Casselberrry/Winter Springs / Tuscawilla Homes with Community Mailbox Community Features

Casselberrry/Winter Springs / Tuscawilla Homes with Community Mailbox Community Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, located in the heart of Seminole County, Florida. This vibrant area is known for its lush landscapes, friendly neighborhoods, and a warm community spirit that invites you to call it home.

Nestled just north of Orlando, Winter Springs boasts an ideal blend of suburban tranquility and urban convenience. Residents enjoy easy access to top-rated schools, shopping centers, and recreational parks, making it a perfect place for families and individuals alike. The charming streets are lined with beautiful homes, many of which feature community mailbox setups that foster a sense of unity among neighbors. Imagine the joy of collecting your mail while catching up with friends or exchanging pleasantries with those who live nearby!

Tuscawilla, a picturesque community within Winter Springs, is particularly renowned for its stunning golf courses and serene lakes. Here, outdoor enthusiasts can indulge in a variety of activities, from hiking and biking to fishing and picnicking in one of the many local parks. The area’s natural beauty is complemented by a vibrant local culture, featuring delightful dining options, boutique shopping, and community events that bring everyone together.

Whether you’re looking for a cozy single-family home or a spacious property with room to grow, the Casselberry/Winter Springs/Tuscawilla region offers diverse housing options to suit your lifestyle. Experience the charm and warmth of this wonderful community—where every day feels like a vacation! Come discover your dream home today!

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

$325,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Welcome to 654 Cypress Lane, a move-in-ready 3-bedroom, 2-bathroom home featuring fresh interior paint throughout. The main entry opens into a bright living room that connects seamlessly to the kitchen, complete with quartz countertops and stainless steel appliances. Designed with a practical split floor plan, the primary bedroom sits on one side of the home with its own en-suite bathroom, while two secondary bedrooms share a second full bath on the opposite side. A dedicated laundry room adds extra convenience. Out back, a screened-in back porch offers a quiet spot to relax, leading to a private, fenced yard framed by mature shade trees. Homeowners will also appreciate the benefit of a low HOA fee, with amenities such as a pool, basketball and tennis court, playground, dog park, and much more! Located in Winter Springs, this home puts you near top-rated Seminole County schools, local parks, and the Cross Seminole Trail. Enjoy easy access to shopping and dining at the Winter Springs Town Center, with quick routes to SR 417 for a smooth commute to UCF, Oviedo, and Orlando.

654 Cypress Lane, 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. The HOA fee is $485 per month. In addition, there is a separate Master Association fee of $436, paid annually at the beginning of the year. 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
$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
$449,000
3 Beds ⋅ 2 Baths ⋅ Fox Glen At Chelsea Parc Tuscawilla Ph 2 SubDv. ⋅ 32708 Zip Code
Welcome to this charming 3-bedroom, 2-bathroom single-family home in desirable Winter Springs, Florida! Freshly painted and move-in ready, this inviting home features beautiful granite countertops in the kitchen and a comfortable, functional layout with ceramic tile flooring throughout the house. The enclosed porch and private backyard provide the perfect setting to relax, unwind, and enjoy your evenings and weekends. Best of all, lawn maintenance is taken care of by the HOA, giving you more time to enjoy your home and community. Residents also have access to wonderful community amenities, including a beautiful clubhouse, swimming pool, jacuzzi, and fitness room. Conveniently located short distance to Sam Smith Park and just a short drive from shopping, dining, and Oviedo Mall, this home offers an excellent combination of comfort and convenience. The property is also located in an area known for highly rated Seminole County schools. Don't miss the opportunity to make this beautiful Winter Springs home your next home!

