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1539 Hawkesbury Court, Winter Garden
$560,000
3 Beds ⋅ 2 Baths ⋅ O6447692 MLS
Welcome to 1539 Hawkesbury Court, located in the desirable Winter Garden area of Central Florida! This single-family home offers an excellent opportunity to enjoy the convenience, amenities, and lifestyle that make Winter Garden a sought-after place to call home. Conveniently located near shopping centers, restaurants, grocery stores, parks, and everyday essentials, residents can enjoy easy access to a variety of local conveniences. Explore the charm of historic Downtown Winter Garden, known for its unique shops, local restaurants, cafés, and welcoming atmosphere. The popular West Orange Trail is nearby, offering miles of scenic paths for walking, jogging, and cycling. Winter Garden Village provides an array of retail stores, dining options, and entertainment for added convenience. The property's location also offers access to major roadways, including Florida's Turnpike and State Road 429, making travel throughout the greater Orlando area convenient. Enjoy proximity to recreational opportunities, golf courses, and outdoor activities, while remaining within reach of Orlando's employment centers, attractions, and entertainment destinations. Whether you're looking for a place to call home or exploring real estate opportunities in the growing Central Florida market, this property presents an opportunity to enjoy the many benefits of the Winter Garden lifestyle.

1539 Hawkesbury Court, Winter Garden

24 W Garden Avenue, Winter Garden
$698,800
4 Beds ⋅ 4 Baths ⋅ O6446518 MLS
Pro pics coming soon.RARE OPPORTUNITY IN THE HEART OF WINTER GARDEN’S HIGHLY SOUGHT-AFTER GOLF CART DISTRICT! Completely remodeled and move-in ready, this impressive 4-bedroom, 4-bath, single-story home sits on an oversized lot directly across from Tanner Hall, Newton Park and the public boat ramp to Lake Apopka—and best of all, there is NO HOA! Extensive renovations have transformed this home with a beautiful new kitchen ( NATURAL GAS RANGE! ), remodeled bathrooms, new flooring, fresh interior and exterior paint, and updated windows, creating a fresh, modern feel throughout. The roof was replaced in 2017 and the water heater in 2013. The spacious open great room floor plan is ideal for both everyday living and entertaining, while the oversized owner’s suite provides a private retreat. Two additional bedrooms feature true ensuite baths, offering exceptional flexibility for family, guests, multigenerational living or a private home office. Step outside to the huge covered and screened rear patio overlooking the expansive backyard with plenty of room to relax, entertain and enjoy the Florida lifestyle. The location is truly hard to beat. Walk across the street to Newton Park, Tanner Hall, the Lake Apopka fishing pier and public boat launch, or hop in your golf cart for a short ride to historic Downtown Winter Garden and everything Plant Street has to offer. Enjoy an incredible collection of restaurants, breweries, coffee shops, boutiques and entertainment, along with year-round festivals, community events and the famous Saturday Winter Garden Farmers Market. Outdoor enthusiasts will love being just a quick bike ride from the popular West Orange Trail and minutes from Lake Apopka. Located in a sought-after K-12 school district with convenient access to SR 429, this location provides an outstanding combination of small-town charm, recreation and accessibility to the greater Orlando area. With four bedrooms, four full baths, extensive renovations, an oversized lot, NO HOA and an exceptional location in the Downtown Winter Garden golf cart district, opportunities like this are increasingly difficult to find. Exceptional value, incredible lifestyle and truly move-in ready—this one is PRICED TO SELL!

24 W Garden Avenue, Winter Garden

923 Colie Alley, Winter Garden
$610,000
3 Beds ⋅ 3 Baths ⋅ O6445624 MLS
Short Sale. ~ IT IS WORTH THE WAIT! Discover the opportunity to own a nearly new David Weekley home in the highly desirable Oakland Park community of Winter Garden. Built in 2022, this SUMMERTON MODEL in McKinnon Square offers the style, space and location buyers are looking for — all within a community known for its beautiful streetscapes and exceptional amenities. The charming FRONT PORCH gives the home a welcoming personality, while inside, soaring ceilings, generous windows and an open layout create an easy sense of space. The kitchen serves as the natural gathering point, with a well-appointed design that connects seamlessly to the dining and living areas — a comfortable setup for both everyday life and entertaining. Upstairs, all of the bedrooms are conveniently grouped together, along with a FLEXIBLE LOFT AREA that can evolve with your needs. Use it as a home office, media room, play space, reading area or simply enjoy the extra room to spread out. Life here extends well beyond the home itself. OAKLAND PARK IS A GOLF-CART-FRIENDLY COMMUNITY with pools, clubhouse facilities, parks, playgrounds, a dog park and plenty of opportunities to enjoy the outdoors. The WEST ORANGE TRAIL AND LAKE APOPKA are nearby, while Historic Downtown Winter Garden is just a golf-cart ride away, putting restaurants, local shops, breweries, coffee spots, entertainment and the popular Farmers Market within easy reach. Location is another standout. Schools are conveniently nearby, including the elementary school approximately .5 miles away, middle school 1.1 miles and high school 3 miles. Orlando Health Hospital is approximately 1.8 miles away, while Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike provide easy access throughout Central Florida — including Disney and the area’s major attractions. NEARLY NEW, MOVE-IN READY AND SET IN ONE OF WINTER GARDEN’S MOST SOUGHT-AFTER COMMUNITIES, this short-sale opportunity is one you’ll want to see before it’s gone! Buyer and buyer agent to verify all data and measurements.

