Winter Garden/Oakland Homes with Sidewalks Community Features

Winter Garden/Oakland Homes with Sidewalks Community Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and vibrant community spirit, this area is a hidden gem that beautifully combines suburban charm with urban conveniences. Winter Garden, with its rich history and quaint downtown, offers a delightful blend of old-world charm and modern amenities. Stroll along the historic Plant Street, where you’ll find an array of unique shops, delightful eateries, and the popular Winter Garden Farmers Market, held every Saturday.

Oakland, just a stone's throw away, is a serene enclave characterized by its lush greenery and tranquil atmosphere. The community is perfect for those who appreciate the great outdoors, with numerous parks and scenic trails that invite exploration and relaxation.

One of the standout features of homes in this region is the presence of sidewalks, which fosters a sense of community and encourages outdoor activities. Picture yourself taking evening walks under the warm Florida sun or enjoying leisurely bike rides with family and friends along the tree-lined streets. The sidewalks not only enhance the aesthetic appeal of the neighborhoods but also promote a healthy, active lifestyle.

Whether you’re looking for a charming bungalow or a spacious family home, Winter Garden and Oakland offer a diverse range of properties to suit every taste and budget. With its friendly atmosphere, excellent schools, and abundant recreational opportunities, this area is truly a wonderful place to call home. Come and experience the magic of Winter Garden and Oakland – where community meets comfort!

Newest Winter Garden/Oakland Homes with Sidewalks Community Features

4 Beds ⋅ 3 Baths ⋅ Orchard Hills Phase 2 SubDv. ⋅ 34787 Zip Code

Welcome to this bright and airy 4-bedroom, 2.5-bath home offering a comfortable and inviting layout. The spacious kitchen opens directly to the living room, creating a great flow for everyday living and entertaining, and features a large island with plenty of room for meal prep or gathering with family and friends. The open feel continues throughout the main living areas, with plenty of natural light adding to the welcoming atmosphere. The primary bedroom offers a private retreat with its own door leading to the balcony, providing a nice spot to step outside and enjoy the fresh air.

14354 Orchard Hills Boulevard, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality. Sample Image

17732 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a versatile loft, providing additional living space or an ideal work-from-home area. With a two-car garage and laundry room conveniently located on the second floor, the Porter combines functionality with comfort, making it a standout home choice. Sample Image!!

17728 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 2 SubDv. ⋅ 34787 Zip Code

Location, location, location!! Incredible opportunity to own a popular Whitman II model in the desirable Oakland Trails community with direct walkable access to the West Orange Trail! Imagine walking or biking to dinner in downtown Winter Garden just minutes away! You're also just minutes from the Florida Turnpike and all the new shopping in Clermont, including Costco just down the road. The location of this home is incredible! From the moment you step through the glass-paneled front door, you are greeted by a bright and airy two story foyer featuring warm luxury vinyl flooring and a contemporary staircase accented with sleek, industrial cable railings. The main level effortlessly transitions into a sun-drenched living space, anchored by large sliding glass doors that open up to an outdoor patio and frame views of the surrounding neighborhood. A neutral color palette and recessed lighting throughout enhance the sophisticated, move-in-ready aesthetic of the home. At the heart of the home is a chef-inspired gourmet kitchen designed for effortless entertaining. The massive central island takes center stage, featuring gleaming white quartz countertops, a deep undermount sink, and comfortable breakfast bar seating for four beneath stylish pendant lighting. Striking dark espresso cabinetry provides an abundance of storage space and beautifully contrasts the modern herringbone tile backsplash. Equipped with premium stainless steel appliances—including a built-in wall oven and microwave combo, a cooktop, and a French-door refrigerator—this kitchen is as functional as it is beautiful, complete with a spacious walk-in pantry nearby. Opposite the main living area, a formal dining space is defined by its soaring high-volume ceiling and a dramatic, modern halo chandelier that casts a warm glow over your dinner parties. Upstairs you'll love the oversized loft area that's open to below - perfect for cozier gatherings with the family. The secondary bedrooms are generously sized and each have their own walk in closets. The primary suite features a grand entrance with french doors leading to the large bedroom with two massive walk in closets, a tray ceiling, and more french doors leading to the spa inspired primary bath. The upstairs laundry room is conveniently placed to complete the home. With major shopping, dining, and entertainment options located within 15 minutes of this community, you have no shortage of lifestyle at your fingertips! You can get to Disney parks in about 20-25 minutes! You're also zoned to A rated schools, and have a very popular charter school - Oakland Avenue Charter School just minutes away. Come tour this home today!

