Casselberry Homes with Sidewalks Community Features

Casselberry Homes with Sidewalks Community Features

Welcome to Casselberry, Florida – a charming city nestled in the heart of Seminole County, where suburban tranquility meets vibrant community living. Known for its lush landscapes and friendly neighborhoods, Casselberry is an ideal location for families, professionals, and retirees alike. With its convenient proximity to Orlando, residents enjoy easy access to world-class attractions while still relishing the peaceful ambiance of a close-knit community.

One of the standout features of Casselberry is its commitment to walkability, exemplified by its homes with sidewalks that weave through picturesque neighborhoods. Imagine leisurely strolls along tree-lined streets, where children can safely ride their bikes, and neighbors can catch up over a friendly wave. The sidewalks not only enhance the aesthetic appeal of the area but also foster a strong sense of community, encouraging outdoor activities and social interactions.

Casselberry is home to a variety of parks, recreational facilities, and community events that bring residents together. From the serene shores of Lake Concord to the vibrant Casselberry Art House, there’s always something happening in this dynamic city. Families can enjoy picnics in the park, while art enthusiasts can explore local exhibitions, ensuring there’s never a dull moment.

Whether you’re looking for a cozy single-family home or a spacious townhome, the homes in Casselberry with sidewalks offer both comfort and convenience. Embrace the charm of this delightful city, where community spirit thrives and every day feels like a breath of fresh air. Discover your dream home in Casselberry today!

Newest Casselberry Homes with Sidewalks Community Features

$519,000
3 Beds ⋅ 3 Baths ⋅ Legacy Park Residential Ph 1 & 2 A Rep SubDv. ⋅ 32707 Zip Code
Welcome home to 629 Legacy Park Drive in Beautiful Casselberry, Florida. This stunning 3-bedroom, 2.5-bath home has it all with a whopping 2500+ square feet overlooking the perfectly situated pond to watch early evening sunsets from the screened patio and fenced backyard. Upon entering this thoughtfully updated home, you will notice the clean, open feel that greets you from the flow of the layout and minimalist touch. There is a direct view to the backyard pond as soon as you enter from the front door, adding even more so to the open feel of this home. With a brand NEW Roof and added moisture barrier (12/2025), 2 NEW A/C Units, NEWER Water Heater and Whole House Water Filtration System, recent Exterior Paint, Updated Kitchen with NEW Quartz Countertops, Backsplash, and Appliances, most of the major expenses have already been handled and waiting for a new owner! Schedule your private showing today!!

629 Legacy Park Drive, Casselberry
$180,900
2 Beds ⋅ 1 Baths ⋅ Summit Village Unit 2 SubDv. ⋅ 32707 Zip Code
Take me home! Updated 2-bedroom, 1-bath single-story end unit in Summit Village, Casselberry—with no upstairs neighbors. The practical layout includes an indoor laundry room with a washer and dryer, spacious bedrooms, and a walk-in primary closet. Enjoy a charming courtyard with sliding glass doors, a welcoming front porch, and community amenities including a clubhouse, tennis courts, and pools. Water, sewer, trash, and lawn maintenance are included in the low HOA. Shopping, restaurants, and public transportation are all nearby. Don't pass up the chance to make this your own! This is a Fannie Mae HomePath property. Contact us today! This one won’t last long.

519 Polaris Loop Unit 109, Casselberry
$270,000
2 Beds ⋅ 3 Baths ⋅ Summerhill Ph 1 SubDv. ⋅ 32707 Zip Code
Investor Special! Fantastic opportunity to transform this spacious 2 bedroom, 2.5 bath townhome in the heart of Casselberry. This property offers great bones, a large, screened patio enclosure private outdoor space, and an excellent location near shopping, dining, parks, and major roadways. The home is in need of renovation and updates, including kitchen, flooring, ceilings, and cosmetic improvements, making it ideal for investors, flippers, or buyers looking to customize a property to their own taste. Bring your vision and unlock the potential of this value add opportunity. Cash or renovation financing recommended. Sold As-Is.

