Casselberrry/Winter Springs / Tuscawilla Homes under $500,000

Casselberrry/Winter Springs / Tuscawilla Homes under $500,000

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area boasts a unique blend of suburban charm and natural beauty, making it an ideal destination for families, retirees, and everyone in between. With its lush landscapes, scenic parks, and a strong sense of community, it’s no wonder that this region is a sought-after place to call home.

Winter Springs is particularly known for its welcoming neighborhoods and excellent schools, providing a nurturing environment for families. The nearby Tuscawilla community offers a touch of elegance with its golf courses and serene lakes, perfect for outdoor enthusiasts and those seeking a peaceful retreat. Casselberry adds to the allure with its beautiful parks, shopping centers, and cultural attractions, creating a well-rounded lifestyle for residents.

For those looking to invest in a home within this delightful area, you’ll be pleased to discover a variety of charming properties available for under $500,000. Whether you’re searching for a cozy single-family home, a modern townhouse, or a spacious condo, the options are plentiful and diverse. Many of these homes feature inviting layouts, updated amenities, and access to community features such as pools, playgrounds, and walking trails.

Embrace the opportunity to live in a region that perfectly marries convenience with tranquility. With its rich community spirit, abundant recreational activities, and affordable housing options, Casselberry, Winter Springs, and Tuscawilla invite you to explore the possibilities of your new home sweet home!

Newest Casselberrry/Winter Springs / Tuscawilla Homes under $500,000

615 Pearl Road, Winter Springs
$350,000
3 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 08 SubDv. ⋅ 32708 Zip Code
Welcome to 615 Pearl Road, a well-loved Winter Springs home ready for its next chapter! Owned by the original family and set on a spacious quarter-acre lot, this three-bedroom, two-bath home offers a wonderful opportunity to bring your own style and make it truly yours. Inside, the comfortable floor plan provides plenty of room to spread out, with a formal living room, formal dining room and additional living space for everyday gathering and entertaining. The two-car garage adds convenient parking and storage, while out back, a large screened porch creates the perfect place for morning coffee, weekend gatherings or simply relaxing while overlooking the beautiful fenced backyard. With plenty of room for pets, play, gardening, outdoor entertaining or creating the backyard you have always envisioned, this outdoor space is one of the home’s standout features. Major updates include a 2019 roof and 2024 AC, offering a great starting point as you add your own finishing touches. Conveniently located near Central Winds Park, Ranchlands Park, Publix, Aldi and everyday shopping and dining, this home combines an established Winter Springs location with space, potential and a backyard that is becoming harder to find. Whether you are searching for your first home, your next home or a property you can personalize over time, 615 Pearl Road is ready to welcome its next owners.

615 Pearl Road, Winter Springs
1436 Winter Wharf Lane, Winter Springs
$399,000
3 Beds ⋅ 4 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to easy, stylish living in Jesup’s Landing, one of Winter Springs’ most desirable communities. This spacious 3 Bedroom, 3 1/2 Bath Townhome features a versatile split-level design that creates a comfortable sense of separation between living areas while still offering plenty of room to gather and entertain. The beautifully appointed kitchen features 42-inch cherry cabinetry, granite countertops, and a spacious prep island, creating an inviting and functional space for cooking, baking, and entertaining. Upstairs, the primary suite offers a generous bedroom, a spacious walk-in closet, and a well-designed primary bath with a double-sink vanity, separate shower, and soaking tub. A second upstairs bedroom also features its own en-suite bath with a walk-in shower and a large walk-in closet, providing added privacy and convenience. The lower level includes an additional secondary bedroom with its own en-suite shower bath, along with access to the two-car garage and extra storage space. New Carpet in the Bedrooms and Stairways was just installed for a MOVE-IN READY transition for the new Owner. The exterior has also been refreshed with New Paint, New Screen on Balcony and the home features a New Roof for added value and peace of mind. The location offers exceptional convenience with Central Winds Park, shopping, dining, SR 417, Orlando Sanford International Airport, UCF, and Seminole State College all within easy reach. Jesup’s Landing residents enjoy a variety of community amenities, including a clubhouse, fitness center, and inviting swimming pool. With its spacious floor plan, recent updates, convenient location, and low-maintenance lifestyle, this home offers a wonderful opportunity to enjoy all that Winter Springs has to offer. ROOF - 2026, A/C and Water Heater - 2014.

