Winter Garden Homes with Community Mailbox Community Features

Winter Garden Homes with Community Mailbox Community Features

Winter Garden is a charming city located in Orange County, Florida. Known for its rich history and small-town feel, Winter Garden offers residents a wonderful place to call home. With its convenient location just a short drive away from Orlando, Winter Garden provides the perfect blend of suburban tranquility and access to urban amenities.

One of the notable features of Winter Garden is its Homes with Community Mailbox Community. This unique community feature offers residents a convenient and centralized location for their mailboxes. No more driving to a separate post office or walking to individual mailboxes scattered throughout the neighborhood. Instead, residents can enjoy the ease and efficiency of a community mailbox system, making it easier to send and receive mail.

Living in a Homes with Community Mailbox Community also fosters a sense of community and connection among neighbors. As residents collect their mail, they have the opportunity to bump into each other, strike up conversations, and build relationships. This creates a friendly and welcoming atmosphere where neighbors can get to know one another and form lasting friendships.

In addition to the Homes with Community Mailbox Community, Winter Garden offers a range of other community features. From beautiful parks and recreational areas to top-notch schools and shopping centers, Winter Garden has something for everyone. Whether you're a nature enthusiast, a foodie, or a shopaholic, Winter Garden has you covered.

If you're considering a move to Winter Garden, you'll find a city that values community, convenience, and quality of life. With its Homes with Community Mailbox Community and other fantastic amenities, Winter Garden is a fantastic place to call home.

Newest Winter Garden Homes with Community Mailbox Community Features

728 Garden West Terrace, Winter Garden
$1,749,000
5 Beds ⋅ 5 Baths ⋅ Garden West SubDv. ⋅ 34787 Zip Code
Welcome to this stunning custom home crafted by the renowned Pioneer Builders in 2022, nestled in one of Winter Garden's most coveted locations. Just steps from the beloved West Orange Trail and the charming Golf Cart District of Historic Downtown Winter Garden, this home offers the best of the Winter Garden lifestyle right at your doorstep. Whether you're pedaling the trail at sunrise or cruising downtown in your golf cart for dinner and live music, this location makes it easy to enjoy everything this vibrant community has to offer. From the moment you step inside, the quality and craftsmanship are undeniable. Engineered hardwood floors flow seamlessly throughout the home, while custom cabinetry adds timeless elegance to every space. The open living areas feature top-of-the-line Fisher & Paykel appliances, blending elevated design with everyday functionality. Plantation shutters throughout the main house add a classic, refined touch, while an automatic gate provides an added layer of privacy and convenience. The main level features a private ensuite bedroom and full bath, ideal for guests or multigenerational living, along with a convenient powder bath for visitors. Upstairs, the primary suite serves as a true retreat, complete with two oversized walk-in closets and a luxurious ensuite bath. Two additional bedrooms share a well-appointed Jack-and-Jill bathroom, while an upstairs laundry room adds everyday convenience. Added in 2024, the private apartment above the garage is a rare and exceptional bonus, complete with a kitchenette, dedicated office space, full bath, and in-unit laundry. Whether envisioned as a private guest suite, in-law quarters, a dedicated work-from-home retreat, or an income-producing rental, the possibilities are endless. Winter Garden's Golf Cart District is more than a novelty—it's a way of life. Residents enjoy cruising to the award-winning Farmers Market, exploring boutique shops and local restaurants, visiting breweries, and taking part in the community events that make Historic Downtown Winter Garden one of Central Florida's most vibrant destinations. The West Orange Trail, spanning more than 22 miles of scenic, paved pathways, is a paradise for cyclists, joggers, and walkers. With this home's prime proximity, outdoor recreation is always within easy reach. This is more than a home—it's a lifestyle. Don't miss the opportunity to own a distinctive property offering timeless finishes, versatile living spaces, added privacy, and an exceptional location in one of Central Florida's most sought-after communities.