923 Colie Alley, Winter Garden

204 Harbor Drive, Winter Garden
$579,000
3 Beds ⋅ 2 Baths ⋅ O6445377 MLS
GOLF CART LIVING IN DOWNTOWN WINTER GARDEN! Welcome to 204 Harbor Drive, a single-story pool home in Winter Garden's sought-after Golf Cart District. Hop in your cart and head to historic Plant Street for dinner, the Saturday Farmers Market, or a morning ride on the West Orange Trail, and leave the car in the garage. This home boasts vaulted ceilings, a skylight, and ceiling fans give the open living area a bright, airy feel. A corner slate-tile fireplace with a wood mantel anchors the room, and a custom built-in wood bookcase wall adds warmth and storage. French doors open to the pool, so indoor and outdoor living flow together. The kitchen features rich wood cabinetry, countertops updated in 2016, a tile backsplash, stainless steel appliances, and a pantry, and it opens to the main living area for easy entertaining. Easy-care tile flooring runs throughout the main living spaces. The screened pool and spa are the centerpiece of the backyard, resurfaced and retiled in 2021, with cafe lighting for evening swims and gatherings. The larger backyard is fully fenced with a 6' white vinyl privacy fence (2020), a double swing gate on one side, and a pedestrian gate on the other. Mature trees and plenty of green space make room for pets, play, or a garden. The two-car garage has a newer door (2018), and the wide driveway offers ample parking. PEACE OF MIND, MAJOR UPDATES DONE: - Whole-home automatic standby generator (2023) with new interior and exterior electrical panels and automatic transfer capability, powered by a buried 500-gallon propane tank - Brand-new HVAC system (2025), a complete replacement with new ductwork and added return air vents - Architectural shingle roof (2016) - Whole-home repipe (2014) LOCATION: Tucked into a quiet neighborhood with green space and a pond nearby, with Lake Apopka visible on the horizon. Winter Garden has grown from a sleepy citrus town into one of Central Florida's most livable communities: - Plant Street and Historic Downtown: brick-paved main street with shops, restaurants, breweries, and the Garden Theatre - Plant Street Market: air-conditioned food hall open seven days a week with 20+ vendors and a craft brewery - Saturday Farmers Market: a beloved weekly tradition - West Orange Trail: 22 miles of flat, shaded, paved trail through downtown - Lake Apopka and Newton Park: a short golf cart ride away - Winter Garden Village: open-air shopping and dining just south of downtown - About 20 minutes to downtown Orlando, with convenient routes to Walt Disney World and major highways A downtown location, golf cart access, a screened pool and spa, a new A/C, and a whole-home generator rarely come together in one home. Schedule your private showing today!

204 Harbor Drive, Winter Garden

517 Garden Heights Drive, Winter Garden
$589,900
4 Beds ⋅ 2 Baths ⋅ O6446560 MLS
Welcome home to 517 Garden Heights Drive, right in the heart of Winter Garden's golf cart district. This fully renovated 4-bedroom, 2-bath modern farmhouse sits on a third of an acre, about a mile from the shops, restaurants, and events on Plant Street, with Lake Apopka views right from your driveway. The big-ticket items are already taken care of: a brand-new roof (July 2025), new water heater (2025), and HVAC replaced in 2021. Inside, nearly 2,000 square feet has been completely refreshed with new tile flooring, fresh paint and texture, and modern wood accent paneling. The open floor plan centers around a shiplap fireplace, with new ceiling fans and light fixtures throughout. The kitchen is the true showpiece, featuring quartz countertops, shaker cabinets, gold hardware, stainless steel appliances, and statement pendant lighting. Both bathrooms were redesigned with custom tile and dual vanities, and the primary suite adds a sliding barn door and a spa-style bathroom. Step out to the screened-in porch with its own wet bar, overlooking a huge backyard made for weekend gatherings or slow mornings with coffee. A 2-car garage gives you plenty of room for storage, tools, and the golf cart. And no HOA! Move-in ready, beautifully updated, and minutes from everything that makes Winter Garden such a special place to call home. Come see it for yourself.

517 Garden Heights Drive, Winter Garden

1442 Coluso Drive, Winter Garden
$585,000
3 Beds ⋅ 2 Baths ⋅ V4951594 MLS
Welcome to this beautifully maintained home in a desirable golf cart community, just 2 miles from historic Downtown Winter Garden! This home offers LVP and tile flooring, double-pane windows, a cozy wood-burning fireplace, a 6-year-old AC system, and a spacious Florida room with sliders for enjoying Florida living. The saltwater pool features a 5-year-old pump and heater, while recent exterior paint adds to the home's appeal. Outdoor amenities include an RV-ready setup with RV connection and a dedicated pad for your boat or RV, plus an oversized shed for additional storage. A whole-home generator, approximately 3 years old, with a 500-gallon propane tank provides added peace of mind. The beautifully landscaped property also features an impressive variety of fruit trees, including 5 peach, 2 plum, 2 nectarine, 1 apple, starfruit, small and large banana, pineapple, and lemon trees. Located in a golf cart-friendly community and minutes from Downtown Winter Garden's shopping, dining, and entertainment, this home offers a wonderful blend of convenience, comfort, and Florida lifestyle.

