Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County, known for its rich history, vibrant community, and picturesque landscapes. Just a stone’s throw away from the bustling city of Orlando, Winter Garden offers a perfect blend of small-town charm and modern conveniences, making it an ideal place to call home.

One of the standout features of Winter Garden is its commitment to community living, exemplified by the Homes with Sidewalks. These thoughtfully designed neighborhoods invite residents to embrace an active lifestyle, with tree-lined sidewalks perfect for leisurely strolls, morning jogs, or family bike rides. Imagine your children playing safely in the front yard while you enjoy a peaceful evening walk, greeting friendly neighbors along the way. The sidewalks foster a sense of connection and camaraderie among residents, creating a warm and welcoming atmosphere.

In addition to the inviting community features, Winter Garden boasts an array of amenities that cater to all ages. The historic downtown area is brimming with delightful shops, delectable dining options, and vibrant farmers' markets, providing a lively backdrop for weekend outings. Outdoor enthusiasts will appreciate the abundance of parks and recreational facilities, including the scenic West Orange Trail, which offers miles of paved paths for biking and walking.

With its excellent schools, diverse housing options, and a strong sense of community, Winter Garden is not just a place to live; it’s a place to thrive. Discover the charm of Winter Garden and find your dream home today in this enchanting Florida city!

Newest Winter Garden Homes with Sidewalks Community Features

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

Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden

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

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. 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

4 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Bellmore. This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a spacious walk in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom. This home features a space to fit all your needs. Like all homes in Waterleigh, the Bellmore includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11923 Shine View Lane, Winter Garden

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

Waterleigh presents the Bellake. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. The kitchen overlooks the dining and great room, while having view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, plentiful cabinet and counter space and stainless steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play and half bathroom. As we head up to the second floor, we are greeted with Bedroom one which includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well. This home features a two car garage located at the rear of the home complete with drop zone as you enter the home. Like all homes in Waterleigh, the Bellake includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16810 Hobe Sound Court, Winter Garden

6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code

Virtually Staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon your family around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code

Luxurious Fully Furnished 5-Bedroom Home in Winter Garden Experience the perfect blend of elegance, comfort, and convenience in this stunning fully furnished two-story home located in the highly desirable Winter Garden area. Designed with both style and functionality in mind, this exceptional residence offers 5 spacious bedrooms, 4 full bathrooms, and 1 half bathroom, providing plenty of room for families of all sizes. The thoughtfully designed open-concept floor plan creates a seamless flow between the expansive living and dining areas, making it ideal for everyday living and entertaining. At the heart of the home is a beautifully appointed kitchen featuring solid wood cabinetry, stone countertops, and a full suite of included appliances, offering both timeless style and modern convenience. The luxurious primary suite serves as a private retreat with a generous walk-in closet and an elegant en-suite bathroom. The additional bedrooms are equally well-designed and include built-in closets, providing excellent storage and comfort for family members or guests. Upstairs, you'll also find a spacious loft that offers endless possibilities as a second living area, media room, home office, or playroom. Step outside to enjoy the convenience of a 2-car attached garage and the peace of mind that comes with owning a meticulously maintained, move-in-ready home. Being fully furnished, this property is perfect for buyers seeking a seamless transition without the hassle of furnishing an entire home. Ideally situated in Winter Garden, this home offers easy access to major highways, shopping, dining, entertainment, and highly rated schools, making it an outstanding choice for those seeking both convenience and an exceptional lifestyle. Don't miss this incredible opportunity to own a beautifully furnished home in one of Central Florida's most desirable communities. Schedule your private showing today and discover everything this remarkable property has to provide.

