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, sparkling lakes, and a plethora of recreational activities, this charming city is an ideal place for families, retirees, and everyone in between.

One of the standout features of Casselberry is its family-friendly atmosphere, particularly in neighborhoods that prioritize community engagement and outdoor fun. Homes with playground community features are a hallmark of this area, providing safe and inviting spaces for children to play and make lifelong memories. These thoughtfully designed communities often include well-maintained playgrounds, walking trails, and picnic areas, ensuring that families can enjoy the great outdoors right at their doorstep.

In addition to its family-centric amenities, Casselberry boasts a rich cultural scene, with art galleries, local events, and a variety of dining options that cater to all tastes. The nearby Casselberry Golf Club and numerous parks offer ample opportunities for recreation, whether you're looking to hit the links or enjoy a peaceful afternoon by the lake.

As a resident of Casselberry, you'll find that the sense of community is palpable, with friendly neighbors and a welcoming atmosphere. Whether you're searching for your first home or looking to settle down in a vibrant community, Casselberry, with its homes featuring playgrounds and family-oriented amenities, is the perfect place to call home. Discover the charm of Casselberry—where community and comfort come together seamlessly!

Newest Casselberry Homes with Playground Community Features

$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
$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
$256,000
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
$479,000
3 Beds ⋅ 2 Baths ⋅ Royal Oaks SubDv. ⋅ 32707 Zip Code
Welcome home to Royal Oaks! This beautifully renovated 3BR/2BA split-plan home is move-in ready, featuring brand new paint throughout, new gorgeous luxury laminate flooring, fully renovated bathrooms, and brand new appliances. New roof (2021) for added peace of mind. Located in the sought-after gated community of Royal Oaks, enjoy a sparkling community pool plus an HOA that covers lawn mowing, manicuring, and outside pest control. Low-maintenance living at its finest — don't miss this one!

1393 Waukon Circle, 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
Start Your Search