Winter Garden Homes with Rain Gutters Exterior Features

4 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

289 Crystal Wood Drive, Winter Garden

$239,000

3 Beds ⋅ 3 Baths ⋅ Grove Resort & Spa SubDv. ⋅ 34787 Zip Code

Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building 1, the condo features a spacious split-bedroom layout, three full bathrooms, a well-equipped kitchen with granite countertops, comfortable living and dining areas, and a screened balcony with elevated views. The Grove delivers the complete Orlando resort experience with Surfari Water Park featuring water slides, a lazy river, splash areas and private cabanas, multiple onsite dining options, a full-service spa, fitness center, arcade, and a 20-acre activity lake offering fishing and water activities. When you're not enjoying the condo yourself, the turnkey rental program provides professional management for vacation rentals. Whether you're looking for your own Orlando getaway or a furnished vacation rental investment near Disney, this top-floor 3-bedroom residence offers an outstanding opportunity at one of Central Florida's most amenity-rich resort destinations.

14501 Grove Resort Ave Unit 1707, Winter Garden

$975,000

5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code

Welcome to 9566 Bolero Rd, where luxury, space, and location come together in one of Central Florida’s most desirable and rapidly growing communities—Winter Garden. Situated on a premium 60-foot lot with beautiful pond views, this impressive North Haven model offers 5 bedrooms, 3.5 baths, a first-floor primary suite, spacious loft, and oversized fenced yard, all tucked away on a quiet cul-de-sac. Step inside through the dramatic two-story foyer and discover a bright, modern floor plan designed for both everyday living and entertaining. The gourmet kitchen features 42” cabinetry with crown molding, upgraded stainless-steel appliances, a vent hood, generous workspace, and an open layout overlooking the family room and picturesque pond beyond. Extend your living outdoors to the spacious backyard featuring a pergola, fenced yard, and tranquil water views—the perfect setting for morning coffee, entertaining, or relaxing at the end of the day. The first-floor primary suite offers privacy and convenience with a spacious walk-in closet and ensuite bath featuring dual vanities, a large walk-in shower, and garden tub. Upstairs, a generous loft provides flexible space for a media room, playroom, home office, or second living area. Bedrooms 2 and 3 share a full bath, while Bedrooms 4 and 5 are connected by a convenient Jack-and-Jill bath. The laundry room is also pre-plumbed for a utility sink. Enjoy the benefits of a resort-style, maintenance-free community while being surrounded by everything that makes Winter Garden such an exceptional place to call home. The area continues to flourish with new restaurants, shopping, grocery stores, entertainment, and everyday conveniences, while still offering the charm and lifestyle Winter Garden is known for. Enjoy easy access to Walt Disney World, Disney Springs, Publix, SR-429, I-4, and SR-417, connecting you to Orlando’s world-class attractions, employment centers, and entertainment. Whether you're enjoying peaceful pond views from your backyard, exploring nearby dining and shopping, or heading out for a day at Disney, 9566 Bolero Rd offers the space, lifestyle, and location you've been looking for. Welcome home!

9566 Bolero Road, Winter Garden

$845,000

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2c-1 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully RENOVATED home, The SEA CLIFF model -One of the largest floorplans in the Waterleigh community.where modern elegance meets comfortable living. The home has been extensively updated with a sophisticated neutral palette, designer lighting, luxury vinyl plank flooring, custom-style cabinetry, quartz countertops, and upgraded fixtures throughout. . This beautiful 2 story home features 4 bedrooms & 3.5 full baths,as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. The show-stopping kitchen is the heart of the home, featuring a large waterfall-edge island, abundant cabinetry, statement backsplash, upgraded appliances, and beautiful accent lighting. The open-concept design seamlessly connects the kitchen, dining, and living spaces, creating an ideal setting for both everyday living and entertaining. bathrooms have been stylishly renovated with contemporary vanities, quartz countertops, modern black fixtures, designer mirrors, and beautiful tile finishes. Additional highlights include custom wall paneling, upgraded trim, elegant lighting, and carefully curated finishes throughout. within walking distance of the community clubhouse and amenities This amazing home is in the highly desirable community “Waterleigh.” Located just off the 429 west of Disney, This community amenities include a huge resort style pool, fitness gym, club house, dog park, huge sports fields, playground, beach volleyball, Tennis, lake view BBQ/picnic area, with sidewalks that wind around the scenic lakes, nature, and community for a relaxing and enjoyable lifestyle with periodic fitness stops if you choose. Fast and easy access anywhere. Hospitals, restaurants and shopping are all nearby. Great schools; Water Spring Elementary, Water Spring Middle, and Horizon Highschool