1436 Winter Wharf Lane, Winter Springs
672 Nighthawk Circle, Winter Springs
$340,000
2 Beds ⋅ 2 Baths ⋅ Greenspointe SubDv. ⋅ 32708 Zip Code
Welcome to 672 Nighthawk Circle, where a beautifully updated interior, NO REAR NEIGHBORS, and a serene, tree-lined setting come together in Winter Springs’ Greenspointe subdivision! This 2-bedroom, 2-bathroom home offers 1,560 square feet of living space, a 2-car garage, and access to the extensive amenities of the Highlands community. Thoughtful improvements include a remodeled kitchen in 2022, a complete plumbing repipe in 2024, bathroom updates in 2026, a water heater replaced in 2021, and exterior painting and fascia repairs completed in 2026. The kitchen is a standout, featuring granite countertops, white cabinetry with crown molding, stainless steel appliances, a subway tile backsplash, recessed lighting, and a wide peninsula overlooking the adjoining living space. A touch-activated faucet and instant hot water dispenser add everyday convenience, while generous cabinetry and counter space provide plenty of room for meal preparation and storage. Luxury vinyl plank flooring extends through the kitchen and dining area, creating a cohesive look that complements the home’s light, neutral finishes. Vaulted ceilings and abundant natural light give the main living areas an open, airy feel, with room to gather, entertain, or simply enjoy the peaceful surroundings. The kitchen’s connection to the living space keeps everyone part of the conversation, while windows overlooking the greenery bring the outdoor setting into view. Both bedrooms feature engineered hardwood flooring. The spacious primary suite includes an updated bathroom with a dual-sink vanity, a soaking tub beneath a large window, and a separate shower. The second bathroom also features recent updates, including a vanity top and faucet. An indoor laundry room, improved in 2023, offers additional cabinetry, counter space, and a tile backsplash, making this hardworking space both practical and attractive. Updated lighting, ceiling fans, and select smart switches add to the improvements throughout the home. Step outside to the covered, screened porch and enjoy a quiet spot for morning coffee or unwinding at the end of the day. An adjoining patio provides additional outdoor seating space, surrounded by mature trees and lush foliage. With no rear neighbors, the backyard offers a wonderfully private atmosphere. The home’s elevated position and established landscaping create a tucked-away feel near the entrance to Greenspointe, a neighborhood distinguished by its tile-roofed homes and mature landscape. As part of the Highlands community, residents enjoy access to a community pool, tennis courts, playground, Audubon Park, a nature trail, and a waterfront park. Whether you prefer a swim, a game of tennis, or time outdoors exploring the neighborhood, there is plenty to enjoy close to home. The property is served by Seminole County schools, including Highlands Elementary, South Seminole Middle, and Winter Springs High. With substantial updates, comfortable single-story living, a private backyard setting, and an impressive collection of community amenities, this Greenspointe home offers a compelling opportunity in Winter Springs. Schedule your private showing today!

672 Nighthawk Circle, Winter Springs
711 Thistle Place, Winter Springs
$284,900
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Welcome to Wildwood! This three-bedroom, two-bath home features ceramic tile flooring throughout, newer windows, siding and water heater, roof replaced in 2016. Enjoy the private, fenced backyard and spacious screened porch—perfect for relaxing or entertaining. This move-in-ready home offers plenty of potential to add your personal touches. The centrally located close to shopping and schools. The community features a pool, playground, tennis courts, and park. Call today for more details or to schedule your private showing.

