Osceola Homes with Sidewalks Community Features

Osceola Homes with Sidewalks Community Features

Welcome to Osceola County, Florida, a vibrant and thriving region that perfectly blends natural beauty with modern convenience. Nestled in the heart of Central Florida, Osceola County is renowned for its picturesque landscapes, diverse wildlife, and an array of recreational opportunities. From the enchanting waters of Lake Tohopekaliga to the lush expanses of the Kissimmee Prairie Preserve, residents enjoy a harmonious connection to nature while being just a stone's throw away from the excitement of Orlando's world-famous attractions.

Osceola County is not only a haven for outdoor enthusiasts but also a community that values family-friendly living. One of the standout features of the neighborhoods here is the abundance of homes with sidewalks. These thoughtfully designed communities encourage residents to embrace an active lifestyle, promoting walking, jogging, and biking as part of daily routines. Imagine leisurely strolls along tree-lined streets, where children can safely play and neighbors can connect. The sidewalks create a welcoming atmosphere, fostering a sense of belonging and community spirit.

Whether you’re looking for a charming single-family home, a modern townhouse, or a spacious estate, Osceola County offers a diverse range of housing options to suit every taste and budget. With top-rated schools, shopping centers, and dining options just around the corner, the convenience of this region is unmatched. Experience the allure of Osceola County, where community, nature, and modern living come together seamlessly. Discover your dream home today and be part of this enchanting Florida paradise!

Newest Osceola Homes with Sidewalks Community Features

$279,000
2 Beds ⋅ 2 Baths ⋅ Northwest Lakeside Groves Ph 2 SubDv. ⋅ 34772 Zip Code
Welcome to 2286 Datura Loop, St. Cloud, FL—a beautifully maintained home offering the perfect combination of comfort, style, and convenience. This inviting residence features a thoughtfully designed floor plan with bright, open living spaces that are ideal for both everyday living and entertaining. The spacious kitchen provides ample cabinet and counter space while overlooking the main living and dining areas, creating a seamless flow throughout the home. The primary suite offers a private retreat with an en-suite bath and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the backyard, offering plenty of room for relaxing, gardening, or outdoor gatherings. Conveniently located near shopping, dining, schools, parks, and major roadways, this home also provides easy access to Lake Nona, Orlando International Airport, Medical City, and Central Florida's world-famous attractions.

2286 Datura Loop, St Cloud
$274,000
3 Beds ⋅ 3 Baths ⋅ Oakwater Condo Ph 7-10 SubDv. ⋅ 34747 Zip Code
ONLY MINUTES FROM WALT DISNEY WORLD! Freshly painted and featuring brand-new carpet, this spacious 3-bedroom, 2.5-bath, two-story condo offers 1,808 square feet of comfortable living space and a private one-car garage. The main level features generous living and dining areas, a convenient powder room, and a well-appointed kitchen with all appliances included, a breakfast bar, closet pantry, and cozy breakfast nook. The adjoining family room opens to a screened lanai overlooking beautifully maintained greenery an inviting setting to relax and unwind. Upstairs, double doors welcome you into the spacious primary suite with a private bath and glass-enclosed shower. Two additional bedrooms share a second full bathroom. Located within the gated, resort-style Oakwater community, residents and guests enjoy exceptional amenities, including a lagoon-style pool, spa, clubhouse, fitness center, game room, playground, splash pad, tennis and basketball courts, sand volleyball, and walking trails. Conveniently located near shopping, dining, major roadways, and Central Florida’s world-famous attractions. With the flexibility to serve as a primary residence, vacation retreat, or short- or long-term rental investment, this property offers an outstanding opportunity in a highly desirable location. Schedule your private showing today!

7509 Pellham Way, Kissimmee
$360,000
3 Beds ⋅ 2 Baths ⋅ Remington Prcl G Ph 2 SubDv. ⋅ 34744 Zip Code
Golf-course investment opportunity in Remington. This well-positioned three-bedroom, two-bath single-family home offers approximately 1,816 square feet of living area, a new roof installed in 2026, direct golf-course views and a covered rear lanai. The property is currently leased at $1,925 per month through February 28, 2027 and is being offered subject to the existing lease. Remington community amenities include golf, recreation facilities, pool, tennis courts and walking trails, subject to HOA confirmation. Conveniently located near Florida’s Turnpike, shopping, schools and dining. Seller will consider up to $5,000 toward buyer closing costs with an acceptable offer, subject to contract terms and lender approval. Property is being sold as-is with the buyer’s right to inspect.

