Casselberry Homes with Playground Community Features

Casselberry Homes with Playground Community Features

Welcome to Casselberry, Florida – a hidden gem 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 a variety of recreational activities, this charming city is an ideal place for families and individuals alike.

One of the standout features of Casselberry is its commitment to creating family-friendly environments. The Homes with Playground Community is a prime example of this dedication. Here, you’ll find beautifully designed residences that cater to the needs of modern families, providing ample space and comfort. But what truly sets this community apart is its emphasis on play and leisure. With well-maintained playgrounds and recreational areas, children can enjoy safe and engaging spaces to explore and socialize, while parents can relax knowing their little ones are having fun just steps away from home.

Beyond the community’s playgrounds, Casselberry boasts a wealth of amenities. Residents can take advantage of nearby shopping centers, delightful dining options, and a variety of outdoor activities, including walking trails and golf courses. The city is also conveniently located just a short drive from the bustling attractions of Orlando, making it easy to enjoy the best of both worlds.

Whether you’re looking for a serene place to raise a family or a vibrant community filled with opportunities for connection and recreation, Casselberry is the perfect choice. Come discover your new home in this welcoming city!

Newest Casselberry Homes with Playground Community Features

$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 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
$345,000
3 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 05 Twnhs SubDv. ⋅ 32730 Zip Code
Located in the quiet community of Lake of the Woods, convenient to shopping and major highways. The "Birch" is a one story corner unit featuring three Bedrooms, two Baths, eat-in-kitchen, large courtyard and two car garage. Many recent renovations and upgrades including new roof HVAC, HWH, re-piping, and others. Amenities include a lakefront pool, fishing pier, basketball and tennis courts, playground and picnic area, fitness center, sauna and clubhouse.

635 Woodridge Dr, 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
$325,000
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
$309,900
3 Beds ⋅ 3 Baths ⋅ Lake Of The Woods Sec 09 Twnhs SubDv. ⋅ 32730 Zip Code
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
$266,000
2 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 05 Twnhs SubDv. ⋅ 32730 Zip Code
Discover the lifestyle and convenience of Lake of the Woods in this inviting 2-bedroom, 2-bath home tucked away on a quiet dead-end street. The open living and dining area features a cathedral ceiling and flows seamlessly to a screened porch, creating a comfortable space to relax or entertain. Both bedrooms offer generous walk-in closets, and one includes a built-in wall unit with abundant shelving and cabinetry—ideal for storage, a home office, or hobby space. A private paved courtyard adds charm and curb appeal, while the 1-car garage provides everyday convenience. Buyers will also appreciate that the special assessment for the new roof installed in 2025 will be paid in full at closing. Lake of the Woods offers resort-style amenities, including an Olympic-size lakefront pool, kiddie pool, tennis courts, basketball court, playground, fishing dock, fitness center, library, game room, and a large, recently renovated clubhouse with a full kitchen available for residents to rent. Ideally located between Maitland, Altamonte Springs, and Casselberry, this home provides easy access to the Sun Rail station, I-4, SR 414, and SR 436, with convenience stores within walking distance and a variety of restaurants and shopping centers nearby.

602 Woodridge Drive, Casselberry
$373,000
3 Beds ⋅ 3 Baths ⋅ Legacy Place SubDv. ⋅ 32707 Zip Code
WHY WAIT TO BUILD when you can have your very own (almost) brand new energy-efficient home ready to move in! This townhouse features 42 Inch Upper Cabinets with Crown Molding. 15x15 Extended Ceramic Tile Flooring. Granite Countertops. Stainless Steel Kitchen Appliances. The kitchen overlooks the spacious great room making entertaining guests a breeze. Enjoy your morning cup of coffee on your front porch or covered lanai. The closet downstairs and walk-in closets in each bedroom provide plenty of storage for everyone. Legacy Place is in the desirable Casselberry submarket only a few miles from SR-417 and I-4 providing easy access to major employment centers. This charming community is a short drive to Oviedo and Winter Park shopping, dining, and entertainment including the Oviedo Mall, Park Avenue and Winter Park Village. Community amenities include a yoga lawn, dog park, putting green, grilling area, and tot lot. The energy-efficient features provide you live a healthier and quieter lifestyle while saving money on utility bills. Home comes with a Level 2 electric car charger. Buyers are motivated to sell!