1442 Coluso Drive, Winter Garden

8836 Lakeshore Pointe Drive, Winter Garden
$1,175,000
4 Beds ⋅ 4 Baths ⋅ O6421088 MLS
Turnkey, Toll Brothers model home in Winter Garden. This property occupies one of Lakeshore Preserve’s most open and airy homesites next to expansive open green space inside Lakeshore Preserve. Expansive open green space extends along the entire south side of the home, creating a valuable advantage. No next-door neighbor on the home’s south side—the dining room, great room, kitchen and outdoor living areas face open green space, offering green views, abundant natural light and added privacy. Additional green space behind the property extends the sense of openness. A dramatic two-story foyer upon entering. Key design and home features: Smart home technology, shiplap wall detailing, rich wood-beam ceilings. Plantation shutters throughout. The kitchen features a massive center island, farmhouse sink, custom backsplash, abundant cabinetry to include deep drawers and natural-gas cooking. Triple sliding glass doors connect the great room to an expansive screened lanai with a fully equipped outdoor summer kitchen. Outdoor dining and lounge spaces enclosed on all sides by motorized retractable screens. Beyond the retractable screens, the backyard features an outdoor putting green and a built-in stone fireplace with modern glass-rock insert. The first floor primary suite is positioned at the rear of the home, and includes a new walk-in closet, a striking primary bath with opposing vanities, a private water closet and a dramatic walk-in shower. Custom tile extends from the floor up the shower walls, with opposing shower systems, multiple shower heads and built-in bench seating. The second floor features a true second living room, three furnished bedrooms and two full baths. One bedroom includes an ensuite bath and full closet, while the other two share a hall bath. When not occupied by guests, the second living room serves as a private lounge, media room, or office space. Turnkey includes: all living area furniture, décor, artwork, rugs, kitchen equipment, dinnerware, glassware and utensils. Utility features to this home: tankless water heater, low-E windows, in-wall pest system and HOA-maintained grounds around the home and inside the fenced in back yard. Lakeshore Preserve amenities include a clubhouse, fitness center, resort-style pool, playgrounds, sand volleyball court. All surrounded by lake. Cable, one-gig internet and ground maintenance are included in the HOA fee. This executive collection home sits on one of the most unique homesites within Lakeshore Preserve. Privacy and sun-drenched light, Toll Brothers coveted upgrades, and this transitional design style fully finished by an interior designer for this model home.

8836 Lakeshore Pointe Drive, Winter Garden

1021 Huntspoint Street, Winter Garden
$865,000
4 Beds ⋅ 4 Baths ⋅ O6445538 MLS
RARE opportunity in Oakland Park, a Parade of Homes-winning community: a 2018 home with approximately $145K in owner upgrades that YOU and your family can enjoy, including a premium SOLAR plus whole-home battery system (paid off at closing). This home is PRICED to MOVE. Offering 4 bedrooms, 3.5 baths, and 2,445 square feet, with a flexible main-floor suite, loft, dining space, tile flooring, newer AC (2024), and a screened balcony, it is built for everyday living, entertaining, and working from home, and is fully fenced for privacy. The main-floor suite is framed by statement doors, with a built-in MURPHY BED and private patio. It works as a 4th bedroom, guest suite, or home office, ideal for multigenerational living. Upstairs, each bedroom enjoys its own en-suite bath, and one opens to the screened balcony. The PRIMARY SUITE includes dual sinks, ample counter space, a soaking TUB, tiled shower, and walk-in closet. The stylish, highly functional kitchen features QUARTZ counters, tile backsplash, custom wood-trim island, and a water filtration system, with APPLIANCES UPDATED in recent years (Bosch dishwasher, LG ThinQ refrigerator, built-in oven and microwave). Just off the kitchen are two pantries, a built-in desk, and extra under-stair storage. CUSTOM finishes add warmth throughout: an electric FIREPLACE with shiplap in the living area, board-and-batten in the primary bedroom, a shiplap accent wall in the secondary bedroom, custom staircase wall, plantation shutters, updated lighting, and a remodeled half bath. Custom closet systems in every bedroom, two linen closets, multiple pantry closets, and added laundry-room cabinetry with a drying rack keep everything organized. The standout garage offers a dedicated mini-split AC, EV charger, epoxy flooring, and abundant built-in storage with an overhead lift system, and connects to the home by a covered walkway, a rarity in the neighborhood. The crown jewel: a premium 12.64 kW solar and whole-home battery system (installed 2024, an approximately $86K value paid off at closing) with 32 Mission Solar panels and four Enphase IQ Battery 5P units (~20 kWh storage) that can power virtually the entire home during outages. Enjoy a monthly energy bill of about $35. A short GOLF-CART ride from Historic Downtown Winter Garden's award-winning restaurants, shopping, farmers market, and events. This golf-cart-friendly waterfront community offers two pools, a clubhouse, parks, playgrounds, a dog park, and access to the 22-mile West Orange Trail, with easy reach to interstates, golf, and world-renowned theme parks. More than a home, it is the Winter Garden lifestyle.

1021 Huntspoint Street, Winter Garden

15614 Espalier Way, Winter Garden
$4,300,000
6 Beds ⋅ 7 Baths ⋅ O6445414 MLS
Welcome to an exceptional lakefront estate in the highly desirable Independence community of Winter Garden. Set on approximately 2.19 acres along the shores of Lake Hancock, this 2022-built residence offers approximately 6,601 square feet of living space, 6 bedrooms, and 6.5 baths, providing an expansive setting for both everyday living and entertaining. The property combines generous indoor and outdoor spaces with a private waterfront setting and an impressive collection of amenities. Features include a dedicated fitness room, private dog kennel, and a beach tennis court scheduled to be completed prior to closing. The expansive grounds provide ample space for recreation, gatherings, and enjoying the lakefront surroundings. The spacious residence and substantial homesite provides flexibility for a variety of lifestyles, while the Lake Hancock frontage provides a distinctive waterfront setting within the community. Located in Winter Garden's Independence community, with convenient access to shopping, dining, entertainment, schools, and major roadways. A rare opportunity to own a spacious lakefront estate on approximately 2.19 acres in one of Winter Garden's sought-after communities.

15614 Espalier Way, Winter Garden

206 N Highland Avenue, Winter Garden
$1,100,000
3 Beds ⋅ 3 Baths ⋅ O6444632 MLS
Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.