119 Southampton Drive, Kissimmee
$360,000
3 Beds ⋅ 3 Baths ⋅ The Terraces At Storey Lake Condo 3 Ph 12 SubDv. ⋅ 34746 Zip Code
Located in the heart of Storey Lake Resort, this fully furnished 3 bedroom, 2 and half bathroom turnkey condo is ready to welcome guests from day one. Thoughtfully designed and fully equipped, it offers investors a seamless opportunity to step into one of Central Florida's most desirable vacation rental markets. Whether you're expanding your investment portfolio, completing a 1031 Exchange, or purchasing your first vacation rental, this property offers the opportunity to own in one of the highest-demand tourist markets in the world. The thoughtfully designed open floor plan features a spacious living area, a modern kitchen with quartz countertops, stainless steel appliances and beautifully appointed furnishings throughout. Everything has been carefully prepared to provide an exceptional guest experience and allow a seamless transition for the next owner. Location is everything and this one delivers. Just minutes from Walt Disney World, Disney Springs, Orlando Vineland Premium Outlets, world-class restaurants, championship golf courses and Central Florida's top attractions, guests enjoy unmatched convenience while owners benefit from one of the region's strongest vacation rental markets. Storey Lake Resort offers an impressive collection of resort-style amenities, including a Clubhouse, Fitness Center, Gated Community with Guard, Resort-Style Pool, Lazy River, Water Park, Restaurant, Playground, and scenic walking paths, creating the kind of guest experience that drives repeat visits and lasting vacation memories. If you're looking for a property that combines location, lifestyle, and investment potential, this fully furnished, move-in-ready condo is an exceptional opportunity to own in one of Orlando's premier short-term rental destinations.

3191 Paradox Circle Unit 208, Kissimmee
$369,900
3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Discover the Perfect Blend of Comfort, Style, and Investment Potential with this beautifully updated Corner-Unit townhome in Regal Oaks Resort, one of Central Florida's most sought-after Gated vacation rental communities. Built during resort's newest development phase, this rare three-bedroom End-unit townhome offers a more Contemporary Design and layout than many of the earlier homes in the community, making it one of the community's most desirable floor plans. Thoughtfully updated throughout, the home features Elegant Decorative Wood Accent Walls, Stylish Wallpaper, Upgraded Lighting, Modern Fixtures, Premium Faucets and Shower Systems, and beautiful Wide-Plank Luxury Vinyl Flooring throughout the entire second floor and staircase, creating a Warm, Contemporary Atmosphere with exceptional durability and easy maintenance. Large windows throughout the home fill every living space with Abundant Natural Light, creating a Bright, Open, and Inviting atmosphere. The spacious open-concept floor plan seamlessly connects the living room, dining area, and kitchen, creating an inviting space for entertaining or relaxing after a day at the parks. The kitchen features Granite Countertops, Stainless-Steel GE Appliances and ample cabinet space. The laundry area includes a modern GE Washer and Dryer, while the home's GE appliances provide quality and consistency throughout the kitchen. Upstairs, the Spacious Owner's Suite overlooks the protected Conservation Area and offers a Private En-suite bathroom with dual vanities, a relaxing soaking garden tub, and peaceful preserve views. Two additional guest bedrooms and another full bathroom comfortably accommodate family and guests. The Screened Lanai provides a peaceful outdoor retreat overlooking the protected preserve, offering privacy with No Rear Neighbors. The home is being sold FULLY FURNISHED and tastefully DECORATED, making it completely Move-In Ready for personal enjoyment or immediate vacation rental use. Regal Oaks Resort offers an outstanding resort lifestyle with a beautiful Clubhouse, resort-style Swimming Pool with Water Slide, Fitness Center, Tennis Courts, Restaurant, Poolside Bar, Arcade, Scenic Lakes, Walking Trails, and 24-hr Guard-Gated security. Daily Valet Trash Collection, Exterior Maintenance, and Lawn Care are all included through the HOA, allowing owners to enjoy a truly low-maintenance ownership experience. Another valuable advantage is that Regal Oaks has no Community Development District (CDD) fees, helping reduce annual ownership costs compared to many competing resort communities. Ideally located in the heart of Kissimmee—Central Florida's Premier Destination for Vacation Homes—the property is approximately 9 miles from Disney Springs and offers convenient access to Walt Disney World, Universal Orlando Resort, Celebration, Sunset Walk, Margaritaville Resort Orlando, Island H2O Water Park, championship golf courses, shopping, dining, and I-4. This property is an established, income-producing vacation rental with an excellent rental history, Outstanding Guest Reviews & Future Reservations already in place. Subject to management continuity existing reservations may transfer to the new owner, allowing rental income to continue immediately after closing with $400 value photo package. Whether you're searching for a FL vacation home or a proven investment in one of Orlando's strongest vacation rental markets, this exceptional Regal Oaks property offers an outstanding opportunity.

