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

$499,000
4 Beds ⋅ 3.5 Baths ⋅ O6246486 MLS ⋅ Na BLDG.
Experience luxury and modern elegance in this breathtaking 3-story corner unit townhome by Dreamfinders Homes. Perfectly positioned to capture serene sunrise and pond views, this residence redefines chic urban living with its expansive layout and chic design. This spacious 4-bedroom, 3.5-bathroom townhome boasts an open-concept floor plan designed to maximize natural light and provide seamless flow across all three levels. The interior is finished in chic ivory tones, creating a contemporary, airy ambiance that complements the home’s sleek lines and designer finishes. The heart of this home is the upgraded gourmet kitchen, designed for both function and style. Featuring top-of-the-line appliances, modern cabinetry, and elegant quartz countertops, it is the perfect setting for culinary exploration and entertaining - a true, Chef-inspired kitchen with an in-cabinet oven and microwave, and flawless range hood. The primary suite offers a luxurious retreat with expansive windows that frame beautiful views of that sunrise, pond, and conservation area, while the spa-inspired ensuite bathroom adds a touch of tranquility to your daily routine. Three additional bedrooms value flexibility for family, guests, or even a home office with one of the bedrooms being on the first floor as a true en-suite with a full bathroom included. With a private front porch overlooking the peaceful pond, this townhome offers an unparalleled outdoor space to enjoy your morning coffee or unwind at sunset. Some final features include a home generator transfer box, garage storage panels, washer and dryer included, and MORE, to truly make this home ready for you to move right in. Set within a vibrant community of Seminole Crossings, this townhome combines the best of luxury living and modern convenience. Don’t miss the opportunity to make this stunning, private townhome a masterpiece your own. Schedule your private tour today!

421 Diamond Dove Cove, Winter Springs
$389,900
4 Beds ⋅ 3.5 Baths ⋅ O6246448 MLS ⋅ N/A BLDG.
Step into Luxury at 279 McLeods Way This gorgeous 4-bedroom, 3-bathroom townhome located in the sought-after Jesups Reserve & offers a rare blend of style, space, & convenience! Recently upgraded with modern touches by a professional interior designer, this home truly stands out. With bedrooms on each floor, there is plenty of room for everyone to spread out and have their private space. Each bedroom has a private bath! Key Features: • Versatile Layout: This spacious home features 4 bedrooms including a primary suite with a private en-suite bath plus another first-floor en-suite that can function as a guest room or in-law space. The third floor offers two large bedrooms with a shared Jack & Jill bathroom, perfect for family or guests. One bedroom even includes an additional 8x7 flex space ideal for a home office, gym, or cozy reading nook! • Gourmet Kitchen: Cook like a chef in the upgraded kitchen featuring new maple cabinets, elegant stone countertops, a sleek tile backsplash, and new stainless steel appliances. Whether preparing a quick meal or hosting a dinner party, this kitchen shines with style and function. • Completely Upgraded Interior: The entire home has been thoughtfully renovated to include new laminate flooring throughout, ceramic tiles in the kitchen, bathrooms, and utility room, and updated bathrooms with new vanities, commodes, light fixtures. There’s no carpet in this home, all upgraded laminate or ceramic tile. • Elegant Details Throughout: Crown molding graces the master bedroom and living room, adding a refined touch to these already impressive spaces. The 17x17 living room is perfect for hosting gatherings or relaxing with family. • New Light Fixtures & Fresh Paint: Every room boasts brand-new, designer-selected light fixtures and fresh neutral paint, providing a modern, clean aesthetic that complements any decor style. • Energy-Efficient Living: Save on utility bills with ENERGY STAR qualified windows, low-flow fixtures, and other energy-efficient upgrades throughout. Outdoor Living & Community Perks: • Step out to your covered front porch, a charming spot to enjoy your morning coffee or evening breeze, even chat with your neighbors. • The 2-car attached garage provides plenty of parking and storage, and guest parking is available as well. • Cool off or socialize in the resort-style community pool, or take the shortys to the City Park, near the schools. • The community is well-maintained with HOA-provided lawn care and exterior maintenance, allowing you to enjoy a low-maintenance lifestyle. Prime Location: • Nestled in the heart of Winter Springs, this home is across from Winter Springs Town Center, where you can enjoy shopping, dining, and entertainment all close by. Also close by is Crunch Gym, Aldi and many other stores! • Easy access to SR 417 makes commuting a breeze to the beach, Orlando International Airport or the parks, and you’re zoned for top-rated Seminole County schools, including Winter Springs High School. • Nearby, you’ll find parks, walking and biking trails, and even a dog park, perfect for those who love outdoor activities and Florida's natural beauty. This townhome offers luxury, convenience, and an ideal location—all in one stunning package. With all these upgrades and improvements, this home is move-in ready and waiting for you!

