, or investors looking for a turnkey property with flexible use potential. Located in Winter Garden, just 11 minutes from Walt Disney World and with easy access to SR-429 and I-4, the best of peaceful lakeside living, with everything nearby. An opportunity that won't come around again!

17152 Arrowhead Boulevard, Winter Garden

17706 Marsh Road, Winter Garden
$1,300,000
3 Beds ⋅ 2 Baths ⋅ Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
LOCATION, ACREAGE, AND ENDLESS POSSIBILITIES! Discover an exceptional opportunity to own 4.98 acres (approximately 216,929 square feet) of prime real estate in the highly desirable and growing Winter Garden area! Whether you are looking for a private residential estate, an agricultural property, an equestrian retreat, or land with future development potential, this unique property offers tremendous possibilities for homeowners, investors, builders, and developers. EXCELLENT POTENTIAL FOR FUTURE DEVELOPMENT! Currently zoned A-1 Agricultural, this expansive parcel offers the opportunity to explore subdivision into up to three individual parcels, subject to Orange County review and approval. Buyers may also investigate the possibility of rezoning for commercial, residential, or other permitted uses through the appropriate application and approval process with Orange County. This flexibility makes the property especially attractive to investors and developers seeking land for future projects in Central Florida. AN ADDED BONUS – AN EXISTING HOME ON THE PROPERTY! The property features a charming single-story residence offering 3 bedrooms, 2 bathrooms, and approximately 1,440 square feet of living space. The home includes tile flooring throughout, granite kitchen countertops, a tile roof, and comfortable living areas. The property also features a pole barn, additional outbuildings, storage sheds, fenced pasture areas, and beautiful mature trees, creating an inviting country atmosphere with plenty of room to enjoy. Retreat to the inviting primary bedroom, featuring elegant marble-look tile flooring, abundant natural light, recessed lighting, and a contemporary ceiling fan. The spacious layout offers room for a desk or sitting area, while generous closet space provides convenient storage. The adjoining bathroom showcases striking marble-look wall and floor tile, a double-sink vanity with cabinetry, gold-tone faucets, and an illuminated mirror. A soaking tub and separate glass-enclosed shower with a rainfall showerhead create a relaxing retreat, complemented by dramatic dark tile accents. THE BEST OF BOTH WORLDS – COUNTRY LIVING WITH CITY CONVENIENCE! Enjoy the privacy, space, and freedom of acreage living while remaining conveniently located near Winter Garden's expanding residential communities, shopping, dining, major roadways, and Central Florida attractions, including Walt Disney World. LIVE, INVEST, OR EXPLORE FUTURE DEVELOPMENT! The existing residence provides immediate residential utility while the surrounding acreage offers opportunities for agricultural activities, equestrian use, a private estate, or potential future development. DON'T MISS THIS OPPORTUNITY TO OWN NEARLY FIVE ACRES IN WINTER GARDEN! Large parcels with an existing home and multiple potential uses are worth exploring. Bring your vision and discover what this exceptional property could become!

17706 Marsh Road, Winter Garden

226 Charlotte Street, Winter Garden
$449,999
3 Beds ⋅ 2 Baths ⋅ East Garden Manor Rep SubDv. ⋅ 34787 Zip Code
UNIQUE PROPERTY OPPORTUNITY!! Nearly of an 1/4 ACRE with NO HOA!! Welcome to this charming 3-bedroom, 2-bathroom home in the heart of Winter Garden! Situated on an oversized lot, this property offers added space and flexibility rarely found in many communities. Inside, enjoy a cozy fireplace, a unique wood accent wall, and an updated kitchen featuring custom cabinetry and convenient hidden storage. Ceramic tile and bamboo flooring, double-pane windows, and a screened front porch add to the home's appeal. The spacious backyard offers two storage sheds, offering plenty of room for outdoor enjoyment, hobbies, and additional storage. Hot water tank 2 years old. Conveniently located walking distance to Downtown Winter Garden, the West Orange Trail. This home combines charm, functionality, and the freedom of homeownership without HOA restrictions!