2679 Corvette Lane, Kissimmee
$1,365,000
5 Beds ⋅ 4 Baths ⋅ Celebration East Village Unit 3 SubDv. ⋅ 34747 Zip Code
Updated 4-bedroom and 3-bath home in Celebration's fantastic East Village, with a private 1-bedroom, 1-bath garage apartment. From the moment you arrive, classic Victorian charm, an inviting front porch, and mature landscaping create an unforgettable first impression. Inside, a convenient floor plan is filled with natural light and thoughtfully designed gathering spaces perfect for everyday living and entertaining. The heart of the home is the extensively improved chef's kitchen, featuring granite countertops, custom cabinetry, a six-burner gas range with pot filler, Bosch dishwasher, Liebherr refrigerator, wine cooler, expanded pantry, coffee bar, and abundant storage. The kitchen opens seamlessly into comfortable living spaces including the family room, dining room, and a bright sunroom/game room that steps out to the private outdoor entertaining area. The first floor also offers a full guest bath and a flexible bedroom that easily functions as a private office. Upstairs, the spacious primary suite has been beautifully enhanced with a fully remodeled bath (2023) featuring a luxurious rain shower, electronic temperature controls, custom lighting, and an updated walk-in closet. Two additional bedrooms upstairs: one bedroom with a murphy bed and the newly added fourth bedroom (2026), a laundry area, an updated guest bath complete the second floor. Outdoor living is equally inviting with a courtyard, paver patio, and pergola, a great place to add an outdoor cooking station. The attached garage includes a completely custom-designed one-bedroom apartment with its own private entrance added in 2017, full kitchen with gas range & quartz countertops, living room, laundry, updated bath, and fenced patio; this gives flexibility for families and guests. This home has been continually improved for comfort and efficiency with a new roof (2018), newer A/C, Anderson double-pane windows, engineered wood flooring, spray foam insulation, fresh air ventilation system, gas water heater, EV charger, and a solar panel system that helps provide exceptionally low electric costs. Located just minutes from Celebration's charming downtown, residents enjoy more than 26 miles of walking and biking trails, neighborhood parks, community pools, year-round events, boutique shopping, restaurants, and convenient access to Disney, I-4, SR-417, and US-192. Homes like this rarely become available—a residence where classic Celebration charm meets today's modern conveniences, creating a home that's as beautiful to live in as it is to admire.

828 Morning Glory Lane, Celebration
$525,000
5 Beds ⋅ 5 Baths ⋅ Paradise Palms Resort Ph 4 SubDv. ⋅ 34747 Zip Code
**Exceptional 5-Bedroom Resort-Style Home in Prime Kissimmee Location!!!!This beautifully upgraded home at 2908 Banana Palm Dr puts you minutes from world-famous theme parks, shopping, restaurants, major roads, and the airport. Welcome to the perfect blend of comfort and convenience in one of Florida's most sought-after vacation destinations. Step inside this spacious 2-story home featuring over 3,000 square feet of thoughtfully designed living space. The grand entry showcases custom tile work and elegant shadow box molding that flows through the living room and dining area. Soaring vaulted ceilings and high ceilings throughout create an open, airy feel you'll love. The completely renovated kitchen is a chef's dream with brand new cabinets and porcelain countertops installed May 2025. Premium Forno appliances include a double wall oven, 36-inch French door electric range with convection, oversized 40-inch refrigerator, and a convenient microwave drawer built into the cabinetry. All five bedrooms offer comfortable retreats, with the primary bath featuring a modern bidet toilet. New LVP flooring runs throughout the entire home, while bedrooms feature cozy carpet. Recent upgrades include a new HVAC system (July 2025), hot water heater (April 2025), pool filter (November 2025), and washer/dryer (April 2025). Relax in your private screened pool and spa with privacy screens, backing up to a peaceful nature preserve. The resort-style community amenities are incredible: clubhouse, fitness center, Tiki bar, pool, two hot tubs, splash park, waterslide, movie theater, sauna, and sports courts. With over $100,000 in upgrades, this move-in ready home is approved for short-term rentals, making it perfect for personal use or investment income. Don't miss this incredible opportunity!

