Casselberrry/Winter Springs / Tuscawilla Homes with Sidewalk Exterior Features

Casselberrry/Winter Springs / Tuscawilla Homes with Sidewalk Exterior Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is renowned for its picturesque landscapes, friendly communities, and an abundance of outdoor activities. With its lush parks, serene lakes, and scenic trails, residents enjoy a lifestyle that beautifully blends nature with suburban charm.

Winter Springs, in particular, is celebrated for its family-friendly atmosphere and top-rated schools, making it an ideal place for families to settle down. The community boasts a variety of amenities, including shopping centers, dining options, and recreational facilities that cater to all ages. Tuscawilla, a sought-after neighborhood within Winter Springs, is known for its stunning golf courses and well-maintained parks, offering a perfect backdrop for outdoor enthusiasts.

One of the standout features of homes in this area is their charming sidewalk exteriors. Many properties are designed with inviting sidewalks that enhance the neighborhood’s appeal, encouraging morning strolls, evening jogs, and friendly chats with neighbors. These sidewalks not only promote an active lifestyle but also foster a sense of community, where families can enjoy the outdoors together.

In this captivating region, you’ll find a diverse array of homes that cater to various tastes and budgets, from cozy single-family residences to luxurious estates. Each home is a gateway to a vibrant lifestyle, where the beauty of Florida living is at your doorstep. Explore the charm of Casselberry, Winter Springs, and Tuscawilla—where your dream home awaits amidst a welcoming community!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Sidewalk Exterior Features

$665,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14a SubDv. ⋅ 32708 Zip Code
Welcome to this exceptional 4-bedroom, 3-bath pool home with a dedicated office, situated on an oversized corner lot in the heart of Tuscawilla in Winter Springs. Featuring a unique three-way split floor plan, generous indoor and outdoor living spaces, and thoughtful updates throughout, this home offers the perfect combination of functionality, privacy, and Florida living. Step inside through the grand foyer, where a spacious dedicated office sits just off the entry and features French doors, crown molding, beautiful flooring, and plantation shutters. Continue into the inviting living room, highlighted by a brick accent wall, vaulted ceilings, and sweeping views of the pool and lanai. Natural light fills the space through an impressive three-panel sliding glass door that disappears into the wall, creating a seamless transition between indoor and outdoor living—perfect for entertaining. The open floor plan flows into a charming breakfast nook and spacious kitchen featuring an abundance of cabinetry and counter space, stainless steel appliances, and a breakfast bar for casual dining. For larger gatherings and special occasions, the separate formal dining room offers plenty of space and is finished with a beautiful statement chandelier. Privately positioned on one side of the home, the primary suite is a true retreat with vaulted ceilings and its own enclosed Florida room—an incredible space for morning coffee, a reading nook, or peaceful space. The expansive primary bathroom features dual vanities, a brand-new Kohler walk-in shower (2026), and a massive walk-in closet with direct access to the bedroom. The home's thoughtful three-way split design provides exceptional privacy. A second wing features two additional bedrooms and a spacious shared bathroom, while the third wing offers a separate bedroom with its own full bathroom and newly renovated shower (2025)—an ideal setup for guests, extended family, or in-law accommodations. Step outside and experience the Florida lifestyle with a sparkling saltwater pool, new pool heater (2025), and a generous covered lanai designed for year-round entertaining. Beyond the pool, the expansive, fully fenced backyard features new pavers (2024) and plenty of room to relax, play, garden, or entertain. Private and serene, this oversized corner lot provides outdoor space that is increasingly hard to find. Additional highlights include no HOA, a new roof and skylights (2019), new salt cell and pool heater (2024) and brand new A/C (2024). Located in sought-after Seminole County, this home is zoned for Oviedo High School and offers convenient access to everything the Tuscawilla community is known for, including walking trails, public parks, and Tuscawilla Country Club with golf, clay tennis courts, a lap pool, fitness center, and dining. With its oversized lot, three-way split floor plan, private pool, dedicated office, flexible living spaces, and incredible Tuscawilla location, this Winter Springs home delivers the space and lifestyle you've been searching for. Call for your private showing today!

