Casselberrry/Winter Springs / Tuscawilla Homes with Two Story Style

Casselberrry/Winter Springs / Tuscawilla Homes with Two Story Style

Welcome to the charming region of Casselberry/Winter Springs/Tuscawilla in Seminole County, Florida. Nestled within the city of Winter Springs, this area boasts a unique blend of natural beauty and modern conveniences, making it a desirable location for homebuyers looking to settle down in a vibrant community.

One of the standout features of the homes in this region is the prevalence of the two-story style, offering both functionality and aesthetic appeal. These homes are not only spacious but also provide a sense of privacy and separation between living and sleeping areas, making them ideal for families or those who enjoy hosting guests.

Living in Casselberry/Winter Springs/Tuscawilla means enjoying a relaxed lifestyle with easy access to an array of amenities. From picturesque parks and recreational facilities to top-rated schools and shopping centers, residents here have everything they need right at their fingertips.

Whether you're looking for a cozy townhouse or a spacious single-family home, the Casselberry/Winter Springs/Tuscawilla region has a diverse range of properties to suit every taste and budget. With its welcoming atmosphere and strong sense of community, this area provides the perfect setting to create lasting memories and truly feel at home. Explore the homes with the two-story style in this region and discover the perfect place to put down roots in beautiful Winter Springs, Florida.

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Two Story Style

$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
$179,900
2 Beds ⋅ 2 Baths ⋅ O6431944 MLS ⋅ 70 BLDG.
Virtually Staged. If you’ve been dreaming of a MOVE-IN READY home where you can enjoy scenic parks, peaceful walking trails, and beautiful green spaces, welcome to Baytree 9, one of the charming communities within the Highlands of Winter Springs. This WELL-MAINTAINED two-story, 2-bedroom, 1½-bath condo offers the perfect blend of comfort, convenience, and carefree Florida living. Ideally located near highly rated schools, top medical facilities, shopping, dining, and major roadways, you’ll enjoy easy access to everything you need while coming home to a peaceful, nature-filled setting. Inside, the thoughtfully designed open floor plan creates an inviting space for everyday living. The kitchen flows into the dining and living areas, while oversized sliding glass doors fill the home with natural light and lead to your private patio – an ideal spot to sip your morning coffee, unwind after a long day, or simply enjoy the tranquil surroundings. The updated kitchen features granite countertops, a breakfast bar, pantry, neutral tile flooring, and all appliances convey. Upstairs, you’ll find a spacious primary suite, a comfortable second bedroom, a shared bath with direct access from the primary suite, and a conveniently located laundry closet designed for everyday ease. Enjoy peace of mind with numerous recent updates, including a NEW A/C in 2023 and, in 2024, a NEW ROOF, WATER HEATER, stainless steel kitchen APPLIANCES, full-size WASHER and DRYER, carpet, blinds, and chair-height toilets. One of the greatest benefits of this home is its low-maintenance lifestyle. The HOA covers exterior and grounds maintenance, giving you more time to enjoy the community’s OUTSTANDING AMENITIES. Spend sunny afternoons at the clubhouse and pool, gather with friends at the picnic areas with grills, explore the scenic nature trails, or enjoy the playgrounds, volleyball, basketball, and tennis courts. Conveniently located just off SR 434 with easy access to SR 436, Highway 17-92, SR 417, and I-4, you can enjoy Cranes Roost Park, Altamonte Mall, Winter Park Village, and the boutiques and restaurants along charming Park Avenue. Whether you’re looking for your first home, an investment, downsizing, or searching for a low-maintenance lifestyle surrounded by nature, this exceptional condo is ready to welcome you home. Schedule your private showing today and discover why so many love calling the Highlands of Winter Springs home! This home may be under audio or video surveillance.

70 Moree Loop Unit 61, Winter Springs
$290,000
3 Beds ⋅ 3 Baths ⋅ O6430311 MLS ⋅ 1329 BLDG.
Built by Beazer Homes in 2010, this beautifully maintained townhome sits in a gated neighborhood and offers an unbeatable location. It is situated just 8 miles from the University of Central Florida & Siemens, 15 miles from downtown, with easy access to the 417 and just a stroll away from shopping, dining, and everyday conveniences. And let's not forget the highly desirable Seminole County schools nearby, making this an exceptional place to call home. Boasting the ideal floor plan, which features an open-concept living, dining, and kitchen area on the first floor, creating the perfect space for entertaining or everyday living. Upstairs, you'll find all three bedrooms thoughtfully tucked away for added privacy, along with a convenient upstairs laundry room. And an attached garage adds even more convenience with an updated smart opener - an app to open it from anywhere. Recent upgrades include a new roof (2020) and A/C (2023) and new oven/stove. Residents of Heritage Commons enjoy access to a community pool as well as a playground. Start enjoying the low maintenance living that townhome living offers, as the HOA handles all exterior maintenance & lawn care, providing the perfect lock-and-leave lifestyle. Don't delay, schedule your showing today!

