Casselberry Homes with Playground Amenities

Casselberry Homes with Playground Amenities

Welcome to Casselberry, Florida—a charming city nestled in the heart of Seminole County. Known for its picturesque landscapes and vibrant community spirit, Casselberry offers a perfect blend of suburban tranquility and urban convenience. With its lush parks, serene lakes, and friendly neighborhoods, this city is an ideal place for families, professionals, and retirees alike.

One of the standout features of Casselberry is its commitment to family-friendly living. Many homes in the area come equipped with delightful playground amenities, making it easy for children to enjoy the great outdoors right in their own backyard. Imagine watching your kids play on swings, slides, and climbing structures while you relax on your patio, sipping a cool drink and enjoying the warm Florida sunshine. These playgrounds foster a sense of community, encouraging families to connect and create lasting memories together.

In addition to its playground amenities, Casselberry boasts a wealth of recreational activities. With numerous parks, walking trails, and sports facilities, residents can stay active and engaged year-round. The city also hosts various community events, from farmers' markets to seasonal festivals, ensuring there’s always something happening to bring neighbors together.

With its prime location just a short drive from the bustling attractions of Orlando, Casselberry offers the perfect balance of peaceful living and easy access to entertainment. Whether you're searching for a cozy family home or a spacious estate, you’ll find a welcoming community that truly feels like home. Explore the charm of Casselberry today—your dream home awaits!

Newest Casselberry Homes with Playground Amenities

629 Woodridge Drive, Fern Park
$339,900
3 Beds ⋅ 3 Baths ⋅ Lake Of The Woods Sec 05 Twnhs SubDv. ⋅ 32730 Zip Code
COME SEE THIS OUTSTANDING TOWNHOME - COMMUNITY POOL OVERLOOKING THE LAKE! Beautiful and spacious 3 bed 3 bath townhome (nearly 1900 SF) in the highly desired Lake of the Woods community. Desirable floor plan features dual master suites upstairs plus another bedroom and bath downstairs. Each bedroom has its own bathroom and walk in closet. Large eat in kitchen and separate dining room open to the courtyard, while the huge living room with volume ceilings views the private setting at the rear of the home. Bright, light and airy throughout, plus a two car garage with a new garage door. Beautifully updated with a new roof in 2025 and low HOA fees. Lake of the Woods offers great amenities owner's love including an Olympic sized pool and kiddie pool that overlook a beautiful lake, tennis/pickleball/basketball courts, playground, fishing pier, fitness room, sauna, game room and clubhouse. Seasonal gatherings throughout the year foster the strong sense of community Lake of the Woods is known for. Conveniently located close to excellent shopping and dining along SR 436, Altamonte Mall, grocery, major roads and nearby Maitland, Altamonte Springs, and Winter Park. Make this your dream home! Schedule your private tour today.

629 Woodridge Drive, Fern Park
2217 Long Derby Way, Casselberry
$525,000
4 Beds ⋅ 2 Baths ⋅ Legacy Park Residential Ph 1 & 2 A Rep SubDv. ⋅ 32707 Zip Code
This cozy, single-story Centex home in Legacy Park features 4 bedrooms, 2 baths, and a split-bedroom floor plan. Recent updates include a new roof (2025), new carpet in all bedrooms (2026), updated appliances (2024), exterior paint (2024), new Carrier A/C (2023), new water heater (2023), a privacy vinyl fence (2023), and custom closet systems installed in three of the four bedrooms. The backyard was transformed in 2024 with a $35,000 improvement project, including tree and stump removal, a travertine patio, and upgraded pet-friendly turf. The turf features enhanced drainage designed for pets and a cooler surface for comfortable use by four-legged family members. Legacy Park offers low-maintenance living with lawn care included through the HOA, plus a community pool and playground. The neighborhood is also conveniently located near desirable schools, including The Geneva School (at the entrance to Legacy Park), Trinity Preparatory School and The Master’s Academy. This home is beautifully and lovingly maintained with major updates already completed, a low-maintenance yard, and an ideal location in Legacy Park. Schedule your showing today!