674 Vistawilla Drive, Winter Springs
$549,000
3 Beds ⋅ 4 Baths ⋅ Seminole Crossing Townhomes SubDv. ⋅ 32708 Zip Code
Welcome to 1166 Spotted Sandpiper Loop in Winter Springs, a spacious three-story, 3-bedroom, 3.5-bath townhome in Seminole Crossing. With a floor plan that offers plenty of room to spread out, this home is one of only two townhomes in the community featuring this unique layout. Its multi-level design gives the home more character and separation than the typical boxy townhome, with gathering spaces and private retreats thoughtfully placed across three floors. The first floor features a private bedroom and full bathroom, making it ideal for guests, extended family, or a home office, along with an oversized rear-facing garage and covered front porch. Upstairs, the main living level brings the gourmet kitchen, dining area, and family room together in an open, light-filled space. Designed with both everyday living and entertaining in mind, the gourmet kitchen features a walk-in pantry, generous prep and storage space, and double ovens. French doors open to an expansive balcony, creating an inviting spot to enjoy some fresh air or unwind at the end of the day. The third floor is home to the primary suite, a second bedroom, and a flexible loft. The primary suite offers a large walk-in closet and spacious bathroom with dual sinks, soaking tub, and separate shower. The second bedroom also has a walk-in closet, with a full bathroom conveniently located just outside the bedroom, while the loft can easily become a lounge, media area, study, or home office. The laundry room is conveniently located nearby. One of the biggest perks of townhome living here is the maintenance-free exterior. The HOA takes care of the outdoor upkeep, including mowing, weeding, flower beds, tree trimming, and more. When the time comes, the HOA is also responsible for exterior painting and roof replacement, giving you even less to worry about. And the location makes everyday errands surprisingly easy. The Cross Seminole County Trail is just a short distance from the home located right outside the neighborhood, while nearby grocery stores and restaurants are also just a walk away. Starbucks is even closer, with Chick-fil-A, Wawa, and Ace Hardware coming soon. Residents also enjoy access to a community pool, sidewalks, and additional recreational spaces, with convenient access to SR 434, Winter Springs Town Center, Oviedo, and surrounding Seminole County. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

1166 Spotted Sandpiper Loop, Winter Springs
$170,000
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 3 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 2-bedroom, 2-bath first-floor condo located at 417 Sheoah Blvd, Apt 17, Winter Springs, FL 32708. This inviting home offers a spacious and comfortable floor plan with plenty of natural light throughout. The renovated kitchen provides a fresh and functional space and comes complete with all appliances. A washer and dryer are also included for added convenience. The home also features renovated bathrooms, adding to its fresh and move-in-ready appeal. The spacious living and dining areas feature tile flooring, creating an open and welcoming space for everyday living and entertaining. The generously sized primary bedroom features wood-look flooring and sliding glass doors that open directly to the outdoor patio, bringing in natural light and providing convenient access to the outdoor space. Enjoy the screened-in back porch and extended paver patio overlooking the community’s mature trees and green space. This inviting outdoor area offers a peaceful setting and added privacy, perfect for enjoying your morning coffee, relaxing outdoors, or entertaining guests. The community offers desirable amenities including a swimming pool and tennis courts. The HOA maintains the building exterior, roof, and community landscaping, providing valuable services for residents. Conveniently located in Winter Springs, this updated first-floor condo offers a wonderful combination of renovated interiors, spacious living areas, inviting outdoor spaces, and community amenities. Enjoy a great location within the desirable Seminole County school district, with convenient access to shopping, dining, parks, and major roadways. Schedule your private showing today and discover everything this beautiful condo has to offer!

417 Sheoah Boulevard Unit 17, Winter Springs
$415,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code
Nestled in the desirable Oak Forest at Tuscawilla community, this 3 bedroom, 2 bathroom home is located near local parks, trails, shops, restaurants, and highly rated Seminole County schools. Inside, a spacious, open floor plan flows effortlessly between the living and dining areas, elevated throughout by custom crown molding and rich wood detailing that add a timeless, tailored feel rarely found at this price point. The lovely kitchen anchors the home with a center island and breakfast bar, perfect for casual meals or entertaining guests. The primary suite offers a peaceful retreat with a generous walk-in closet, while the additional bedrooms are equally impressive, each offering generous space and an abundance of natural light. Outside, a screened patio invites year-round outdoor living, and an attached 2 car garage completes this beautiful Winter Springs residence.

