Casselberry Homes with Private Pool type

Casselberry Homes with Private Pool type

Welcome to Casselberry, Florida, a hidden gem nestled in the heart of Seminole County! Known for its vibrant community spirit and lush landscapes, Casselberry offers a delightful blend of suburban charm and urban convenience. Just a stone’s throw away from the bustling city of Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping, while relishing the peaceful ambiance of this picturesque city.

One of the standout features of homes in Casselberry is the availability of properties with private pools. Imagine stepping out into your own backyard oasis, where you can unwind under the warm Florida sun, host unforgettable summer barbecues, or simply take a refreshing dip in your private pool. These homes are perfect for families, entertainers, or anyone looking to enjoy the ultimate Florida lifestyle.

The real estate market in Casselberry boasts a variety of styles and sizes, ensuring that there’s something for everyone. From charming single-family homes to spacious modern designs, many properties come equipped with beautifully landscaped yards, providing a serene backdrop for your outdoor activities. Plus, the community is dotted with parks, walking trails, and recreational facilities, making it an ideal place for families and nature enthusiasts alike.

Whether you’re seeking a tranquil retreat or an active lifestyle, Casselberry’s homes with private pools offer the perfect sanctuary. Discover the joys of living in this inviting city and make your dream of owning a home with a private pool a reality in Casselberry, Florida!

Newest Casselberry Homes with Private Pool type

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

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

4 Beds ⋅ 2 Baths ⋅ Camelot Unit 2 SubDv. ⋅ 32707 Zip Code

Welcome to this lovingly maintained, one-owner home offering an exceptional combination of quality updates, thoughtful features, and an unbeatable location in the heart of Casselberry. Major improvements provide peace of mind, including a new HVAC system (2025), new gas water heater (2026), new range, dishwasher, microwave, and garbage disposal (2026), roof replaced (2017), and exterior painted (2022). The home also features replacement windows with a lifetime warranty, hurricane shutters, a transferable termite bond, irrigation with reclaimed water, security system wiring, and natural gas service with a gas heat pump, gas water heater, and range. Inside, you'll find a cozy wood-burning fireplace and a versatile enclosed garage that could easily serve as a fifth bedroom, home office, or bonus room. One of the bathrooms offers direct access to the back porch, making it ideal as a future pool bath. The fully vinyl-fenced backyard includes a private rear gate providing direct access to the newly renovated Dew Drop Park, where you'll enjoy basketball and tennis courts, a playground, pavilion, dock, and open green space just steps from your backyard. This rare opportunity combines decades of meticulous ownership with outstanding updates and an incredible park-side setting that is difficult to find.

1391 Avalon Boulevard, Casselberry

4 Beds ⋅ 6 Baths ⋅ Crystal Bowl Add SubDv. ⋅ 32707 Zip Code

Welcome to a truly one-of-a-kind waterfront estate where the tranquility of country living meets the convenience of city life. Nestled on nearly one acre of private lakefront property in the heart of Casselberry, this exceptional multigenerational home is an incredibly rare opportunity to own a custom-built retreat unlike anything else on the market. Designed with both everyday living and unforgettable entertaining in mind, this expansive residence offers incredible flexibility with multiple living areas and up to three potential primary suites, making it ideal for extended families, guests, or those seeking dedicated work-from-home space. Rich Brazilian hardwood floors add warmth and elegance to the formal living and dining rooms, while the spacious kitchen features a generous island with abundant prep space, creating the perfect gathering place for family and friends. The oversized bonus room offers endless possibilities as a home theater, fitness studio, game room, or creative space. Just outside, an elevated deck overlooks the sparkling pool, creating a seamless connection to the beautifully renovated detached guest residence. The detached suite is a true highlight, offering approximately 864 square feet of beautifully updated living space complete with one bedroom, one and a half bathrooms, & private accommodations ideal for multigenerational living, long-term guests, a home office, or gym. The convenient half bath also provides direct access from the pool area, making outdoor entertaining effortless. Mature trees provide a peaceful canopy over the nearly one-acre homesite. Whether you enjoy gardening, relaxing with a morning coffee, or simply taking in the serene surroundings, this property offers an outdoor lifestyle that is difficult to find. A spacious workshop shed provides the perfect space for hobbies, woodworking, storage, or DIY projects, complementing the detached two-car garage with additional parking for a boat, RV, trailer, and ample guest parking courtesy of the circular driveway. Enjoy private access to Lake Crystal Bowl, where fishing, kayaking, paddle boarding, and other non-gas-powered boating activities await. It's a peaceful waterfront setting that feels miles away from the city, yet places you in one of Central Florida's most convenient locations. Thoughtfully updated throughout, the home features six beautifully remodeled bathrooms, four air conditioning systems, three of which have been replaced within the last five years, new roof, new electrical panels & outlets, new garage door, updated knockdown ceilings, energy-efficient LED recessed lighting, a new sprinkler system, updated main primary bathroom, new windows, and so much more! Perfectly situated in a quiet, established neighborhood within the sought-after Winter Springs High School district, this extraordinary property is within walking distance to quality schools and just minutes from shopping, dining, major highways, two golf courses, scenic bike trails, and Butterfly Park directly across the street. Rarely does a property combine nearly an acre of waterfront, a detached guest home, extensive updates, exceptional parking, workshop space, beautiful gardens, and an unbeatable location into one extraordinary offering. This is more than a home—it's a legacy property designed to bring generations together while offering the privacy, flexibility, and lifestyle today's buyers are searching for.