206 N Highland Avenue, Winter Garden

745 Cascading Creek Lane, Winter Garden
$700,000
3 Beds ⋅ 3 Baths ⋅ O6444131 MLS
Some homes just have a way of making everyday life feel a little easier—and this is one of them. Located in a gated Winter Garden community, this 3-bedroom, 2.5-bath pool home offers the kind of space and flexibility that works for real life. From the moment you step inside, the home feels open, bright, and remarkably spacious, with plenty of room to gather, unwind, work from home, or simply spread out. A DEDICATED OFFICE adds even more flexibility without sacrificing any of the three bedrooms. Out back, the SCREENED-IN POOL creates your own private Florida retreat. Start the morning with coffee by the water, spend an afternoon cooling off in the pool, or settle in for an evening outside without ever leaving home. The pool pump and heater have both been replaced recently, adding to a list of important updates that includes a BRAND NEW ROOF in 2026 and an A/C system that's just four years old. And the lifestyle extends well beyond the backyard. The GATED COMMUNITY features its own pool, basketball courts, tennis courts, and a dock with access to the lake—giving you plenty of ways to enjoy the outdoors close to home. Then there's the location. You're less than 10 minutes from Downtown Winter Garden, where weekends can mean grabbing breakfast, exploring the shops, visiting the farmers market, or meeting friends for dinner. Shopping, everyday conveniences, and highway access are also nearby, making it easy to get around Central Florida while still coming home to a neighborhood that feels tucked away from it all. If you've been searching for a Winter Garden pool home with a dedicated office, gated-community amenities, lake access, major recent updates, and a location close to Downtown Winter Garden, 745 Cascading Creek brings all of it together—with the space to make it your own.

745 Cascading Creek Lane, Winter Garden

1032 Galston Alley, Winter Garden
$1,650,000
6 Beds ⋅ 5 Baths ⋅ O6441542 MLS
Built by RCB Custom Homes as the builder’s personal residence, this exceptional 5-bedroom, 5-bath residence offers 3,506 square feet of thoughtfully designed luxury in the highly desirable Oakland Park neighborhood. Completely remodeled within the past two years, no detail was overlooked in creating a home that is as refined as it is comfortable. Beautiful new hardwood flooring, custom wood beams, designer wallpaper, upscale tile selections, custom cabinetry, premium appliances, and an antique barn wood fireplace treatment create distinctive character throughout. Custom automated blinds and a complete repaint add the finishing touches to this beautifully curated home. Designed for both everyday living and entertaining, the home features inviting screened front and side porches, with an outdoor kitchen. The premium lot faces a long green park with views of Lake Apopka, adjacent to the community clubhouse & amenities . Beyond the beautiful finishes are the exceptional behind-the-scenes upgrades that truly set this home apart, including a whole-home generator, spray foam insulation for impressive energy efficiency, an expansive climate-controlled attic offering valuable conditioned storage, and wiring in place for a future water treatment system. Enjoy all that Oakland Park has to offer, including two community pools and a prime location within the golf cart district. A complete list of upgrades and improvements is available upon request. This is a rare opportunity to own a meticulously remodeled custom residence where luxury, craftsmanship, comfort, and thoughtful design come together.

1032 Galston Alley, Winter Garden

9845 Emerald Berry Drive, Winter Garden
$1,050,000
5 Beds ⋅ 5 Baths ⋅ O6441968 MLS
Stunning Mediterranean-style home in the sought-after Watermark community of Winter Garden! This 5-bedroom, 4.5-bath home offers a spacious open layout with custom finishes throughout, including custom wood paneling with LED accent lighting, designer curtains and light fixtures, and luxury vinyl plank flooring on every floor. The gourmet kitchen features KitchenAid appliances (built-in oven, built-in microwave, cooktop, dishwasher), double sink, walk-in pantry, and a bright breakfast nook overlooking the living area. The living room boasts a custom electric fireplace with built-in wood shelving. A dedicated den/office with custom cabinetry and a formal dining room with custom cabinetry and built-in wine fridge add versatility. One bedroom and full bath are located downstairs — perfect for guests — while upstairs offers four bedrooms including a luxurious primary suite with his-and-hers vanities flanking a built-in soaking tub, separate shower, and private water closet. The upstairs loft comes complete with a projector and screen, ideal for a home theater. Enjoy Florida living at its finest in the screened lanai, complete with a summer kitchen (grill, sink, refrigerator) and motorized retractable screen. Additional highlights include a laundry room with utility sink, screened pool, and a 2-car garage with paver driveway. Watermark residents enjoy access to a community pool and clubhouse for just $160/month HOA. Don't miss this move-in-ready gem!

