Casselberrry/Winter Springs / Tuscawilla Homes with Private Pool type

Casselberrry/Winter Springs / Tuscawilla Homes with Private Pool type

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is not just a place to live; it's a lifestyle defined by lush landscapes, serene lakes, and a welcoming community spirit. With its prime location just north of Orlando, residents enjoy a perfect blend of suburban tranquility and easy access to urban amenities.

Winter Springs is renowned for its family-friendly atmosphere, top-rated schools, and an array of recreational opportunities. The picturesque parks, including the expansive Central Winds Park, offer ample space for outdoor activities, picnics, and community events. Tuscawilla, a charming neighborhood within Winter Springs, is particularly celebrated for its golf courses and scenic views, making it a haven for golf enthusiasts and nature lovers alike.

One of the most alluring features of homes in this region is the availability of properties with private pools. Imagine relaxing in your own backyard oasis, soaking up the Florida sunshine while enjoying the luxury of a refreshing dip at any time. These homes with private pools not only enhance your lifestyle but also provide a perfect setting for entertaining friends and family or simply unwinding after a long day.

Whether you're seeking a cozy single-family home or a spacious estate, the real estate options in Casselberry, Winter Springs, and Tuscawilla cater to diverse tastes and budgets. With its warm climate, vibrant community, and beautiful homes, this region is truly a hidden gem waiting to be discovered. Come explore your new home in this delightful corner of Florida!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Private Pool type

$850,000
6 Beds ⋅ 6 Baths ⋅ Huntridge SubDv. ⋅ 32708 Zip Code
You will find this gem in a conveniently located smaller community on a beautiful corner lot with side entry oversized two car garage. This address will afford new owners a comfortable lifestyle in a spacious home for everyday, formal and entertaining living. The kitchen is a focal point with top of the line stainless steel appliances, double oven and solid wood cabinets and soft-close drawers. Enjoy your everyday meals in a separate eating area. The adjoining family room, complete with built-in book shelves and wood burning fireplace, will be the place for your relaxing hours. The larger than average six bedrooms (one currently used as office) with primary and office (or bedroom) downstairs will impress. The primary bedroom has two closets and an ensuite bathroom with double sinks, tub and separate shower. Plus there's a separate sitting area that can be used as office space, a reading nook or a quiet time retreat. Remaining four bedrooms (upstairs) include two with Jack and Jill full bathroom featuring dual sinks in between. Another upstairs full bath compliments the floor plan. All upstairs bedrooms are big and have large closets. Other outstanding features include a formal dining room and living room, and an all weather sunroom with adjoining outdoor kitchen that has a Jenn-Air grill. There is also an outside covered patio area. Last but certainly not least, the screened-in pool right outside your back sliding doors will provide welcomed cooling off on hot days and add to the many joyful memories this home will give you, your loved ones, friends and guests. Double-paned windows, separate air conditioning units (upstairs/downstairs) to help control temperature regulation and costs. Roof less than ten years old and new water heater. Enjoy the convenience of a downstairs laundry room (with sink), ceiling fans, central vac, lots of storage throughout and Rainbird lawn irrigation. Combine this well kept, move-in ready home with a location that affords easy access to major highways, airports (Orlando, Daytona, Sanford), beaches, central FL attractions, shopping, restaurants and UCF. This home is bound to exceed your expectations!

224 Huntridge Way, Winter Springs
$375,000
4 Beds ⋅ 3 Baths ⋅ North Orlando Terrace Unit 1 Sec 3 SubDv. ⋅ 32708 Zip Code
POOL HOME WITH PRIVATE IN-LAW SUITE! Welcome to this beautifully updated 4-bedroom, 3-bath home in the heart of Winter Springs. This move-in-ready property features an open floor plan, tile flooring throughout, a remodeled kitchen with granite countertops, wood cabinetry, and stainless steel appliances. The private mother-in-law suite offers its own kitchenette, bedroom, full bath, and separate living space, making it perfect for multi-generational living, guests, or rental potential. Step outside to your screened lanai overlooking the sparkling pool and fully fenced backyard—ideal for entertaining or relaxing year-round. With a 2017 roof, new water heater, fresh paint, and no HOA, this home is conveniently located near top-rated Seminole County schools, shopping, dining, and major highways. This is Florida living at its best!

