Casselberrry/Winter Springs / Tuscawilla Condos for Sale

Casselberrry/Winter Springs / Tuscawilla Condos for Sale

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Florida’s Seminole County. Known for its vibrant community, lush landscapes, and a plethora of recreational activities, this area is a hidden gem that perfectly balances suburban tranquility with urban convenience.

Winter Springs is renowned for its family-friendly atmosphere, excellent schools, and stunning parks, making it an ideal place for families, young professionals, and retirees alike. The nearby Tuscawilla neighborhood offers a picturesque setting with beautiful golf courses, scenic lakes, and winding trails, perfect for outdoor enthusiasts. Casselberry, with its charming boutiques and delightful dining options, adds a touch of local flair to the region, ensuring that residents have access to everything they need right at their fingertips.

If you’re in the market for a new home, you’ll be delighted to discover the array of condos for sale in this area. These modern residences offer a blend of comfort and style, featuring open floor plans, updated amenities, and community features such as pools, fitness centers, and walking trails. Whether you’re seeking a cozy retreat or a spacious family condo, there’s something for everyone in this thriving community.

With its strategic location just a short drive from Orlando, residents can easily access world-class attractions, shopping, and dining options while enjoying the peaceful ambiance of suburban life. Explore the condos for sale in Casselberry, Winter Springs, and Tuscawilla today, and discover your dream home in this captivating Florida paradise!

Newest Casselberrry/Winter Springs / Tuscawilla Condos for Sale

$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
$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
$178,900
2 Beds ⋅ 2 Baths ⋅ Indian Ridge SubDv. ⋅ 32708 Zip Code
Virtually Staged. Enjoy life in this beautiful, recently renovated 2 bedroom, 2 bathroom patio home located in the beautiful Indian River community in Winter Springs. Welcome to a low maintenance lifestyle with the Condo Assn maintaining the lawn, sparkling community pool and clubhouse, tennis courts. This Central Florida location, near roads 434, 419 and 17/92, provides convenient access to the Winter Park restaurant and shopping district, other restaurants, shopping such as Publix, plus the Oviedo Mall and Advent Hospital. It is also only a 25 minute drive to the University of Central Florida and, so, is perfect for Faculty or Students! There are multiple parks in the area, such as Mount Greenwood Park and Big Tree Park, which host many activities throughout the year. The newly installed kitchen and freshly painted interior looks beautiful. One of the standout features of this home is the private outdoor space. The fenced patio area creates a comfortable spot for morning coffee....... ......container gardening, pets, outdoor dining, or relaxing at the end of the day. The included storage shed at 6 ft by 4 ft adds valuable functionality, offering extra space for tools, bikes, surfboards, or outdoor equipment. Indian River offers a peaceful residential setting known for its convenient access to parks, trails, shopping and dining. With its newly renovated interior, efficient 2-bedroom layout, private fenced outdoor space, storage shed, and desirable Winter Springs location, this condominium patio home offers comfort, convenience, and low-maintenance living in one of Seminole County's most appealing areas.

311 San Miguel Street Unit 311, 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
$140,000
1 Beds ⋅ 1 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Virtually Staged. Price improvement for the perfect starter home, investment opportunity or downsizing. Excellent condition! Not every condo feels like HOME the moment you walk in—but this one does. EXCELLENT CONDITION! Tucked beneath the canopy of mature oaks in The Highlands of Winter Springs, this beautifully UPDATED FIRST FLOOR ONE BEDROOM/ONE BATH condominium offers the perfect blend of comfort, convenience, and carefree Florida living. Forget carrying groceries upstairs or tackling weekend projects. This move-in ready home has ceramic tile flooring throughout the main living areas, new luxury vinyl in the bedroom, new appliances, updated lighting, modern ceiling fans, a new water heater - A/C system replaced in 2019. The bedroom features custom-built closet organizers that maximize storage, while two additional exterior storage closets provide room for bicycles, holiday décor, tools, and outdoor gear. In 2010 all interior elements of the building were replaced with new electric, plumbing, doors, windows and all drywall and studs. One of the home's best features is the oversized screened porch—a private outdoor living space where you can sip your morning coffee, read a book, or unwind at the end of the day while enjoying the peaceful, tree-lined setting that has made The Highlands one of Winter Springs' most beloved communities. Life here extends well beyond your front door. Residents enjoy miles of scenic walking and nature trails, a community pool, tennis courts, pickleball courts, clubhouse, playground, and beautifully landscaped common areas that encourage an active outdoor lifestyle. Whether you're taking an evening stroll beneath the oak trees, meeting neighbors for a game of pickleball, or spending the afternoon poolside, you'll quickly see why so many people love calling The Highlands home. Located in the heart of Winter Springs, you'll be just minutes from top-rated Seminole County schools, shopping, dining, medical facilities, parks, and major roadways including SR 434, SR 417, and US 17-92, making commuting to Orlando, Winter Park, Lake Mary, and the surrounding area simple and convenient. Whether you're searching for your first home, a winter retreat, an investment property, or an easy, low-maintenance lifestyle, this updated Winter Springs condo delivers exceptional value in a location that continues to be one of Central Florida's most desirable places to live.

