Casselberrry/Winter Springs / Tuscawilla Homes with Three+ Story Style

Casselberrry/Winter Springs / Tuscawilla Homes with Three+ Story Style

Welcome to the charming region of Casselberry/Winter Springs/Tuscawilla, nestled in the heart of Seminole County, Florida. Boasting a serene environment and a strong sense of community, this area is perfect for those seeking a peaceful yet vibrant place to call home.

Winter Springs, a city within this region, offers a perfect blend of suburban tranquility and modern amenities. With top-rated schools, beautiful parks, and a variety of dining and shopping options, Winter Springs provides an ideal setting for families and individuals alike.

One of the unique features of the homes in this region is the prevalence of properties with three or more stories. These homes offer not only ample space for living and entertaining but also stunning views of the surrounding landscape. Imagine waking up to panoramic vistas of lush greenery or enjoying a quiet evening on a rooftop terrace under the starlit sky.

Whether you are looking for a spacious family home or a luxurious retreat with multiple levels, the Casselberry/Winter Springs/Tuscawilla region has a diverse range of properties to suit your needs. With easy access to major highways, top-rated schools, and an array of recreational activities, this area truly offers the best of Florida living.

Come and explore the homes with three or more stories in this picturesque region, and find your perfect oasis in Winter Springs.

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Three+ Story Style

$395,000
3 Beds ⋅ 4 Baths ⋅ O6428194 MLS ⋅ 227 BLDG.
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
$360,000
3 Beds ⋅ 4 Baths ⋅ TB8504740 MLS ⋅ Jesups Landing BLDG.
Virtually Staged. BACK ON MARKET THROUGH NO FAULT OF SELLER! Buyer financing fell through. Do not miss out on this opportunity for a spacious, tastefully updated, move-in ready townhome in the heart of Winter Springs! This is a low maintenance 3-bed, 3.5 bath unit with quaint landscaping leading you up the stairs to your classy entry. The interior boasts recent vinyl flooring and no carpet anywhere, perfect for all season in FL. The kitchen and living room are on the main level creating a seamless relaxing or entertaining experience with the ability for residents and guests to have privacy in bedrooms. All modern stainless steel appliances convey! The spacious primary bed/bath is on the 3rd floor and provides a large walk-in closet and dual sinks. Enjoy paradise from your key west style balcony above the 2-car garage. The community amenities include a fitness center and pool overlooking the neighborhood pond. Enjoy quick and easy access to shopping, dining, outdoor activities and entertainment, many of these steps from your front door.

1384 Mill Stream Lane, Winter Springs
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