Casselberry Homes with Pool Community Features

Casselberry Homes with Pool Community Features

Welcome to Casselberry, Florida—a hidden gem nestled in the heart of Seminole County. Known for its picturesque lakes, lush parks, and friendly neighborhoods, Casselberry offers a perfect blend of suburban tranquility and vibrant community life. With its strategic location just a short drive from Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping, while still relishing the charm of a close-knit community.

One of the standout features of Casselberry is its array of homes with pool community options. Imagine coming home to your very own oasis, where you can unwind beside a sparkling pool after a long day or entertain friends and family during those warm Florida evenings. These homes not only offer the luxury of private pools but also come with fantastic community amenities such as well-maintained parks, playgrounds, and recreational facilities. Whether you’re looking for a cozy single-family home or a spacious townhome, the options in Casselberry are diverse and cater to various lifestyles.

In addition to its beautiful homes, Casselberry boasts a rich array of activities and attractions. Explore the scenic walking trails at Secret Lake Park or enjoy a leisurely afternoon at the Casselberry Art House, where local artists showcase their talents. With a strong sense of community and a welcoming spirit, Casselberry is not just a place to live—it’s a place to thrive. Come discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Casselberry Homes with Pool Community Features

$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
$179,000
2 Beds ⋅ 1 Baths ⋅ Summit Village Unit 2 SubDv. ⋅ 32707 Zip Code
Welcome to 513 Polaris Loop in Casselberry — easy, maintenance-free living at its finest in this beautifully maintained single-story end-unit condo. This charming 2-bedroom, 1-bathroom home features no carpet throughout, laundry room, an updated bathroom, new windows, and a newer sliding glass door that fills the space with natural light. As an end unit, you’ll also enjoy added privacy and a bright, open feel. True low-maintenance living awaits: the HOA covers exterior maintenance, grounds care, sewer, trash, and water so you can focus on enjoying life. Residents have access to three community pools, tennis courts, and a clubhouse for recreation and socializing. Ideally located near shopping, dining, and everyday conveniences, with easy access to Winter Park and Altamonte Springs. This move-in-ready condo offers the perfect blend of comfort, convenience, and relaxed Central Florida living. Don’t miss this opportunity — schedule your private showing today!

513 Polaris Loop Unit 101, Casselberry
$315,000
2 Beds ⋅ 2 Baths ⋅ Lake Of The Woods Sec 11 Twnhs SubDv. ⋅ 32730 Zip Code
Welcome Home to this warm and inviting townhome in a popular, established neighborhood. This home is a 2 bedroom, 2 bath, 1 car garage. It has been updated and features luxury vinyl planking throughout. Light and Bright kitchen with stone counters, custom cabinets with pull-out drawers, storage closet, and stackable washer and dryer. Vaulted ceiling in living room and dining area is perfect for entertaining. Split bedroom floor plan gives everyone privacy. Both bedrooms offer walk-in closets for all of your storage needs. To add to the enjoyment of the Florida lifestyle, the enclosed porch can be enjoyed year-round. The community amenities include a Clubhouse, Fitness Center, Playground, Tennis Courts.

407 Meadowood Boulevard, Fern Park
$135,000
2 Beds ⋅ 2 Baths ⋅ Ashwood Condo SubDv. ⋅ 32730 Zip Code
Welcome to easy Florida living—without the stairs! This inviting 2-bedroom, 2-bathroom condo is conveniently located on the first floor of a gated community in the desirable 32730 area. Say goodbye to going up and down stairs and enjoy the ease of single-level living! The spacious layout offers comfortable living and dining areas, well-sized bedrooms, and plenty of natural light. Relax and unwind by the community pool, perfect for enjoying sunny Florida days. Conveniently located near shopping, dining, entertainment, major roadways, and everyday amenities, this condo is an excellent opportunity for a first-time buyer, downsizer, or investor. First-floor convenience, gated-community privacy, and a community pool—this is Florida living made easy. Come see why this one deserves a spot at the top of your list!

1000 Lake Of The Woods Boulevard Unit 105E, Fern Park
$180,900
2 Beds ⋅ 1 Baths ⋅ Summit Village Unit 2 SubDv. ⋅ 32707 Zip Code
Take me home! Updated 2-bedroom, 1-bath single-story end unit in Summit Village, Casselberry—with no upstairs neighbors. The practical layout includes an indoor laundry room with a washer and dryer, spacious bedrooms, and a walk-in primary closet. Enjoy a charming courtyard with sliding glass doors, a welcoming front porch, and community amenities including a clubhouse, tennis courts, and pools. Water, sewer, trash, and lawn maintenance are included in the low HOA. Shopping, restaurants, and public transportation are all nearby. Don't pass up the chance to make this your own! This is a Fannie Mae HomePath property. Contact us today! This one won’t last long.