220 Moree Loop Unit 2, Winter Springs
$199,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath condominium nestled in the highly desirable Highlands community of Winter Springs. Offering the perfect blend of comfort, style, and convenience, this move-in-ready home features an updated kitchen with granite countertops, stainless steel appliances, and ample cabinetry. The spacious floor plan is complemented by updated bathrooms, well-maintained interiors, and an inviting atmosphere throughout. Whether you're relaxing at home or hosting guests, you'll appreciate the thoughtful upgrades and pride of ownership evident in every room. Step outside and enjoy the exceptional resort-style amenities the community has to offer, including a sparkling pool, tennis and pickleball courts, scenic walking trails, playgrounds, and picturesque water views. The HOA provides added peace of mind by covering exterior maintenance, roof care, and common area upkeep, allowing for a low-maintenance lifestyle. Conveniently located near parks, shopping, dining, top-rated Seminole County schools, and major roadways, this home offers easy access to everything Central Florida has to offer. Don't miss this opportunity to enjoy resort-style living in one of Winter Springs' most sought-after communities!

429 Sheoah Boulevard Unit 9, Winter Springs
$165,000
2 Beds ⋅ 2 Baths ⋅ Indian Ridge SubDv. ⋅ 32708 Zip Code
Welcome to this freshly painted 2-bedroom, 2-bathroom condominium located in the desirable Deer Song community in Winter Springs. Offering a low-maintenance lifestyle in a convenient Central Florida location, this residence is a great fit for a first-time buyer, downsizer, seasonal resident, or investor looking for a well-positioned property with everyday comfort and community appeal. Inside, the home features a practical layout with 945 square feet of living space, offering comfortable living areas and a functional design that makes the most of the space. The freshly painted interior provides a clean, refreshed feel and gives the next owner a neutral starting point to make the home their own. With two bedrooms and two full bathrooms, the layout offers flexibility for guests, a home office setup, or shared living arrangements. One of the standout features of this home is the private outdoor space. The fenced patio area creates a comfortable spot for morning coffee, container gardening, pets, outdoor dining, or relaxing at the end of the day. The included storage shed adds valuable functionality, offering extra space for tools, bikes, seasonal items, or outdoor equipment. Deer Song offers a peaceful residential setting known for its established neighborhoods, mature surroundings, and convenient access to parks, trails, shopping, dining, and everyday essentials. The community is located near Winter Springs Town Center, Torcaso Park, the Cross Seminole Trail, Oviedo Mall, Publix, restaurants, and major roadways for easier commuting throughout Central Florida. With its freshly painted interior, efficient 2-bedroom layout, private fenced outdoor space, storage shed, and desirable Winter Springs location, this Deer Song condominium offers comfort, convenience, and low-maintenance living in one of Seminole County’s most appealing areas.

343 San Miguel Street Unit 343, Winter Springs
$167,777
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 1 SubDv. ⋅ 32708 Zip Code
WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy, with sliding doors from the primary suite leading to a charming brick patio, ideal for enjoying your morning coffee or unwinding in the evening. The kitchen has been beautifully renovated with new appliances, updated countertops, and ample workspace. The primary bathroom features a walk-in shower with safety grab bars, while the guest bathroom includes a tub, with a convenient laundry area located in the guest bath closet. A bright and airy enclosed Florida room with A/C provides flexible space for a home office, reading nook, or additional living area. Step outside to your private patio with room for outdoor furniture, plants, or even your own garden retreat, all overlooking a peaceful wooded conservation area. Additional highlights include approximately 1,196 square feet including the enclosed porch, a newer A/C and water heater, fresh interior paint in a modern light gray, and no carpet throughout. Located in The Highlands, a quiet and friendly community offering a pool, tennis courts, parks, walking trails, scenic water views, reserved parking, and community mailboxes. HOA fees include high-speed internet, cable, pest control, and full grounds maintenance, with weekly lawn care and twice-weekly trash pickup. The home is situated in a top-rated school district with schools nearby and is just minutes from shopping, dining, and everyday conveniences. Schedule your private showing today, this one won’t last long!

