Casselberry Homes with Sidewalk Exterior Features

Casselberry Homes with Sidewalk Exterior Features

Welcome to Casselberry, Florida – a charming city nestled in the heart of Seminole County, just a stone's throw away from the vibrant pulse of Orlando. Known for its picturesque landscapes and welcoming community, Casselberry offers a delightful blend of suburban tranquility and urban convenience. With its lush parks, serene lakes, and a variety of recreational activities, this city is an ideal setting for families, young professionals, and retirees alike.

One of the standout features of homes in Casselberry is their inviting sidewalk exterior. Imagine strolling through tree-lined streets, where friendly neighbors greet you with a wave as you enjoy your evening walk. The sidewalks not only enhance the aesthetic appeal of the neighborhood but also promote a healthy, active lifestyle. Whether you’re out for a morning jog or an evening stroll with your loved ones, these well-maintained pathways create a safe and enjoyable environment for all.

Casselberry is not just a place to live; it’s a community where memories are made. The city boasts a range of local shops, restaurants, and cultural attractions, ensuring that residents have everything they need within reach. With its strong sense of community, excellent schools, and convenient access to major highways, Casselberry is the perfect place to call home.

Discover the charm of Casselberry and explore the beautiful homes with sidewalk exteriors that invite you to enjoy the outdoors. Experience a lifestyle where community and comfort come together in perfect harmony. Welcome home!

Newest Casselberry Homes with Sidewalk Exterior Features

$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
$359,900
3 Beds ⋅ 2 Baths ⋅ Orange Grove Park Unit 2 SubDv. ⋅ 32707 Zip Code
Some homes ask you to imagine the possibilities. This one lets you move in and start living while you do. The open floor plan keeps the main living spaces connected, creating an easy rhythm for weeknight dinners, weekend gatherings and everything in between. Three bedrooms and two baths offer a comfortable, functional layout, while the move-in-ready interior gives you the freedom to layer in your own style and make the space feel unmistakably yours. Out back, a spacious screened patio becomes an extension of the home—a breezy spot for morning coffee, game-day spreads or lingering over dinner as the sun goes down. Beyond it, the expansive fenced yard is ready for whatever comes next: a garden, firepit, play space or the backyard retreat currently living on your inspiration board. Set near Red Bug Lake Park, outdoor recreation is practically part of the neighborhood, with trails, playgrounds, sports fields, courts and fishing nearby. Shopping, dining and everyday conveniences are also close at hand, with easy access to Winter Springs, Oviedo, Winter Park and the greater Orlando area. The yard is big, the floor plan flows and the possibilities are entirely yours.

854 N Jerico 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
$477,000
4 Beds ⋅ 2 Baths ⋅ Camelot Unit 2 SubDv. ⋅ 32707 Zip Code
Welcome to this lovingly maintained, one-owner home offering an exceptional combination of quality updates, thoughtful features, and an unbeatable location in the heart of Casselberry. Major improvements provide peace of mind, including a new HVAC system (2025), new gas water heater (2026), new range, dishwasher, microwave, and garbage disposal (2026), roof replaced (2017), and exterior painted (2022). The home also features replacement windows with a lifetime warranty, hurricane shutters, a transferable termite bond, irrigation with reclaimed water, security system wiring, and natural gas service with a gas heat pump, gas water heater, and range. Inside, you'll find a cozy wood-burning fireplace and a versatile enclosed garage that could easily serve as a fifth bedroom, home office, or bonus room. One of the bathrooms offers direct access to the back porch, making it ideal as a future pool bath. The fully vinyl-fenced backyard includes a private rear gate providing direct access to the newly renovated Dew Drop Park, where you'll enjoy basketball and tennis courts, a playground, pavilion, dock, and open green space just steps from your backyard. This rare opportunity combines decades of meticulous ownership with outstanding updates and an incredible park-side setting that is difficult to find.