1329 Heritage Commons Drive, Winter Springs
$498,000
4 Beds ⋅ 4 Baths ⋅ O6430088 MLS
Virtually Staged. Pond view!! Beautifully maintained 4-bedroom, 3.5-bath home located in the highly sought-after Tuscawilla community. Offering nearly 2,500 sq. ft. of thoughtfully designed living space, this home features an ideal floor plan with two primary suites—one on the first floor and another upstairs—providing exceptional flexibility for multi-generational living or guests. Enjoy an outstanding lifestyle with resort-style community amenities, including a community pool and direct access to scenic walking and biking trails right within the neighborhood. Conveniently located with top-rated Seminole County schools, easy access to major highways, shopping, dining, and everyday conveniences. Surrounded by mature landscaping and a peaceful atmosphere, Tuscawilla is one of Central Florida’s most desirable communities. Property Highlights: 4 Bedrooms | 3.5 Bathrooms Nearly 2,000 Sq. Ft. Two Primary Suites (First & Second Floor) Functional, Open Floor Plan Beautifully Maintained & Move-in Ready Resort-Style Community Pool Walking & Biking Trails Within the Community Excellent School District Easy Access to Major Highways, Shopping & Dining Move in and enjoy the perfect combination of comfort, convenience, and the exceptional Tuscawilla lifestyle!

225 Gentle Breeze Lane, Winter Springs
$850,000
6 Beds ⋅ 6 Baths ⋅ O6428821 MLS
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
$406,990
3 Beds ⋅ 3 Baths ⋅ O6428779 MLS ⋅ 9 BLDG.
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
$350,000
3 Beds ⋅ 3 Baths ⋅ O6429343 MLS ⋅ 617 BLDG.
Welcome to the beautiful, tree-lined, gated community of Barclay Reserve. This 3 bedroom, 2.5 bathroom, end unit townhome is offered fully furnished and move in ready. Brand new A/C July 2025, new refrigerator April 2025 and new washer & dryer May of 2023. Enjoy a waterfront view with the soothing fountain sound from the living space and two bedrooms. Both the original owner and current owner used the property as a second home which means less wear and tear. The property is less than 10 minutes away from Ovideo on the Park and 15 minutes away from UCF, making the home a perfect purchase for parents needing student housing. It’s only 2 minutes from SR-417 for easy access to the airport, 408 and I-4. 33 guest parking spaces are distributed around the circle so you don’t have to worry about dodging street parking. Peace, security and a prime location seeking its next owner.

617 Pinebranch Circle, Winter Springs
$2,794,500
5 Beds ⋅ 6 Baths ⋅ O6428801 MLS
NEW $165k BONUS! - With acceptable contract seller will credit buyer up to $100,000 for roofing allowance and pay off $65k solar financing balance at closing. 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 views include 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
$350,000
2 Beds ⋅ 2 Baths ⋅ O6427178 MLS
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 ⋅ O6428353 MLS ⋅ 472 BLDG.
Delightful 2 story townhouse - backs up to pond. New appliances, Granite counters, New Carpet - MOVE-IN READY.

472 Harbor Winds Court, Winter Springs
$263,000
3 Beds ⋅ 3 Baths ⋅ O6427882 MLS ⋅ 3880 BLDG.
Welcome to Heritage Commons, a gated community in the heart of Winter Springs, where comfort, convenience, and low-maintenance living come together. This 3-bedroom, 2.5-bathroom townhome with a one-car garage offers an excellent opportunity to make it your own and add your personal touches. Step inside to a bright, open floor plan filled with natural light. The spacious living and dining areas flow seamlessly into the well-appointed kitchen, featuring ample cabinetry, generous counter space, a breakfast bar, and a closet pantry — ideal for everyday living and entertaining. Upstairs, you’ll find all three generously sized bedrooms, including a spacious primary suite with a private en-suite bathroom. Two additional bedrooms share a well-appointed full bathroom, providing flexibility for guests, a home office, or additional living space. Enjoy the convenience of an interior laundry area, plenty of storage, and a private outdoor space perfect for relaxing after a long day. Heritage Commons offers a community pool and a convenient location close to shopping, dining, parks, top-rated Seminole County schools, and major roadways. Experience the best of Winter Springs living with easy access to Central Winds Park, the Cross Seminole Trail, and everything the area has to offer. Don’t miss the opportunity to make this wonderful townhome your own!

3880 White Birch Run, Winter Springs
$489,900
2 Beds ⋅ 3 Baths ⋅ O6426798 MLS ⋅ 1541 BLDG.
Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs
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