964 Legacy Winds Way, Casselberry
$615,000
4 Beds ⋅ 4 Baths ⋅ Oakhurst Reserve Unit Two SubDv. ⋅ 32707 Zip Code
Welcome to this spacious and light-filled 4-bedroom, 3.5-bath POOL home located in the gated community of Oakhurst Reserve. With all bedrooms conveniently located upstairs and an ideal layout for both everyday living and entertainment, this two-story home offers room to spread out and enjoy Florida living. Tile flooring flows throughout the downstairs living areas. The open living and dining room combination welcomes you upon entry and is adjacent to a bonus room (currently used as private office) with views of the covered front porch. An abundance of windows throughout fill the home with natural light, creating a bright and inviting atmosphere. The heart of the home is the open kitchen, dinette, and family room combination overlooking the pool and backyard. The kitchen features plenty of cabinetry, a stainless appliance package, a large center island, and additional prep area that can serve as a breakfast bar, coffee station, or desk space. The adjoining dinette with bay window offers the perfect spot for casual dining while enjoying views of the backyard oasis from the family room. Upstairs, the spacious primary suite offers a relaxing retreat with a garden tub, separate shower, double vanities, and a private water closet. Bedroom two features its own ensuite bath with tub/shower combination and single vanity, while bedroom three enjoys direct access to the shared hall bath. An upstairs laundry room adds convenience to daily life. Outside, enjoy your own private backyard retreat featuring a sparkling pool with water feature, paver deck, covered patio, and a large fully fenced yard with plenty of room for pets, play, or gardening. ROOF 2018, A/C 2023, WATER HEATER 2024 Residents of Oakhurst Reserve enjoy the security of a GATED entrance along with community amenities including a pool, playground, and shaded pavilion area. Ideally located near top-rated schools, Red Bug Lake Park, shopping, dining, banking, hospitals and major roadways, this home offers the perfect blend of comfort, convenience, and Florida lifestyle.

2013 Crossvine Lane, Casselberry
$329,000
3 Beds ⋅ 3 Baths ⋅ Lake Of The Woods Sec 08 Twnhs SubDv. ⋅ 32730 Zip Code
3-bedroom, 2.5-bath home centrally located between Winter Park, Altamonte Springs, and Casselberry. Features a private courtyard entry and an attached 2-car garage with direct access to the kitchen. Open layout with good natural light. Split bedroom floor plan with an oversized primary suite. Screened patio provides additional outdoor space. Community amenities include pool, fitness center, tennis courts, and more

459 Meadowood Boulevard, Fern Park
$159,000
2 Beds ⋅ 1 Baths ⋅ Cabana Key A Condo SubDv. ⋅ 32707 Zip Code
Enjoy living in this charming 2-bedroom, 1-bath first-floor condominium located in the desirable Cabana Key community. This well-maintained unit offers a screened patio perfect for relaxing, an interior laundry area, a spacious primary bedroom with a walk-in closet and separate vanity, plus an additional storage room for added convenience. Recent updates include newer windows, a new front door, a replaced patio screen, and updated flooring installed approximately one year ago. Residents of Cabana Key enjoy access to a community pool, spa, and clubhouse, creating the perfect setting for both relaxation and recreation. This home also offers convenient access to shopping, dining, and everyday essentials. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this move-in-ready condo offers comfort, and convenience.