728 Garden West Terrace, Winter Garden
2199 White Feather Loop, Oakland
$489,900
3 Beds ⋅ 3 Baths ⋅ Oakland Trails Ph 1 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Oakland
618 Sigler Drive, Winter Garden
$685,240
3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Bayview floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

618 Sigler Drive, Winter Garden
622 Sigler Drive, Winter Garden
$604,580
3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Gardenia floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, Calacatta countertops, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

622 Sigler Drive, Winter Garden
620 Sigler Drive, Winter Garden
$697,240
4 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Bayview floor plan, offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

620 Sigler Drive, Winter Garden
15613 Boggy Oak Circle Unit 110A, Winter Garden
$299,900
2 Beds ⋅ 2 Baths ⋅ Tucker Oaks Condo SubDv. ⋅ 34787 Zip Code
MAINTENANCE-FREE LIVING IN DESIRABLE TUCKER OAKS! Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo with an attached single car garage, ideally located in the sought-after Tucker Oaks community. Situated on a quiet, lightly traveled cul-de-sac-style road with a dog parkconveniently located directly across the street, this home offers comfort, convenience, and an easy Florida lifestyle.This is one of the newer-built models in the community and features an expanded kitchen layout with additional counter space and a convenient eat-in area. The kitchen is equipped with stainless steel appliances, including a French-door refrigerator, dishwasher, microwave, and range, alongwith upgraded counters, sink, and faucet. The appliances are approximately four years old. Additional kitchen conveniences include pull-out/roll-out cabinet shelving and upper and lower cabinet lighting.The spacious family room features a beautiful focal wall with a floating shelf, electric fireplace, and wall-mounted flat-screen TV, creating a warm and inviting space to relax or entertain. Step outside to the larger upper-level balcony, the perfect spot to enjoy your morning coffee or unwind at the end of the day.The second bathroom features a walk-in shower for added convenience. An interior laundry room includes installed shelving for additional storage.The attached garage offers storage shelving, a painted and sealed floor, and convenient attic storage for seasonal items and belongings.Tucker Oaks offers an array of amenities, including a community pool, basketball courts, playground, dog park, and picnic/BBQ area. Enjoy an unbeatable location close to Winter Garden Village, restaurants, shopping, the farmers market, and Central Florida’s world-famous attractions. Witheasy access to the Florida Turnpike, SR 429, SR 408, and Highway 50, getting around Central Florida is quick and convenient.Come enjoy low-maintenance living, wonderful community amenities, and an incredible location—all in one great condo!

15613 Boggy Oak Circle Unit 110A, Winter Garden
900 Allendale Lane, Oakland
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Oakland Parkb-2 SubDv. ⋅ 34787 Zip Code
Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.

900 Allendale Lane, Oakland
14743 Field Daisy Drive, Winter Garden
$654,718
3 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Loft | Balcony. New Construction - December Completion! Welcome to the Newberry at 14743 Field Daisy Drive in Harvest at Ovation! Welcome to this stunning two-story home. Thoughtfully designed for both comfort and flexibility, this spacious floor plan features three bedrooms, four-and-a-half bathrooms, a versatile loft, an expansive game room, and a two-car garage. The open-concept main living area seamlessly connects the great room, designer kitchen, casual dining space, and lanai, creating an inviting setting for everyday living and entertaining. Upstairs, the private primary suite offers a relaxing retreat with a spacious bath and generous walk-in closet, while the loft provides additional space for work, play, or gathering. A secondary bedroom and bath on the upper level, plus an oversized game room with its own bathroom on the top floor, provide privacy and flexibility for guests or multigenerational living. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: 8' interior doors, tray ceiling package, wet bar at game room and shower in place of tub at bath 2. Photos are for representative purposes only. MLS#O6450084

