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 parks, serene lakes, and vibrant community spirit, Casselberry offers an ideal blend of suburban tranquility and urban convenience. With its close proximity to Orlando, residents enjoy easy access to world-class dining, shopping, and entertainment, while still relishing the charm of a smaller town.

One of the standout features of living in Casselberry is the abundance of family-friendly amenities, particularly in neighborhoods that boast playground community features. These communities are designed with families in mind, providing safe and engaging spaces for children to play and grow. Imagine your little ones laughing and making friends at the playground just steps from your front door, while you relax in the shade of nearby trees or join them for a fun afternoon of outdoor activities.

In addition to playgrounds, many homes in these communities feature spacious backyards, perfect for family gatherings, barbecues, and weekend fun. The sense of camaraderie among neighbors fosters a welcoming atmosphere, making it easy to form lasting friendships. Whether you’re strolling through the local parks, participating in community events, or enjoying the scenic views of the nearby lakes, Casselberry truly embodies the essence of a close-knit community.

With its charming neighborhoods, excellent schools, and a wealth of recreational opportunities, Casselberry stands out as a fantastic place to call home. Come explore the beauty and warmth of this delightful city, and discover the perfect home for your family in Casselberry’s playground communities!

Newest Casselberry Homes with Playground Community Features

$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
$164,900
Secret Lake Shores SubDv. ⋅ 32707 Zip Code
Virtually Staged. Rare 0.91-acre Secret Lake waterfront homesite in Casselberry with no HOA, R-12.5 residential zoning, approximately 95 feet of paved street frontage, and expansive views toward Secret Lake Park. The current boundary/topographic survey identifies approximately 6949 sq. ft. of upland, 6928 sq. ft. of wetland, and 25,640 sq. ft. of other surface waters. Significant pre-development due diligence has been completed: FDEP Formal Determination No. 0426404-001-FD establishes wetland and surface water boundaries through January 26, 2028; an environmental report, geotechnical exploration, tree study, 3D-drone mapping, and conceptual architectural plans for a 2,416 sq. ft. conditioned residence are available for review. Seller reports city water, public sewer, reclaimed water, fiber internet, and underground electric are available at the frontage. Buyer must independently verify availability, connection requirements, capacity, fees, zoning, setbacks, floodplain requirements, wetlands, permits, foundation design, and intended use. Convenient to Secret Lake Park, Casselberry City Hall/Lake Concord, Cross Seminole Trail access, shopping, dining, and recreation. Conceptual plans are not permitted or approved, and no representation is made that any particular design or development approval is guaranteed. Reclaimed water is reported available at the frontage but is not connected; buyer to independently verify availability, capacity, connection requirement and fees.

233 Secret Way, Casselberry
$449,000
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. 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
$187,500
2 Beds ⋅ 2 Baths ⋅ Oxford Square Condo SubDv. ⋅ 32707 Zip Code
Welcome to easy Florida living in this spacious first-floor 2-bedroom, 2-bath condo in the desirable Oxford Square community of Casselberry. With approximately 1,126 square feet, the thoughtfully designed layout offers comfortable living and dining spaces, generous bedrooms, and the convenience of single-level living. The kitchen features granite countertops, while the screened-in patio creates a relaxing spot to enjoy your morning coffee or unwind at the end of the day. Community amenities add to the appeal, with a pool, fitness center, clubhouse and tennis facilities available for residents. The location puts everyday conveniences, shopping, dining, recreation and major Central Florida roadways within easy reach, making trips throughout Casselberry, Winter Park, Maitland, Altamonte Springs and surrounding areas convenient. Whether you're looking for a comfortable primary residence, a low-maintenance Florida lifestyle or an investment opportunity, this condo offers a compelling combination of space, amenities and location. Come see why 648 Kenwick Circle deserves a place on your must-see list!

648 Kenwick Circle Unit 102, 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
$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
$333,000
3 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 05 Twnhs SubDv. ⋅ 32730 Zip Code
Virtually Staged. 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
$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
$369,000
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
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