Winter Garden Homes with Gated Community - No Guard Community Features

Winter Garden Homes with Gated Community - No Guard Community Features

Welcome to Winter Garden, Florida—a vibrant city that beautifully blends the charm of small-town living with the conveniences of modern life. Nestled just a short drive from the bustling attractions of Orlando, Winter Garden offers a serene escape with its picturesque landscapes, thriving downtown, and an array of recreational activities. With its rich history, charming brick-lined streets, and a strong sense of community, it’s no wonder that Winter Garden is a sought-after destination for families, retirees, and everyone in between.

One of the most appealing aspects of living in Winter Garden is the availability of homes within gated communities. These neighborhoods provide a perfect blend of privacy and security, allowing residents to enjoy a peaceful lifestyle while fostering a close-knit community atmosphere. The gated community features in Winter Garden, although lacking a guard, still offer a sense of exclusivity and safety. Residents can relish the tranquility of their surroundings, with well-maintained landscapes and beautifully designed homes that reflect the area's aesthetic charm.

In addition to the security and privacy that these gated homes provide, Winter Garden is also known for its excellent schools, parks, and recreational facilities. Families can take advantage of the local farmer's market, enjoy outdoor activities at the West Orange Trail, or indulge in the vibrant dining and shopping options that downtown Winter Garden has to offer.

If you're looking for a place that combines the warmth of community with the beauty of nature, Winter Garden’s gated communities are the perfect choice. Come discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Winter Garden Homes with Gated Community - No Guard Community Features

5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code

Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden

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

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 5 bedrooms, 4 full bathrooms, a loft, 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, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a 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. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth 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.

285 Crystal Wood Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Ests/Lakeview Preserve SubDv. ⋅ 34787 Zip Code

This is a rare opportunity to find a popular Roseland floorplan loaded with upgrades, perfectly located on a quiet cul-de-sac on a private lot with no rear neighbors and extra space on this oversized lot! Best of all, you can enjoy picturesque views of Johns Lake right from the front yard! Inside, you are greeted with a beautiful double glass door entry, soaring dramatic ceilings, and elevated light fixtures that create an immediate sense of openness and grandeur. Luxury vinyl plank floors throughout bring warmth to the home. To the right, you have an oversized flex room with French doors, making a perfect home office, play area, or home gym. The formal dining room provides a great space to gather around meals for family nights or holiday hosting. The butler's pantry features a wine fridge and added cabinets, while the walk-in pantry is truly impressive with built-in shelving. The kitchen is truly the heart of the home, featuring stunning quartz countertops, cream cabinets, upgraded lighting, and a beautiful tile backsplash. Transom windows in the backsplash pour natural light into the kitchen. The open breakfast area is perfect for enjoying quick meals with the family and overlooks the great room, which has custom accent walls and an elevated light fixture to enhance the space. Triple windows above brighten the room, & the 12ft slider door overlooks the extended lanai and huge flat yard—with plenty of space to add a pool and outdoor kitchen! Downstairs features a massive guest suite that can serve as a second master bedroom, complete with its own ensuite bath, upgraded shower, and large walk-in closet—perfect for in-laws or guests to have their own retreat! There is also another full-sized bath downstairs with a shower and a door leading out to the lanai for quick access from the future pool area. Heading upstairs, there are 4 additional bedrooms, 3 full baths, and the laundry room. Elegant open railings bring added character across the catwalk over the living room. Directly at the top of the stairs, French doors lead to your primary retreat. You are greeted by a sitting area with a large window and a massive primary suite with a tray ceiling and picturesque windows looking over the yard and trees beyond. To the left is your stunning ensuite bathroom with split vanities, lots of natural light, a soaking tub, a large walk-in shower with a bench, and dual closets (one with built-ins). The other three oversized bedrooms add similar quality, each with direct ensuite access to a bathroom (including two sharing a Jack-and-Jill bath). The laundry room features built-in cabinets and two washer/dryer sets side by side, allowing you to handle two loads at a time—perfect for large or busy families! Over in the garage, vehicle enthusiasts and storage seekers will marvel at the pristine three-car garage, complete with sleek epoxy flooring, heavy-duty overhead storage racks, and a private car wash station for ultimate convenience. The exclusive gated community offers resort-style amenities including a clubhouse, swimming pool, splash pad, and playground—all with a low HOA fee and no CDD. The community is perfectly located on the border of Clermont and Winter Garden, offering access to all both cities have to offer! You are just 15 minutes from Winter Garden Village for shopping, dining, and SR-429 access into Orlando, and within 20 minutes from both downtown Clermont and downtown Winter Garden. Come tour this stunning property today!