1048 Crystal Bowl Circle, Casselberry

2 Beds ⋅ 2 Baths ⋅ Deer Run Unit 11 SubDv. ⋅ 32707 Zip Code

Charming Dual-Master Retreat in Deer Run! Welcome to 1552 Cougar Ct, a beautifully functional 2-bedroom, 2-bathroom home in the heart of Casselberry's sought-after Deer Run community. Thoughtfully designed with a dual master suite layout, this 1,315 sq ft residence offers privacy and flexibility ideal for roommates, multigenerational living, guests, or a dedicated home office setup — each bedroom enjoys its own full en-suite bath. Step outside to your own private oasis: a screened-in pool paired with a covered patio, perfect for year-round Florida entertaining, morning coffee, or simply unwinding after a long day without the hassle of bugs or excess sun. Deer Run is known for its established tree-lined streets, community amenities, and convenient access to shopping, dining, and major roadways — putting Winter Springs, Winter Park, and Downtown Orlando all within easy reach. Whether you're a first-time buyer, downsizer, or investor, this move-in-ready gem offers a rare combination of privacy, functionality, and outdoor living in one of Casselberry's most desirable neighborhoods. Don't miss your chance to make 1552 Cougar Ct your own — schedule your private showing today!

1552 Cougar Court, Casselberry

3 Beds ⋅ 2 Baths ⋅ Carriage Hill Unit 1 SubDv. ⋅ 32707 Zip Code

Welcome to 4 Carriage Hill Circle, a spacious and inviting pool home nestled on a generously sized lot in the established Carriage Hill community. This well-designed residence features a versatile split-bedroom floor plan with multiple living spaces, including separate living, dining, and family rooms, offering flexibility for entertaining, relaxing, or working from home. Additional highlights include a spacious bonus room, a large indoor laundry room with plenty of storage, dual-zone air conditioning for improved comfort and efficiency, and mature landscaping that enhances the home's curb appeal. Conveniently located near shopping, dining, major roadways, parks, and top-rated Seminole County schools, this home offers the perfect blend of space, comfort, and convenience. Don't miss the opportunity to make this versatile Florida pool home your own!

