Casselberrry/Winter Springs / Tuscawilla Homes with Pool

Casselberrry/Winter Springs / Tuscawilla Homes with Pool

Welcome to the beautiful region of Casselberry/Winter Springs/Tuscawilla, located in Seminole County, Florida. This area is known for its stunning natural landscapes, family-friendly neighborhoods, and a warm and welcoming community.

Winter Springs, the main city in this region, offers a perfect blend of suburban charm and urban convenience. With its picturesque lakes, lush green spaces, and well-maintained parks, Winter Springs provides residents with ample opportunities for outdoor activities and relaxation. The city also boasts excellent schools, making it an ideal place for families to settle down.

One of the standout features of homes in this area is the availability of properties with pools. Whether you enjoy lounging by the water, hosting pool parties, or just want a refreshing dip on a hot summer day, owning a home with a pool in Casselberry/Winter Springs/Tuscawilla is a fantastic option. Imagine having your own private oasis right in your backyard, where you can unwind and create lasting memories with family and friends.

From cozy single-family homes to spacious estates, the real estate market in this region offers a variety of options to suit different preferences and budgets. With a home with a pool, you can enjoy the benefits of both indoor and outdoor living, creating a space that is perfect for entertaining and relaxation.

If you're searching for a place that offers a high quality of life, natural beauty, and the luxury of a pool, Casselberry/Winter Springs/Tuscawilla is the perfect region for you. Explore the available properties and find your dream home with a pool in this wonderful part of Florida.

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Pool

$549,000
4 Beds ⋅ 3 Baths ⋅ O6436090 MLS
Spacious 4 bedroom, 3 bathroom pool home off of Tuskawilla Rd! This home features two story ceiling in the formal living and dining room. The staircase and second story walkway over look the entrance and formal areas. The family room has a fireplace and is joined with the kitchen. On the first floor are also three large bedrooms, two of the bedrooms have attached baths. The primary bedroom is upstairs and has double walk in closets, and an oversized en suite bathroom. The pool has a screen enclosure and the yard is fenced. Roof replaced in 2022, complete Replumb ins 2023.

1142 Oday Drive, Winter Springs
$650,000
4 Beds ⋅ 3 Baths ⋅ O6435785 MLS
UPDATED WINTER SPRINGS POOL HOME IN THE HIGHLY DESIRABLE TUSKAWILLA AREA! Welcome to 4951 Courtland Loop, where timeless character, extensive upgrades and the Florida lifestyle come together. This impressive .38-acre homesite is surrounded by beautiful mature oaks. TUSKABAY is located in the heart of TUSCAWILLA, one of ORLANDO's Best COMMUNITIES. Offering 4 bedrooms, 3 full baths and 2,562 square feet, this is the MOVE-IN READY Winter Springs home you've been waiting for. Top features include a desirable FIRST-FLOOR PRIMARY & Sec.Bedrooms, Gourmet KITCHEN, SIDE-ENTRY GARAGE, spacious living areas and impressive indoor-outdoor layout designed for entertaining. Main entry offers view of large living area with cozy, BRICK WOOD BURNING FIREPLACE with POOL & YARD VIEWS. OPEN CONCEPT DINING- LIVING ROOM COMBO flanking the kitchen, primary and secondary downstairs' bedrooms flows.The PRIMARY BEDROOM boasts CATHEDRAL CEILINGS, DOUBLE CLOSETS, TRANSOM/FULL LENGTH WINDOWS, immersing the room in natural light. Warm, wood style flooring contrasts the lighter finishes exquisitely and leads to the ENSUITE, LUXURY BATHROOM. The remodeled primary bath adds another touch of luxury with QUARTZ COUNTERTOPS, GOLD FINISHES, FARMHOUSE-STYLE SINK and GLASS ENCLOSED SHOWER with SUBWAY TILE. At the heart of the home is a beautifully RENOVATED KITCHEN offering a timeless look,appealing to discriminating buyers. Crisp, LIGHT CABINETRY with clean lines offers abundant storage, complemented by EXPANSIVE QUARTZ COUNTERTOPS and a classic backsplash. The butcher-block island compliments the STAINLESS STEEL APPLIANCES package including the JennAir range, low maintenance KitchenAid appliances with double oven, dishwasher, wine and beverage cooler. This kitchen was created for everyday living and entertaining, blending style and practicality. Upstairs you'll find two large, private bedrooms with a bathroom and loft view of the downstairs. Through the FRENCH DOORS to the outside you'll discover your own backyard retreat. Enjoy the swaying oak trees from your private lanai, in-ground POOL, expansive PAVER PATIO, extended walkways, over .38 ACRE FENCED YARD and mature landscaping provide an incredible setting for weekend gatherings, quiet mornings and year-round outdoor living. Enjoy the parklike feel from the comfort of home. Even more impressive is the investment already made in the home's major systems available to a buyer without having to assume the payment or finance a new roof or solar system. Buy HASSLE FREE, no insurance issues here with a 2021 installed roof, seller-owned 11.745 kW solar system, TESLA POWERWALL BATTERY, DOUBLE PANE WINDOWS, high-efficiency heat-pump water heater, WHOLE-HOME WATER FILTRATION AND SOFTENER, Nest thermostats and EV CHARGING combine modern technology with energy-conscious living. The sellers' transfer offers an incredible opportunity for a savvy buyer to buy an outstanding home at an even better VALUE. Too many improvements like upgraded irrigation, newer gutters and additional improvements to mention that make this home truly stand apart. If you've been searching for a WINTER SPRINGS POOL HOME, Tuskawilla home, updated 4-bedroom home, energy-efficient home or move-in-ready home in Seminole County, 4951 Courtland Loop deserves to be at the top of your list. Space. Pool. Upgrades. Energy efficiency. Exceptional Winter Springs LIFESTYLE. This is the home buyers have been waiting for—schedule your private showing today.