10169 Shallow Water Drive, Winter Garden

$365,000

3 Beds ⋅ 3 Baths ⋅ Orchard A1-A26 B1 B2 C D1-D4 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2.5-bath townhome with a 2-CAR GARAGE in the GATED Orchard community of Winter Garden! Recent improvements include FRESH INTERIOR PAINT, UPDATED KITCHEN & BATHS, LUXURY VINYL PLANK FLOORING throughout the main level, BRAND NEW CARPET upstairs, stylish NEW LIGHT FIXTURES, a NEW GARAGE DOOR OPENER, and UPDATED ROOF (2024), creating a home that feels fresh, modern, and truly MOVE IN READY. Inside, the light-filled OPEN CONCEPT floor plan is designed for both everyday living and entertaining. The modern flooring creates a cohesive feel throughout the main living areas, while the kitchen - delivering ample storage and counter space, STAINLESS STEEL APPLIANCES and a breakfast bar - overlooks the spacious living and dining areas, keeping everyone connected. A convenient half bath completes the first floor. Upstairs, the PRIMARY SUITE is ideally situated at the back of the home and offers a generous WALK-IN CLOSET and a private en-suite bath. Bedrooms two and three are positioned at the front of the home, with the third bedroom also featuring its own walk-in closet. The guest bath and second-floor laundry closet are centrally located for added convenience. Step outside to enjoy a rear patio overlooking a sizable green space with NO REAR NEIGHBORS, creating a peaceful setting for relaxing outdoors. Charming curb appeal, a COVERED FRONT PORCH with an arched entry, and well-kept landscaping enhance this home's appeal. The Orchard offers the LOW MAINTENANCE lifestyle you have been looking for, with the HOA covering exterior maintenance while residents enjoy a GATED ENTRANCE, COMMUNITY POOL, playground, and tree-lined streets. Located just minutes from Winter Garden Village, you will love having exceptional shopping, dining, entertainment, TOP-RATED SCHOOLS, and easy access to SR 535, SR 50, the Florida Turnpike, and SR 429, putting everything Central Florida has to offer within easy reach. This is the perfect opportunity to enjoy stylish, low-maintenance living in one of Winter Garden's most desirable communities. Call today to schedule a tour and let Golden Russet Drive welcome you HOME!

13765 Golden Russet Drive, Winter Garden

$599,900

4 Beds ⋅ 2 Baths ⋅ Orchard Hills Phase 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 4-bedroom, 2-bath home in the highly desirable Orchard Hills community of Winter Garden. Thoughtfully designed with an open-concept floor plan, this home offers a perfect blend of comfort, style, and functionality. The spacious kitchen is the centerpiece of the home, featuring granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and seamless flow into the living and dining areas—ideal for entertaining or everyday living. Wood-look tile flooring enhances the main living spaces, while large windows fill the home with natural light. Step outside to your private outdoor oasis featuring a screened lanai, an extended paver patio, custom pergola, built-in outdoor bar, and fire pit—creating the perfect space for weekend gatherings or relaxing evenings at home. The spacious primary suite provides a peaceful retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Residents of Orchard Hills enjoy exceptional resort-style amenities, including a stunning zero-entry pool, clubhouse, fitness center, playgrounds, walking trails, and beautifully maintained green spaces. Ideally located in the heart of Horizon West, you're just minutes from Hamlin Town Center, top-rated schools, shopping, dining, SR-429, Walt Disney World, and all that Winter Garden has to offer. Don't miss your opportunity to own this exceptional home in one of Winter Garden's most sought-after communities.