1067 Chokecherry Drive, Winter Springs
$210,000
2 Beds ⋅ 2 Baths ⋅ Moss Cove SubDv. ⋅ 32708 Zip Code
Virtually Staged. Charming Winter Springs Townhouse – Perfect for Buyers or Investors! Welcome to 113 Kristi Ann Court, a beautifully maintained 2BR/1.5BA townhouse in the highly sought-after Winter Springs area. Offering 898 sq ft of thoughtfully designed living space, this home features a bright, open living area and a well-appointed kitchen optimized for everyday comfort. Step outside to your private, screened-in patio—the perfect spot to relax and enjoy the Florida lifestyle. Superb location provides seamless access to premier shopping, local dining, parks, top-rated schools, and major roadways for an easy commute. An exceptional opportunity for first-time homebuyers, downsizers, or savvy investors looking for excellent rental potential. Immediate income producing opportunity for investors. No detail overlooked, functional layout, and unbeatable location. Schedule your private tour today!

113 Kristi Ann Court, Winter Springs
$512,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Beautifully Upgraded Sofia Model Townhome on a Premium Conservation Lot! Welcome home to this exceptional Sofia Model townhome, featuring one of the community’s most desirable floorplans—with the primary suite conveniently located on the first floor and two additional bedrooms upstairs. This thoughtfully designed layout is ideal for families, first-time buyers, those looking to downsize, or anyone seeking comfortable living with flexibility for guests, a home office, or additional living space. Situated on a premium lot backing to a peaceful conservation/green area, this home offers a wonderful sense of privacy and a tranquil natural backdrop. Inside, numerous builder upgrades and thoughtful custom enhancements create a beautiful blend of modern style, classic elegance, and everyday functionality. Upgrades include enhanced tile, bathrooms, and kitchen finishes, complemented by a custom-designed stair railing that adds a distinctive touch of sophistication. The spacious primary suite features a custom-built walk-in closet, maximizing storage and organization. An Ecobee Smart Thermostat system with Smart Sensors provides efficient, convenient control of the home's comfort while helping manage energy usage. Premium professionally installed ceiling fans in every room provide excellent air circulation and year-round comfort. The home is also professionally wired for rear surround-sound speakers, making it ready for an enhanced entertainment experience. All the rooms have plenty of natural lights! The garage is equally practical, featuring large custom-built ceiling-hung storage, providing valuable additional space while keeping vehicles and everyday belongings organized. Enjoy an outstanding location within Hickory Grove. The community pool and dog park are just down the street, while the Cross Seminole Trail can be easily accessed just outside the community—perfect for walking, jogging, or biking. The Magnolia Square Fountain and Park and The Winter Springs Town Center are both approximately a five-minute walk away, with roughly a dozen food-and-beverage places within walking distance or a short drive away. Central Winds Park is only about a 10-minute drive away. Access to 417 is about 7-minute drive away. With its highly sought-after first-floor primary suite, premium conservation lot, extensive upgrades, custom touches, and exceptional walkable location, this townhome offers a rare combination of comfort, style, privacy, and convenience.

1378 Tarflower Drive, Winter Springs
$499,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Virtually Staged. Live the Florida lifestyle in the beautiful gated community of Parkstone! This 4-bedroom, 3-bath pool home offers the perfect combination of comfort, convenience, and resort-style living. Spend sunny afternoons relaxing by your own private screened pool, enjoy morning walks or bike rides along the nearby Cross Seminole Trail, or take advantage of Parkstone’s community pool, tennis and volleyball courts, playgrounds, and lakefront dock on Lake Jesup. Even better, lawn care is included through the HOA, giving you more time to enjoy everything the community has to offer. Inside, the open and inviting layout is designed for both everyday living and entertaining, with spacious gathering areas and easy access to the covered outdoor living and pool area. A downstairs bedroom and full bath provide flexibility for guests, a home office, or multigenerational living, while the spacious primary suite upstairs creates a comfortable private retreat. The home has also been thoughtfully cared for with approximately $5,000 invested in new gutters and an extensive underground drainage system, including underground downspouts and dual French drains. Approximately two tons of river rock, a side-yard walkway, refreshed landscaping in 2026, and refreshed tile grout in all three bathrooms add to the home’s move-in-ready appeal. Whether it’s coffee by the pool, an evening walk through the neighborhood, a bike ride on the trail, or a day enjoying the community amenities, 909 Devon Creek offers more than a home—it offers an easy, active Florida lifestyle.