226 Charlotte Street, Winter Garden

505 N Boyd Street, Winter Garden
$618,000
3 Beds ⋅ 2 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
CHARMING VINTAGE HOME IN DOWNTOWN WINTER GARDEN — NO HOA! Huge DOUBLE LOT offers more space for all your dreams! Welcome to the heart of Downtown Winter Garden! This well-maintained, classic Florida style 3-bedroom, 2-bath home offers timeless character, a cozy atmosphere, and an incredible location in Winter Garden’s highly desirable Golf Cart District. Inside, you’ll find a warm and inviting living room featuring a real wood-burning brick fireplace, a comfortable living and dining combination, and a convenient pass-through to the kitchen. The spacious, covered, screened-in room provides the perfect setting for entertaining guests, enjoying your morning coffee, or relaxing from the Florida sunshine. There are actually two primary suite bedrooms and a large home office or third bedroom. The home is situated on a corner, double lot so there is room for growth. The home is being offered for purchase AS IS. Enjoy the best of downtown living, where you can stroll or hop on your golf cart to explore the popular Plant Street Market, local restaurants, charming boutiques, cozy cafés, and the beloved Winter Garden Farmers Market. Take a short ride to Veterans Memorial Park for a game of pickleball, enjoy a swim at Farnsworth community pool, stroll or bike along the scenic West Orange Trail, or discover the natural beauty of nearby Lake Apopka and Newton Park. Historic downtown Winter Garden is an official Hallmark Christmas Town for 2026! Come experience the beauty of this friendly town. With NO HOA, a sought-after downtown location, and easy access to major highways, this home offers a wonderful opportunity to enjoy the unique blend of small-town charm and modern convenience that makes Winter Garden so special. Orlando’s attractions, including Walt Disney World, Universal, SeaWorld and multiple water parks are also within convenient driving distance. Only 30 minutes to Orlando airport (MCO). Don’t miss your opportunity to own a home in one of Central Florida’s most loved downtown communities! Schedule your private showing today and experience the charm and lifestyle of Downtown Winter Garden!

505 N Boyd Street, Winter Garden

13151 Calming Breeze Way, Winter Garden
$489,900
3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code
NEWER CONSTRUCTION. SHOWS LIKE A MODEL HOME + BUILT IN 2024 + SCREENED LANAI + FULLY FENCED BACKYARD + MINUTES FROM DISNEY! Welcome to 13151 Calming Breeze Way, a beautifully maintained 3-BEDROOM, 2.5-BATH HOME offering 2,096 SQ FT of stylish living space in the desirable SERENADE AT OVATION community of Horizon West in Winter Garden! With its modern finishes, thoughtfully designed OPEN-CONCEPT FLOOR PLAN, and exceptional attention to detail, this home offers the appeal of newer construction with valuable upgrades already completed by the current owners! Inside, experience the bright, inviting atmosphere created by HIGH CEILINGS, LUXURY VINYL FLOORING, and spacious living areas designed for both everyday comfort and entertaining. The beautiful GOURMET-STYLE KITCHEN is the heart of the home, featuring STONE COUNTERTOPS, A LARGE CENTER ISLAND, generous cabinetry, and an effortless connection to the dining and gathering areas. The open bungalow-style layout creates a welcoming space for hosting friends or simply relaxing at home. Upstairs, the spacious PRIMARY SUITE offers a comfortable private retreat with a walk-in closet and en-suite bathroom. Two additional generously sized bedrooms provide flexibility for guests, a HOME OFFICE, or additional living space. One of this home's standout features is its beautifully enhanced outdoor living area! Unlike many newer homes where these improvements are still on the wish list, the current owners have already invested in a SCREENED-IN COVERED LANAI AND PRIVACY FENCING, creating an inviting backyard retreat. Enjoy morning coffee, outdoor dining, or relaxing evenings in your own private space. Additional upgrades include WINDOW BLINDS AND CEILING FANS, adding comfort and convenience from day one. LOCATION, LOCATION, LOCATION! Situated in the thriving HORIZON WEST / WINTER GARDEN area, this home offers exceptional convenience to WALT DISNEY WORLD, with Disney's theme parks, resorts, dining, and entertainment just a short drive away. Enjoy easy access to FL-429, nearby shopping, restaurants, and everyday essentials, along with the charm of Historic Downtown Winter Garden. Even better, SERENADE AT OVATION OFFERS A LOW HOA AND NO CDD FEE, making this an attractive opportunity for buyers seeking newer construction in one of Central Florida's most desirable and growing locations. Why wait for new construction when you can enjoy a beautifully finished, MOVE-IN READY HOME with the outdoor upgrades already in place? SELLER OFFERING $10,000 TOWARDS BUYERS CLOSING COSTS. Schedule your private showing and see for yourself why this home truly shows like a model! Mortgage savings may be available for buyers of this listing. Ask for details.