2217 Long Derby Way, Casselberry
624 Legacy Park Drive, Casselberry
$527,000
4 Beds ⋅ 2 Baths ⋅ Legacy Park Residential Ph 1 & 2 A Rep SubDv. ⋅ 32707 Zip Code
Welcome home to 624 Legacy Park Drive in beautiful Casselberry, Florida. This 4-bedroom, 2-bath home is unique to the neighborhood being one of only a few single-story homes in Legacy Park with 4 bedrooms while also boasting its own private pool. From the moment you enter this gorgeous home you will notice the care and upkeep that could only come from having ONE owner since built in 2007. Wood-look porcelain tiles were recently laid throughout the home with complimenting tile in the bedrooms. A formal dining room with an additional room ready for an office, study, den, or playroom. ***The Seller is willing to remove additional room to create more space if Buyer needs.*** The split bedroom layout is ideal for separating any noise or commotion and retreating to the primary bedroom and ensuite. The kitchen was recently renovated with stainless steel appliances, quartz countertops, and an oversized breakfast bar that spills into the welcoming family room with plenty of space for entertaining. The layout flows from there onto the screened porch and out to the spa-inspired private pool to enjoy the Florida weather. The roof is only 7 years old! The pool was built in 2020! The kitchen and appliances were renovated in 2025! This home is ready for a new owner!

624 Legacy Park Drive, Casselberry
420 Nantahala Court, Casselberry
$359,000
4 Beds ⋅ 2 Baths ⋅ Seminole Sites SubDv. ⋅ 32707 Zip Code
Virtually Staged. Seller is very motivated to sell! Offering a $5,000 concession for the buyers!! Welcome to 420 Nantahala Ct, Casselberry, FL Welcome home to this beautifully updated 4-bedroom, 2-bathroom home tucked away on a quiet cul-de-sac in Casselberry. Featuring a desirable open floor plan, remodeled flooring, and a private vinyl-fenced backyard, this home offers a comfortable and inviting layout designed for both everyday living and entertaining. Step inside to a spacious living area with remodeled floors that provide a fresh, modern look and a seamless flow throughout the main living spaces. The open-concept design connects the living, dining, and kitchen areas, creating an ideal setting for family gatherings and entertaining guests. The four-bedroom, two-bathroom layout provides plenty of flexibility for family, guests, a home office, or additional living space. Enjoy the Florida lifestyle in the private backyard, enclosed by a vinyl privacy fence that provides added seclusion and creates a great space for outdoor entertaining, pets, or simply relaxing. The home also features a water softener system installed in 2019, which was professionally serviced in July 2025, providing added convenience and comfort for the next homeowners. Conveniently located near shopping, dining, parks, schools, and major roadways, 420 Nantahala Ct offers the perfect combination of updated interior living, outdoor privacy, modern conveniences, and a convenient Casselberry location. Move-in ready and thoughtfully improved, this home is ready for its next chapter. Come see everything 420 Nantahala Ct has to offer!

420 Nantahala Court, Casselberry
638 Sausalito Boulevard Unit B5, Casselberry
$250,000
2 Beds ⋅ 2 Baths ⋅ Sausalito SubDv. ⋅ 32707 Zip Code
Welcome to this charming one-story condo offering comfortable, easy living with an inviting open floor plan and a desirable view of the community pool. Featuring 2 bedrooms and 2 baths, this home also includes a double carport for convenient covered parking. The fully enclosed porch adds valuable living space, complete with a vaulted ceiling and laundry facilities. The well-appointed kitchen features white appliances, solid-surface countertops, and a stunning tiled accent wall, while the oversized breakfast-bar island creates the perfect gathering spot for meals, entertaining, or casual conversation. With its versatile living spaces, thoughtful layout, and poolside outlook, this condo is ready to welcome you home.