4951 Courtland Loop, Winter Springs
$289,900
3 Beds ⋅ 3 Baths ⋅ O6435344 MLS ⋅ 00 BLDG.
Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the desirable gated community of Heritage Park in Winter Springs. Designed for comfortable, low-maintenance living, this home features an open-concept floor plan with wood flooring throughout—no carpet! The kitchen overlooks the living and dining areas and features stainless steel appliances, a tile backsplash, 42-inch crown-topped cabinetry, a closet pantry, and breakfast bar, creating a functional layout for everyday living and entertaining. Upstairs, the spacious primary suite offers a walk-in closet and en-suite bath with dual sinks. Two additional bedrooms, a remodeled full bath, and a conveniently located second-floor laundry room with washer and dryer included complete the upper level. Additional highlights include a 2023 roof, attached one-car garage, and screen-enclosed porch perfect for enjoying the Florida lifestyle. Heritage Park residents enjoy access to a community pool and playground, all within a gated setting. Conveniently located near Winter Springs Town Center, shopping, dining, and major roadways, and zoned for A-rated Seminole County schools.

476 Tradition Lane, Winter Springs
$439,000
3 Beds ⋅ 2 Baths ⋅ O6435377 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bath POOL home nestled on a quiet, tree-lined street in the highly sought-after Country Club Village of Tuscawilla. This inviting home offers a versatile floor plan ideal for both everyday living and entertaining, with volume ceilings, abundant natural light, and attractive, low-maintenance tile and luxury vinyl plank flooring throughout. The spacious living and dining areas provide wonderful flexibility and can easily be arranged to complement your lifestyle. At the heart of the home, the kitchen overlooks the dinette and family room and features stainless steel appliances, ample prep and storage space, pull-out drawers, a built-in pantry and built-in wine rack. Its thoughtful location also offers possibilities to open or expand the kitchen toward the rear of the home, creating an even greater connection to the outdoor living and pool area. A charming greenhouse window in the dinette is perfect for growing fresh herbs or displaying your favorite plants. The spacious owner's suite provides a relaxing retreat with direct access to the back porch, a beautifully updated shower and vanity with granite countertop, an oversized window overlooking the atrium, and generous closet space. Two sizable secondary bedrooms are located toward the front of the home, with one offering direct access to the charming atrium. Step outside and enjoy your morning coffee or unwind at the end of the day on the private back patio overlooking the sparkling pool and hot tub, all tucked behind a privacy wall to create your own peaceful outdoor retreat. The pool screen was replaced in 2022 for added peace of mind. The OVERSIZED two-car garage is another standout feature, offering an extended workshop area with ample room for a golf cart, along with built-in shelving, attic stair access and a convenient rear-exit door. Country Club Village offers the perfect combination of a peaceful neighborhood setting and exceptional convenience. Located adjacent to Tuscawilla Country Club, optional memberships provide access to golf, tennis, fitness facilities, social activities, clubhouse amenities and more. Enjoy nearby parks and nature trails, highly rated Seminole County schools, shopping and dining, along with convenient access to UCF, Seminole State College, Orlando Sanford International Airport, Orlando International Airport and major roadways 417, 408, 528 and I-4. Don't miss the opportunity to make this exceptional Tuscawilla pool home your own—schedule your private showing today!