9845 Emerald Berry Drive, Winter Garden

128 N Highland Avenue, Winter Garden
$965,000
4 Beds ⋅ 3 Baths ⋅ O6442723 MLS
Welcome to a piece of history, right in the Winter Garden's golf cart district! This stunning Craftsman bungalow is nestled in the Historic District, where timeless character meets extensive modern updates. Set on a 0.34-acre lot beneath grandfather oaks, this home creates an atmosphere that feels peaceful while placing you just steps from the energy of downtown. From the moment you arrive, you're greeted by a gravel driveway(2021) that leads to the front of the property, while outdoor lighting (2021) creates a welcoming glow as the sun goes down. Step through the beautiful leaded glass front door into a home filled with warmth and character. Rich heart pine floors, 9-foot ceilings, and crown molding create a timeless backdrop that is sure to make everyone feel at home.The front living and dining area provides a comfortable place to entertain or settle in with loved ones. Nearby, a flexible room can function as a bedroom or home office, and includes its own half bath, giving you the freedom to shape the space around your family's needs. At the center of the home, the farmhouse-inspired kitchen includes real wood cabinetry, granite countertops, and a convenient side entry to make everything from everyday cooking to hosting dinners feel effortless. The side entrance also makes bringing in groceries especially convenient. Down the hall, two bedrooms create comfortable retreats and share a guest bathroom with subway tile detailing. The guest bathroom tub drain line was replaced in 2025, while extensive flooring and subfloor improvements completed throughout the home provide a refreshed foundation from room to room. Upstairs, you’ll find the new flooring that was installed in 2025, along with recessed lighting (2018), and a bright and inviting loft space with flexibility for a reading area or home office. The primary bedroom was remodeled in 2025 and includes a custom built-in closet for exceptional organization. The upstairs bathroom was also remodeled in 2025, creating a beautifully updated space to begin and end your day. The home has received extensive upgrades, providing the new owners with peace of mind that this home was truly cared for. Upgrades include a downstairs HVAC system (2023), a replacement of the downstairs ductwork (2025), foundation support installed beneath the rear half of the home with concrete footers (2024), and a new water heater (2025). The home's exterior has been refreshed as well, including Artificial turf (2021) for easy upkeep, new exterior paint (Dec, 2024) and a new roof (2023). Heading outside, you're bound to love the private fenced in backyard space. Whether you're imagining weekend gatherings, letting little ones play, or simply enjoying a quiet afternoon outdoors, there's room to create the backyard you've always wanted. The detached 25' x 25' garage and workshop adds another layer of flexibility, complete with 100-amp electrical service. For a hobbyist, craftsman, or anyone who needs additional storage and workspace, this building can become whatever your lifestyle requires.This is a home with character you simply can't recreate, paired with the extensive updates and improvements. And perhaps best of all, you're living in the heart of Historic Downtown Winter Garden, where morning walks, farmers markets, local dining, shopping, live entertainment, and community events can become part of your daily routine. Don't wait on this amazing home, schedule your private showing TODAY!

128 N Highland Avenue, Winter Garden

1118 Maidenmoor Road, Winter Garden
$460,000
4 Beds ⋅ 2 Baths ⋅ O6440167 MLS
Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

1016 Catori Road, Winter Garden
$800,000
4 Beds ⋅ 4 Baths ⋅ O6440957 MLS
Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Winter Garden

16924 Tradewind Point, Winter Garden
$719,999
4 Beds ⋅ 4 Baths ⋅ O6439183 MLS
FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden

1553 Spring Ridge Circle, Winter Garden
$449,500
3 Beds ⋅ 2 Baths ⋅ S5156629 MLS
Live in Winter Garden’s Golf Cart District! This charming 3 bed, 2 bath home with an office/den in one of Winter Garden’s most desirable communities, Crown Point Springs. This home has an open floor plan with split bedrooms, an enclosed patio, fenced yard, inside laundry room and a two-car attached garage. The foyer will welcome you into the home with the formal dining on your left and the French door enclosed office/den on your right (currently being used as a game/theatre room. You will love the ceramic tile floors in the formal dining and family rooms. Walk further into the heart of the home - the kitchen, that features painted cabinets and counters, a new stainless steel stove, dishwasher and fridge. The breakfast nook overlooks the yard. The kitchen is open to the family room that has a brick front wood burning fireplace. A French door leads to the enclosed patio – what a great space to enjoy your morning coffee or relax after a long day! The spacious yard is fenced in and there’s plenty of room for a pool. The owner’s suite is off the kitchen and features and en-suite bath with an updated “adult height” vanity with two sinks, a glass enclosed shower and a walk-in closet. The guest bedrooms are on the other side of the home and share the guest bath that features an updated “adult height” one sink vanity and a tub/shower combo. This home has been lovingly maintained! Additional updates include a new roof (2026), new garage door, new fan in the family room, interior paint, cabinets for additional storage in the laundry room and the washer & dryer are included! This home has leased solar panels that the Buyer will have to take over, making the electricity bill low. Community is located minutes away from downtown Winter Garden, half a mile from the West Orange Trail, close to Chapin Station where you can enjoy picnic areas, playground, a tennis and basketball court. Crown Point Springs is also close to Newton Park where you’ll find a boardwalk, boat ramp, grills, picnic tables and playground, etc. Take your golf cart to Plant Street’s restaurants, boutiques, theater, festivals, and the popular Saturday farmer’s market. Close to top-rated schools, Winter Garden Village, AdventHealth, Publix, 429, and the Florida Turnpike. Don't miss this chance to own a home in one of Central Florida’s most desirable communities. Schedule your showing today!

1553 Spring Ridge Circle, Winter Garden

16260 Silver Grove Blvd, Winter Garden
$950,000
5 Beds ⋅ 5 Baths ⋅ O6437986 MLS
Welcome to a beautifully maintained home offering modern style, thoughtful design, and comfortable everyday living. The bright, open layout features a gourmet kitchen with an oversized island, white cabinetry, striking blue island cabinets, elegant pendant lighting, beautiful backsplash, generous counter space, and a spacious pantry. The expansive living area is filled with natural light and opens to a versatile additional room, ideal for a home office, media room, playroom, or hobby space. The spacious primary suite offers a relaxing retreat with an ensuite bath featuring dual sinks, ample cabinetry, and a separate tub and shower. Generously sized secondary bedrooms, well-appointed bathrooms, and excellent storage add to the home's functionality. A large walk-in closet with built-in organization, dedicated laundry room, and oversized garage provide even more convenience. Outside, enjoy a large backyard with abundant green space and a covered patio, perfect for entertaining, play, gardening, or relaxing. Located in an attractive residential community surrounded by green space and neighborhood amenities, this home delivers the ideal combination of style, space, storage, and livability.Situated in an attractive residential community surrounded by green space and neighborhood amenities, this home offers the combination of style, space, storage, and livability that today's buyers are looking for.