2996 Lowell Court, Casselberry
$425,000
4 Beds ⋅ 2 Baths ⋅ Sterling Park Unit 04 SubDv. ⋅ 32707 Zip Code
Some homes simply check the boxes. Others invite you to slow down, settle in, and imagine the life waiting for you inside. Welcome to 304 Shadow Oak Drive—a thoughtfully designed single-story, 4-bedroom, 2-bathroom pool home nestled in one of Casselberry's established communities, where abundant natural light, generous living spaces, and timeless character come together. As you step through the front door, you're welcomed by an open, airy atmosphere filled with sunshine streaming through oversized windows. The spacious living room draws you in with its warm gas fireplace, creating an inviting focal point for cozy evenings, gatherings, or quiet moments of relaxation. Designed with a desirable split-bedroom floor plan, the home offers a functional layout that balances openness with privacy. The expansive dining area provides exceptional flexibility for everyday dining, entertaining, or special occasions, while the adjoining living spaces flow seamlessly, creating an inviting environment for both everyday living and hosting guests. Tucked away for added privacy, the spacious primary suite serves as a peaceful retreat at the end of the day—a comfortable space to relax, recharge, and make your own. The additional bedrooms offer flexibility for a variety of needs, while the thoughtful floor plan makes the home feel both spacious and connected. Step outside and discover what truly makes this property shine. The backyard unfolds into your own private Florida oasis, where the sparkling in-ground swimming pool and attached spa invite you to unwind beneath the Florida sunshine. Surrounded by a fully fenced backyard, this outdoor space offers the perfect setting for entertaining, relaxing, gardening, or simply enjoying the year-round Florida lifestyle. Whether you're hosting weekend barbecues, gathering around the pool, or savoring a quiet morning outdoors, this backyard was designed to be enjoyed. A large driveway provides ample parking for multiple vehicles and guests, while the low HOA adds convenience within this well-established neighborhood. Ideally located in the heart of Casselberry, Florida, this home offers convenient access to Red Bug Lake Road, State Road 436, US Highway 17-92, Interstate 4, and SR-417, placing you just minutes from Winter Park, Altamonte Springs, Longwood, Lake Mary, Downtown Orlando, Orlando Sanford International Airport, shopping, dining, parks, recreation, grocery stores and everyday conveniences. If you've been searching for a single-story pool home in Casselberry with 4 bedrooms, 2 bathrooms, a split floor plan, a gas fireplace, a fully fenced backyard, low HOA, and generous living spaces, 304 Shadow Oak Drive offers the perfect opportunity to add your own personal style while enjoying all the comfort, space, and convenience this Central Florida location has to offer. Schedule your private showing today and experience everything 304 Shadow Oak Drive has to offer today.

304 Shadow Oak Drive, Casselberry
$495,000
4 Beds ⋅ 3 Baths ⋅ Deer Run Unit 9a SubDv. ⋅ 32707 Zip Code
The updates you'll notice are great. The ones you won't have to think about are even better. Here, the big-ticket items have already been taken care of. Roof replaced in 2024. Brand new HVAC in 2025. Renovated bathrooms. Updated kitchen. Fresh interior paint. And to top it off, the seller is paying off the solar panels at closing, so you'll get the benefit of lower electric bills without taking on a solar payment. Inside, you'll find four bedrooms, two and a half bathrooms, and over 2,100 square feet. The split-bedroom floor plan gives the primary suite a little separation from the secondary bedrooms, while the flex room near the front of the home can easily become a home office, playroom, workout space, or whatever fits your life. The kitchen opens to the main living areas, making it easy to stay connected whether you're cooking dinner, helping with homework, or catching up with friends. The primary suite is bigger than most, with sliding glass doors leading straight to the lanai, a beautifully updated bathroom with a large walk-in shower, and dual closets, giving you plenty of room without having to share every inch of storage. Out back is where this home really shines. The covered lanai is the kind of space you'll actually use, with skylights, ceiling fans, and a full outdoor kitchen complete with a built-in grill, refrigerator, prep space, and bar seating. Whether it's football on the TV, burgers on the grill, or everyone ending up outside after dinner, this is where people naturally gather. The pool screen enclosure was completely replaced including new hardware in 2025, giving the entire outdoor space a fresh, updated feel. There's plenty of deck space around the pool, and there's still fenced backyard beyond the enclosure, plus a storage shed for all the extras. Deer Run has been one of Casselberry's favorite neighborhoods for years, with mature trees, a low HOA, and nearly 140 acres of green space that's becoming a public park with walking trails. The neighborhood also provides direct access to the Casselberry Greenway Trail, giving you miles of paved trails right in your backyard. Just around the corner, you'll find the recently renovated Dew Drop Park with basketball, pickleball and tennis courts, a fishing dock, playground, and park. The elementary school is also just half a mile away. You're just minutes from Winter Park, Altamonte Springs, the 417, shopping, restaurants, and everything else that makes day-to-day life a little easier.