1162 E Winged Foot Circle, Winter Springs
$270,000
3 Beds ⋅ 3 Baths ⋅ O6431829 MLS ⋅ Unit 11 BLDG.
Welcome to Tuscany Place in the heart of sought after Tuscawilla! This townhouse styles condo offers a open floor plan with abundant natural light, generous living and dining areas, peaceful green back yard and spacious kitchen perfect for everyday living and entertaining. All bedrooms are upstairs with 2 full bathrooms and laundry. Enjoy the greenery, calmness of the shaded outdoor patio; ideal for relaxing after a long day or lounging. This popular gated community offers many amenities including a community pool, beautifully maintained grounds, located within walking distance to Trotwood Park & little shops AND close to all major roads, amenities, schools, medical facilities, shopping, dining, schools, golf course and parks. A fantastic opportunity to enjoy the Winter Springs lifestyle! Great opportunity to enjoy this community & put your personal touches to this home. Priced to sell Motivated seller, bring your offers!

600 Northern Way Unit 1108, Winter Springs
$298,900
3 Beds ⋅ 2 Baths ⋅ O6433718 MLS
SINGLE FAMILY HOME. Stunningly Renovated Gem in Winter Springs. Looking for the perfect blend of modern comfort and community living? Look no further! This spectacular, Renovated home in the desirable Wildwood community is ready for its new owners. Brand New Solar Panel System, Green energy. Paid off. This almost 1,300 sq. ft. residence has been thoughtfully updated with high-end finishes throughout. Offers New roof in 2022. New cabinets and stunning granite countertops. Modern Baths with Porcelain wall tiles, new vanities, and upgraded faucets. Fresh paint inside and out, new baseboards, and elegant tile flooring. Resently replace water heater, A/C unit 2018 . 3 Bedrooms, 2 Bathrooms, spacious living and dining areas, plus a garage and carport. Community & Location Benefits: Enjoy the active Wildwood lifestyle with access to a pool, playground, tennis court, and volleyball court. You will be perfectly positioned in a top-rated school district with easy access to major highways (434, 17-92, I-4, 417, 436) and minutes away from the Altamonte Mall, Lake Mary, premier shopping, dining, and healthcare.

736 Summerland Drive, Winter Springs
$178,900
2 Beds ⋅ 2 Baths ⋅ V4950741 MLS ⋅ 311 BLDG.
Virtually Staged. Enjoy life in this beautiful, recently renovated 2 bedroom, 2 bathroom patio home located in the beautiful Indian River community in Winter Springs. Welcome to a low maintenance lifestyle with the Condo Assn maintaining the lawn, sparkling community pool and clubhouse, tennis courts. This Central Florida location, near roads 434, 419 and 17/92, provides convenient access to the Winter Park restaurant and shopping district, other restaurants, shopping such as Publix, plus the Oviedo Mall and Advent Hospital. It is also only a 25 minute drive to the University of Central Florida and, so, is perfect for Faculty or Students! There are multiple parks in the area, such as Mount Greenwood Park and Big Tree Park, which host many activities throughout the year. The newly installed kitchen and freshly painted interior looks beautiful. One of the standout features of this home is the private outdoor space. The fenced patio area creates a comfortable spot for morning coffee....... ......container gardening, pets, outdoor dining, or relaxing at the end of the day. The included storage shed at 6 ft by 4 ft adds valuable functionality, offering extra space for tools, bikes, surfboards, or outdoor equipment. Indian River offers a peaceful residential setting known for its convenient access to parks, trails, shopping and dining. With its newly renovated interior, efficient 2-bedroom layout, private fenced outdoor space, storage shed, and desirable Winter Springs location, this condominium patio home offers comfort, convenience, and low-maintenance living in one of Seminole County's most appealing areas.

311 San Miguel Street Unit 311, Winter Springs
$510,000
3 Beds ⋅ 2 Baths ⋅ P4939571 MLS
Property is well maintained, had been owned by a former major league baseball prayer. Adjacent to a nice secluded pond. The pool and lanai area is wonderful for quiet sitting, meditation, reading and then jump into the pool for a refreshing dip. The subdivision is one minute from a convenience store and access to Rt 417 highway to all parts of Central Florida. Spacious master bedroom with very big walk-in closet. This is in move-in condition subject only to your color decorations. Part of the Tuscawilla Master Community !!

