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 city of Orlando. Known for its picturesque landscapes and friendly community atmosphere, Casselberry offers a perfect blend of suburban tranquility and urban convenience. With its lush parks, serene lakes, and a variety of recreational facilities, this city is an ideal haven for families, retirees, and everyone in between.

One of the standout features of homes in Casselberry is the abundance of properties adorned with beautiful sidewalk exterior features. Imagine stepping out of your front door and strolling along tree-lined sidewalks, where friendly neighbors greet you and children play in the lush green yards. These sidewalks not only enhance the aesthetic appeal of the community but also promote a healthy, active lifestyle. Whether you’re out for a morning jog, an evening walk with your furry friend, or simply enjoying the fresh Florida air, these pathways invite you to explore your neighborhood.

The homes in Casselberry are as diverse as its residents, with options ranging from cozy single-family homes to spacious townhouses. Many of these properties boast modern amenities, open floor plans, and inviting outdoor spaces, making them perfect for entertaining guests or enjoying quiet evenings at home. With its welcoming community, excellent schools, and convenient access to shopping and dining, Casselberry is more than just a place to live; it’s a place to thrive. Come discover the charm of Casselberry and find your dream home today!

Newest Casselberry Homes with Sidewalk Exterior Features

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

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 was resurfaced in 2025 and the screen enclosure was completely replaced 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

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

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 income-producing potential. 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

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

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

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

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

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

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

2 Beds ⋅ 2 Baths ⋅ Sausalito Sec 3 SubDv. ⋅ 32707 Zip Code

Welcome to 670 Stanhope Drive in Casselberry, a charming home located in the desirable Sausalito community near Lake Howell. This property offers a comfortable layout with plenty of potential for a primary residence, second home, or investment property. This 2 bedroom and 2 bath home features NO flooding, new roof 2023, oversized 2 car garage and a screened in porch with a fully fenced in back yard. One of the biggest highlights is the community lifestyle. Residents enjoy access to recreational amenities including pickleball/tennis courts, a community boat ramp and dock, playground and clubhouse, making it easy to enjoy time outdoors and on the water. The community also offers optional boat and RV storage, a valuable feature for buyers who want convenient space for their recreational vehicles. Nearby listings in the same Sausalito community confirm access to a private/community boat ramp, dock and recreational facilities. Conveniently located in Casselberry with easy access to shopping, dining, schools and the greater Orlando area, this home offers a great combination of neighborhood amenities and Central Florida living. Bring your boat, RV and pickleball paddle and start enjoying the Florida lifestyle at 670 Stanhope Drive!

670 Stanhope Drive, Casselberry

3 Beds ⋅ 2 Baths ⋅ Heftler Homes Orlando Sec One SubDv. ⋅ 32707 Zip Code

Virtually Staged. – $329,999 522 Wilshire Dr, Casselberry, FL 32707 Move-in ready 3-bedroom, 2-bath home in a fantastic Casselberry location! This beautifully updated home 1,274 sq. ft. of living space on a spacious 7,500 sq. ft. lot. Major updates have already been completed, including a new A/C (2025), new roof (2026), and fresh interior paint throughout, making this home truly move-in ready. Step outside to enjoy the large covered back porch (300 sq ft), brand-new paver patio (400 sq ft), and fully fenced back yard—great for entertaining, grilling, pets, or relaxing with family and friends. Prime location: • Walking distance to the newly renovated Casselberry Aquatics Center & Park (formerly Wirz Park) • Walking distance to the Casselberry Greenway Trail • Convenient access to shopping, dining, schools, and major highways Features: 3 Bedrooms 2 Bathrooms 1,274 Sq. Ft. 7,500 Sq. Ft. Lot New Roof (2026) New A/C (2025) Fresh Interior Paint Large Covered Back Porch Brand-New Paver Patio Fully Fenced Back Yard $329,999 Some photos have been virtually rendered.

522 Wilshire Drive, Casselberry

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