4 Carriage Hill Circle, Casselberry

4 Beds ⋅ 2 Baths ⋅ Howell Cove 2nd Sec SubDv. ⋅ 32707 Zip Code

Dreams Do Come True... by you know who! WATERFRONT • LAKE ACCESS • ALMOST ½ ACRE • POOL HOME! County owned industrial seawall Welcome to Howell Cove, where waterfront living meets everyday luxury! This one-of-a-kind property sits on an incredible nearly half-acre lot with direct access to beautiful Howell Creek, leading through majestic cypress trees to the exclusive 401-acre Lake Howell. Whether you enjoy fishing, kayaking, paddleboarding, boating, or simply relaxing on the water, this is the Florida lifestyle you've been dreaming of! From the moment you arrive, you'll be captivated by the home's outstanding curb appeal, meticulously manicured landscaping, and welcoming presence. Inside, you'll discover a beautifully updated home featuring wood-style flooring, knockdown ceilings, recessed lighting, remodeled bathrooms with granite countertops, and spacious living areas designed for comfort and entertaining. The chef's kitchen is a showstopper with granite countertops, a 5-burner gas range, high-volume exterior vent hood, and updated appliances (2018). The inviting family room features a cozy wood-burning fireplace, custom built-in home theater cabinetry, and a convenient dry bar. Step outside to your own private paradise! The oversized 19' x 20' screened lanai overlooks a sparkling swimming pool and an expansive backyard perfect for entertaining family and friends. Relax under the 9' x 21' pavilion, launch your kayak from the 8' x 20' Trex dock, or enjoy the peaceful waterfront setting that makes this property truly special. Additional features include: 4 Bedrooms, 2 Bathrooms Spacious primary suite with walk-in closet New roof (2022) with transferable warranty and skylights Trane heat pump (2020) & Carrier heat pump (2022) New gas water heater (2019) PEX whole-house re-pipe with manifold Whole-house water filtration system Wired security camera system Pool with variable-speed pump Lake-fed irrigation system Fenced backyard 10' x 14' finished air-conditioned shed 10' x 20' workshop with electricity The location is just as impressive! Situated directly across from Red Bug Lake Park, you're only minutes from Walmart Neighborhood Market and approximately 20 minutes from both Winter Park and the University of Central Florida. Properties offering this combination of waterfront living, private lake access, premium upgrades, outdoor amenities, and an unbeatable location are incredibly rare. Don't miss your opportunity to own this exceptional Florida waterfront retreat—schedule your private showing today!

3589 Jericho Drive, Casselberry

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

3 Beds ⋅ 3 Baths ⋅ Buttons Sub Amd SubDv. ⋅ 32707 Zip Code

Welcome to a rare lakefront retreat offering privacy, space, and an exceptional lifestyle with NO HOA! Tucked away at the end of the road in Casselberry, this two-story single-family home offers 3 bedrooms, 2.5 bathrooms, 1,793 square feet of living space, and a fully screened saltwater pool overlooking the beautiful waters of Lake Azalea. NEW ROOF 2026. One of the most impressive features of this property is the expansive backyard, which stretches all the way from the home to the lake, creating a private waterfront setting that is increasingly difficult to find. The fully screened pool area features a covered patio space along with plenty of additional screened-in pool deck for enjoying Florida's year-round outdoor lifestyle. Beyond the pool, the spacious yard offers a fire pit area, room to relax and entertain, and a large side yard with ample space to park a boat, RV, or other recreational equipment. Inside, the welcoming foyer opens to a front living room with a custom wallpaper accent wall and offers excellent flexibility as a formal sitting area, home office, or additional living space. The kitchen features stainless steel appliances, updated cabinet hardware, and an open connection to the main living areas. From the downstairs living spaces, enjoy beautiful sightlines through the screened pool enclosure and beyond to the lake, creating a seamless connection between the interior and the spectacular outdoor setting. A switchback staircase with decorative spindles leads to the second floor, where the oversized primary suite is privately positioned at the rear of the home and offers wonderful views toward the lake. The spacious primary bathroom features dual vanities, a glass-enclosed shower, and a full garden tub. Two additional bedrooms and a full bathroom are also located upstairs, along with a generously sized laundry room for added convenience. Fresh interior paint and new lighting and fans throughout. Whether you're looking for a private lakefront residence, a home with room for a boat or RV, or simply a property where you can enjoy a pool and expansive backyard without HOA restrictions, this unique Casselberry property offers an exceptional opportunity to enjoy the best of Florida living on Lake Azalea. Make an appointment to see this home today!