4817 Fair Winds Court, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Wintermere Harbor Ph 02 48 21 SubDv. ⋅ 34787 Zip Code

Welcome home to this one-story pool home situated on an oversized lot that overlooks a pond! ***NEW WINDOWS, NEW COMMODES, 2022 ROOF, 2020 SMART POOL*** Tucked into the back of this gated community, this spacious oasis is ready for its next owners. One of Florida's most popular floor plans features a formal living space at the entrance of the home, casual living space in the middle of the home, the primary suite privately on one side of the home, and the 3 secondary bedrooms on the other side of the home. Choose to repurpose the "formal living space" into whatever your wants and needs may be, or use them as the formal living room and formal dining room as the builder intended. The primary suite has an extension included and is ready to be used as yet another flex space. French doors open from this extension right onto the covered outdoor living space. The primary bathroom boasts a soaking tub, dual vanities, and 2 custom closets. The casual living space is open and inviting with the kitchen, large dining nook, and family room, and lots of natural light brightens this space up even more by way of a wall of sliding glass doors that lead to the outdoor living space, another door with a window that also leads to the outdoor living space, and a set of bay windows in the dining nook. Bedrooms 2 and 3 are located down a hallway off of the casual living space and have a full bathroom they share. The 4th bedroom is in the back of the home with its own bathroom. Step out back to the screened in patio which holds a gorgeous pool with a sun shelf and waterfall, covered portion, and extension under the screen for total and full enjoyment opportunities! Continue outside of the screen enclosure to the fully fenced in backyard that overlooks a pond. Whether looking for peace and serenity or fun and activity, this home has a solution to it all! Inquire today to for a private viewing to see if this gem will become your next home!

2039 Harbor Cove Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

ONE-YEAR HOME WARRANTY AVAILABLE WITH A FULL-PRICE OFFER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom FIRST-FLOOR condo in the gated Southern Pines community of Winter Garden. Featuring a FRESH INTERIOR REPAINT (2026), UPDATED FIXTURES, a bright, open-concept layout, and NO CARPET THROUGHOUT FOR EASY MAINTENANCE, this home is truly move-in ready. Step inside to a spacious open living area offering a dedicated dining room and breakfast nook just off the kitchen. The kitchen features STAINLESS STEEL APPLIANCES, GRANITE COUNTERTOPS, NEUTRAL CABINETRY, and a pantry offering additional storage. The desirable split-bedroom floor plan provides added privacy, with the primary suite positioned on one side of the home and two additional bedrooms with a guest bathroom on the opposite side. All three generously sized bedrooms feature walk-in closets, providing plenty of storage throughout the home. Ideal as a primary residence or investment property, this low-maintenance condo offers excellent rental potential in a desirable Winter Garden location. HOA dues include internet and basic cable, adding further value and convenience. Southern Pines offers an impressive collection of resort-style amenities, including a pool and spa, fitness center, tennis courts, indoor basketball and volleyball courts, playground, dog park, clubhouse, theater room, billiards room, BBQ area, resident car wash station, and on-site management. Conveniently located near highly regarded public schools, Publix, Winter Garden Village, the West Orange Trail, and vibrant Downtown Winter Garden, with easy access to SR-429, Florida’s Turnpike, and major Orlando attractions. Whether you're searching for a comfortable primary residence or a great investment opportunity, this well-located Winter Garden condo delivers space, convenience, amenities, and value.

431 Southern Pecan Circle Unit 101, Winter Garden

1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Resort style living in Winter Garden close to everything. Enjoy an impressive array of resort-style community amenities, including a state-of-the-art fitness center, indoor basketball and racquetball courts, tennis courts, and a beautifully appointed clubhouse featuring a private movie theater and dedicated workspace. Relax by the resort-style swimming pool and spa, or entertain outdoors with a fully equipped kitchen and grilling area. The community also offers a park and playground, providing something for everyone to enjoy. This 1bed/1 bathroom with a flex room boast commercial grade luxury vinyl plank flooring, crown molding throughout, granite counter tops throughout the kitchen and bathroom, dedicated dining room, indoor laundry room with washer and dryer included, neutral interior wall paint, excellent natural light, ensuite bathroom, ample size primary suite walk-in closet, and more. Conveniences to be noted in the association fees are: Water, Cable, Trash, Pest Control, Roof, Exterior Building Maintenance, and Pool. Live just minutes from Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail. Getting around Central Florida is easy with quick access to SR-429, the Florida Turnpike, SR-408, and SR-50. Everyday shopping is also close by, with Publix and Costco Just minutes away. Low maintenance living at it's finest. Come see this condo today.