13151 Calming Breeze Way, Winter Garden

215 S Woodland Street, Winter Garden
$425,000
4 Beds ⋅ 2 Baths ⋅ Fries Survey Of Winter Garden SubDv. ⋅ 34787 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION! Just ONE BLOCK SOUTH OF PLANT STREET in the heart of historic Downtown Winter Garden, this is the kind of opportunity that doesn’t come around every day! With a 6,933-square-foot lot, an existing four-bedroom, two-bathroom home, and a mother-in-law suite, this property offers something increasingly difficult to find: a prime downtown address with incredible possibilities for the future. In real estate, you can change almost anything about a property, but you can never change its location. And this one is exceptional! Situated just steps from the charm, character, and energy of Downtown Winter Garden, you’ll find yourself surrounded by some of Central Florida’s most beloved restaurants, coffee shops, boutiques, breweries, and community gathering spots. Spend your Saturday mornings exploring the award-winning Winter Garden Farmers Market, enjoy an afternoon along the West Orange Trail, or take an evening stroll down Plant Street for dinner and live entertainment. This is the walkable, golf-cart-friendly downtown lifestyle so many buyers dream about! The existing residence offers 1,685 square feet of living space with four bedrooms, two bathrooms, and the added flexibility of a mother-in-law suite. Whether you’re looking for a home with room for extended family, a property to personalize, or a place to establish your roots in one of Central Florida’s most desirable communities, there’s plenty of opportunity to make this address your own. But perhaps the most exciting feature isn’t just what’s standing on the property today. It’s the LAND and the LOCATION! With approximately 6,933 square feet just one block from Plant Street, this parcel presents a compelling opportunity for buyers who recognize the long-term appeal of owning property in the heart of Downtown Winter Garden. Bring your creativity, explore renovation possibilities, or investigate future improvements and redevelopment options, subject to city zoning and approval requirements. As Downtown Winter Garden continues to attract buyers seeking character, convenience, and a true sense of community, opportunities to secure property this close to the center of it all are especially appealing. Whether you’re a homeowner with a vision, an investor seeking a desirable location, or someone who’s always dreamed of living steps from Plant Street, this property deserves your attention. THE LOCATION IS ALREADY PERFECT. THE POSSIBILITIES ARE YOURS TO EXPLORE. Don’t miss your opportunity to own a piece of Downtown Winter Garden!

215 S Woodland Street, Winter Garden

704 Caterpillar Run, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code
Don't miss this one-of-a-kind, move-in-ready corner home featuring 4 bedrooms, 3 full baths, a dedicated office, and a 3-car attached garage, all on one level! Built in 2019, this spacious 3,000+ sq. ft. home offers an open, functional floor plan with vinyl flooring throughout, ceramic tile in wet areas, window treatments that convey and high ceilings. The home features separate living and dining areas, a spacious family room, and an open kitchen with granite countertops, center island, stainless steel appliances, and built-in oven and cooktop. The primary suite offers a large walk-in closet, double vanity, walk-in shower, separate soaking tub, and sliding glass door access to the oversized screened lanai. Additional bedrooms include a convenient guest suite with private bath. Enjoy the extended, full-length screened lanai with two ceiling fans, perfect for relaxing or entertaining. The sellers have made numerous improvements, including gutters, exterior paint (2022), epoxy-coated garage floor, built-in workbench, wall storage systems, and four overhead storage racks. The outdoor space features paver walkways and grilling pad, artificial turf with stepping stones, and a variety of fruit trees, including avocado, papaya, grapefruit, orange, and key lime, along with raised garden beds and an underground irrigation system. A transferable termite bond adds peace of mind. This beautifully maintained home offers space, functionality, and numerous upgrades. Schedule your private showing today!