1391 Avalon Boulevard, Casselberry
$949,900
4 Beds ⋅ 6 Baths ⋅ Crystal Bowl Add SubDv. ⋅ 32707 Zip Code
Welcome to a truly one-of-a-kind waterfront estate where the tranquility of country living meets the convenience of city life. Nestled on nearly one acre of private lakefront property in the heart of Casselberry, this exceptional multigenerational home is an incredibly rare opportunity to own a custom-built retreat unlike anything else on the market. Designed with both everyday living and unforgettable entertaining in mind, this expansive residence offers incredible flexibility with multiple living areas and up to three potential primary suites, making it ideal for extended families, guests, or those seeking dedicated work-from-home space. Rich Brazilian hardwood floors add warmth and elegance to the formal living and dining rooms, while the spacious kitchen features a generous island with abundant prep space, creating the perfect gathering place for family and friends. The oversized bonus room offers endless possibilities as a home theater, fitness studio, game room, or creative space. Just outside, an elevated deck overlooks the sparkling pool, creating a seamless connection to the beautifully renovated detached guest residence. The detached suite is a true highlight, offering approximately 864 square feet of beautifully updated living space complete with one bedroom, one and a half bathrooms, & private accommodations ideal for multigenerational living, long-term guests, a home office, or gym. The convenient half bath also provides direct access from the pool area, making outdoor entertaining effortless. Mature trees provide a peaceful canopy over the nearly one-acre homesite. Whether you enjoy gardening, relaxing with a morning coffee, or simply taking in the serene surroundings, this property offers an outdoor lifestyle that is difficult to find. A spacious workshop shed provides the perfect space for hobbies, woodworking, storage, or DIY projects, complementing the detached two-car garage with additional parking for a boat, RV, trailer, and ample guest parking courtesy of the circular driveway. Enjoy private access to Lake Crystal Bowl, where fishing, kayaking, paddle boarding, and other non-gas-powered boating activities await. It's a peaceful waterfront setting that feels miles away from the city, yet places you in one of Central Florida's most convenient locations. Thoughtfully updated throughout, the home features six beautifully remodeled bathrooms, four air conditioning systems, three of which have been replaced within the last five years, new roof, new electrical panels & outlets, new garage door, updated knockdown ceilings, energy-efficient LED recessed lighting, a new sprinkler system, updated main primary bathroom, new windows, and so much more! Perfectly situated in a quiet, established neighborhood within the sought-after Winter Springs High School district, this extraordinary property is within walking distance to quality schools and just minutes from shopping, dining, major highways, two golf courses, scenic bike trails, and Butterfly Park directly across the street. Rarely does a property combine nearly an acre of waterfront, a detached guest home, extensive updates, exceptional parking, workshop space, beautiful gardens, and an unbeatable location into one extraordinary offering. This is more than a home—it's a legacy property designed to bring generations together while offering the privacy, flexibility, and lifestyle today's buyers are searching for.

1048 Crystal Bowl Circle, Casselberry
$234,900
2 Beds ⋅ 2 Baths ⋅ Deer Run Unit 14b SubDv. ⋅ 32707 Zip Code
Virtually Staged. Dreams Do Come True... By You Know Who! Bring your DPA, FHA, VA offers! WATERFRONT VIEWS • TWO PRIMARY SUITES • EXPANSIVE SCREENED LANAI Wake up every day to peaceful water views and the feeling of your own private retreat! Nestled among mature trees and lush landscaping, this beautifully maintained waterfront townhome offers the perfect blend of comfort, privacy, and low-maintenance living. Designed with flexibility in mind, this spacious residence features two private primary suites—one conveniently located on the first floor and another upstairs, making it ideal for guests, roommates, or multigenerational living. The heart of the home is an open-concept Great Room where oversized sliding glass doors frame the tranquil pond and flood the living space with natural light. Step outside to the massive screened lanai, an incredible extension of your living space that's perfect for morning coffee, evening wine, outdoor dining, or simply relaxing while enjoying the calming sights and sounds of nature. The kitchen shines with brand-new premium stainless steel appliances, all still under transferable warranty, plus a sunny breakfast nook for casual meals. A generous dining area easily accommodates family dinners and holiday gatherings while overlooking the beautiful waterfront scenery. Additional features include an in-unit washer and dryer, outdoor storage closet, and carefree living with exterior maintenance handled for you. The community offers outstanding amenities including a sparkling swimming pool, clubhouse, and resurfaced tennis courts—giving you the lifestyle you deserve without spending your weekends doing yard work. Whether you're searching for your primary residence, a seasonal escape, or a smart investment, this waterfront gem delivers the perfect combination of peaceful surroundings, resort-style amenities, and everyday convenience. Don't miss your opportunity to own a slice of paradise!