16260 Silver Grove Blvd, Winter Garden

15680 Panther Lake Drive, Winter Garden
$1,950,000
5 Beds ⋅ 6 Baths ⋅ O6438584 MLS
Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an environment that caters to both entertaining and every day life. The first floor is open and has 2 sets of triple pane sliding glass doors that fully open to your personal oasis. Beyond the covered lanai is a beautiful pool, spa and cabana area, perfect for a mid day swim or watching Disney fireworks at night. The kitchens, indoor and outdoor, and sure to impress even the most fastidious of chefs with the natural gas cooktop, multiple mounted range hoods, quartz countertops and more. This property is not only a "smart home" but also environmentally conscientious with newly installed solar panels and an electric car charger. All furniture is included with the sale of this home, the only thing you need is the keys to begin living your best central Florida life. Virtual Tour Available.

15680 Panther Lake Drive, Winter Garden

14776 Magnolia Ridge Loop, Winter Garden
$839,900
4 Beds ⋅ 4 Baths ⋅ O6434178 MLS
Welcome to your Dream home with a private Pool, located in Orchard Hills Community! This stunning residence perfectly blends elegance, comfort, and functionality in Winter Garden's most sought-after neighborhoods. This home offers 4 bedrooms, 3 full bathrooms, and a 1/2 pool bath bath with a bonus /flex room off of the kitchen and thoughtfully designed living spaces ideal for both everyday living and entertaining. A beautifully appointed gourmet kitchen, complete with a large island, elegant granite countertops, and ample cabinetry. The kitchen seamlessly flows into the expansive open-concept living and dining areas, creating the perfect setting for gatherings with family and friends. A charming front porch welcomes you and provides the perfect place to relax. Step through the sliding glass doors and discover your own private outdoor retreat. The backyard features a spectacular covered gourmet outdoor living area and a beautiful private pool, offering the ideal space for entertaining, relaxing, and enjoying year-round outdoor living. Living in Orchard Hills means enjoying an exceptional lifestyle with resort-style amenities, including a clubhouse, fitness center, resort-style swimming pool, dog park, playgrounds, walking trails, and community events throughout the year. Ideally located, this home is just minutes from Hamlin Town Center, Winter Garden Village, top-rated schools, shopping, dining, grocery stores, and major highways, including SR-429 making this Central Florida residence such a desirable place to live.

14776 Magnolia Ridge Loop, Winter Garden

301 Valencia Court, Winter Garden
$695,000
4 Beds ⋅ 3 Baths ⋅ NS1089084 MLS
Welcome to 301 Valencia Ct., a well maintained 4bedroom 2.5 bath home situated on a large, beautifully landscaped lot with mature trees and established landscaping in desirable Winter Garden. This inviting home offers a comfortable and functional floor plan with plenty of space for everyday living, entertaining and hosting family and friends. Inside a beautiful stone fireplace creates a warm and inviting focal point, while the interior laundry room adds everyday convenience. Step outside to enjoy the spacious backyard, with plenty of room to add a pool, creating the opportunity to design your own private Florida retreat. One of the property’s standout features is its location within the Winter Garden golf cart district, allowing you to enjoy the sought after golf cart lifestyle. Take a golf cart ride toward historic downtown Winter Garden and enjoy its popular restaurants, shops, Farmers market, entertainment, community events and small town charm.Numerous updates have been made to the home to include a new roof in 2021, A/C 2020, master bathroom,guest bathroom remodel in 2023 and Kitchen 2017.

301 Valencia Court, Winter Garden

2491 Prairie View Drive, Winter Garden
$925,000
5 Beds ⋅ 3 Baths ⋅ O6436619 MLS
5 bedrooms. 3 full baths. Nearly 3,740 SF. 3-car garage. Private screened pool. Gated community. Newer roof and A/C. Minutes from Winter Garden Village, AdventHealth, SR-429, the Florida Turnpike, Historic Downtown Winter Garden, and convenient to Walt Disney World. This is the combination buyers spend months trying to find. Set behind the gates of Wintermere Pointe, 2491 Prairie View Drive brings together a flexible five-bedroom floor plan, multiple living and entertaining spaces, private outdoor living, and a connected Winter Garden location with shopping, dining, healthcare, major roadways, and entertainment within easy reach. Step inside and the scale is immediately apparent. Soaring ceilings rise above formal living and dining rooms, leading to a spacious family room anchored by a striking dual staircase. Large sliding glass doors frame the greenery and blue waters of the pool beyond. At the center of the home, the updated gourmet-style kitchen offers stainless steel appliances, abundant cabinetry and counter space, a prep island, casual seating, and views toward the pool and backyard — creating a natural flow between cooking, gathering, and outdoor entertaining. A first-floor bedroom and nearby full pool bath provide valuable flexibility for guests, extended family, multigenerational living, or a private office. Upstairs, two separate loft areas provide space for a media room, game room, second living area, or quiet retreat. The larger opens directly onto an expansive second-story balcony overlooking the pool. An oversized bonus bedroom above the garage, incorporated as a builder upgrade, joins two additional bedrooms and a shared full bath. The naturally bright primary suite features dual walk-in closets and an ensuite with separate vanities, soaking tub, and walk-in shower. Outside, the Florida lifestyle takes over. A private screened pool and covered lanai extend the living space outdoors, with additional yard beyond the enclosure and the second-story balcony above. A generous driveway and three-car garage provide valuable parking and storage, while a newer roof and A/C add two significant improvements already in place. Wintermere Pointe offers the privacy of an established gated community with Winter Garden Village, AdventHealth, shopping, dining, and everyday conveniences nearby. Quick access to SR-429 and the Florida Turnpike keeps Central Florida connected, with Historic Downtown Winter Garden and Walt Disney World conveniently accessible. What makes this home compelling isn't any one feature. It's how rarely they come together. Nearly 3,740 SF. Five bedrooms. First-floor guest space. Two lofts. Oversized bonus bedroom. Expansive balcony. Private screened pool and lanai. Three-car garage. Newer roof and A/C. Gated community. Prime Winter Garden location. You don't have to choose between space and location, indoor and outdoor living, or rooms for everyone and places to come together. It's already here. If this is the combination you've been waiting to find, 2491 Prairie View Drive deserves to be seen.