704 Caterpillar Run, Winter Garden

17984 Adrift Road, Winter Garden
$899,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Stunning lake views set the tone for this upgraded 5-bedroom, 4.5-bath home in Waterleigh, one of Horizon West’s most sought-after communities. Offering 3,225 square feet of living space, this home goes well beyond the standard build. Upgraded cabinetry, countertops, appliances, and flooring create a refined, cohesive look, while custom office cabinetry delivers a polished, built-in workspace. Custom closets add smart, organized storage. Location makes it even better, with Water Spring Elementary and Water Spring Middle within walking distance. Waterleigh offers a resort-style lifestyle with two clubhouses, multiple pools, fitness centers, tennis, pickleball, beach volleyball, mini golf, dog parks, and walking trails. All of this comes with a lake view you’ll never get tired of. Schedule your private showing today.

17984 Adrift Road, Winter Garden

17906 Hither Hills Circle, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Lake Apopka Sound SubDv. ⋅ 34787 Zip Code
3.99 ASSUMABLE MORTGAGE OPPORTUNITY! Built in 2022, this four-bedroom home in Lake Apopka Sound offers single-story living, a three-car garage, and an open layout perfect for entertaining. The spacious kitchen features an oversized island, granite countertops, stainless steel appliances, and ample storage overlooking the inviting great room. A split-bedroom design provides privacy, while the primary suite includes dual vanities, a soaking tub, separate shower, and walk-in closet. Enjoy nearby outdoor adventures at the West Orange Trail and Oakland Nature Preserve, plus dining, boutiques, Plant Street Market, and the Saturday farmers market in historic Downtown Winter Garden. Shopping at Winter Garden Village and access to Florida’s Turnpike, SR 429, and Highway 50 add everyday convenience. Schedule your private showing today! Mortgage assumption subject to lender approval, buyer qualification, and applicable loan terms.

17906 Hither Hills Circle, Winter Garden

17778 Sedona Street, Winter Garden
$814,139
3 Beds ⋅ 4 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Deep Backyard | 1st Floor Primary Bedroom | Loft | Dedicated Study. New Construction – April Completion! Welcome to the Genoa at 17778 Sedona Street in Esplanade at McKinnon Groves! This thoughtfully designed two-story home offers a spacious and inviting layout with a stunning great room that flows seamlessly into the dining area, gourmet kitchen, and expansive lanai, perfect for everyday living and entertaining. The first floor features a private primary suite with large walk-in closet and well-appointed bath, a secondary bedroom suite, half bathroom, and a study, while upstairs includes a versatile loft, flex room, additional bedroom, and full bathroom. Additional Highlights Include: 10' ceilings at first floor, whole house 8' interior doors, door at primary closet to laundry room, outdoor kitchen rough-in, and whole house blinds. Photos are for representative purposes only. MLS#O6455189 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

17778 Sedona Street, Winter Garden

2827 Sanctuary Lane, Winter Garden
$2,349,000
3 Beds ⋅ 3 Baths ⋅ Lake Avalon Groves SubDv. ⋅ 34787 Zip Code
**BUILD YOUR DREAM HOME ON 9 ACRES IN BEAUTIFUL WINTER GARDEN, FLORIDA!** **A Rare Opportunity to Own Your Own Piece of Paradise!** Imagine waking up every morning surrounded by nature, privacy, and endless possibilities! This incredible **9-acre property in desirable Winter Garden, Florida**, offers the perfect opportunity to create the custom estate you've always dreamed of. Whether you envision a luxurious custom-built residence, a stunning modern farmhouse, a private family retreat, or a peaceful country estate, this expansive property provides the space to bring your vision to life. Enjoy the beauty and tranquility of spacious country living while remaining close to everything that makes Winter Garden one of Central Florida's most sought-after communities, including charming Downtown Winter Garden, shopping, dining, entertainment, and major highways. **9 ACRES. ENDLESS POSSIBILITIES. ONE INCREDIBLE OPPORTUNITY.** Land of this size in Winter Garden is a remarkable find. Don't settle for someone else's dream home when you can create your own masterpiece! **Your Dream. Your Land. Your Legacy.** Schedule your private showing today and discover the possibilities this extraordinary property has to offer!

2827 Sanctuary Lane, Winter Garden

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