279 Mcleods Way, Winter Springs
$420,000
3 Beds ⋅ 3.5 Baths ⋅ V4938333 MLS
This stunning 3-bedroom, 3.5-bathroom townhome offers spacious living across three levels in the desirable Jesup's Landing community of Winter Springs. The open-concept kitchen is perfect for entertaining, with stainless steel appliances and modern finishes. Relax on your private attached balcony or enjoy the convenience of a 2-car garage. Residents of Jesup's Landing enjoy access to a variety of amenities, including a community pool, clubhouse, gym, and direct access to the scenic Cross Seminole Trail. With its blend of comfort and convenience, this home is a must-see! Ready to make this townhome yours? Reach out today for a showing!

1157 Orange Avenue, Winter Springs
$395,000
3 Beds ⋅ 4.5 Baths ⋅ O6237923 MLS ⋅ 412 BLDG.
Welcome to this meticulously maintained and spaciously cozy home with 1844 square feet of living space in the sought after Jesups Reserve community. The only reason the family is moving is because they have outgrown the house and need more space, but they have loved living there. Your new 3 story home includes 3 bedrooms each with its own full bathrooms (3 total) with an oversized 2 car garage (with storage hooks to keep you organized); there is even a garage closet for additional storage space. You won’t have to worry about making upgrades to the main systems of the house because the AC was replaced in 2023, the roof was replaced in 2022 and the garage door had maintenance performed in 2024. This home features a fabulous split bedroom floor plan that is great for multi-generational living or for families that like to entertain guests. When you enter the home, there is a full bedroom and bath on the first floor; as well as a back entrance to the garage (which you enter from the alley). Upstairs on the second floor, you will find your spacious, open floor plan living area with room for dining, relaxing and cooking in your oversized kitchen with breakfast bar and stainless steel appliances (less than 5 years). The laundry room is also located on the second floor for convenience. Brand new stair railing. The third floor has the large owner’s suite, which has a master tub and shower, large walk in closet and private bathroom. You will also find the laundry room and linen closets. The three outdoor seating areas have hosted many dinner parties and family gatherings. You have a porch on the first floor and a patio on the 2nd floor (which was completely updated) and a 3rd floor balcony. All of these will allow you to enjoy romantic outdoor dinners listing to the music from the wine bar across the street. Additional features include: laminate flooring - no carpet throughout the house; community pool is well maintained and equipped with a jacuzzi for those days when you need to relax and chill and there is a beautiful pond with a family of friendly ducks. You will enjoy living in this safe community with friendly neighbors. The house has been professionally cleaned and the exterior pressure washed to give you that move-in ready feeling. Priced to sell. Bring us your offers. Jesups Reserve is conveniently located across from Winter Springs Town Center. You have every convenience you can need either in walking distance or within a quick car ride. The community is close to trails, including Trotwood, Centralwinds, Friendship, Winding Hollow, Sam Smith and Torcaso Parks. There is a nearby dog park for you fur babies. You have your choice of fitness centers that are 1 to 5 minutes away (Crunch, Planet Fitness and Zoo Fitness). Shopping and restaurants nearby include Publix, Spill, Aldi, Dollar Tree, Water to a Tea, Ice cream parlor and more. It is so easy to get to Lake Mary or Sanford shopping areas without having to use 417, but 417 is right there for convenience and you are in a great school zone! Priced to sell. Make your appointment today and see this beautiful home for yourself.