711 Thistle Place, Winter Springs
725 Adidas Road, Winter Springs
$365,000
2 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code
Enjoy peaceful pond views from this 2-bedroom, 2-bath Winter Springs home that blends thoughtful updates with genuine character. Exposed wood beams and a fireplace anchor the living room, while the kitchen was renovated in 2021 with butcher block counters and new wood cabinetry. New exterior paint in September 2026! The home was fully repiped in 2024, and the primary bath features an updated shower. The enclosed porch, cooled by its own mini-split AC, adds flexible space for a home office, reading nook, or entertaining. Step outside to a 14' x 14' brick paver patio overlooking the pond. Conveniently located near Trotwood Park, Seminole County schools, and SR 417, making it easy to get anywhere in Central Florida. Schedule your showing today!

725 Adidas Road, Winter Springs
1024 Dinero Drive, Winter Springs
$394,900
3 Beds ⋅ 2 Baths ⋅ Sunrise Estates Unit 2 SubDv. ⋅ 32708 Zip Code
Welcome to one of the best-priced pool homes in Winter Springs! Sitting directly across from an oak-shaded park, playground, and scenic pond, this light-filled 3-bedroom, 2-bathroom pool home with a 2-car garage delivers the ultimate Florida lifestyle from the very moment you pull into the driveway. Step through the welcoming front door into an open-concept layout packed with natural light, soaring vaulted ceilings, and warm, durable floors that run throughout the main living areas. The front dining space features a charming picture window seat overlooking the park across the street—a sunny spot to sip your morning coffee before flowing straight into an expansive family room built for relaxing or hosting around the classic stone wood-burning fireplace. If you love to cook or entertain, this kitchen is ready for you. It features crisp cabinetry with plenty of deep, ample storage for all your kitchen gadgets and pantry items, paired with rich granite countertops and modern electric appliances. Recessed lighting keeps the space bright, while a gooseneck faucet over the sink looks out a big picture window toward the screened patio. Dual pass-through counter cutouts connect the kitchen directly to both the dining space and living room, so you can easily chat with family or hand off snacks while keeping the energy open and social. Tucked behind a stylish sliding barn door, the primary suite feels like its own quiet retreat with high ceilings, a double-sink granite vanity, a walk-in closet with built-in wire shelving, and a tiled step-in shower with a rain showerhead. For ultimate convenience on pool days, a private exterior door right in the primary bathroom leads straight out to the pool deck so no one ever tracks wet feet through the house. The secondary bedrooms offer wonderful flexibility for whatever your lifestyle needs. Whether you picture them as future kids' rooms, a cozy nursery, a dedicated home office, a hobby space, or a welcoming guest room, there’s plenty of room to grow. One room comes already styled with a cheerful, sunlit wall mural that kids or guests will love, while both rooms enjoy plush finishes, built-in recessed lighting, and bright windows. Nearby, the updated second full bath features a crisp vanity and a tiled step-in shower with a flexible handheld sprayer. Step out back and your personal backyard paradise takes center stage. The deep covered screened patio is complete with a ceiling fan to keep things cool, opening up to a wide concrete pool deck and a sparkling private chlorine pool with an attached heated spa. Surrounding the pool is a fully wood-fenced yard with raised stone garden beds, tropical plants, a hammock nook, and plenty of grassy lawn for pets or play. Practical updates give you total peace of mind, including a roof replaced in 2021, a pool/spa heater replaced in 2020, an attached 2-car garage with laundry space, and a handy garden shed in the backyard that stays if you'd like. It’s an incredible home in a friendly, beautiful location that's ready to welcome you!