1714 Fox Glen Court, Winter Springs
$267,500
3 Beds ⋅ 3 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to Tuscany Place in the heart of sought after Tuscawilla! This townhouse styles condo offers a open floor plan with abundant natural light, generous living and dining areas, peaceful green back yard and spacious kitchen perfect for everyday living and entertaining. All bedrooms are upstairs with 2 full bathrooms and laundry. Enjoy the greenery, calmness of the shaded outdoor patio; ideal for relaxing after a long day or lounging. This popular gated community offers many amenities including a community pool, beautifully maintained grounds, located within walking distance to Trotwood Park & little shops AND close to all major roads, amenities, schools, medical facilities, shopping, dining, schools, golf course and parks. A fantastic opportunity to enjoy the Winter Springs lifestyle! Great opportunity to enjoy this community & put your personal touches to this home. Priced to sell Motivated seller, bring your offers!

600 Northern Way Unit 1108, Winter Springs
$275,000
3 Beds ⋅ 2 Baths ⋅ Deersong 2 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bath home in the desirable Deer Song community of Winter Springs! Offering 1,105 square feet of thoughtfully designed living space, this move-in-ready home combines modern updates, smart-home technology, energy efficiency, and comfortable Florida living. Step inside to a bright, welcoming interior featuring fresh paint throughout and an updated kitchen with stainless steel appliances and a Samsung Smart Refrigerator with Family Hub Touchscreen. Both bathrooms have been fully updated with modern finishes and smart mirrors, adding style and technology throughout the home. Major improvements include a complete whole-home re-pipe in 2023, and an HVAC UV light system designed to support indoor air quality. Step outside to the screened-in back porch with newly finished epoxy flooring—the perfect place to relax and enjoy the private backyard. A separate storage shed provides additional space for tools, outdoor equipment, and more. Energy-efficient living is made easier with solar panels that help keep monthly electric costs low Enjoy access to the community pool and a convenient Winter Springs location near shopping, dining, parks, recreation, A-Rated Seminole County Public schools, and more. Come see what makes 272 San Gabriel Street such a sweet place to call home!

272 San Gabriel Street, Winter Springs
$234,900
2 Beds ⋅ 3 Baths ⋅ Casa Park Villas Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to 611 Casa Court, Unit A, a well-located 2-bedroom, 2.5-bath condo offering 1,156 square feet of living space and a great opportunity for an investor or future owner-occupant. The two-story layout provides comfortable separation between the main living areas and bedrooms, with a convenient half bath downstairs and private baths upstairs. Enjoy outdoor space just outside your door along with the benefits of a community setting and shared amenities. Conveniently located near shopping, dining, major roadways, and everything the surrounding Orlando area has to offer, this property provides easy access for everyday living. Whether you're looking to add to your rental portfolio or purchase a property with long-term potential, Unit A offers an affordable opportunity in a convenient Central Florida location.

611 Casa Park A Court, Winter Springs
$179,900
2 Beds ⋅ 2 Baths ⋅ Bay Tree Sec 09 SubDv. ⋅ 32708 Zip Code
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
$339,900
3 Beds ⋅ 3 Baths ⋅ Barclay Reserve Twnhms SubDv. ⋅ 32708 Zip Code
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
$489,900
2 Beds ⋅ 3 Baths ⋅ Greens At Tuscawilla SubDv. ⋅ 32708 Zip Code
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
$365,000
3 Beds ⋅ 3 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this beautifully maintained townhome in desirable Jesup’s Landing, offering a wonderful combination of style, convenience, and community amenities. The open-concept main level features a bright living area, gourmet kitchen with an oversized walk-in pantry equipped for a kegerator, half bath, and attached two-car garage. Upstairs, the spacious primary suite includes a custom walk-in closet, private balcony, and ensuite bath with dual vanities, along with two additional bedrooms. A brand-new roof and freshly painted exterior add peace of mind, while crown molding, custom window treatments, designer lighting, and extensive smart-home technology enhance the interior. Smart features include Brilliant Home Control, Nest thermostat, Philips Hue lighting, August Smart Locks, Ring doorbell, myQ garage control, Alexa integration, and pre-wired surround sound and security. Jesup’s Landing residents enjoy a resort-style pool, fitness center, clubhouse with full kitchen, and game room. Conveniently located near SR 417 with easy access to shopping, dining, parks, and scenic walking and biking trails.

457 Gee Hammock Lane, Winter Springs
Start Your Search