133 Redtail Place, Winter Springs
$275,000
3 Beds ⋅ 2 Baths ⋅ S5155512 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in the desirable Deer Song community of Winter Springs! Offering 1,105 square feet of thoughtfully designed living space, this move-in-ready home combines modern updates, smart-home technology, energy efficiency, and comfortable Florida living. Step inside to a bright, welcoming interior featuring fresh paint throughout and an updated kitchen with stainless steel appliances and a Samsung Smart Refrigerator with Family Hub Touchscreen. Both bathrooms have been fully updated with modern finishes and smart mirrors, adding style and technology throughout the home. Major improvements include a complete whole-home re-pipe in 2023, and an HVAC UV light system designed to support indoor air quality. Step outside to the screened-in back porch with newly finished epoxy flooring—the perfect place to relax and enjoy the private backyard. A separate storage shed provides additional space for tools, outdoor equipment, and more. Energy-efficient living is made easier with solar panels that help keep monthly electric costs low Enjoy access to the community pool and a convenient Winter Springs location near shopping, dining, parks, recreation, A-Rated Seminole County Public schools, and more. Come see what makes 272 San Gabriel Street such a sweet place to call home!

272 San Gabriel Street, Winter Springs
$244,900
2 Beds ⋅ 3 Baths ⋅ O6431044 MLS ⋅ 1 BLDG.
Welcome to 611 Casa Court, Unit A, a well-located 2-bedroom, 2.5-bath condo offering 1,156 square feet of living space and a great opportunity for an investor or future owner-occupant. The two-story layout provides comfortable separation between the main living areas and bedrooms, with a convenient half bath downstairs and private baths upstairs. Enjoy outdoor space just outside your door along with the benefits of a community setting and shared amenities. Conveniently located near shopping, dining, major roadways, and everything the surrounding Orlando area has to offer, this property provides easy access for everyday living. Whether you're looking to add to your rental portfolio or purchase a property with long-term potential, Unit A offers an affordable opportunity in a convenient Central Florida location.

611 Casa Park A Court, Winter Springs
$245,000
2 Beds ⋅ 2 Baths ⋅ O6432480 MLS ⋅ 1307 BLDG.
Nice Casa Park 2 bedroom 1.5 bath townhome located in beautiful and upscale Tuskawilla! New carpet and fresh interior paint. The townhome features separate living and dining rooms with a half bath downstairs and sliding glass doors leading out to the back patio with a outdoor closet for storage. Off the living is a huge bay window letting in tons of natural light! The kitchen offers tons of cabinet space for all those kitchen essentials! Upstairs has 2 spacious bedrooms with a full bath between them. Located across the street from Trotwood Park, soccer fields, tennis courts, basketball, pavilion for picnics, and much more! Just a 5-minute walk from both Keeth Elementary and Indian Trails Middle Schools. Take a walk to Central Winds Park or ride your bike on the Cross-Seminole Trail. Have fun with your dog at the Doggie Park with a view of Lake Jessup! Tuskawilla Country Club minutes away! What are you waiting for...Check it out today!

1307 Park Villa Place, Winter Springs
$374,900
3 Beds ⋅ 3 Baths ⋅ O6432123 MLS
Welcome to this beautifully updated 3 bedroom, 3 bath home nestled in an established Winter Springs community! Conveniently located near shopping, dining, parks, and major roadways, including SR 417 and I-4, this home combines comfort, style, and an incredibly versatile floor plan. Freshly painted inside and out, the home features new carpet, updated bathrooms, and spacious living areas filled with natural light. The beautifully updated kitchen showcases soft close cabinetry, quartz countertops, stainless steel appliances, and a modern tile backsplash. A unique kitchen opening overlooks the adjacent nook and provides views of the outdoors, creating an open and connected feel. The spacious living room is designed for both relaxing and entertaining, featuring a wood burning fireplace, ceiling fan, and large windows overlooking the lush backyard. The versatile bedroom layout is truly a standout feature. One bedroom and a full bathroom are located downstairs, while the two upstairs bedrooms each feature their own private en-suite bathroom, providing excellent privacy and flexibility for family, guests, or a dedicated home office or guest space. Sliding glass doors lead to an impressive elevated balcony, while the lower level provides additional patio space for enjoying the peaceful outdoor setting. Step outside and enjoy a private backyard surrounded by mature tropical landscaping and no rear neighbors, creating a peaceful Florida retreat. A two car garage and durable tile roof add even more appeal. With its stylish updates, unique floor plan, private outdoor spaces, and exceptional bedroom configuration, this Winter Springs home is a rare find that combines space, comfort, privacy, and functionality. Schedule your private showing today!

662 Nighthawk Circle, Winter Springs
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