2908 Banana Palm Drive, Kissimmee
$695,000
5 Beds ⋅ 6 Baths ⋅ Reunion West Ph 1 East SubDv. ⋅ 34747 Zip Code
Welcome to 7564 Marker Avenue, an outstanding turnkey investment and lifestyle opportunity in the highly desirable gated resort community of Encore at Reunion, just minutes from Walt Disney World and Orlando’s world-class attractions. This fully furnished, professionally themed 5-bedroom, 5.5-bath luxury home offers over 3,300 square feet of thoughtfully designed living space, blending comfort, style, and strong short-term rental potential. The open-concept main level features a spacious family room, dining area, and modern kitchen, with the primary suite conveniently located on the first floor for added privacy and functionality. Upstairs, guests will find additional themed bedrooms and a versatile bonus/game room, creating an immersive vacation experience that consistently appeals to short-term rental guests. The home is designed for maximum occupancy appeal while still offering a warm and inviting feel for personal use. Step outside to your private resort-style pool and spa, complete with outdoor lounging space ideal for relaxing or entertaining after a day at the parks. All furnishings are included, making this a true turnkey purchase opportunity ready for immediate enjoyment or rental income. Located within Encore at Reunion, residents and guests enjoy world-class amenities including a water park, clubhouse, fitness center, tennis courts, and 24-hour gated security. With its prime location, strong vacation rental demand, and resort-style features, this property represents an exceptional opportunity for both personal enjoyment and income-producing investment.

7564 Marker Avenue, Kissimmee
$1,375,000
6 Beds ⋅ 5 Baths ⋅ Waterside Vista SubDv. ⋅ 34771 Zip Code
Virtually Staged. Mediterranean Elegance Meets Waterfront Luxury in the Exclusive Gated Community of Waterside Vista. Experience luxury, privacy, and convenience in this stunning Mediterranean-inspired estate nestled within the exclusive gated enclave of a private boating community of only 24 custom residences. This one-of-a-kind property features a residential elevator, breathtaking canal views, direct access to the Chain of Lakes, a heated saltwater pool, a rare five-car split garage, and an extended driveway accommodating up to 11 vehicles, perfect for your boats, cars, RVs, and all your recreational toys. Enjoy the benefit of lower St. Cloud taxes while being adjacent to Lake Nona, just minutes from world-class dining, shopping, and only 20 minutes from Orlando International Airport. Situated on a .64-acre waterfront homesite, this 5,193-square-foot estate offers 6 bedrooms, 5 bathrooms, and two versatile flex rooms ideal for a home office, gym, playroom, or additional guest space. Enjoy breathtaking canal views with direct access to Fells Cove, East Lake Tohopekaliga, and the Chain of Lakes. The deep-water canal offers the opportunity to build your own private dock and enjoy the ultimate Florida boating lifestyle. From the moment you arrive, the home's striking Mediterranean architecture commands attention. A dramatic two-story turreted entrance, reminiscent of a castle, welcomes you into a spectacular 24-foot foyer with an elegant Juliet balcony. The home's impressive curb appeal is further enhanced by an extended driveway that comfortably accommodates accommodates up to 11 vehicles and is complemented by a rare five-car split garage, perfect for car enthusiasts, boat owners, or multigenerational living. The garage also features both a Tesla charger and an EVBox charging station. The open-concept floor plan is designed for entertaining and everyday living, featuring a chef's kitchen with an oversized granite island, upgraded countertops, stainless steel appliances, gas cooktop, and separate butler's pantry. An oversized laundry room offers abundant cabinetry, while thoughtful accessibility features including a residential elevator and front entry ramp provide comfort and convenience. The first-floor owner's suite is a private retreat featuring a custom walk-in closet with built-in organizers. A second first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs offers a spacious living room with wet bar, a dedicated theater room, and four oversized bedrooms, including one with its own Juliet balcony. Step onto the second-floor balcony and take in beautiful canal views. Outdoor living shines with a heated saltwater pool, recently replaced pool motor, and a brand-new screened enclosure. More than 84 solar panels will convey with the home to help minimize electric costs, while a whole-home water treatment system enhances everyday comfort and efficiency. This exceptional home combines luxury waterfront living, private boating access, energy-efficient upgrades, accessibility features, abundant parking, and an unbeatable location next to Lake Nona. Contact the listing agent today to schedule your private tour or RSVP for the upcoming Open House.