50 Sheoah Boulevard Unit 33, Winter Springs
$170,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
One or more photo(s) has been virtually staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute. Step inside to a bright, open-concept living and dining area featuring a wall of windows and two sets of triple sliding glass doors, filling the space with natural light and providing seamless access to a large screened balcony with peaceful garden views—perfect for relaxing or entertaining. The kitchen is well-equipped with stainless steel appliances, ample cabinet and countertop space, and easy-care tile flooring. The spacious primary suite offers a comfortable retreat, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Additional highlights include in-unit laundry and extra storage off the balcony. Residents of Baytree Village enjoy well-maintained amenities and close proximity to local parks, including Audubon Park just minutes away. Seller is willing to cover up to six (6) months of the buyer’s Homeowners Association (HOA) dues with an acceptable offer. Whether you're a first-time buyer, downsizing, or investing, this is an opportunity you won’t want to miss. Schedule your private showing today!

240 Moree Loop Unit 3, Winter Springs
$301,000
4 Beds ⋅ 3 Baths ⋅ Highland Patio Homes Amended Plat SubDv. ⋅ 32708 Zip Code
**Fannie Mae approved** Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and low-maintenance living. From the moment you arrive, you’ll appreciate the private courtyard entry—perfect for morning coffee or relaxing evenings, along with multiple outdoor spaces, including a screened-in porch and two fenced areas ideal for pets or gardening. Inside, the home features warm wood accents, soaring ceilings, and an abundance of natural light throughout. The updated kitchen is equipped with a gas double oven, modern appliances, pantry storage, and flows seamlessly into the main living areas. An interior laundry/utility room adds everyday convenience. Bathrooms have been tastefully renovated with updated vanities, tilework, and glass shower enclosures. Recent upgrades provide peace of mind, including re-piping, updated HVAC system, water heater, garage door, and energy-efficient windows and doors. Additional improvements include updated flooring, custom closet shelving, and enhanced finishes throughout the home. Located within The Highlands, residents enjoy a wide range of amenities, including a community pool, clubhouse, tennis courts, playgrounds, and miles of scenic walking trails and boardwalks. The HOA maintains exterior elements such as the roof, paint, and landscaping, allowing for easy, low-maintenance living

702 Glasgow Court, Winter Springs
$272,000
3 Beds ⋅ 2 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New roof (2023) •New AC (2016) •Washer/dryer (2026) •Primary bedroom with walk-in closet, en-suite, and balcony access •Split floor plan for privacy. Seize this opportunity to own a beautifully updated condo in a prime location! FHA Approved Condo complex.

600 Northern Way Unit 1608, Winter Springs
$274,900
3 Beds ⋅ 2 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this maintained 3-bedroom, 2-bathroom ground-floor condominium offering 1,425 square feet of comfortable, low-maintenance living in a desirable gated community in the heart of Tuscawilla, perfect for investors or those seeking a primary residence. Step inside to a FRESHLY painted inviting open floor plan highlighted by tile flooring throughout the main living areas, creating a seamless space for both everyday living and entertaining. The kitchen is thoughtfully designed with NEW stainless steel appliances, stone countertops, an eat-in dining area, and a convenient laundry closet nearby for added functionality. Privately situated at the rear of the home, the spacious primary suite offers a peaceful retreat complete with a walk-in closet, and a RENOVATED bathroom dual vanity sinks, and a standalone shower. Sliding glass doors provide direct access to your own private patio — the perfect spot to enjoy your morning coffee. Down a separate hallway, you’ll find two additional bedrooms and a guest bathroom featuring an updated vanity and a tub/shower combination, offering comfort and privacy for family or guests. The living area also opens through sliding doors to a covered rear lanai overlooking tranquil green space, creating an ideal setting for relaxing or entertaining outdoors. Residents enjoy access to a beautiful community pool and cabana, enhancing the ease of Florida living. Conveniently located by Trotwood Park, featuring a pavilion, playground, splash pad, tennis courts, and sports fields. The nearby Seminole County Cross Trail offers miles of scenic biking and walking paths. This exceptional condo combines comfort, convenience, and an unbeatable location — a wonderful opportunity to enjoy everything Tuscawilla has to offer.

600 Northern Way Unit 201, Winter Springs
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