1459 Azalea Avenue, Casselberry

4 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 6 SubDv. ⋅ 32730 Zip Code

Welcome home to this solid block pool home in one of Seminole County's most desirable neighborhoods! Step inside to find spacious living areas. The kitchen provides ample cabinets plus a pantry and eat in-counter. The adjoining dining and living areas provide the perfect setting for everyday living or entertaining. The split bedroom floor plan provides privacy and flexibility, making this home ideal. Enjoy outdoor living with the screened pool, covered porch area and workshop building! Huge yard for families and pets! Walk to Kewannee Park, a county park that offers walking trails, a boardwalk, fishing ponds, basketball court and play-grounds! A-Rated Seminole County Public School district.

1921 Winnebago Trail, Fern Park

3 Beds ⋅ 2 Baths ⋅ Coach Light Estates SubDv. ⋅ 32730 Zip Code

Welcome to this breathtaking home nestled under the canopy of mature oak trees in one of the area's most sought-after neighborhoods. Coach Light Estates of Fern Park checks all the boxes! This well established home is centrally located but, is still in a hard to find, old Florida neighborhood. This single-story masterpiece blends well thought out spaces sitting on .27 acre lot, with natural light throughout — ready for immediate move-in. Bonus* there are two additional buildings for storage or fun outside! The larger of these even has ac! The striking facade features a combination of stacked stone, slanted wood panels, beneath a sleek roofline. A dramatic entryway door, 2-car garage, and lush green lawn with newly laid sod, framed by beautifully aged oaks give this home incredible presence and charm. Step through the stunning glass panel front door into a bright, airy foyer that flows seamlessly into the home. Beautifully Updated Kitchen The showstopping freshly updated kitchen features quartz countertops and seating for four, white shaker cabinetry, a stainless steel double sink and stainless steel appliances. Glass panel french-doors open directly to the backyard and pool — perfect for entertaining. Living Areas. Open-concept living and dining areas are bathed in natural light with clean bright neutral walls, recessed lighting, and ceiling fans making this are a comfortable practical gathering space. The space is fresh, bright, and move-in ready. All three bedrooms feature engineered hardwood flooring, generous closet space. The bedrooms are spacious and filled with natural light. The inspired bathrooms feature tile flooring. A wrap-around shower in the primary bedroom completes the luxurious feel. A dedicated laundry room comes equipped with a washer and dryer, and plenty of storage space right next to the garage. Outside Oasis The fully fenced backyard features a glorious pool with brick paver surround, sun shelf and fountain water feature. The removal fence is also available to ensure safety. Plenty of privacy and relaxation to be had by all (including furry family members.) Steps away from the pool is a wonderful green space for gardening or other outdoor pursuits. The additional building also has easy access to the pool allowing you to jump right in after working or working out. Additional Features 2-car attached garage newer roof (2022) Within walking distance of Kewannee Trail Fresh landscaping with newly planted sod

773 Coach Light Drive, Fern Park

4 Beds ⋅ 2 Baths ⋅ English Woods 1st Add SubDv. ⋅ 32730 Zip Code

Virtually Staged. No HOA! Welcome to this beautifully maintained 4-bedroom, 2-bathroom pool home offering the perfect blend of comfort, style, and outdoor living. Ideally located within walking distance to the elementary school, this exceptional property features elegant travertine and bamboo flooring throughout, soaring sloped ceilings that create a bright and open atmosphere, and a thoughtfully designed layout perfect for everyday living and entertaining. The spacious kitchen is equipped with granite countertops, stainless steel appliances, and ample cabinetry, making it a functional and inviting space for cooking and gathering. Retreat to the spacious primary suite, complete with a generously sized bedroom and an ensuite bathroom designed for comfort and privacy. Three additional bedrooms and another full bathroom provide plenty of space for family, guests, or a home office. Step outside to your own private backyard oasis. Relax on the expansive covered lanai overlooking the huge sparkling dark-bottom custom pool with a built-in spa, all surrounded by beautiful Coral Tile decking. The fully equipped outdoor kitchen makes entertaining effortless, while the custom Jacuzzi provides the perfect place to unwind after a long day. With its impressive indoor features, resort-style outdoor amenities, and prime location within walking distance to the elementary school and just minutes from shopping, dining, and major roadways, this home offers the Florida lifestyle you've been searching for—all with no HOA. Roof 2022, Re-piped, AC about 10 years old, Water Heater age is unknown with recent service.

217 Yarmouth Road, Casselberry

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