3756 Idlebrook Circle Unit 108, Casselberry
$390,000
3 Beds ⋅ 3 Baths ⋅ Legacy Place SubDv. ⋅ 32707 Zip Code
Welcome to Legacy Place—where style, function, and low-maintenance living come together in this beautifully maintained townhome. Built in 2022 and offering 3 bedrooms, 2.5 bathrooms, 1,806 square feet, and an attached 2-car garage, this move-in ready home delivers the benefits of newer construction without the wait.  Step inside to a bright open-concept floor plan where abundant natural light streams through oversized windows and sliding glass doors, creating a warm and inviting atmosphere throughout. Designed for both comfortable everyday living and effortless entertaining, the spacious living, dining, and kitchen areas flow seamlessly together, enhancing the home's sense of openness and connection.  The kitchen is a true focal point of the home, appointed with 42-inch solid wood cabinetry, stainless steel appliances, granite countertops, a large center island with breakfast bar seating, a dedicated coffee bar, and an oversized walk-in pantry. Both elegant and highly functional, the space is perfectly suited for everyday living, effortless entertaining, and gathering with those who matter most.  Beautiful wood-plank tile flooring extends throughout the first floor, creating a clean, cohesive designer feel. Sliding glass doors seamlessly blend indoor and outdoor living, leading to a private patio—an inviting extension of the home that's perfect for grilling, morning coffee, or relaxing around a fire pit on cooler Florida evenings.  The first floor features all main living areas along with a conveniently located guest bath, while the upstairs layout offers privacy and separation from the home's entertaining spaces. The spacious primary suite serves as a peaceful retreat, featuring a generous walk-in closet, dual-sink vanity, walk-in shower, and private water closet. Two additional bedrooms, a full guest bath, and the conveniently located upstairs laundry area complete the second floor.  Storage is abundant throughout the home, offering practical solutions that make everyday living easy and organized.  Additional highlights include a ROOF, A/C, and WATER HEATER all NEW in 2022 providing valuable peace of mind and long-term value. Ideally located in Legacy Place, residents enjoy quick access to SR-417 and I-4, providing convenient connections to Winter Park, Oviedo, downtown Orlando, shopping, dining, and major employment centers. Community amenities include a dog park, playground, grilling area, putting green, Yoga lawn, community exercise path, and a permanent cornhole set-up, creating opportunities to enjoy the Florida lifestyle close to home.  Beautifully maintained, thoughtfully designed, and perfectly located—this exceptional townhome offers the ideal combination of comfort, convenience, and modern living. Don't miss this opportunity!  Schedule your private showing today.

942 Legacy Winds Way, Casselberry
$405,000
4 Beds ⋅ 2 Baths ⋅ Sterling Park SubDv. ⋅ 32707 Zip Code
This is a rare opportunity to own a Large 4 bedroom 2 bath home inside the quiet neighborhood of Deer Run / Sterling Park Community, only minutes to Maitland, Altamonte Springs Winter Park and downtown Orlando. As you enter, you'll immediately notice the soaring ceilings in the spacious living and dining areas, along with the oversized pass-through breakfast bar that connects the kitchen to the formal dining room. All bedrooms are generously sized, especially the primary suite, which features a large vanity and a separate glass-enclosed shower. Newer luxury vinyl plank flooring extends throughout several of the bedrooms, while tile flooring leads from the entryway through the kitchen and informal dining area—meaning there is no carpet anywhere in the home. The kitchen offers abundant cabinet and counter space, a large walk-in pantry, and newer stainless steel appliances. Just beyond the Living room, a 20-foot screened porch provides the perfect setting for morning coffee, outdoor dining, and weekend grilling. Storage is plentiful with an attic access stairwell, built-in garage shelving plus workbench and a 12' x 10' aluminum shed that can easily accommodate tools, equipment, and outdoor gear. Recent updates include: * High-efficiency Carrier A/C system (less than 5 years old) * Side-by-side refrigerator with ice and water dispenser in the door (less than 2 years old) * Newer shingle roof (2021) * Luxury vinyl flooring (2022) * All new exterior paint (2026) * Washer and Dryer * Paddle fans throughout Residents of Sterling Park enjoy access to a community picnic and playground area, a secure swimming pool, and a basketball court. Future recreational opportunities are on the horizon as the former Deer Run Golf Course is being transformed into The Deer Run Community Park. Planned amenities include more than four miles of trails and boardwalks, along with a renovated community center, creating an exceptional outdoor destination within Seminole County's natural landscape. All schools are close by and Sterling Park Elementary is inside the neighborhood for easy access. Make your appointment to see this today!

298 Quail Court, Casselberry
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