Casselberry Homes with Playground Amenities

Casselberry Homes with Playground Amenities

Welcome to Casselberry, Florida – a hidden gem nestled in the heart of Seminole County! Known for its lush landscapes, friendly neighborhoods, and vibrant community spirit, Casselberry offers a perfect blend of suburban charm and modern conveniences. With its close proximity to Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping while savoring the tranquility of a peaceful residential atmosphere.

One of the standout features of Casselberry is its commitment to family-friendly living. The city is home to numerous parks and recreational facilities, making it an ideal location for families seeking homes with playground amenities. Imagine your children laughing and playing just steps away from your front door, where well-maintained playgrounds and green spaces create a safe and enjoyable environment for outdoor activities.

The real estate market in Casselberry is diverse, offering a variety of homes that cater to different lifestyles and budgets. Whether you’re searching for a cozy single-family home or a spacious townhome, you’ll find properties equipped with playground amenities that encourage community interaction and outdoor fun. These homes not only provide a place to live but also foster a sense of belonging, as families gather for picnics, parties, and playdates.

With its warm climate, excellent schools, and a plethora of recreational opportunities, Casselberry is a fantastic choice for anyone looking to plant roots in Central Florida. Come discover the charm of Casselberry, where your dream home awaits amidst friendly neighbors and delightful amenities!

Newest Casselberry Homes with Playground Amenities

$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
$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
$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
$210,000
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
$294,900
2 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 10 Twnhs SubDv. ⋅ 32730 Zip Code
Welcome to this beautifully updated 2-bedroom, 2-bath townhome located in the highly sought after community of Lake of The Woods. This home offers comfortable living with modern upgrades throughout. Step inside to find new luxury vinyl flooring, a tastefully updated kitchen featuring refreshed finishes and ample cabinet space. The open and functional floor plan with cathedral ceilings provides a welcoming atmosphere perfect for everyday living or entertaining guests. Enjoy coffee on the screened in patio, or open the French doors to expand your living space on the cool evenings. One of the biggest benefits for the new owner is a brand-new roof, providing added value and peace of mind. Conveniently located near shopping, dining, parks, major roadways/highways, and everything Central Florida has to offer. This move-in-ready home is an excellent opportunity for first-time buyers, downsizers, or investors. The community offers a lakefront pool, fitness center, sauna, clubhouse/recreation center, fishing pier, tennis courts, playground and picnic area, and a basketball court. Don’t miss your chance to own this updated gem in a community with so many amenities.

1016 Sherrywood Street, 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
$560,000
5 Beds ⋅ 3 Baths ⋅ Oakhurst Reserve Unit One SubDv. ⋅ 32707 Zip Code
Inside the gated community of Oakhurst Reserve, step into this inviting single-story home to discover a spacious open living-room and dining-room combo. The first hallway to the right leads to a large primary bedroom, with an attached bathroom and a large walk-in closet! Past the well-appointed kitchen, with ample cabinet space and modern appliances, is a second hallway to the right. This hallway leads down to three more rooms (two carpeted bedrooms, and the third bonus room), as well as a second full bathroom. Toward the back of the house is an additional entertainment room, which shares an open concept with the kitchen. Beyond that is a third hallway, with an additional two bedrooms and a third full bathroom. This addition makes the house ideal for multi-generational living. This home has many updates, including new windows throughout, flooring and screened in lanai all done in 2024. As well as a water heater installed in 2022, a roof in 2021, and a Lennox 23 SEER HVAC system in 2020, ensuring worry-free living for years to come. The fenced backyard offers privacy and space for outdoor activities, making it ideal for entertaining guests or simply relaxing in the sunshine. Furthermore, the property includes an 8x12 storage shed, offering 100sq/ft of storage space to keep all your lawn equipment neatly organized, ensuring that your garage remains free for parking your cars. The Rainsoft EC5 water treatment system, valued at approximately $7500, will remain with the house. This system provides added value and convenience for the new homeowners, ensuring clean and fresh water throughout the home. The home is only a few houses down the street from the beautiful community pool and playground.

1737 Setting Sun Loop, Casselberry
$264,900
2 Beds ⋅ 3 Baths ⋅ Sausalito SubDv. ⋅ 32707 Zip Code
Recently updated 1,492 square foot, 2 bedroom, 2.5 bath condo in the Sausalito Condominium community in Casselberry. Designed in a relaxing and airy contemporary style. Numerous glass sliders and outdoor patios for cheerful, sun-filled spaces. Bamboo wood flooring, and porcelain and travertine tile. New paint and trim. Ready to move in. Perfect for indoor and outdoor living, entertaining, and relaxation. Beautiful ~600 square foot private outdoor courtyard living space with outdoor landscape lighting and irrigation system. Great for parties, BBQs, relaxing, and a secure pet or play area. All new Energy Star certified PGT ProtecSure Max windows (Low E, argon filled with transferable lifetime warranty). Attic upgrade with blown in insulation, foam sealing, and radiant barrier. Beautiful updated kitchen with stainless steel Kitchenaid appliances, premium granite countertops, and ample counter space. All bathrooms have been updated. Indoor or outdoor laundry room with Samsung washer and dryer (stackable). These are currently installed indoors. Smart water heater, new circuit breaker panel, and recently coated epoxy floor in oversized 2 car carport. You really should plan to see for yourself how this beautiful condo could be the perfect home for you. The Sausalito Condominium community also has many features and amenities. Many of these are listed below. There are also additional long term improvement projects planned. Spectrum Internet Spectrum cable TV Lake access and boat launch for 400 acre Lake Howell Playground and covered pavilion Roof and building exterior insurance Includes exterior termite and pest control Grounds upkeep and exterior irrigation RV, trailer, and boat parking area Tennis/pickleball courts Swimming pool Clubhouse

108 Madrid Drive Unit D, Casselberry
$289,900
2 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 08 Twnhs SubDv. ⋅ 32730 Zip Code
Welcome to this charming 2 bedroom, 2 bath townhome located in the desirable Lake of the Woods community in Fern Park, FL. This well-maintained home offers comfortable living with a functional layout, perfect for first-time buyers, downsizers, or investors. Enjoy the convenience of a 1-car garage and a prime location just minutes from shopping, dining, and major highways for an easy commute throughout Central Florida. Residents of Lake of the Woods enjoy an exceptional lineup of resort-style amenities, including a stunning lakefront pool, fishing pier, basketball and tennis courts, playground, and picnic area. Stay active and relax at the community fitness center, sauna, and clubhouse — all designed to elevate your everyday lifestyle. With its unbeatable location, comfortable living spaces, and outstanding community features, this townhome offers tremendous value. Don't miss your opportunity to call Lake of the Woods home — schedule your private showing today!

497 Meadowood Boulevard, Fern Park
Start Your Search