Casselberrry/Winter Springs / Tuscawilla Homes with Pool Community Features

Casselberrry/Winter Springs / Tuscawilla Homes with Pool Community Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is known for its lush landscapes, family-friendly atmosphere, and a myriad of recreational opportunities that make it a perfect place to call home.

Winter Springs, with its charming neighborhoods and strong sense of community, offers a tranquil suburban lifestyle while still being conveniently close to the excitement of Orlando. The area boasts an array of parks, trails, and lakes, making it ideal for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the scenic beauty of this region will captivate you.

One of the standout features of homes in this community is the abundance of properties with private pools. Imagine relaxing in your own oasis on a warm Florida day, hosting summer barbecues, or enjoying a refreshing swim in the comfort of your backyard. These homes with pool community features not only provide a luxurious lifestyle but also create a perfect space for family gatherings and entertaining friends.

Tuscawilla, in particular, is renowned for its golf courses and well-maintained neighborhoods, offering a blend of leisure and luxury. Residents here enjoy a tight-knit community, with access to top-rated schools, shopping centers, and dining options.

If you're looking for a place where community spirit thrives and outdoor adventures await, Casselberry, Winter Springs, and Tuscawilla offer the perfect backdrop for your next chapter. Come explore the beauty and warmth of this remarkable region and discover your dream home today!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Pool Community Features

$406,990
3 Beds ⋅ 3 Baths ⋅ Hickory Grove SubDv. ⋅ 32708 Zip Code
Under Construction. Final opportunity! Don't miss your chance to make this beautiful property yours! As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a large walk-in closet, providing plenty of storage for your wardrobe and personal items. With two additional bedrooms, this townhome provides flexibility for a growing family, a home office, or a guest room.

225 Spindle Palm Cove, Winter Springs
$425,000
3 Beds ⋅ 4 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Discover refined living in the sought-after Jesup's Landing community of Winter Springs. This elegant 3-bedroom, 3.5-bathroom split-level townhome offers exceptional privacy, with thoughtfully designed living spaces that maximize comfort and separation. Beautiful new wood laminate flooring enhances the home's modern appeal, while the spacious layout is ideal for both everyday living and entertaining. Outside is a freshly painted exterior and new roof! Perfectly situated near Central Winds Park, premier shopping, SR 417, Sanford International Airport, the University of Central Florida, and Seminole State College, this residence combines luxury with convenience. Residents also enjoy resort-style amenities, including a clubhouse, state-of-the-art fitness center, and sparkling community pool. Experience low-maintenance living in one of Winter Springs' most desirable communities.

1380 Mill Stream Lane, Winter Springs
$279,900
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
Beautifully remodeled 3-bedroom, 2-bath home with a 1-car garage. This charming home features: Brand-new kitchen cabinets with elegant quartz countertops. Updated bathrooms with new vanities and modern lighted mirrors. New lighting fixtures throughout. Stylish tile flooring and waterproof luxury vinyl plank flooring. Low HOA. Enjoy all the amenities this wonderful community has including a community pool, tennis courts, pickleball courts, and basketball courts. Conveniently located near highly rated schools, shopping, dining, and more. Don't miss this opportunity—this one won't last long! Schedule your showing today!

236 Panorama Dr, Winter Springs
$350,000
2 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Great Opportunity in Winter Springs! This single family home has 2 bedrooms, 2 bathrooms, and a large upstairs bonus room - great for an office (or used as another bedroom!). Upon entry you'll be impressed with the high vaulted ceilings and wide open view to the living and dining room. The Primary Bedroom is well sized, and the bathroom features a large walk-in closet, dual sinks, and a shower garden tub. The kitchen has newer appliances and solid wood cabinets. Check out the back yard - it's one of the largest lots in the community - with beautiful grass and a new fence! There's also a screened-in back porch and a large shed - great for storage. 2021 ROOF! Amazing Seminole County Schools!