519 Polaris Loop Unit 109, Casselberry
$270,000
2 Beds ⋅ 3 Baths ⋅ Summerhill Ph 1 SubDv. ⋅ 32707 Zip Code
Investor Special! Fantastic opportunity to transform this spacious 2 bedroom, 2.5 bath townhome in the heart of Casselberry. This property offers great bones, a large, screened patio enclosure private outdoor space, and an excellent location near shopping, dining, parks, and major roadways. The home is in need of renovation and updates, including kitchen, flooring, ceilings, and cosmetic improvements, making it ideal for investors, flippers, or buyers looking to customize a property to their own taste. Bring your vision and unlock the potential of this value add opportunity. Cash or renovation financing recommended. Sold As-Is.

2996 Lowell Court, 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
$234,900
2 Beds ⋅ 2 Baths ⋅ Deer Run Unit 14b SubDv. ⋅ 32707 Zip Code
Virtually Staged. Dreams Do Come True... By You Know Who! Bring your DPA, FHA, VA offers! WATERFRONT VIEWS • TWO PRIMARY SUITES • EXPANSIVE SCREENED LANAI Wake up every day to peaceful water views and the feeling of your own private retreat! Nestled among mature trees and lush landscaping, this beautifully maintained waterfront townhome offers the perfect blend of comfort, privacy, and low-maintenance living. Designed with flexibility in mind, this spacious residence features two private primary suites—one conveniently located on the first floor and another upstairs, making it ideal for guests, roommates, or multigenerational living. The heart of the home is an open-concept Great Room where oversized sliding glass doors frame the tranquil pond and flood the living space with natural light. Step outside to the massive screened lanai, an incredible extension of your living space that's perfect for morning coffee, evening wine, outdoor dining, or simply relaxing while enjoying the calming sights and sounds of nature. The kitchen shines with brand-new premium stainless steel appliances, all still under transferable warranty, plus a sunny breakfast nook for casual meals. A generous dining area easily accommodates family dinners and holiday gatherings while overlooking the beautiful waterfront scenery. Additional features include an in-unit washer and dryer, outdoor storage closet, and carefree living with exterior maintenance handled for you. The community offers outstanding amenities including a sparkling swimming pool, clubhouse, and resurfaced tennis courts—giving you the lifestyle you deserve without spending your weekends doing yard work. Whether you're searching for your primary residence, a seasonal escape, or a smart investment, this waterfront gem delivers the perfect combination of peaceful surroundings, resort-style amenities, and everyday convenience. Don't miss your opportunity to own a slice of paradise!

4008 W Maryland Place, 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
$135,000
1 Beds ⋅ 1 Baths ⋅ Oxford Square Condo SubDv. ⋅ 32707 Zip Code
Ground floor one -Bedroom, 1-Bath Condo in the Oxford Square Community of Casselberry! This charming first-floor condo has all kitchen appliances, plus a washer and dryer. The property has been well maintained and features a recently replaced roof, a new flooring, ceramic tile flooring throughout, and is in great condition. The HOA fee includes water, trash collection, exterior maintenance, and access to community amenities, including two swimming pools, a community center, and tennis courts. Don't miss this excellent opportunity to own your home. This property is move-in-ready home in a desirable location! Close to main roads, UCF, shopping in winter park and only a short drive to downtown Orlando Business district.

660 Kenwick Circle Unit 104, Casselberry
$220,000
3 Beds ⋅ 2 Baths ⋅ Summit Village Unit 2 SubDv. ⋅ 32707 Zip Code
This well-maintained 3-bedroom, 2-bath condo offers a fantastic opportunity for both first-time homebuyers and investors. Recently painted and move-in ready, the home shows beautifully with a functional layout and comfortable living spaces. Conveniently located just minutes from Winter Park, Oviedo, Altamonte Springs, and Maitland, you’ll enjoy easy access to shopping, dining, major roadways, and everyday conveniences. The association fee includes water, sewer, and trash, adding extra value and convenience for homeowners. Whether you’re looking for a place to call home or a great investment property, this condo is one you won’t want to miss.

509 Polaris Loop Unit 101, Casselberry
Start Your Search