212 S Cortez Avenue, Winter Springs
$2,795,000
5 Beds ⋅ 7 Baths ⋅ Sturbridge Oaks SubDv. ⋅ 32708 Zip Code
Beyond the gates of an intimate seven-home enclave, a winding drive beneath a canopy of sculpted oaks introduces one of Winter Springs' most compelling lakefront estates. Set on more than two private acres with 150 feet of frontage on Little Lake Howell, the property pairs an exceptionally functional floor plan with a setting that has become increasingly difficult to find. Designed for both everyday living and effortless entertaining, the residence offers five bedrooms, five-and-one-half baths, a private study, dedicated home theater with professional-grade audio and projection, and nearly 5,800 square feet of thoughtfully designed living space. The primary suite occupies its own private retreat on the first floor, complete with a sitting room overlooking the lake, an expansive walk-in closet with direct access to the laundry room, and a spacious bath. A second en suite bedroom on the main level provides ideal accommodations for guests or multigenerational living. At the heart of the home, the open kitchen and family room flow naturally to the outdoor living spaces, while a soaring two-story gathering room and open second-floor gallery fill the home with natural light and create a remarkable sense of openness. Upstairs, three additional bedrooms and a screened terrace spanning the rear of the home provide exceptional flexibility while capturing sweeping views across the water. Outdoor living is equally inviting. A recently installed screened enclosure surrounds the pool, spa, and summer kitchen, while the covered dock with boat lift invites boating, skiing, paddleboarding, or quiet mornings on one of Central Florida's most beautifully maintained lakes. The usable grounds have been thoughtfully cleared and enhanced to create generous lawn, garden, and recreation space, complemented by mature fruit trees and preserve land bordering the southern property line for an extraordinary sense of privacy. The eastern shoreline offers unforgettable sunrises, rocket launches rising over the horizon, seasonal fireworks reflected across the lake, and frequent visits from native wildlife—creating a setting that feels remarkably peaceful despite being just minutes from everyday conveniences. Completing the estate are two separate two-car garages, three HVAC systems, and an expansive solar array that significantly reduces energy costs. It is a combination of land, privacy, and livability that is becoming increasingly difficult to find in Central Florida.

2117 Sturbridge Court, Winter Springs
$384,900
3 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 02 SubDv. ⋅ 32708 Zip Code
Welcome to this charming 3-bedroom, 2-bathroom home in the desirable North Orlando Ranches neighborhood. This home features a classic, traditional floor plan that provides distinct and comfortable living spaces. The heart of the home is a cozy living room anchored by a beautiful fireplace, perfect for relaxing evenings. The kitchen has been thoughtfully updated, boasting durable countertops and modern stainless-steel appliances. The primary bedroom offers plenty of storage with a large walk-in closet. Step outside to discover your own private pool, creating a wonderful outdoor retreat for cooling off and unwinding. The location is exceptionally convenient, situated near top-rated schools, shopping, dining, and major highways for an easy commute to local essentials and employment hubs. Schedule your private showing today!

629 Alton Road, Winter Springs
$689,900
4 Beds ⋅ 3 Baths ⋅ Howell Creek Reserve Ph 3 SubDv. ⋅ 32708 Zip Code
THERE ARE HOMES YOU SEE...and HOMES YOU FEEL! Privacy, space, and a peaceful conservation setting come together in this 4-bedroom, 3-bath pool home in the gated community of Howell Creek Reserve. Backing to conservation with no rear neighbors, the backyard feels like your own private retreat—perfect for relaxing by the pool or entertaining family and friends. Inside, the thoughtfully designed triple-split floor plan offers exceptional privacy, while soaring ceilings, crown molding, and updated lighting create an inviting, open atmosphere. The spacious primary suite features a tray ceiling, sitting area, walk-in closet, and an additional closet for extra storage. The kitchen offers granite countertops, a newer refrigerator and dishwasher, and opens seamlessly to the living spaces. Two bathrooms were renovated in 2020, and major updates include newer roof (2019), new HVAC (2026), newer water heater (2024), and a newer pool pump. Located just minutes from the Cross Seminole Trail, parks, shopping, dining, and top-rated Seminole County schools, this home offers the perfect balance of comfort, convenience, and Florida outdoor living. CALL TODAY to schedule your private Showing.

197 Nandina Terrace, Winter Springs
$546,000
4 Beds ⋅ 2 Baths ⋅ Deer Run Unit 21a SubDv. ⋅ 32708 Zip Code
Don’t miss your chance to own this luxury 4-bedroom, 2-bath pool home retreat in the highly sought-after Tuscawilla Forest, featuring a BRAND NEW ROOF upon signed contract. Beautifully designed for everyday living and comfortable formality, this home offers an open layout with multiple living spaces. Walk in to a formal conversation area followed by a chef's kitchen with all granite countertops, and backsplashes. A spacious primary bedroom with an en suite spa like bathroom featuring large his and hers walk-in closets, a custom carrara quartz double vanity, and tied together with modern organic finishes. Have peace of mind with updated plumbing throughout. Step outside to your private fully fenced backyard oasis, featuring a sparkling pool and expansive outdoor area perfect for relaxing evenings, weekend gatherings, and enjoying the Florida nature. Ideally located near shopping, dining, parks, top-rated schools, and major roadways, this home provides the perfect combination of convenience, comfort, and modern luxury.