638 Sausalito Boulevard Unit B5, Casselberry
1610 Grand Rue Drive, Casselberry
$342,999
3 Beds ⋅ 3 Baths ⋅ Legacy Place SubDv. ⋅ 32707 Zip Code
Welcome home to this beautifully maintained 2022 end-unit townhome in the desirable Legacy Place community! Offering 3 bedrooms, 2.5 bathrooms, a versatile loft, and a private patio, this move-in-ready home showcases true pride of ownership while delivering exceptional value. Step inside to a bright, open-concept floor plan filled with natural light from energy-efficient double-pane tinted windows. The chef-inspired kitchen is the heart of the home, featuring 42-inch shaker-style cabinetry, granite countertops, a spacious center island, walk-in pantry, stainless steel appliances, and stylish LED track lighting. Ceramic tile flooring flows throughout the main living areas, kitchen, and bathrooms, creating a clean, modern feel. The spacious primary suite offers a relaxing retreat with a walk-in closet and a private en-suite bath featuring dual vanities and a walk-in shower. A split-bedroom layout provides added comfort and privacy for family members or overnight guests, while the upstairs loft offers flexible space for a home office, media room, or play area. Enjoy peaceful mornings and relaxing evenings on your private patio overlooking the conservation area and walking trail, with no rear neighbors for added privacy. The home is equipped with an ADT Smart Home Security System and a Rain Soft whole-home water filtration system for added comfort and peace of mind. Additional features include a one-car garage with private driveway parking, a high-capacity smart front-load washer and dryer, a second refrigerator in the garage, and all drapes and window treatments. Residents enjoy a low HOA that includes lawn maintenance, along with outstanding community amenities including a playground, dog park, yoga lawn, picnic area, putting green, and scenic walking trails. Conveniently located near shopping, dining, SR 417, and the Cross Seminole Trail, and zoned for top-rated Seminole County schools, this exceptional home offers the perfect blend of style, comfort, convenience, and low-maintenance living. Don't miss your opportunity to own one of Legacy Place's most desirable end-unit homes! Schedule your private showing today!

1610 Grand Rue Drive, Casselberry
1442 Canterbury Circle, Casselberry
$434,900
3 Beds ⋅ 2 Baths ⋅ Camelot Unit 2 SubDv. ⋅ 32707 Zip Code
Virtually Staged. Welcome to this beautifully updated **3-bedroom, 2-bath pool home, Roof (2022)** offering the perfect combination of comfort, style, and convenience, all in a desirable **NO-HOA community**. Step inside to a bright, freshly painted interior featuring **luxury vinyl plank flooring throughout**. The thoughtfully designed floor plan includes a cozy family room, separate dining room, and a versatile **office/flex room**, providing plenty of space for both everyday living and working from home. Decorate vernada in the front with flowers, coffee table at the front entrance or enjoy the spacious large sun-room in the back. The **upgraded kitchen** is sure to impress with beautiful **quartz countertops, new cabinetry, and stainless steel appliances**, creating a clean and modern space for cooking and entertaining. Step outside and enjoy your own private Florida retreat. The **covered patio overlooks a resurfaced swimming pool**, surrounded by beautiful palms, mature trees, and a variety of fruit trees that create a peaceful and relaxing atmosphere. The **fully fenced backyard** offers added privacy and plenty of room for entertaining, pets, gardening, or simply enjoying the outdoors. Additional highlights include a **2022 roof, 2-car garage, paved driveway, and fresh interior and exterior paint**, making this home truly move-in ready. The location adds even more appeal. **Walk or bike to Dew Drop Park**, reach **Wirz Park in approximately six minutes**, or enjoy a round at **Casselberry Golf Club just eight minutes away**. The home is also conveniently located near **Casselberry Elementary School and South Seminole Academy**, as well as restaurants, grocery stores, shopping, and everyday conveniences. With its **updated interior, private pool, NO HOA, spacious fenced backyard, and convenient Casselberry location**, this beautifully cared-for home offers everything you need to enjoy the Florida lifestyle. **Schedule your private showing today!**

1442 Canterbury Circle, Casselberry
3740 Idlebrook Circle Unit 102, Casselberry
$137,000
1 Beds ⋅ 1 Baths ⋅ Cabana Key A Condo SubDv. ⋅ 32707 Zip Code
Virtually Staged. Welcome to this first-floor, 1-bedroom, 1-bathroom condo located in the gated community of Cabana Key. This unit offers a functional open layout and a desirable location within the community, with views of the pool and amenities. The unit is in move in conditions, giving the next owner the opportunity to update and personalize it to their taste. Most importantly, it is PRICED TO SELL and positioned as an excellent value for a buyer looking for an affordable home or investment opportunity. Enjoy Cabana Key’s community amenities, including a swimming pool, clubhouse, fitness center, playground, and gated entrance. Recent improvements to the complex include newer roofs, composite siding, exterior paint, energy-efficient windows, refreshed landscaping, and a resurfaced asphalt parking lot. Centrally located in Casselberry with convenient access to UCF, Seminole State College, Full Sail University, Red Bug Lake Park, restaurants, grocery stores, SR 436, and the 417 Expressway. Whether you're looking for your own place or an investment property, this first-floor condo offers location, convenience, and value. Priced for a quick sale—schedule your showing today!