909 Devon Creek Road, Winter Springs
$409,900
3 Beds ⋅ 2 Baths ⋅ Tusca Oaks SubDv. ⋅ 32708 Zip Code
MULTIPLE-OFFER SITUATION: The sellers have requested that all highest and best offers be submitted by Friday, September 11. Discover the comfort and convenience of Tusca Oaks, located within the sought-after Tuscawilla Community in Winter Springs and zoned for highly regarded Seminole County schools. This 3-bedroom, 2-bath home offers over 1,600 square feet of inviting living space, featuring a welcoming foyer, open-concept design, and vaulted ceilings that create a bright, spacious feel throughout the main living areas. The kitchen features Formica countertops, matching appliances, generous cabinet storage, and a convenient flow into the dinette, making it ideal for both everyday living and entertaining. The home features a combination of tile and laminate flooring, with carpet in one guest bedroom. The primary suite offers a walk-in closet and an ensuite bathroom with a separate shower and garden tub. The interior laundry room includes a window for natural light, along with a bumped-out space across from the washer and dryer that offers a great opportunity for a future built-in. Recent updates include a re-roof in 2021, a water heater approximately three years old, and brand-new interior and exterior paint completed in August 2026. The A/C is approximately 20 years old. A screened-in back porch overlooks the backyard, offering a comfortable space for outdoor dining, entertaining, pets, play, or simply enjoying the Florida sunshine. The backyard provides additional space to enjoy the outdoors. Tusca Oaks residents enjoy a low HOA fee and access to a community pool, while the home’s location within Tuscawilla puts you close to Trotwood Park, Tuscawilla Country Club, Tuscawilla Square, Bear Creek Nature Trail, Cross Seminole Trail for biking and recreation, and Sam Smith Park. Shopping, dining, major roadways, and highly regarded Seminole County schools are also conveniently nearby.

519 Pleasant Grove Drive, Winter Springs
$369,500
3 Beds ⋅ 4 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
Welcome to 412 Blue Bayou, your beautifully refreshed oasis in Jessups Reserve in Winter Springs! This exceptional home stands out with 3 fully en-suite bedrooms and a carpet-free interior featuring laminate flooring throughout and a brand-new stair railing. The downstairs bedroom can be used as a guest bedroom, office or flex space. Complete peace of mind comes standard thanks to major recent capital upgrades, including a ROOF replacement (2022), a brand-new A/C system (2023), and professional garage door maintenance (2024). The primary suite, situated on the third floor for added privacy, features a large walk-in closet, a soaking tub and separate shower, offering a peaceful retreat away from the home's common areas Enjoy effortless Florida living while cooling off in the community pool and soak away the stress of life in the spa. Unwind at the end of the day in three distinct outdoor spaces: a welcoming front porch, a renovated second-floor patio, and a private third-floor balcony. Convenient location is a bonus: walk across the street to Publix when you run out of sugar, check out the live music at Wine Lounge or hit your fitness goals at Crunch Fitness. The main level boasts a bright, open-concept living and dining area, along with a spacious kitchen equipped with stainless steel appliances in excellent condition and a generous breakfast bar; a convenient laundry area is also located on this floor. A spacious two-car garage comes fully equipped with additional smart storage solutions to keep your life organized and functional. Additional bonuses can be found at the Winter Springs Town Center (Aldi, Hiking/Biking Trails and more). Perfectly priced at $369,500, this turn-key property is ready for its next chapter!

412 Blue Bayou Lane, Winter Springs
$399,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Built in 2024 and located in the desirable Hickory Grove community of Winter Springs, this move-in-ready home offers modern style, low-maintenance living, and everyday convenience. Featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage, the home welcomes you with an open-concept layout filled with natural light. The modern kitchen is designed for both entertaining and everyday living with stainless steel appliances, quartz countertops, and a large center island overlooking the main living area. Upstairs, the spacious primary suite provides a private retreat with an en-suite bathroom and generous closet space, while two additional bedrooms offer plenty of flexibility for family, guests, or a home office. Enjoy maintenance-free living with an impressive list of community amenities just steps from your front door, including a resort-style pool and cabana, playground, dog park, serene green spaces, fountains, and walking paths. Monthly HOA dues include landscaping, irrigation, weed control, exterior paint, roof maintenance, 1GB high-speed internet, and a premium cable package. Conveniently located across the street from Winter Springs Town Center, you’ll have shopping, dining, and everyday conveniences just steps away, all while being near top-rated schools and everything Winter Springs has to offer. With its like-new condition, remaining builder warranty, and sought-after location, this home is ready for its next owner!