4008 W Maryland Place, Casselberry
$365,000
2 Beds ⋅ 2 Baths ⋅ Deer Run Unit 11 SubDv. ⋅ 32707 Zip Code
Charming Dual-Master Retreat in Deer Run! Welcome to 1552 Cougar Ct, a beautifully functional 2-bedroom, 2-bathroom home in the heart of Casselberry's sought-after Deer Run community. Thoughtfully designed with a dual master suite layout, this 1,315 sq ft residence offers privacy and flexibility ideal for roommates, multigenerational living, guests, or a dedicated home office setup — each bedroom enjoys its own full en-suite bath. Step outside to your own private oasis: a screened-in pool paired with a covered patio, perfect for year-round Florida entertaining, morning coffee, or simply unwinding after a long day without the hassle of bugs or excess sun. Deer Run is known for its established tree-lined streets, community amenities, and convenient access to shopping, dining, and major roadways — putting Winter Springs, Winter Park, and Downtown Orlando all within easy reach. Whether you're a first-time buyer, downsizer, or investor, this move-in-ready gem offers a rare combination of privacy, functionality, and outdoor living in one of Casselberry's most desirable neighborhoods. Don't miss your chance to make 1552 Cougar Ct your own — schedule your private showing today!

1552 Cougar Court, 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
$499,900
3 Beds ⋅ 3 Baths ⋅ Indian Hills Unit 2 SubDv. ⋅ 32730 Zip Code
This renovated and updated 3 bedroom, 2 and a half bath pool home is truly move-in ready. The layout perfect for entertaining, whether in the large kitchen space, by the fireplace in the Living Room, spending game day in the Family Room or time out enjoying the pool and the private backyard. You will not want to leave once you enter the home, it's that inviting. From the large Kitchen, to the cozy Living Room with a fireplace or the Family Room for spending time with friends and family. There is an indoor utility room and a infrared sauna as well. You can spend time on the front porch or evenings on the screened lanai. Kewannee park is around the corner as well as a bike trail. The roof was replaced in 2021 and the home just got a brand new HVAC system installed. Did I say it even has a infrared sauna?!

1903 Collier Drive, Fern Park
$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
$375,000
3 Beds ⋅ 2 Baths ⋅ Deer Run Unit 7a SubDv. ⋅ 32707 Zip Code
Welcome to 1275 Bridlebrook Drive, a fantastic single-family home in the heart of Seminole County. This beautifully maintained 3-bedroom, 2-bathroom home with a 2-car garage offers the perfect blend of comfort, style, and low-maintenance living. From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious screened-in porch overlooks a professionally installed turf backyard (2021), creating an attractive outdoor space that's easy to enjoy year-round while keeping maintenance to a minimum. Inside, you'll find an updated kitchen with granite countertops, both bathrooms beautifully renovated in 2023, custom built-in closets, fresh interior paint completed in 2026. Major mechanical updates provide added peace of mind, including a new roof in 2021, a new water heater in 2022, and an A/C system that's only about 10 years old, plus all new ductwork in 2024. Cozy up on cool evenings beside the wood-burning fireplace, adding warmth and character to the living space. Whether you're a first-time homebuyer, an investor, or looking to downsize without sacrificing quality, this move-in-ready home offers exceptional value in a desirable Casselberry location close to shopping, dining, parks, and top-rated Seminole County schools.

1275 Bridlebrook Drive, Casselberry
Start Your Search