Winter Garden Homes with Attached Property Description

Winter Garden Homes with Attached Property Description

Welcome to Winter Garden, Florida, a charming city that beautifully marries small-town warmth with modern conveniences. Nestled just a short drive from the bustling attractions of Orlando, Winter Garden boasts a rich history, vibrant community, and a picturesque downtown area that invites leisurely strolls along its tree-lined streets. With its historic buildings, delightful shops, and an array of dining options, you'll find that this city offers a welcoming atmosphere that feels like home.

The heart of Winter Garden is its stunning West Orange Trail, a 22-mile-long recreational path perfect for walking, biking, or jogging while soaking in the natural beauty of the area. The city also hosts a variety of community events throughout the year, including farmers' markets, art festivals, and seasonal celebrations, making it an ideal place for families and individuals alike.

As for real estate, Winter Garden is home to an impressive selection of homes with attached properties, catering to diverse lifestyles and preferences. Whether you’re seeking a quaint townhouse with a cozy patio or a spacious duplex with modern amenities, you’ll find a range of options that suit your needs. These homes often come with charming outdoor spaces, perfect for entertaining or simply enjoying Florida’s sunny climate.

With its delightful blend of community spirit, recreational opportunities, and attractive homes, Winter Garden is not just a place to live—it's a place to thrive. Discover your dream home in this enchanting city and experience everything that Winter Garden has to offer!

Newest Winter Garden Homes with Attached Property Description

$710,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! 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. 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.

13527 Fox Glove Street, Winter Garden
$505,435
4 Beds ⋅ 4 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in November 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 4 bedrooms, 3 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your 4th bed with ensuite bathroom. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15153 Groveside Road, 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
$400,000
3 Beds ⋅ 2 Baths ⋅ Regal Pointe Ph 02 47/133 SubDv. ⋅ 34787 Zip Code
Hidden Gems Don't Stay Hidden Long. 234 Grand Royal Circle is the kind of home that stops buyers mid-scroll and makes them say out loud that they did not expect this. Character is the first thing you feel when you walk through the door. Arched doorways carry you through the layout with a warmth and elegance that newer construction spends years and significant money trying to recreate. Rich laminate flooring runs through the main living spaces. Vaulted ceilings create volume and light that make every room feel intentional. And the details, a gallery mirror wall at the entry, a dramatic arched window flooding the flex room with natural light. The kitchen has been updated throughout. Shaker cabinetry, granite countertops, a tile backsplash, stainless steel appliances, upgraded hood and a peninsula with bar seating that opens to the living area and keeps everyone connected. The primary ensuite delivers a double vanity, soaking tub, and clean cabinetry in a bath that feels calm and considered. The flex room is a genuine bonus space, bright, private, and ready to become whatever the next owner needs it to be. The fenced backyard, and a footprint that gives you real outdoor space in one of the most walkable and sought after corridors in Winter Garden. The mature oak canopy makes it feel even larger and is the kind of backyard that earns its own conversation. And then there is the location. Plant Street, Winter Garden's celebrated downtown heart, is right here. The farmers market, award winning restaurants, craft breweries, and community events that make this the most desirable city in Central Florida are not a drive away. They are a walk away. This home is an awesome opportunity in the truest sense of the word. The right buyer is going to recognize exactly what this is the moment they step inside.

234 Grand Royal Circle, Winter Garden
$494,890
3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in November 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your spacious flex space. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15159 Groveside Road, Winter Garden
$420,000
2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Corner Lot | Close to Park | Dedicated Study | Spacious Kitchen. New Construction – September Completion! Welcome to the Caicos at 11275 Silver Trumpet Loop in Esplanade at McKinnon Groves! This thoughtfully designed home features an open-concept layout that blends the great room, dining area, and spacious kitchen into one inviting living space. The kitchen offers plenty of room for meal preparation and entertaining, while the covered extended lanai creates a seamless connection to outdoor living. Tucked away at the rear of the home, the private primary suite features a well-appointed bath and generous walk-in closet. A secondary bedroom, full bath, and versatile study provide flexible space for guests, hobbies, or a home office. A convenient laundry room and two-car garage add everyday functionality. Additional Highlights Include: double pocket doors at study, extended lanai, garden fence, and extended tile flooring. Photos are for representative purposes only. MLS#O6427248. Esplanade at McKinnon Groves offers resort-style living in Winter Garden with beautifully designed homes and exceptional amenities. Residents enjoy a fitness center, movement studio, resort-style pool and spa, Bahama bar, pickleball, tennis and bocce courts, yoga lawns, a bark park, rose garden, and scenic trails. Concierge services and year-round social events create a vibrant lifestyle focused on wellness, recreation, and connection, all within a gated community convenient to everyday essentials.

11275 Silver Trumpet Loop, Winter Garden
$432,318
2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Dedicated Study | Close to Park. New Construction - September Completion! Welcome to the Caicos at 11279 Silver Trumpet Loop in Esplanade at McKinnon Groves! This thoughtfully designed home offers an open-concept layout where the great room, kitchen, and dining area come together to create a bright and inviting space for everyday living and entertaining. The covered lanai extends the living area outdoors, providing the perfect place to relax and enjoy Florida's beautiful weather. The private primary suite features a well-appointed bath and spacious walk-in closet, while a secondary bedroom and full bath offer comfortable accommodations for guests. A versatile study is ideal for a home office, hobby room, or reading retreat. A convenient laundry room and two-car garage add everyday functionality. Additional Highlights Include: garden fence, laundry package, GE refrigerator, 8' interior doors, and extended vinyl flooring. Photos are for representative purposes only. MLS#O6427229. Esplanade at McKinnon Groves offers resort-style living in Winter Garden with a gated setting and exceptional amenities designed for wellness, recreation, and connection. Residents enjoy a fitness center, movement studio, resort-style pool and spa, Bahama bar, pickleball, tennis and bocce courts, yoga lawns, a bark park, rose garden, and scenic walking trails. Concierge services and year-round social events create a vibrant lifestyle, making it easy to stay active, meet neighbors, and enjoy every day in a beautiful natural setting.