4855 Palmetto Park Drive, Winter Garden

$1,100,000

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code

Welcome to your LAKEFRONT dream home and backyard oasis! This popular “Delmar” floor plan with 120’ of DOCKABLE lake frontage on skiable Hickory Nut Lake which expends 403 acres. You will love the lake lifestyle enjoying boating, waterskiing, kayaking, or fishing! This is a great fishing lake known for it’s Largemouth bass, Bluegills, and Spotted Gars. When you’re done boating, you can finish the day in your heated swimming pool or spa. The pool and spa have all the works, including an electric AND solar heater, plus pool lights for night swimming. This home features a sizable covered lanai perfect for dining a la fresca by the pool enjoying the lake views with all the privacy having no rear neighbors. When night time comes, you will enjoy your nightly DISNEY fireworks view. A bonus of this lot is that it is pie shaped, so there is a spacious yard beside the pool that is fenced in for your furry friends. This sprawling 1 story home is located on a small alcove offering privacy from the main access road. You can sit on the covered front porch enjoying sunset views. The interior of this home is perfect for entertaining, featuring an open concept living area complete with family room/kitchen/dining combo. The stunning kitchen features a wall oven and wall microwave, cooktop, and large walk-in pantry. This “emerald series” house has all the upgrades including tile roof, custom built in closets, custom woodwork and wainscoting, 8 ft interior doors, tray ceilings, whole house water softening system, luxury LVP all throughout (no carpets!), trim lights built into the soffit for all of your holiday lighting needs, and a new dishwasher. The exterior was hand painted in August 2026, so this is truly a turn key home! Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, water view, walking trails, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. Don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh provides!

10043 Little Alcove Loop, Winter Garden

$879,900

4 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Stunning Home in Winter Garden – Prime Location! Welcome to this beautifully maintained 4-bedroom, 3-bathroom home offering an exceptional combination of modern design, comfort, and thoughtful upgrades. The home opens to a spectacular open-concept living, dining, and kitchen area. The dramatic two-story living room features soaring ceilings, abundant natural light, elegant floor-to-ceiling window treatments, and luxury vinyl plank flooring throughout the main living areas, while all bedrooms feature upgraded carpeting for added comfort. At the heart of the home is a stunning gourmet kitchen featuring abundant white cabinetry extending to the ceiling, quartz countertops, a beautiful waterfall-design island, and a full suite of Samsung appliances, including a built-in microwave and oven, cooktop, and modern stainless-steel range hood. A separate beverage station with a built-in wine fridge adds both style and convenience. Additional premium upgrades include a whole-house water filtration system, automated blinds, and window treatments throughout. The spacious primary suite offers dual sinks with quartz countertops, a beautifully tiled walk-in shower, automated shades, and an impressive custom walk-in closet with extensive built-in shelving, drawers, and hanging space. The garage is equally well-appointed with an upgraded epoxy floor and an EV charger for convenient at-home electric vehicle charging. Step outside to an exceptional outdoor living area featuring an expansive screened enclosure, paver patio, low-maintenance artificial turf, and a covered lanai with a ceiling fan—perfect for entertaining, relaxing, and enjoying Florida living year-round. The home also features a solar panel system that will transfer to the new owner. Residents enjoy resort-style community amenities, including a swimming pool, playground, and scenic sidewalks. Ideally located near Walt Disney World, Hamlin Town Center, Horizon West, top-rated schools, shopping, dining, and major highways, this highly upgraded Winter Garden home delivers an outstanding combination of space, style, comfort, and convenience. Don’t miss this exceptional opportunity—schedule your private showing today!

17018 Seville Orange Road, Winter Garden

$549,500

3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 3a SubDv. ⋅ 34787 Zip Code

Welcome HOME to this beautifully upgraded Bellake floorplan located in the HIGHLY sought-after Waterleigh community in the heart of Horizon West! From the moment you walk through the front door, you'll be welcomed by a bright, open-concept layout designed for both everyday living and effortless entertaining. Just off the entry, the ENCLOSED FLEX ROOM offers the perfect space for a home office, playroom or media room. The heart of the home is the kitchen, where you'll find stainless steel appliances, a stylish subway tile backsplash, an updated faucet, upgraded lighting, and elegant crown molding throughout. Overlooking the spacious dining and living areas, this inviting space makes it easy to stay connected whether you're hosting family gatherings or enjoying a quiet evening at home. Upstairs, escape to your spacious primary suite, thoughtfully designed to feel like your own private retreat. Custom touches including a MODERN ACCENT WALL, CROWN MOLDING, and a custom walk-in closet with built-in shelving. Two additional bedrooms provide flexibility for family, guests, or hobbies, while the upgraded laundry room features added cabinets and shelving for exceptional organization. Step outside to your EXTENDED COVERED LANAI with an ALUMINUM ROOF, creating the perfect outdoor living space for morning coffee, weekend barbecues, or relaxing Florida evenings. The home has been beautifully updated with FRESH EXTERIOR PAINT completed in MAY 2026 and a professionally repainted interior, offering a modern, MOVE-IN-READY feel from the moment you arrive! Additional upgrades include GUTTERS, upgraded ceiling fixtures, NO CARPET DOWNSTAIRS or on the lower portion of the staircase, and a garage featuring EPOXY FLOORS and overhead storage racks. Living in Waterleigh means enjoying more than just a beautiful home, it's a lifestyle. This community offers the convenience of NO CDD and HOA-maintained landscaping! Residents enjoy access to FOUR resort-style amenity centers featuring pools, fitness centers, clubhouses, playgrounds, sports courts, scenic walking trails, community events, and a GOLF CART FRIENDLY atmosphere. You'll even enjoy views of Walt Disney World fireworks and NASA rocket launches from within the community. Located just minutes from Walt Disney World, you'll also be close to shopping, dining, major highways, the newly opened Horizon West Regional Park, the new Horizon West Library opening soon, and the highly anticipated Lifetime Fitness coming soon. This home has been thoughtfully upgraded, meticulously maintained, and is ready for its next owners to make lasting memories. Schedule your private showing TODAY and discover why so many families love calling Waterleigh home!