1406 Blumberg Boulevard, Winter Springs
$335,000
3 Beds ⋅ 3 Baths ⋅ Harbor Winds SubDv. ⋅ 32708 Zip Code
Welcome to 518 Harbor Winds Ct! A beautifully maintained and move-in-ready townhome nestled within a very desirable gated community. Featuring 3 bedrooms, 2.5 bathrooms, an attached 2-car garage, primary suite on the first floor, and backs up to a GORGEOUS POND VIEW! The home features soaring ceilings and a bright open-concept! The kitchen features granite countertops, 42-inch wood cabinets, stainless steel appliances, a pantry, and breakfast bar. The view from the living room and kitchen of the serene conservation and pond from your patio area is soothing! The primary suite has plenty of room for a king-size bedroom set features a large walk-in closet and private ensuite bathroom with dual vanities, a jetted tub, and separate shower. The townhome community has a newer roof and gutters, a resort-style community pool, and beautifully maintained surroundings. Easy access to shopping, dining, parks, nature trails, major highways, and highly regarded Seminole County schools. Look forward to your visit soon!

518 Harbor Winds Court, Winter Springs
$779,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 12a SubDv. ⋅ 32708 Zip Code
A rare opportunity awaits in the heart of Tuscawilla. Welcome to 992 Sleeping Rock Court, a distinctive 4 bedroom, 2.5 bath Parade of Homes model pool home offering approximately 2,701 square feet of beautifully updated living space on an oversized .38 acre cul de sac homesite with the exceptional freedom of NO HOA. Designed with character, warmth and impressive architectural detail, this custom Parade of Homes model home immediately stands apart. Striking vaulted tongue and groove cedar ceilings in both the family room and primary suite create a rich, inviting atmosphere, while the beautifully updated wood burning fireplace serves as a dramatic centerpiece to the main living area. The spacious split bedroom floor plan provides privacy and functionality for both everyday living and entertaining. The primary suite feels like a private retreat, showcasing vaulted tongue and groove cedar ceilings, smart LED lighting, a remote controlled smart ceiling fan, custom closet shelving and an ensuite bath overlooking a private atrium. Throughout the home, thoughtful improvements include updated flooring, crown molding, baseboards, interior doors, electrical outlets, faucets and new ceiling fans. The kitchen features 36 inch cabinetry and updated black stainless steel appliances, including a 2025 dishwasher, along with a generous walk in pantry offering excellent storage. A dedicated laundry room, updated hall and half baths, custom closet systems and numerous smart home upgrades add convenience throughout. Step outside and discover an exceptional setting designed for the Florida lifestyle. The expansive covered lanai creates an impressive outdoor living and entertaining space overlooking the private pool with a beautiful natural rock waterfall, mature landscaping and oversized yard. Whether hosting friends, enjoying a quiet evening or relaxing poolside to the sound of the waterfall, this backyard offers the space, privacy and atmosphere that are increasingly difficult to find. The exterior has also received extensive improvements, including new brick pavers, updated fencing, cedar fascia, updated gutters and soffits, refreshed pool equipment with a Pentair pool pump, updated irrigation with a smart WiFi controller and a new mailbox. Major improvements have already been completed, providing tremendous value for the next owner. Updates include a 2019 roof and skylights, 2020 A/C, electrical panel, ductwork repairs and partial replacement, 2023 windows and three sliding glass doors with a Home Depot lifetime warranty, a new front door and a 2024 water heater. Technology and security have also been thoughtfully incorporated throughout the home with fiber internet, CAT8 wiring, a Nest thermostat, Ring doorbell, Nest Yale keypad front entry, keypad garage entry and Ring spotlight video cameras positioned at the front of the property. This home offers the rare combination buyers are searching for: a substantial homesite, a private pool with natural rock waterfall, mature landscaping, architectural character, extensive updates, impressive outdoor living space, Parade of Homes distinction and NO HOA restrictions or monthly HOA dues. It is a distinctive, non cookie cutter property filled with character, thoughtful upgrades and exceptional indoor and outdoor living spaces. Homes offering this combination of size, privacy, improvements, architectural personality and freedom from an HOA are increasingly difficult to find.

992 Sleeping Rock Court, Winter Springs
Start Your Search