2491 Prairie View Drive, Winter Garden

16273 Taliesin Street, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ S5156149 MLS
Welcome to this beautifully maintained home in the desirable Hawksmoor community of Winter Garden! Built in 2019, this bright and inviting residence offers modern style, thoughtful design, and comfortable living in one of the area’s sought-after communities. From the moment you arrive, the charming curb appeal and beautifully landscaped front yard create a warm welcome. Inside, you’ll find an open and airy layout filled with natural light, recessed lighting, and stylish finishes throughout. The spacious living area features a modern fireplace and large windows with elegant window treatments, creating the perfect space to relax or entertain. A thoughtfully enclosed flex space features beautiful sliding glass doors, creating a private and beautifully finished home office that is perfect for working from home, studying, or a variety of lifestyle needs. The contemporary kitchen offers modern cabinetry, stainless steel appliances, a generous island with seating, and plenty of workspace, flowing seamlessly into the dining and living areas. Sliding glass doors extend the living space to a screened-in lanai, providing a wonderful indoor-outdoor setting for morning coffee, dining, or entertaining while enjoying the Florida lifestyle. The home's neutral finishes, beautiful tile flooring, and well-maintained interiors make it truly move-inready. Located in Hawksmoore, this home offers the perfect combination of modern comfort, community living, and the highly desirable Winter Garden lifestyle. Don't miss the opportunity to make this beautiful home your own!

16273 Taliesin Street, Winter Garden

2202 Redmark Lane, Winter Garden
$824,900
5 Beds ⋅ 4 Baths ⋅ O6435919 MLS
Welcome to a home where thoughtful design, elevated finishes, and effortless Florida living come together. This exceptional 5-bedroom, 3.5-bath residence offers an impressive blend of space, functionality, and custom detail, complete with a bonus room, private office, formal dining room, spacious living room, and a stunning great room that truly serves as the heart of the home. Primary bedroom is located on the first floor offering a split floor plan and privacy. This is a smoke free, pet free home. Interior laundry room with utility sink. The great room seamlessly opens to the expansive kitchen, featuring generous cabinetry, abundant storage, and a comfortable eat-in space designed for everyday gatherings. Custom built-ins, an electric fireplace surrounded by beautiful stone, and ceiling speakers create an inviting atmosphere for both relaxing and entertaining. Throughout the home, Pottery Barn curtain rods, crown molding, upgraded lighting, and an abundance of closet and storage space showcase the attention to detail. Fresh interior paint adds a crisp, move-in-ready feel, while the custom-built office provides an ideal space for working from home. Upstairs, an upgraded wrought-iron staircase creates a striking architectural focal point while adding a sophisticated touch to the home's aesthetic. The versatile bonus room offers additional space for a media room, playroom, fitness area, or second living space—the possibilities are endless. Step outside through the double-sided sliders to your own private retreat. The screened and covered lanai overlooks a sparkling saltwater pool with a sheer-fall water feature, creating the perfect setting for Florida afternoons and beautiful sunsets to top off the evening entertaining possibilities. The outdoor living area is thoughtfully pre-wired for television and equipped for speaker connectivity, making it easy to create the ultimate outdoor entertainment space. The home also delivers an impressive list of functional upgrades,whole-house surge protector, newer water heater (2024) ,new exterior paint (2026) , and a new HVAC (1/26) system with a damper system and remote-control capability thermostat. A spacious 3-car garage and elegant paver driveway provide both convenience and curb appeal. A transferable termite bond (Massey) adds another layer of confidence for the next homeowner. Located within a gated community, residents enjoy added peace of mind along with an outstanding selection of amenities, including a playground, tennis and pickleball courts, soccer field, and picnic area. Beyond the community, Winter Garden offers an exceptional lifestyle with an abundance of dining, shopping, entertainment, and recreation options. Convenient access to 429, the Florida Turnpike, OIA 33 miles, and 535 makes commuting throughout Central Florida a breeze.

2202 Redmark Lane, Winter Garden

7693 Green Mountain Way, Winter Garden
$2,600,000
6 Beds ⋅ 6 Baths ⋅ O6432738 MLS
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 7693 Green Mountain Way in Winter Garden, an impressive two-story lakefront home offering 6 bedrooms, 6 bathrooms, dual primary suites, a spacious loft, balcony, and multiple indoor and outdoor living areas. Designed to accommodate both everyday living and large-scale entertaining, this expansive residence combines flexible living spaces with standout waterfront amenities and scenic lake views. The interior provides an abundance of space across two levels, highlighted by two primary bedrooms that offer added flexibility for multigenerational households, extended guests, or those who simply prefer multiple private retreats. Four additional bedrooms and six full bathrooms provide generous accommodations throughout the home. A large loft adds another dedicated living area that can easily function as a media room, game room, secondary family room, or entertainment space. The balcony extends the living area outdoors and provides another inviting place to unwind while taking in the surrounding views. Multiple gathering areas throughout the home allow plenty of room for entertaining while still providing separation and privacy when desired. The outdoor spaces are designed to make the most of the home's scenic lakefront setting. A welcoming front porch adds curb appeal, while the rear of the home opens to a covered patio, spacious deck, and outdoor kitchen, creating a well-equipped setting for dining, grilling, and entertaining. The centerpiece is the in-ground infinity pool and spa overlooking the lake, where the water's edge blends beautifully with the waterfront backdrop. With dedicated areas for cooking, lounging, swimming, and gathering, the combination of the outdoor kitchen, covered patio, deck, infinity pool, spa, and expansive lake views creates a resort-inspired outdoor retreat ideal for both everyday relaxation and entertaining. Situated in Winter Garden, the property offers access to a vibrant Central Florida community known for its parks, recreational opportunities, shopping, dining, and convenient connections to major roadways and Orlando-area destinations. With six bedrooms, dual primary suites, six bathrooms, a loft, balcony, expansive outdoor living areas, and a lakefront infinity pool and spa, 7693 Green Mountain Way delivers exceptional space, flexibility, and waterfront living in one impressive property