16091 Silver Brook Way, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Lift Station/Cobblestone/Winte SubDv. ⋅ 34787 Zip Code

Bright, open living meets a polished, move-in-ready feel in Winter Garden. A flowing tile-floor plan creates an effortless backdrop for daily living and entertaining, anchored by a standout kitchen with crisp white cabinetry, stainless steel appliances, dramatic stone countertops and backsplash, recessed lighting, and an oversized waterfall island with seating. The generous primary retreat offers a large walk-in closet and an en-suite bath with dual sinks, a soaking tub, and a separate tiled shower. Well-proportioned secondary bedrooms offer versatile space, while the interior laundry room and two-car garage add everyday convenience. Sliding glass doors open to a covered, screened lanai, an inviting spot for morning coffee, outdoor dining, or relaxing with views of the expansive backyard. The home’s welcoming curb appeal is enhanced by an arched entry, shutters, and established landscaping. Enjoy the best of Winter Garden living, with Historic Downtown Winter Garden’s boutiques, dining, farmers market, and community events, plus the beloved West Orange Trail for walking, biking, and exploring.

356 Black Springs Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Li SubDv. ⋅ 34787 Zip Code

**Spacious 3-bedroom, 3-bathroom fully-furnished condo located on the fourth floor of the beautiful Grove Resort and Water Park! This condo has a full kitchen, full washer and dryer, large primary bedroom with sitting area, large primary bathroom with dual sinks and separate shower and tub, a second bedroom with its own ensuite bathroom, and a third bedroom and bathroom. The screened-in balcony overlooks the central fountain area, so the location is only a short stroll away from any amenities! You have the Surfari water park with a large heated pool, lazy river, water slides, splash area, and the Flowrider surfing experience! The Longboard Bar and Grill is located inside the water park for delicious meals, snacks and drinks! Or visit the Springs Pools area which has three further pools, and the relaxing hot tub! Located next to the Valencia Restaurant, the outdoor bar is also located there, and the 24/7 gym! Take a stroll down to Lake Austin and try your hand at fishing, kayaking, or paddle a swan boat!! For indoor fun visit Flip Flops, the 6000 sf games arcade with glow-in-the-dark mini golf!! For your convenience for food, gifts and sundries, we have the Marketplace, located at the Front Desk area. A free daily shuttle to the Disney parks is also provided for owners and guests. Enjoy ownership of a vacation condo, while having the onsite management company place bookings in your unit while you are not there! It is a completely hands-free experience! Call now for more details!!**

14501 Grove Resort Avenue Unit 3401, Winter Garden

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

Under Construction. Toll Brothers new construction in Winter Garden, Horizon West. Estimated completion in 2027. The Montpelier bungalow offers a thoughtfully designed layout with a covered entry leading to a spacious foyer and a private guest suite. The main living area features an open-concept design with a dining area, breakfast bar, great room, and access to the courtyard, creating a comfortable space for everyday living and entertaining. The second floor includes two secondary bedrooms and a private primary suite featuring a large walk-in closet and a well-appointed bath with dual vanities, separate shower, and private water closet. Additional highlights include the functional bungalow design, inviting courtyard space, and the opportunity to personalize select design features based on the stage of construction

13020 Sunset Garden Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to this beautifully designed new construction bungalow by Toll Brothers in the desirable Winter Garden/Horizon West area, with estimated completion in April 2027. A covered front entry welcomes you into a spacious foyer that opens to a versatile flex space, ideal for a home office or additional living area. The open-concept floor plan features a well-appointed kitchen with a breakfast bar overlooking the dining area and a great expansive room, creating the perfect setting for everyday living and entertaining. Enjoy seamless indoor-outdoor living with access to the private courtyard. The spacious primary suite offers a large walk-in closet and a luxurious bath complete with dual vanities, a separate shower, and a private water closet. Experience thoughtfully designed living in one of Central Florida's most sought-after communities.

13056 Sunset Garden Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to this stunning new construction home by Toll Brothers in the highly sought-after Winter Garden/Horizon West area, with estimated completion in April 2027. Designed with both everyday living and entertainment in mind, this thoughtfully crafted floor plan offers an open-concept great room, kitchen, and dining area that seamlessly flow together. A covered front entry welcomes you inside, while the covered lanai and spacious private courtyard create the perfect outdoor retreat with convenient access to the detached 2-car garage. The luxurious primary suite features a generous walk-in closet and a spa-inspired bath with dual vanities, a separate shower, and a private water closet. Don't miss this opportunity to own a beautifully designed new home in one of Central Florida's most desirable communities.

13038 Sunset Garden Lane, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden

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