14743 Field Daisy Drive, Winter Garden
12934 Harvest Rain Avenue, Winter Garden
$750,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | 3 Full Baths. New Construction - February Completion! Welcome to the Ozark at 12934 Harvest Rain Avenue in Harvest at Ovation! This thoughtfully designed one-story home offers three bedrooms, three and a half bathrooms, and a private study off the foyer. The open-concept layout centers around a spacious gathering room that flows seamlessly into the dining area and gourmet kitchen with a walk-in pantry, creating the perfect space for everyday living and entertaining. The private primary suite features a spacious bathroom and large walk-in closet, while the secondary bedrooms provide comfort and flexibility for guests or hobbies. Enjoy outdoor living on the covered extended lanai and the convenience of a two-car garage with tandem storage space. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: pocket sliding glass door at great room, tray ceiling package, whole house 8' interior doors, quartz countertops, whole house blinds, and outdoor kitchen rough-in. Virtually staged photos are for representative purposes only. MLS#O6450081

12934 Harvest Rain Avenue, Winter Garden
17590 Japonica Bloom Drive, Winter Garden
$824,000
4 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Reduced rate promotion with preferred lender! Welcome to the Eliot design, new luxury home by RockWell Homes in Northlake at Ovation lot 234. Thoughtfully crafted new home offering a balance of comfort, style, and flexibility. This popular floorplan includes 4 bedrooms, 3.5 bathrooms, and a spacious gameroom, with parcel entry. The exterior design enhances curb appeal and functionality, featuring a covered front porch and an oversized covered backyard lanai ideal for outdoor living. The extended entryway leads to a versatile den or home office, creating a flexible space for work or relaxation. The chef-inspired kitchen anchors the home and includes a large island, solid-surface countertops, and stainless-steel appliances including a cooktop, oven, microwave, dishwasher, and vent hood. Additional kitchen features include an undermount sink with a Delta faucet, ceramic tile backsplash, upgraded 42-inch cabinets, a walk-in pantry, upgraded flooring and lighting throughout the main living areas. The open-concept living space is filled with natural light from a 9-foot sliding glass door and dual-pane energy-efficient windows, offering seamless access to the covered lanai. The primary suite is located on the first floor and features a dual-sink vanity, ceramic tile flooring, a tiled shower with glass enclosure, Delta faucets, a lighting package, and a walk-in closet. Upstairs includes a gameroom, pocket office, three secondary bedrooms with walk-in closets, and two secondary bathrooms with ceramic tile flooring and tub shower surrounds, Delta faucets, towel bars, solid surface countertops, upgraded cabinets and undermount sinks. Energy-efficient block construction, full landscaping package, full gutters, a garage door opener, and a 10-year new home structural warranty complete this home. The Eliot design by RockWell Homes offers a luxurious living experience with an array of high-end finishes, ample space, and an elegant layout. Whether you're relaxing in the spacious living areas or enjoying the beauty of the covered lanai, this home is perfect for modern living. Homeowners enjoy quick access to highways, downtown Orlando, Walt Disney World Theme Parks, resort style pool, play park, green spaces, water features, pet areas and walking trails.

17590 Japonica Bloom Drive, Winter Garden
1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden
14747 Field Daisy Drive, Winter Garden
$573,147
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | Gas Range | 1st Floor Guest Suite. New Construction - December Completion! Welcome to the Newberry at 14747 Field Daisy Drive in Harvest at Ovation! This thoughtfully designed two-story home offers three bedrooms, three-and-a-half baths, and inviting spaces that blend comfort with everyday convenience. The bright kitchen with a spacious island opens to the casual dining area and great room, creating a warm and welcoming setting for gathering with family and friends. A first-floor secondary bedroom with an ensuite full bath is perfect for guests, while upstairs, the private primary suite provides a peaceful retreat with a generous walk-in closet and well-appointed bath. A versatile loft adds flexible living space, and the covered lanai is ideal for relaxing or enjoying time outdoors. Complete with a two-car garage, this home is as functional as it is charming. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Shower in place of tub at secondary bath, 8' interior doors, pre-plumb for future laundry tub, LVP flooring throughout, and whole house blinds. Photos are for representative purposes only. MLS#O6449322

14747 Field Daisy Drive, Winter Garden
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