324 Ringwood Circle, Winter Springs
$850,000
4 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 01 SubDv. ⋅ 32708 Zip Code
Motivated Seller! This custom 4 bedroom, 2.5 bathroom pool home nestled on a gated 2.6 acres in the sought-after Ranchlands Community is a must see! The 40ft long front porch overlooks the nature's paradise with views you must see to appreciate. Oak trees and mature landscaping line the private entrance and make up the bulk of this serene property. An entertainer's paradise features pool with custom waterfall, poolside cabana with fireplace, bar and grill, pergola leading to cabana, romantic gazebo with power, nature trails, tri-level balcony, covered back porch (29x12) overlooking pool and 2 story playhouse/gym. You'll notice the craftmanship and attention to detail throughout the property with custom carpentry and designer touches both inside and out. Kitchen (19x12) with lots of granite counter space boasts solid wood cabinets, modern hardware, stainless steel appliances with range hood, flat top range, stone backsplash, rolling island, and pendant lighting over bar seating while overlooking the beautiful pool oasis. The owner's suite (14x13) offers laminate flooring, walk-in closet, pool views, French doors leading to private balcony and a private study (14x10) perfect for relaxing with a good book. Master bathroom features gorgeous standup shower, waterproof vinyl flooring and lovely tile work. Home features massive family room (39x32) with tile flooring and separate living room (20x13) with wood-exposed cathedral ceilings and gas fireplace. Upstairs you'll find two bedrooms with a shared bathroom in addition to the master bedroom retreat. Laundry room, half bath and fourth bedroom are located on first floor. Upgrades include extending trusses and roof line to add carport, gutters, entire paver driveway, automatic wrought iron gate, sprinklers in front yard, gazebo with power, and a wrought iron fence. Two single car detached garages (20x10) plus additional workshop (20x10) with power, water and exhaust fan, two covered sheds and additional storage space (10x10) located below playhouse/gym provide ample storage to go along with oversized attached carport (33x14). No HOA.

230 E Panama Road, Winter Springs
$425,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code
Virtually Staged. Discover 963 Sequoia Dr, recently updated with fresh interior paint and partial flooring replacement throughout the residence. The kitchen includes all stainless steel appliances, complementing the updated interior. The exterior features a patio, fully fenced in backyard, a practical storage shed, and an in ground pool. This updated residence provides comfort and an exceptional outdoor retreat ready for everyday enjoyment.. Included 100-Day Home Warranty with buyer activation

963 Sequoia Drive, Winter Springs
$450,000
3 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code
Welcome to 1454 King Court - this is an ideal POOL home or rental property for those seeking an updated living space. This renovated home has 3 bedrooms with 2 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated luxurious bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2026 and Newer Water Heater! This home also has a newly painted interior/exterior. Quiet Neighborhood, Close to all Major Highways, and Shopping Centers. Also an excellent rental investment opportunity.

1454 King Court, Winter Springs
$630,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 5-bedroom, 2-bath pool home in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this spacious home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you'll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, and a whole-house water filtration system, two mini-split air conditioning systems (2025) —providing enhanced comfort and energy efficiency year-round. The backyard has also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you're entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don't miss your opportunity to own this exceptional waterfront home in one of Winter Springs' most desirable communities!

216 Tavestock Loop, Winter Springs
$749,000
5 Beds ⋅ 3 Baths ⋅ Winter Spgs Unit 4 SubDv. ⋅ 32708 Zip Code
Beautiful 5 bedroom, 3 full bath home, in highly sought after Tuscawilla golf community, on a large lot with desirable side entry 2-car garage. The home boast neutral paint and flooring décor, abundant natural light with views of the lake. The primary bedroom sits on one side of the house and has an adjoining room that can be used as an office or gym area. The remodeled kitchen is a chef’s dream, which includes granite countertops, an oversized pantry, a pot filler and two ovens, plus a large island with a prep sink along with an eating area to entertain.  You can sit by your pool overlooking a large backyard with a lake view. The home was recently updated with a new roof, gutters, exterior paint and new fencing in 2026. There are 2 central heat and air systems and a whole house water filtration system. Volunteer HOA with no HOA restrictions. Zoned for Seminole county A-rated school system.

1209 Deer Run Drive, Winter Springs
$3,499,000
7 Beds ⋅ 7 Baths ⋅ Dunmar Estates SubDv. ⋅ 32708 Zip Code
Rare opportunity to own a private estate in the heart of Central Florida. Situated on nearly 6 acres in Dunmar Estates community of Winter Springs, this exceptional property is fully fenced BY METAL FENCE AND SOLID WALL FENCE FROM 6ft to 10 ft and gated, offering outstanding privacy, security, and a true retreat-like setting. The main residence features over 12,000 square feet of living space, including 7 bedrooms, multiple living and entertaining areas, and a unique indoor heated pool that can be enjoyed year-round regardless of weather. Expansive grounds and mature landscaping create a peaceful and secluded environment rarely found in today’s market. A standout feature of the property is its two separate Mother-in-Law Suites, ideal for multigenerational living, extended family, long-term guests, caregivers, private offices, or flexible living arrangements. Additional amenities include a tennis court, circular driveway, 6-car garage, and abundant outdoor space, offering endless opportunities for customization, renovation, and creating a truly one-of-a-kind family compound. Conveniently located just minutes from top-rated schools, shopping, dining, and major highways, this estate combines the tranquility of private country-style living with the convenience of city access. A rare offering with exceptional space, privacy, and unlimited potential.

593 Dunmar Circle, Winter Springs
Start Your Search