321 Kirkcaldy Drive, Winter Springs
$329,000
3 Beds ⋅ 3 Baths ⋅ Harbor Winds SubDv. ⋅ 32708 Zip Code
Delightful 2 story townhouse - backs up to pond. New appliances, Granite counters, New Carpet - MOVE-IN READY.

472 Harbor Winds Court, Winter Springs
$395,000
3 Beds ⋅ 4 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
Experience maintenance-free living in the heart of Winter Springs at Jesup's Reserve, where charming streetscapes, walkability, and everyday convenience come together. Perfectly positioned with peaceful pond views from the front porch and both upper-level balconies, this three-story townhome offers over three levels of thoughtfully designed living space just steps from Winter Springs Town Center. The versatile floor plan begins with a private first-floor bedroom and full bath—ideal for guests, multigenerational living, or a home office. Upstairs, the expansive main living level is designed for entertaining, featuring an open-concept living and dining area that flows seamlessly into the spacious kitchen. Complete with stone countertops, abundant 42” cabinetry, stainless steel appliances, a large center island, and generous prep space, it's a layout equally suited for everyday living and hosting friends and family. The third floor is home to two spacious bedroom suites, including a generous primary retreat with its own private balcony overlooking the water. The en-suite bath features dual vanities, a soaking tub, separate walk-in shower, and large walk-in closet, creating a true owner's sanctuary. Additional highlights include: Roof (2023), AC (2026) with transferrable warranty, fresh interior paint (2026), a convenient second-floor laundry room, powder bath, and attached two-car garage. Beyond your front door, enjoy resort-style amenities including a community pool, spa, and beautifully maintained grounds. Located directly across from Winter Springs Town Center, you'll have Publix, Aldi, restaurants, coffee shops, fitness centers, boutiques, and everyday conveniences just a short walk away. Outdoor enthusiasts will appreciate being minutes from Central Winds Park and the Cross Seminole Trail, while commuters enjoy quick access to SR-417, US-17/92, and top-rated Seminole County schools. Whether you're searching for a low-maintenance primary residence or a lock-and-leave lifestyle without sacrificing space or location, this Jesup's Reserve home delivers the perfect combination of comfort, convenience, and scenic surroundings. Easy to see. Call/Text for your private showing today!

227 Mcleods Way, 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
$370,000
2 Beds ⋅ 2 Baths ⋅ Greenspointe SubDv. ⋅ 32708 Zip Code
Welcome home to this impeccably maintained 2-bedroom, 2-bath home in the highly desirable area of Winter Springs, Florida! From the moment you step inside, you'll appreciate the open floor plan, soaring vaulted ceilings, and spacious living area centered around a stunning wood-burning fireplace—creating the perfect setting for both relaxing evenings and entertaining guests. The heart of the home is the completely remodeled kitchen (2024), featuring timeless Shaker cabinetry, beautiful butcher-block countertops, an oversized undermount sink, under-cabinet LED accent lighting, and a full suite of high-end stainless-steel appliances. The adjacent pass-through adds both convenience and connectivity, making entertaining effortless. Both bedrooms are generously sized, offering comfortable retreats with ample flexibility to suit your lifestyle. Whether you're hosting overnight guests, creating a dedicated home office, or simply enjoying extra space to unwind, these well-appointed rooms provide endless possibilities. The impressive updates continue with a fully remodeled bathroom (2024), new flooring throughout (2023), a new 40-year clay tile roof (2023), and a new garage door (2022), providing peace of mind for years to come. Outside is a well-kept backyard featuring a generously sized patio with a partially covered seating area—ideal for year-round outdoor dining, entertaining, or simply relaxing with your morning coffee or evening beverage. The low-maintenance outdoor space offers plenty of room to enjoy as-is while still providing endless possibilities for personalization and for creating your own backyard retreat. Ideally located near shopping, dining, parks, and recreation, this home also offers easy access to SR 417 and I-4 for a convenient commute. Situated within an A-rated school district and a community with fantastic amenities, this exceptional home offers the perfect combination of style, comfort, convenience, and pride of ownership. Don't miss your opportunity to make this beautifully updated, truly turnkey home your own! Schedule your showing today as this wont last long.