1539 Elf Stone Drive, Casselberry
$405,000
3 Beds ⋅ 2 Baths ⋅ Wil O' Wik SubDv. ⋅ 32707 Zip Code
Don’t miss this beautifully updated 3-bedroom, 2-bathroom home located in the highly desirable Wil O Wik neighborhood of Seminole County with $25K in UPGRADES! Tucked away on a quiet dead-end street and zoned for top-rated schools, this charming property offers the perfect blend of comfort, convenience, and style. The welcoming living room offers a cozy space to relax and unwind, while the sleek eat-in kitchen centrally located at the heart of the home boasts a newly renovated kitchen (2024) with soft close white shaker cabinets, granite countertops, a large deep stainless-steel sink & a spacious island with built-in storage ideal for cooking, dining and entertaining. Natural light fills the space through large windows, French doors, and sliding glass doors, creating a fresh and airy atmosphere throughout the main living areas. A generous dining space easily accommodates a large table, perfect for family meals or entertaining guests. The spacious primary suite boasts vaulted ceilings, views of the backyard, two walk-in closets, and a private en-suite bathroom with a walk-in shower. On the opposite side of the home are two additional bedrooms, a full guest bathroom, and a convenient laundry closet. The guest bathroom provides access to the screened-in lanai already “pool planned” and full of backyard potential. Step outside and enjoy Florida living year-round on the lanai, overlooking a fully fenced backyard with mature landscaping and plenty of room to relax, garden, or play. Recent updates include the freshly painted interior (2025), original Spanish tile flooring revealed and restored in living areas (2024), NEW waterproof luxury vinyl installed in the bedrooms (2024), Roof (2018) with NEW gutters (2024), and a NEW HVAC (2024). This home combines classic Florida charm with modern updates in a prime location just minutes from everything Orlando has to offer!

818 Wil O Wik Drive, Casselberry
$370,000
3 Beds ⋅ 2 Baths ⋅ Sterling Park Unit 01 SubDv. ⋅ 32707 Zip Code
Short Sale. Welcome to the heart of Casselberry's desirable Deer Run community, where this beautifully maintained 3-bedroom, 2-bathroom pool home perfectly blends comfort, functionality, and peace of mind. Designed with an open floor plan, the home features tile flooring in the kitchen, bathrooms, foyer, and living room, with durable laminate running throughout the main living areas. The kitchen offers a brand-new refrigerator and is pre-wired for a microwave, which will be included with the home. Fresh interior paint (2024) and updated interior doors in all bedrooms and one bathroom add a fresh, modern touch. The spacious family room flows seamlessly to a large screened-in patio—refinished in 2025 with sleek new concrete flooring—perfect for relaxing or entertaining while enjoying views of the private, mulched backyard. Safety and convenience are top-of-mind with a newly installed pool safety fence (2024) and a new pool pump (2025). This home also offers major updates for long-term peace of mind, including a new roof (2024), full home repipe (2024), updated outlets and switches (2024), water heater (2021), and an A/C unit with a brand-new fan motor (2024). A transferable 2-10 Home Warranty is included through May 2026, making this home truly move-in ready. Don’t miss your chance to own this gem in a well-established neighborhood!

623 Swallow Drive, Casselberry
$330,000
4 Beds ⋅ 2 Baths ⋅ Laurelwood SubDv. ⋅ 32730 Zip Code
Welcome to 2510 Driftwood Drive, Fern Park, FL! Nestled on a spacious corner lot, this charming single-family home offers the perfect blend of comfort, convenience, and location. Whether you're a first-time homebuyer, growing family, or investor, you'll appreciate everything about this property! Ideally situated just minutes from a variety of shopping, dining, and everyday conveniences, you'll enjoy easy access to local favorites while still being tucked away in an established neighborhood. Outdoor enthusiasts will love the nearby lakes, parks, and recreational opportunities that make Central Florida living so desirable. Families will appreciate the home's location within highly regarded Seminole County schools, known for their strong academic reputation. With its desirable corner-lot setting, convenient location, and access to excellent schools, parks, and local amenities, 2510 Driftwood Drive is a wonderful opportunity to call home. Schedule your private showing with Thomas today and discover all that this Fern Park gem has for you!

2510 Driftwood Drive, Fern Park
$135,000
1 Beds ⋅ 1 Baths ⋅ Oxford Square Condo SubDv. ⋅ 32707 Zip Code
Ground floor one -Bedroom, 1-Bath Condo in the Oxford Square Community of Casselberry! This charming first-floor condo has all kitchen appliances, plus a washer and dryer. The property has been well maintained and features a recently replaced roof, a new flooring, ceramic tile flooring throughout, and is in great condition. The HOA fee includes water, trash collection, exterior maintenance, and access to community amenities, including two swimming pools, a community center, and tennis courts. Don't miss this excellent opportunity to own your home. This property is move-in-ready home in a desirable location! Close to main roads, UCF, shopping in winter park and only a short drive to downtown Orlando Business district.