5229 Waterside Vista Lane, St Cloud
$380,000
4 Beds ⋅ 2 Baths ⋅ Saratoga Park SubDv. ⋅ 34743 Zip Code
Move in ready 4 bedroom, 2 bathroom home in the desirable Saratoga Park community! Featuring a 2021 ROOF, December 2018 HVAC, 2019 water heater, and included water softener system, this well maintained home offers peace of mind from day one. Freshly painted for the new owners, the open concept floor plan showcases vaulted ceilings, quality ceramic tile flooring throughout the main living areas, and a spacious kitchen that flows seamlessly into the living and dining spaces, making it perfect for everyday living and entertaining. The split bedroom layout provides a private primary suite with a walk in closet and en suite bathroom. A new garbage disposal adds to the home's move in ready appeal, and the seller is willing to contribute toward the buyer's closing costs to replace the bedroom flooring. Enjoy relaxing on the screened covered lanai overlooking the water view backyard. Complete with a 2 car garage, low HOA, and a prime location near Florida's Turnpike, Orlando International Airport, Lake Nona, shopping, dining, and Orlando's world famous attractions, this home offers the perfect combination of comfort, convenience, and value.

2608 Deck Avenue, Kissimmee
$389,900
3 Beds ⋅ 2 Baths ⋅ East Lake Preserve Ph 3 SubDv. ⋅ 34744 Zip Code
Welcome to this beautifully designed 3-bedroom, 2-bath home plus a versatile bonus room featuring a walk-in closet; ideal as a home office, playroom, guest room, or 4th bedroom. Enjoy indoor and outdoor living with a welcoming front porch and a covered screened lanai overlooking the fenced backyard. The open concept layout offers a spacious living area, ideal for everyday living and entertaining. The kitchen features granite countertops, a large island, espresso 42-inch cabinetry with crown molding, stainless steel appliances, undermount sink, and ample storage. The private owner's suite includes a walk-in closet and an en-suite bath with dual granite vanities and glass enclosed shower. Two additional bedrooms, a second full bathroom, and a generously sized utility room complete the home. Additional highlights include in-wall pest control, dual-pane windows, and barrier roof sheathing for energy efficiency. Community amenities include a pool, playground, dog park, and internet service included in the HOA dues. Ideally located with easy access to SR-417, this home is just 5 miles from Boxi Park and Lake Nona Medical City, 7 miles from Orlando International Airport, and short distance to shopping, dining, and top-rated schools. Experience the perfect combination of modern comfort, community amenities, and great location.

2732 E Lake Pointe Drive, Kissimmee
$325,000
3 Beds ⋅ 3 Baths ⋅ Storey Lake Tr K SubDv. ⋅ 34746 Zip Code
Virtually Staged. Welcome Home to 2935 Theme St! Move-in ready, this 3-bedroom, 2.5-bath townhome offers 1,859 sq ft of open-concept living in the heart of Central Florida. From the moment you arrive, the home's charming coastal-craftsman exterior — with paver driveway and manicured landscaping — sets the tone for what's inside... Step through the front door into a spacious great room that flows seamlessly into the kitchen and dining area, all finished with tile flooring throughout the main level. The kitchen features espresso cabinetry, stainless steel appliances, a subway tile backsplash, and a center island with pendant lighting. Upstairs, the primary suite offers a peaceful retreat with a tray ceiling, walk-in closet, and en-suite bath, while two additional bedrooms provide flexible space for family, guests, or a home office. A convenient half bath downstairs and in-unit laundry add everyday functionality. Outside, enjoy a private patio and an insulated 2-car garage that stays cool year-round. HOA includes access to a community pool, dog park, cable, and WiFi. Located just minutes from Orlando's world-famous attractions, shopping, dining, and major highways, this townhome combines comfort, style, and unbeatable convenience. Don't miss this one and schedule your private showing today!

2935 Theme Street, Kissimmee
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