655 Nighthawk Circle, Winter Springs
$230,000
3 Beds ⋅ 2 Baths ⋅ Deersong 2 SubDv. ⋅ 32708 Zip Code
Opportunity knocks in Winter Springs! If you've been waiting for an affordable way to own in a desirable Central Florida community, this is it This 3-bedroom, 2-bath home offers 1,105 square feet with a very functional layout. This makes it an excellent opportunity for homeowners ready to build equity or investors looking for their next project. The biggest expense has already been taken care of with a 2018 roof, giving you peace of mind where it counts most. Inside the home is clean and with plenty of potential to make it your own; the home has been priced below market to account for some repair needed. Cash or conventional financing only. Schedule your showing today and imagine the possibilities!

118 Deer Song Drive, Winter Springs
$386,990
3 Beds ⋅ 3 Baths ⋅ Hickory Grove SubDv. ⋅ 32708 Zip Code
Under Construction. Final opportunity! Don't miss your chance to make this beautiful property yours! As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a large walk-in closet, providing plenty of storage for your wardrobe and personal items. With two additional bedrooms, this townhome provides flexibility for a growing family, a home office, or a guest room.

233 Spindle Palm Cove, Winter Springs
$299,900
3 Beds ⋅ 3 Baths ⋅ Heritage Park Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to 162 Constitution Way, a well-maintained 3-bedroom, 2.5-bath townhome in the highly desired gated Heritage Park community of Winter Springs. This home features an open-concept floor plan with a kitchen overlooking the living and dining areas, 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, while two additional bedrooms, a full bath, and an upstairs laundry room complete the second level. Additional highlights include an attached one-car garage and low-maintenance living with access to community amenities, including a pool and playground. Conveniently located near Winter Springs Town Center, Central Winds Park, shopping, dining, major roadways, and highly rated Seminole County schools, this property is an excellent opportunity for first-time buyers, young families, or investors.

162 Constitution Way, Winter Springs
$370,000
3 Beds ⋅ 3 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this beautifully upgraded townhome in the highly sought-after Jesup's Landing community! Designed for both comfortable everyday living and effortless entertaining, this home features an open-concept floor plan, a two-car attached garage, and three bedrooms, all located on the second floor. Adding to its value and peace of mind, the home features a brand-new roof and has been freshly painted on the exterior, enhancing both its curb appeal and long-term durability. The first floor offers a bright and inviting living space that flows seamlessly into the gourmet kitchen, complete with an oversized walk-in pantry that is already set up for your own kegerator, making it easy to enjoy your favorite craft beer on tap at home. A convenient half bath completes the main level. Upstairs, the luxurious primary suite is thoughtfully designed with a custom walk-in closet featuring a stylish barn door, a private balcony for morning coffee or evening cocktails, and a spa-inspired ensuite bath with dual vanities. Every detail has been carefully considered, from crown molding and custom window treatments to designer lighting controlled by wireless smart switches. Smart home features include a Brilliant Home Control System with touch panels in the living room and primary bedroom, a Nest Smart Thermostat, Aquanta Smart Water Heater Controller, Philips Hue smart lighting throughout the home, August Smart Locks on both exterior doors, a Ring Video Doorbell, myQ Smart Garage Door Opener with Amazon Key compatibility, Amazon Alexa integration throughout the home, pre-wired surround sound for Dolby 5.1 in the living room with additional in-ceiling speakers upstairs and in the primary bedroom, and a pre-wired security system. Residents of Jesup's Landing enjoy exceptional community amenities, including a resort-style pool, fitness center, clubhouse with a full kitchen, and game room—perfect for entertaining, gatherings, and special occasions. Conveniently located just minutes from SR 417, this home offers easy access to shopping, dining, parks, and scenic bike and walking trails, combining modern living with an exceptional location.

457 Gee Hammock Lane, Winter Springs
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