1315 Eastern Pecan Place Unit 202, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Villas/Tucker Oaks SubDv. ⋅ 34787 Zip Code

Welcome to your beautifully updated home in the gated community of Winter Garden. This charming residence offers 3 bedrooms, 2.5 baths, 2-car garage, and approximately 1,737 sq. ft. of comfortable living space. In 2025, this home underwent a $53K renovation, featuring a modern kitchen with 42” shaker white cabinets with undermount lighting and quartz counters, stainless steel appliances, and a double oven for added convenience. The renovation also includes kitchen and bathroom upgrades, frameless shower doors, LVP flooring on the upstairs level and stairs, interior and exterior paint, new drapes, and elevated finishes throughout. Additional details include crown molding and 5” baseboards. Enjoy peace of mind with an A/C unit (3 years old) and a new roof (2025). Relax or entertain on the screen-covered patio with pond views. The garage floors feature non-slip coating, and the home includes all-new light fixtures, ceiling fans, and updated lighting. Additional benefits include a security system for added safety and convenience. Community amenities include a pool, playground, dog park, basketball courts, BBQ grills, and walking trails, perfect for everyday enjoyment. Located near Downtown Plant St, Fowler’s Grove, and with convenient access to 429 and the Florida Turnpike, you’re close to dining, shopping, entertainment, and major travel routes. Schedule your showing today!

1424 Scarlet Oak Loop, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Waterside/Johns Lk-Ph 1 SubDv. ⋅ 34787 Zip Code

Virtually Staged. With a whisper of Tuscan charm, Waterside on Johns Lake is a private GATED community featuring this impressive 6 BEDROOM (w/additional 7th room) 4.5 BATHROOM estate. As you pull up you will be welcomed by curb appeal, thoughtful landscaping, entry courtyard, 2 CAR GARAGE, and separate BOAT/TOY GARAGE. Inside the ceilings soar: with lots of NATURAL LIGHT, specialty molding, WOOD BEAMS, iron railings, built-ins, and a balance of both open concept & compartmentalized spaces. Downstairs you will find the 2-story ceiling Living Room, both FORMAL & CASUAL DINING space, Laundry Quarters, Butlers Pantry, Nanny's Workspace, Office, IN-LAW SUITE, and Primary Bedroom with SPA STYLE ENSUITE featuring a massive RAINSHOWER, GARDEN TUB, DOUBLE WALK IN CLOSETS, and separate vanities. And let's take a moment to discuss the CHEF'S KITCHEN that you will no longer have to envy, because as the new owner of this home you can whip up family meals or dinner party delights using your KITCHENAID 5 BURNER RANGE, convenient POT-FILLER set into glass tile backsplash, INDUSTRIAL DOUBLE REFFIGERATOR, oversized kitchen island, coffee bar, desert bar, KITCHENAID DOUBLE WALL OVEN, built-in Convection Oven/Microwave, and walk-in Pantry. Up the stairway lined with ironwork and over the landing, you reach the SUPERSIZED LOFT before leading to the 4 MORE BEDROOMS and 2 bathrooms. Currently one of the bedrooms is being used as an in-home gym and another as a craft room. The other 2 are joined by a JACKNJILL BATHROOM, perfect for kiddos or SECONDARY IN-LAW SUITE/Living space combo. With so much space, this home will suit most any lifestyle needs. For outdoor living you will find a large FENCED YARD off a COVERED LANAI with NO REAR NEIGHBORS and privacy bushes. Space for a future pool and outdoor entertaining customized just how you like it. For existing outdoor recreation, Waterside on Johns Lake offers a clubhouse, fitness center, community pool, trails, playgrounds, and a community dock perfect for watching cotton candy sunsets. Zoned for A rated public schools & nearby private school options. Nearby there is an abundance of restaurants, shopping, convenience, and the sought after Downtown Winter Garden lifestyle. Come see this spacious estate that you will want to call home soon. FLOORPLAN IN ATTACHMENTS