412 Blue Bayou Lane, Winter Springs
$397,000
3 Beds ⋅ 3.5 Baths ⋅ O6231156 MLS
Welcome to Your Dream Home in Winter Springs! This stunning, modern 3-story townhouse is the epitome of style, convenience, and comfort. Located in the highly sought-after Jesups Reserve community, this 3-bedroom, 3.5-bathroom home offers an unbeatable location just steps away from Winter Springs Town Center. Imagine having Publix, diverse restaurants, lively bars, and even Crunch Fitness right around the corner. Plus, with top-rated Seminole County schools, including Winter Springs High School, and the 23-mile Cross Seminole Trail for outdoor enthusiasts, this is the perfect place for families and active lifestyles. Step inside and be greeted by an open-concept layout drenched in natural light. The first floor features a cozy bedroom with a walk-in closet and a full bathroom, ideal as a guest suite, home office, or bedroom. On the second floor, expansive living and dining areas await, perfect for entertaining. The gourmet kitchen is a chef's delight, boasting sleek stainless steel appliances, granite countertops, and wood cabinetry. A convenient half bath and a full laundry room with washer and dryer complete this level. Retreat to the third floor, where you'll find serene bedrooms, including the luxurious primary suite. This tranquil oasis features a private balcony, a large walk-in closet, and a spa-like bathroom with a soaking tub, separate walk-in shower, and double vanity. An additional ensuite bedroom with a traditional tub and shower is also located on this floor. Outdoor living is a breeze with multiple balconies and a front porch, offering peaceful spots to enjoy your morning coffee or watch the sunset. The community pool and hot tub provide additional relaxation options, while the two-car garage with high ceilings adds practicality and convenience. With quick access to 17-92 and 417, commuting is easy, allowing you more time to enjoy the vibrant community around you. Don’t miss your chance to own this gorgeous townhouse that perfectly combines modern living with a prime location.

384 Innisbrook Lane, Winter Springs
$398,000
3 Beds ⋅ 3.5 Baths ⋅ O6215575 MLS ⋅ 371 BLDG.
Location, Location, Location...Enjoy maintenance free living in this beautiful and highly sought-after community of Jesups Reserve in Winter Springs. Fitness and family fun is within walking distance, or just a bike ride away. Whether it is at one of two gyms or one of the numerous lovely parks offering pickleball, fishing, tons of ball fields as well as all trails that Seminole county is known for. Welcome home to this well-maintained 3-story townhouse with community pool and hot-tub. This move-in ready property features 3 bedrooms, 3.5 baths & a 2 car garage. Each level grants easy access to outdoor living. Enjoy a cup of coffee or socialize with neighbors on the front porch, entertain family & friends on the balcony, directly off the living room, or watch the sunset from the third floor owners suite. Enter the tall front door to a small foyer with soaring ceiling & easily accessible first of three ensuite bedrooms, perfect as a kids’ room, guest-room or home office. Head up the stairs to the main level, where you’re greeted with a bright, open living/dining room space, full kitchen featuring granite countertops, solid wood cabinets, stainless-steel appliances, a full laundry room with new washer & dryer, across from the half bath. On the top floor, you will find the owner’s suite, with walk-in closet, access to the balcony & a spacious bath, featuring soaking tub & shower. Across the way, is the third on-suite bedroom. A walk across the street is the Winter Springs Town Center, with grocery shopping, dining options, establishments for socializing & entertainment. Conveniently located on Rt 434, enjoying Florida life will be easy with access to bus stops, top rated schools and route 417.

371 Innisbrook Lane, Winter Springs
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