660 Kenwick Circle Unit 104, Casselberry
$299,900
2 Beds ⋅ 3 Baths ⋅ Cassel Creek Ph 1 SubDv. ⋅ 32707 Zip Code
Welcome to 2577 Derbyshire Circle, a beautifully freshly painted 2-bedroom, 2½-bath townhome offering 1,768 square feet of comfortable living space in the desirable Cassel Creek community of Casselberry. This spacious two-story home offers a warm and inviting floor plan designed for both everyday living and entertaining. The generous living room is highlighted by a wood-burning fireplace, creating a cozy focal point for relaxing evenings at home. Large windows fill the living and dining areas with natural light, creating a bright, open atmosphere. The spacious kitchen offers abundant cabinet storage and generous countertop space, making meal preparation and entertaining both convenient and enjoyable. A convenient half bath on the main level is perfect for guests. Upstairs, you'll find two generously sized bedrooms, each with its own private full bathroom, providing comfort and privacy for family members or overnight guests. Fresh interior paint gives the home a clean, updated look, making it truly move-in ready. Whether you're looking for your first home, downsizing, or searching for an excellent investment opportunity, this townhome offers the perfect combination of comfort, functionality, and value. Located in the established Cassel Creek community, residents enjoy a low-maintenance lifestyle with convenient access to shopping, restaurants, medical facilities, parks, and major roadways, making it easy to enjoy everything Central Florida has to offer. With its spacious layout, wood-burning fireplace, fresh interior paint, and outstanding location, 2577 Derbyshire Circle is ready to welcome its next owner. Schedule your private showing today!

2577 Derbyshire Circle, Casselberry
$274,900
2 Beds ⋅ 3 Baths ⋅ Summerhill Ph 2 SubDv. ⋅ 32707 Zip Code
Welcome home to the highly desirable Summerhill community in Casselberry! This charming townhome offers 2 spacious bedrooms, 2.5 bathrooms, and 1,223 square feet of comfortable living space, complete with inviting interiors and a private backyard retreat. Major updates include a new roof in 2024 and fresh exterior paint, offering peace of mind and curb appeal. Step inside to a bright and airy living room filled with natural light from two large picture windows. The thoughtfully designed layout flows into the dining area, which overlooks and opens to the private backyard—perfect for relaxing or entertaining. The kitchen offers ample cabinet storage and comes fully equipped with all appliances included. Conveniently located in the kitchen is a laundry closet with washer and dryer, both conveying in as-is condition. Enjoy your own outdoor oasis featuring a brick patio, decorative planters, and a fully fenced backyard with a private gate—ideal for morning coffee, gardening, or unwinding at the end of the day. Upstairs, a winding staircase leads to two spacious en-suite bedrooms, providing privacy and comfort. One bathroom features a tub/shower combination, while the other offers a walk-in shower. Residents of Summerhill enjoy access to a beautiful community pool with a large covered cabana, low-maintenance landscaping, irrigation, and plenty of parking. Conveniently located near Red Bug Road, this home offers easy access to shopping, dining, parks, and highly rated schools. As an added bonus, with an acceptable executed contract, the seller will install a brand-new HVAC system prior to closing.

838 Commonwealth Court, Casselberry
$239,000
3 Beds ⋅ 2 Baths ⋅ Hunters Chase Condo Ph 1 SubDv. ⋅ 32707 Zip Code
Welcome home to this beautiful, ground-floor condo tucked inside the peaceful, gated community of Hunters Chase! This desirable 3-bedroom, 2-bathroom first-floor unit offers over 1,100 sq. ft. of comfortable living space with a bright, open floor plan. The kitchen overlooks the main living area, creating an ideal layout for both daily living and entertaining. Enjoy your morning coffee or unwind in the evening on the private, screened-in rear patio which also features handy extra space. As a resident, you'll have access to fantastic community amenities, including a refreshing pool, clubhouse, and fitness center. Strategically located just off Red Bug Lake Road, you are only minutes away from Red Bug Lake Park, shopping, dining, Publix, and Starbucks, with easy access for SR-436 and the 417. Whether you are looking for a low-maintenance primary residence or a stellar investment opportunity in Seminole County, this condo is a must-see!

1141 Exceller Ct. Unit 105, Casselberry
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