16730 Rusty Anchor Road, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code

WELCOME HOME TO BLACK LAKE PARK — a gated community where every day feels like a retreat. As you pass through the gates, you're welcomed by the community's stunning 10-acre park, complete with a charming white gazebo and wide-open green space that instantly sets the tone. There's a sense of warmth and connection here that's hard to put into words — you simply feel it. Pulling into the driveway and stepping through the inviting front door, you already know this is more than just a house... it's home.Offering over 1,923 square feet of thoughtfully designed living space, this move-in-ready 3-bedroom, 2-bath home with a 2-car garage has everything you need. Inside, natural light pours through the windows, highlighting the open layout and laminate flooring throughout the main living areas. If you love to cook, gather, and entertain, the remodeled kitchen will absolutely capture your heart, featuring quartz countertops, a glass cooktop, and built-in double ovens. Whether you're hosting a holiday gathering or enjoying a quiet morning coffee, this kitchen truly delivers. Sliders open to the patio — perfect for relaxing evenings or weekend get-togethers.Down the hall, bedrooms 2 and 3 offer comfortable accommodations and share a beautifully appointed guest bath. The primary suite is your private retreat, complete with a spacious walk-in closet, while the en-suite bath features a dual-sink vanity and a walk-in shower — your own personal escape at the end of the day.Living in Black Lake Park means enjoying an array of amenities, including a playground, fitness area, volleyball court, swimming pool, tennis courts, basketball court, pickleball courts, soccer field, private boat ramp and dock, and sidewalks throughout the neighborhood. Imagine ending your day with a walk to the community dock to watch breathtaking sunsets over the water, or enjoying seasonal fireworks lighting up the sky on the 4th of July. The community also hosts memorable events throughout the year, including a Halloween Costume Parade, Christmas caroling and movie night in the park, Easter egg hunts, organized garage sales, and more — creating opportunities to connect and build lasting memories.Location truly completes the package — just minutes from Downtown Winter Garden, Winter Garden Village, and major highways including the 429, the Florida Turnpike, and the 408, and conveniently close to Walt Disney World and other world-class attractions.This is more than a home. It's a lifestyle filled with comfort, connection, and everyday moments that turn into lasting memories.

502 First Cape Coral Dr, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hickory Hammock Ph 1c SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome Home to 15163 Orange Harvest Drive! YOUR oportunity to live in this incredible neighborhood, is HERE! Move-in ready and beautifully maintained, this townhome offers 3 bedrooms, 2.5 baths, and a bright, open layout perfect for modern living. A paver driveway and charming stucco exterior with mature landscaping set the tone before you even step inside. The main level features a spacious open-concept living and dining area with tile flooring throughout. Sliding glass doors lead out to a private patio, offering a peaceful spot to unwind while overlooking green common space. The kitchen is a standout, showcasing rich espresso cabinetry, gleaming granite countertops, a designer mosaic tile backsplash, stainless steel appliances, and a large island with pendant lighting — ideal for entertaining or casual family meals. Upstairs, the generously sized primary suite includes plush carpet and an en-suite bath with dual sinks, a walk-in shower, and a linen closet. A second full bath serves the additional bedrooms with a dual-sink vanity and a tub/shower combo, and a convenient half bath is located on the main level for guests. As part of a sought-after community, residents enjoy resort-style amenities including a sparkling community pool, tennis courts, a playground, and scenic lakefront views — all just minutes from Winter Garden's shops, dining, and amazing schools. Don't miss your chance to own this stylish, low-maintenance townhome in one of Winter Garden's most desirable communities!

15613 Orange Harvest Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lake Cove Pointe 46/58 SubDv. ⋅ 34787 Zip Code

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

5 Beds ⋅ 4 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code

Welcome to 2027 Rickover Place, located in the highly desirable gated community of Bronson’s Landing in Winter Garden! This beautiful home offers a spacious and versatile floor plan designed for both comfortable everyday living and entertaining. The home features split living spaces, providing flexibility and plenty of room to spread out. Upstairs, you'll find a spacious loft that can easily be transformed into a home office, media room, game room, playroom, or additional living area—the possibilities are endless. A three-car garage provides ample space for vehicles, storage, or hobbies. Bronson’s Landing offers an inviting, well-maintained neighborhood setting with a welcoming community atmosphere, creating a wonderful place to enjoy all that Winter Garden has to offer. Enjoy the convenience of being just minutes from Winter Garden Village, with an abundance of shopping, dining, and entertainment nearby. Easy access to SR-429 makes traveling throughout Central Florida convenient, while the home’s location near area schools adds to its appeal. With its gated community, flexible living spaces, three-car garage, and fantastic Winter Garden location, this home has so much to offer. Schedule your private showing today!

2027 Rickover Place, Winter Garden

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