2273 Standing Rock Circle, Oakland

3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code

Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden

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

MOVE-IN READY! BRAND-NEW CONSTRUCTION, NEVER LIVED IN! Located in the highly desirable Waterleigh community in Winter Garden, this beautiful Ibis townhome offers 3 bedrooms, 2.5 bathrooms, a one-car garage, and a long driveway providing additional parking space. With modern finishes and a bright, open-concept design, this home is ready for its first owner! Step inside through the welcoming foyer and into an open living space where the kitchen, dining area, and living room flow seamlessly together. The kitchen features upgraded stainless steel appliances, quartz countertops, ample cabinetry, and convenient bar seating, making it ideal for everyday living and entertaining. The living area overlooks a covered patio, offering additional space to relax and enjoy the Florida lifestyle. A powder room and rear-entry garage complete the first floor. Upstairs, you’ll find all three bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite features a walk-in closet, double-sink vanity, and generously sized shower. Two additional bedrooms and a full guest bathroom provide flexibility for family, guests, or a home office. The home also includes a Smart Home technology package, allowing convenient control of compatible home features from your smart device whether you’re home or away. Located in Waterleigh, one of Horizon West’s sought-after master-planned communities, residents enjoy an exceptional lifestyle with resort-style amenities and convenient access to shopping, dining, entertainment, and major Central Florida destinations. SR-429 is nearby, providing easy connectivity throughout the Orlando area. With attractive curb appeal, modern finishes, newer construction, and a low-maintenance townhome lifestyle, this Ibis offers an excellent opportunity to own a move-in-ready home in Winter Garden. Schedule your private showing today!

16570 Barbours Creek Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code

Located in the desirable Winding Bay community in Horizon West, this impeccably maintained home offers 3 spacious bedrooms, 2.5 bathrooms and a versatile flex room that can easily serve as a home office, playroom or potential 4th bedroom. Luxury tile flooring, upgraded in 2025, flows throughout the entire home for a clean and consistent look that is stylish, durable and easy to maintain. The kitchen serves as the centerpiece of the main living space, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, hard-wired under-cabinet lighting and abundant counter and storage space. Crown molding, oversized baseboards, decorative columns, and custom finishes bring an elevated feel and distinctive detail to the interior. The spacious owner’s suite features plantation shutters and a beautiful en-suite bathroom, fully upgraded in 2026 with floor-to-ceiling tile, modern finishes and a large walk-in closet. The two secondary bedrooms share a convenient Jack-and-Jill bathroom. Double sliding doors lead to the screened lanai with sun shades, overlooking the fully fenced backyard with iron fencing. In the evening, relax outdoors and enjoy views of the Disney fireworks in the distance, adding a special touch to the Florida lifestyle. Additional features include an extended driveway with pavers, gutters, whole-home security camera system, whole-home water softener, reverse osmosis filtration in the kitchen and a dedicated garage outlet for an additional refrigerator or freezer. Solar panels provide an added energy-efficiency benefit, with electric bills averaging approximately $34 during the hot summer months. With no carpet, extensive upgraded tile flooring, flexible living space, a renovated owner’s bathroom, solar panels, and numerous thoughtful upgrades, this Horizon West home is truly move-in ready. This home offers convenient access to shopping, dining, schools, major roadways, and the many amenities throughout Winter Garden and West Orange County. Schedule your showing today!

10750 Petrillo Way, Winter Garden

3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Oakland

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

Virtually Staged. Welcome to this impressive 5-bedroom, 4-bath home with a 3-car garage in the highly desirable Hawksmoor community of Horizon West. Built in 2021, this beautifully designed two-story home offers an exceptionally flexible floor plan, generous indoor and outdoor living spaces, peaceful water and natural views, plus an outstanding energy feature a Tesla whole-home backup power system with solar.One of the home's most valuable upgrades is its Tesla backup battery and solar system designed to provide whole-home backup power. The sellers currently enjoy an electric bill of approximately $34 per month, and the entire solar and battery system will transfer to the new buyer at no additional cost, providing an exceptional combination of energy efficiency, backup power and long-term value.From the moment you arrive, the home makes a great first impression with attractive architectural details, mature landscaping, a paver driveway and three-car garage. Step inside to a welcoming foyer and a dedicated private office, providing an ideal space for working or studying from home.The heart of the home is the expansive open-concept living area, where the kitchen, dining and family rooms flow seamlessly together. The spacious kitchen features an oversized center island with abundant seating, extensive cabinetry and counter space, gas cooktop, built-in oven and microwave, stainless steel appliances and a separate walk-in pantry. Large sliding glass doors fill the living area with natural light and create a wonderful connection to the outdoor living space.The first floor also features a bedroom and full bath, offering excellent flexibility for overnight guests, extended family or multigenerational living.Upstairs, the oversized primary suite provides a relaxing retreat with a tray ceiling, multiple windows and beautiful views. The spacious primary bath features dual vanities, a soaking tub and separate walk-in shower. Additional bedrooms and baths provide plenty of room, while the conveniently located upstairs laundry room makes everyday living easier.An expansive upstairs loft/family room provides an entirely separate living area with endless possibilities as a media room, game room, playroom, fitness area or second family room.Outdoor living is another standout feature. Large sliding doors open to an extended covered lanai overlooking the spacious fenced backyard, water and natural green space beyond. Whether enjoying your morning coffee, entertaining friends or relaxing at the end of the day, this peaceful setting provides an inviting extension of the home with plenty of usable yard space.Beyond the property, Hawksmoor offers an amenity-rich lifestyle with a resort-style community pool, clubhouse, fitness center, playground and outdoor recreation. Located in Horizon West, the community provides convenient access to shopping, dining and entertainment at Hamlin, area parks and trails, SR-429, Walt Disney World and the many attractions of Central Florida. Historic Downtown Winter Garden, with its restaurants, shops, farmers market and West Orange Trail, is also within easy reach.

16773 Wingspread Loop, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Oakland

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