3740 Idlebrook Circle Unit 102, Casselberry
623 Swallow Drive, Casselberry
$355,000
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
805 Westwind Lane, Fern Park
$294,900
3 Beds ⋅ 3 Baths ⋅ Lake Of The Woods Sec 09 Twnhs SubDv. ⋅ 32730 Zip Code
Virtually Staged. "Price Improvement" Welcome to 805 Westwind Lane, a spacious 3-bedroom, 3-bathroom townhome located in the desirable Lake of the Woods community of Fern Park. Each bedroom features its own private bathroom, including a convenient first-floor bedroom that may serve as a primary suite, guest retreat, or flexible home office. A private entrance and inviting courtyard create a warm welcome, while the eat-in kitchen offers generous counter space and plenty of room for casual dining. Sliding glass doors throughout the first level fill the living spaces with natural light and provide easy access to the outdoor areas. Upstairs, a distinctive landing with high-set windows offers an elevated view of the surrounding scenery and leads to two additional spacious bedrooms, each with its own en suite bathroom. The home also features an enclosed screened porch, an attached two-car garage, a newer A/C system installed in 2022, and a new roof completed in 2025. Residents enjoy access to an expansive community pool and clubhouse with a fitness room, sauna, billiards room, and grand ballroom. The home may also be purchased furnished, offering added convenience for a seasonal residence or move-in-ready lifestyle. Conveniently located near shopping, dining, entertainment, sports venues, and Central Florida’s renowned attractions. Schedule your private tour today and discover everything this exceptional townhome and community.

805 Westwind Lane, Fern Park
612 Woodridge Drive, Casselberry
$280,000
2 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 05 Twhs SubDv. ⋅ 32730 Zip Code
Updated Lake of the Woods Town House. This 2-bedroom, 2-bath home (1,296 sq ft) in Lake of the Woods offers an updated kitchen, replumbed, New Cabinets, new Quartz countertops, light fixtures, new appliances with updated bathrooms, engineered hardwood in the living and dining rooms, and vaulted ceilings, and a bright open floorplan. A skylight brings in additional natural light, and the enclosed Florida room adds flexible living space just off the main living area. Outside, the home includes an irrigation system and sits within easy reach of Winter Park and Altamonte Springs shopping and dining. With its unbeatable location, comfortable living space, and outside community features: Playgrounds, Tennis, Pool, Fitness Center, Fishing Pier, and Basketball. Don't miss your opportunity to call Lake of the Woods home-schedule your private showing today!

612 Woodridge Drive, Casselberry
3716 Idlebrook Circle Unit 212, Casselberry
$200,000
3 Beds ⋅ 2 Baths ⋅ Cabana Key A Condo SubDv. ⋅ 32707 Zip Code
Welcome to Cabana Key, a highly desirable gated community in the heart of Casselberry where comfort, convenience and lifestyle come together. This beautifully updated condo is move-in ready and features modern upgrades throughout, including stainless steel appliances, updated cabinetry, refreshed bathrooms, an in-unit washer and dryer, and durable flooring with no carpet. Residents of Cabana Key enjoy access to gated community amenities, including a sparkling resort-style pool, fitness center and playground, all designed to enhance everyday living. The HOA adds exceptional value by covering trash service and exterior building maintenance, including roof replacement, helping to keep ownership costs low and maintenance responsibilities to a minimum. The location is second to none, with an abundance of restaurants, shopping, grocery stores and daily conveniences located just minutes away. Commuters will also love the quick and easy access to SR 417, providing seamless connectivity throughout Central Florida. Whether you're seeking a primary residence, seasonal retreat, or investment opportunity, this home offers outstanding value in one of Casselberry's most convenient and desirable communities. Don't miss your chance to enjoy low-maintenance living in Cabana Key, where everything you need is just minutes from your front door. Some photos have been virtually staged to illustrate the potential use and layout of the home. Furnishings and décor shown are for illustrative purposes only and are not included in the sale.

3716 Idlebrook Circle Unit 212, Casselberry
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