9462 Komika Lane, Winter Garden

$949,000

3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Welcome to this **better-than-new Renown model by Del Webb**, beautifully maintained and only used seasonally. Located on a premium wooded conservation homesite with open green space, this exceptional home offers privacy, breathtaking nature views, and magical nightly Disney fireworks. This spacious home features 3 bedrooms, 3 full baths, a powder room, flex room, and a 3-car garage with abundant storage. The open-concept floor plan is perfect for entertaining, showcasing a gourmet kitchen, white and gray cabinets with Kitchenaid Stainless Steel appliances including NATURAL GAS stove top, DOUBLE Convection ovens, built-in microwave, refrigerator, wine refrigerator, oversized island, 42" soft-close cabinetry, Lyra quartz countertops, mosaic tile backsplash, and walk-in pantry. The gathering room opens through dramatic zero-corner sliding glass doors to an extended covered paver lanai with panoramic screen enclosure and outdoor kitchen plumbing, creating seamless indoor/outdoor living. You'll be spending lots of time enjoying this gorgeous view! The private Owner's Suite features oversized walk-in closets, dual quartz vanities, linen closet, and an upgraded Super Shower. Two additional guest suites each include walk-in closets and private en-suite baths. Luxury upgrades include Plantation shutters, top-down/bottom-up cellular shades, solar shades, designer lighting, upgraded interior doors, luxury vinyl plank flooring, porcelain tile baths, Smart Thermostat, HVAC air quality package, utility sink in the garage, full rain gutters, and LG pedestal washer and gas dryer included, Tankless Natural Gas Water Heater. Enjoy the award-winning Del Webb Oasis 55+ lifestyle with a 12,000+ sq. ft. clubhouse, resort-style pool, fitness center, pickleball and tennis courts, walking trails, coffee bar, wine room, arts & crafts studio, social clubs, and a full-time Lifestyle Director. HOA includes lawn maintenance, landscaping, gated entry, and high-speed fiber internet with streaming TV. Ideally located in Horizon West, just 6-8 miles from Walt Disney World®, 2.4 miles to AdventHealth ER, and minutes to Flamingo Crossings shopping, dining, and entertainment. Move-in ready and truly better than new, experience luxury, comfort, and resort-style living at its finest!

15031 Canopy Cover Drive, Winter Garden

$859,500

5 Beds ⋅ 4 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to your dream home in the highly desirable community of Wincey Groves! This stunning 5-bedroom, 3.5-bath single-family residence, built in 2021, boasts contemporary design and upscale finishes throughout. Enjoy soaring 10-foot ceilings with elegant fascia, and a chef-inspired modern kitchen featuring luxurious quartz countertops and top-of-the-line stainless steel appliances. Experience custom-built cabinetry and exquisite upgraded millwork that add character and style to every room. The spacious primary suite offers generous walk-in closets, a versatile bonus fifth bedroom, perfect for guests or a home office. Step outside to an upgraded back patio and balcony, where you'll find a fully equipped outdoor kitchen with a wine fridge, refrigerator, built-in grill, and a cozy fire pit—ideal for entertaining or relaxing under the stars. Ideally situated just one mile from Hamlin Town Center, you'll have easy access to premier shopping, dining, and entertainment options.

5128 Breezy Acres Street, Winter Garden

$615,000

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

**Virtual staging in formal living and dining rooms. Video available.** Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW with a distant golf course view. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, Winter Garden

Winter Garden Homes with Rain Gutters Exterior Features

Newest Winter Garden Homes with Rain Gutters Exterior Features