7693 Green Mountain Way, Winter Garden

208 3rd Street, Winter Garden
$435,000
8 Beds ⋅ 3 Baths ⋅ O6435284 MLS
8 bedrooms. 3 full baths. Approximately 1,750 SF. Just blocks from Plant Street. Space and location set this property apart. Offering 8 bedrooms and 3 full baths across approximately 1,750 SF, the home sits on a 9,431 SF fully fenced lot—a combination of interior space and land increasingly difficult to find this close to Historic Downtown Winter Garden. Built in 1925 and sold as-is, the home presents an opportunity to update and personalize to your own vision. The flexible room count provides options for bedrooms, guest space, home offices, or additional living needs, while the generous 75' x 125' lot leaves plenty of outdoor space to create a garden, entertaining area, or backyard retreat. No HOA, city utilities, and R-2 zoning add to the property's flexibility and long-term appeal. Location is the part that cannot be renovated. Enjoy being just blocks from Plant Street, the Saturday farmers market, restaurants, cafés, shops, entertainment, and the West Orange Trail, with Lake Apopka, SR-429, and Florida's Turnpike conveniently nearby. Currently income producing, the property offers the flexibility to maintain its existing rental use or be delivered vacant upon request. 8 Bedrooms. 3 Full Baths. Approx. 1,750 SF. 0.22 Acres. 9,431 SF Lot. 75' x 125'. No HOA. Bring your vision and make the space your own in a location that's increasingly difficult to replicate. Schedule your private showing today.

208 3rd Street, Winter Garden

427 Tierra Verde Lane, Winter Garden
$849,988
4 Beds ⋅ 3 Baths ⋅ O6435267 MLS
Virtually Staged. Welcome to this beautifully maintained custom home located in the gated community of Lake Cove Pointe, within the Winter Garden Golf Cart District. Conveniently located just minutes from Historic Downtown Winter Garden, this home offers easy access to dining, shopping, theater, entertainment, and local avente. A paver driveway and path lead to the charming front porch and welcoming entry. Inside, this nearly 2, 400-square-foot home features 4 bedrooms, 3 full baths, and a spacious three-way split floor plan designed for comfort and privacy. The main living areas feature attractive wood-look ceramic tile, with carpet in the family room and bedrooms. The well-appointed kitchen offers white cabinetry, beautiful countertops, and glass-pane display cabinets for added character and storage. The spacious Owner's Suite includes custom closets, a comfortable sitting area, and French doors leading to the screened-in patio. The Owner's Bath features a large shower and freestanding soaking tub. Enjoy Florida outdoor living from the screened-in patio, complete with a convenient wet bar and sink, making it an ideal space for entertaining or relaxing. The property also offers an immaculate two-car garage with new epoxy flooring, plus a separate third golf cart garage/workshop combination, providing excellent flexibility for golf cart storage, hobbies, or additional workspace. Recent updates include a 2019 roof, 2019 A/C, a Rheem 60-gallon hybrid water heater installed approximately nine months ago, and lifetime garage door springs! installed last summer. Located in a desirable gated community and close to Historic Downtown Winter Garden, this well-maintained home combines a thoughtful floor plan, attractive updates, excellent garage space, and convenient access to all that Winter Garden has to offer.

427 Tierra Verde Lane, Winter Garden

208 3rd Street, Winter Garden
$435,000
O6435218 MLS
Most Winter Garden listings sell on charm. This one sells on the rent roll. Eight rooms currently rented — seven at $175 weekly and one at $200 — generating $1,425 per week / $74,100 annualized gross income at current rents. In place, occupied, and income producing. The land adds another layer to the opportunity. Situated on approximately 0.22 acres / 9,500+ SF with a 75' x 125' lot, the fully fenced property offers R-2 zoning, no HOA, city water and city sewer, along with ample yard space and future flexibility. Hold the existing income while exploring the property's longer-term expansion or redevelopment potential, subject to applicable zoning requirements and City approvals. The location carries its own value. Just a few blocks from Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shops, restaurants and the farmers market, with SR-429, Florida's Turnpike and Lake Apopka nearby. The surrounding area continues to evolve with renovated properties and new construction. 0.22 Acres. 9,500+ SF Lot. R-2. Eight Rented Rooms. $1,425/Week Gross. Income in place. Land underneath. Future upside ahead. A rare opportunity to own all three near Downtown Winter Garden—schedule your private showing today.

208 3rd Street, Winter Garden

9056 Morgana Court, Winter Garden
$2,050,000
5 Beds ⋅ 5 Baths ⋅ O6432897 MLS
Welcome to 9056 Morgana Ct, perfectly positioned on one of the most desirable lakefront homesites in the community, offering expansive water views and an exceptional setting on Hickorynut Lake. Designed to take full advantage of its waterfront location, the home features expansive windows and open living spaces that frame the lake from the moment you step inside. The views continue outdoors, where a resort-style pool and spa, covered outdoor living, and summer kitchen create a seamless connection between the home and the water. Beyond the pool, the backyard leads to a private covered dock with boat and jet ski lifts, making days on the lake effortless. Whether enjoying quiet mornings by the water, entertaining poolside, or watching the sunset over the lake, this is Florida waterfront living at its finest. Inside, soaring ceilings, abundant natural light, sophisticated finishes, and generously sized living spaces create a luxurious yet inviting atmosphere. With its remarkable lake views, private waterfront setting, and resort-style outdoor living, this is truly one of the premier lakefront opportunities in the community.

9056 Morgana Court, Winter Garden