11279 Silver Trumpet Loop, Winter Garden
$465,000
3 Beds ⋅ 3 Baths ⋅ Emerald Ridge SubDv. ⋅ 34787 Zip Code
*Walkthrough Video Available* Welcome to the gated Emerald Ridge neighborhood that is conveniently located near the 429, Turnpike, shopping and restaurants in Winter Garden, Horizon West and Windermere as well as the charming downtown Winter Garden Plant Street and all of the local activities it brings. Cool off in the COMMUNITY POOL and enjoy staying active on the sidewalks that run throughout the neighborhood. This home has an OPEN FLOOR PLAN that greets you as soon as you enter. The spacious living room has nice natural lighting and opens to the eat-in kitchen which was recently remodeled. You’ll find NEW CABINETRY with soft-close doors, a TILE BACKSPLASH and STAINLESS STEEL appliances. The WALK-IN PANTRY is a dream as it gives storage space for kitchen wares and laundry needs. Sliding doors open to the SCREENED PATIO so you can enjoy the evening breeze. There’s a SPACIOUS LOFT upstairs which makes for a fantastic 2nd living room, home office, play space, or home gym. The primary suite in this model is extra large giving room for a sitting area! The WALK-IN CLOSET offers plenty of space to keep your wardrobe organized and the en-suite bathroom has a garden tub and separate shower. The secondary bedrooms share a hall bathroom. The ROOF, AC, AND WATER HEATER WERE REPLACED IN 2018. Additional upgrades include CROWN MOLDING and canned lighting throughout the home.

1830 Morning Sky Drive, Winter Garden
$1,800,000
6 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 34787 Zip Code
TWO HOMES FOR THE PRICE OF ONE.... Explore this stunning 10-acre lakefront estate in southwest Winter Garden with everything you’ve been dreaming of within 20 minutes of all the major theme parks in Central Florida. This beautiful tree-lined property offers privacy, shade, and plenty of space for both you and your animals. The owners have enjoyed using the land as a family ranch and oasis for many years, making it an ideal home for horse owners or those who just want to get away to relax and create lasting memories. You’ll also love the peaceful waterfront setting, where you can enjoy breathtaking sunsets. Beyond the incredible land, the property includes a spacious 3,196-square-foot main home with four bedrooms, three bathrooms, fireplace, screened patio and swimming pool with outdoor spa. In 2017 owners built a 1,200-square-foot guest house with a two-car garage, perfect for visitors or extra living space. Both homes are equipped with metal roof and screened porches. Despite its peaceful country feel, you’re still conveniently close to hospitals, restaurants, and shopping. If you’re looking for a property that combines the beauty of ranch living with laid back comfort and convenience, this is the perfect place to call home. Video https://youtu.be/FU5ZvzJ_3PM

16945 W Phil C Peters Road, Winter Garden
$290,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code
**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden
$489,890
4 Beds ⋅ 4 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in October 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 4 bedrooms, 3 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your 4th bed with ensuite bathroom. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15165 Groveside Road, Winter Garden
$1,099,000
6 Beds ⋅ 5 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code
Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases beautifully appointed living spaces throughout both floors, making it ideal for multigenerational living or hosting extended family and guests. A dramatic second-floor loft overlooks the main living area, creating an open and inviting atmosphere while providing additional living space. Upstairs also features a second primary suite, three additional spacious bedrooms, a dedicated theater/media room, and a flex room that serves perfectly as a home office, den, or playroom. At the heart of the home is a chef-inspired gourmet kitchen designed to impress, featuring stainless steel appliances, a gas cooktop, double wall ovens, quartz countertops, and an oversized center island with an undermount sink, generous seating, and double-sided cabinetry that provides exceptional storage for both everyday living and entertaining. Motorized shades throughout the main living area add a touch of sophistication and everyday convenience. The spacious family room opens effortlessly to the outdoor living space through triple pocket sliding glass doors, creating a seamless indoor-outdoor lifestyle. Relax year-round on the screened lanai overlooking peaceful conservation views or entertain with ease around the sparkling pool and fully equipped outdoor kitchen featuring a Paradise Grill, built-in sink, and refrigerator. Luxurious owner's suite is a private retreat featuring a spa-inspired bath with dual vanities, a relaxing garden tub, a zero-entry walk-in shower with seamless glass enclosure, and double-door entry to an expansive custom-designed walk-in closet that is sure to impress. A private hallway just off the main living area leads to a spacious guest suite with direct access to the pool, along with a generously sized laundry room for added convenience. Upstairs, you'll find a second primary suite, three additional bedrooms, an expansive loft, a dedicated theater/media room, and a versatile flex room—offering abundant space for family, guests, a home office, fitness room, or additional living area. Additional highlights include a three-car tandem garage offering abundant storage and ample room for a home gym, workshop, or hobby space. LOCATED just minutes from Downtown Winter Garden, the award-winning Winter Garden Farmers Market, Winter Garden Village, shopping, dining, top-rated schools, and major roadways including State Road 429 and Florida’s Turnpike, this exceptional home offers the perfect blend of luxury, comfort, convenience, and location *** This is a rare opportunity to own one of Cypress Reserve’s premier residences and experience the very best of the Winter Garden and true Florida lifestyle. ***

14067 Jomatt Loop, Winter Garden
Start Your Search