1024 Dinero Drive, Winter Springs
855 Benchwood Drive, Winter Springs
$499,000
4 Beds ⋅ 3 Baths ⋅ Oak Forest Unit 3 SubDv. ⋅ 32708 Zip Code
**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.** Welcome to 855 Benchwood Drive in Winter Springs, a spacious 4-bedroom, 3-bathroom home situated in the established Oak Forest community. Offering approximately 2,268 square feet of living space, the home features an open floor plan designed to bring the main gathering areas together while providing flexibility for everyday living and entertaining. One of the four bedrooms is currently used as a home office, creating a dedicated workspace that can easily adapt to other needs. The interior offers generous living areas filled with natural light, along with a functional connection between the kitchen, dining, and main living spaces. The bedrooms provide plenty of room for family and guests, while three full bathrooms add convenience throughout the home. The flexible office can also serve as a guest room, hobby space, or additional bedroom as needed. Outside, the backyard is designed for enjoying the Florida lifestyle with a private in-ground pool and spa, surrounded by an expansive pool deck with plenty of space for lounging and entertaining. A covered patio provides a shaded area for outdoor dining and relaxing, while mature landscaping adds character to the outdoor setting. Public listing records also note the property sits on approximately 0.37 acre, providing additional yard space around the outdoor living areas. Located in Oak Forest, the home is close to neighborhood recreation, including Trotwood Park, as well as shopping, dining, and everyday conveniences throughout Winter Springs. The location also provides convenient access to Tuskawilla Road, SR 434, SR 417, and I-4, making surrounding Seminole County and Greater Orlando destinations easily accessible.

855 Benchwood Drive, Winter Springs
1120 Dappled Elm Ln Lane, Winter Springs
$419,900
3 Beds ⋅ 2 Baths ⋅ Wedgewood Unit 3 SubDv. ⋅ 32708 Zip Code
LOCATION! LOCATION! LOCATION! Perfectly maintained Move-In ready home is situated on a quite cul-de sac in the Wedgewood Golf Villas in Tuscawilla. Top rated golf course in the area! Home contains 3-bedrooms, 2-full baths, open floor plan with attached 2 car garage with workbench Covered breezeway is located between the home and garage for additional area to relax. Living and dining areas under beautiful, vaulted wood ceilings with rock faced fireplace. Large back screened patio overlooks the nicely appointed garden area. Large open kitchen / dinette area with sliding door leading to front porch. Offers a comfortable layout with sliding glass door leading out to private patio courtyards from all three bedrooms as well as the dining room. Primary bedroom contains a large a walk in closest. ROOF IS 2018 / KITCHEN APPLIANCES UPDATED IN 2017. Washer and Dryer included. Very convenient location in Tuscawilla / Winter Springs area close to golf courses, shopping, hospitals, restaurants, county and state parks. 30 - 45 minutes to UCF, Rollins College, International airport, downtown Orlando, Winter Park and Sanford. 1 hour to the Atlantic beaches. Call today to schedule your tour!

1120 Dappled Elm Ln Lane, Winter Springs
131 Kristi Ann Court, Winter Springs
$206,999
2 Beds ⋅ 2 Baths ⋅ Moss Cove SubDv. ⋅ 32708 Zip Code
Welcome to this charming 2-bedroom, 1.5-bath townhome in the established Moss Cove community of Winter Springs! Offering 898 square feet of comfortable living space, this two-story home features a functional open living and dining area, easy-care luxury vinyl flooring, and plenty of natural light. The kitchen offers ample cabinet and counter space along with a full appliance package, while both bedrooms are privately located upstairs. Step outside to the covered and screened rear porch—a great spot for morning coffee, relaxing at the end of the day, or simply enjoying the peaceful green surroundings. The home also features an enclosed front porch, interior laundry closet, ceiling fans, central A/C, and no rear neighbor immediately behind the screened porch. Association fees include exterior and grounds maintenance, helping make this an appealing low-maintenance option for homeowners. Conveniently located in Winter Springs with easy access to SR-434, shopping, dining, schools and major Central Florida roadways. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this affordable Moss Cove townhome offers plenty of potential and is ready for its next chapter!

131 Kristi Ann Court, Winter Springs
45 Hayes Road, Winter Springs
$465,000
3 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 02a SubDv. ⋅ 32708 Zip Code
Picture coming home to more than a third of an acre in Winter Springs, where the trees are tall and the pace slows the moment you arrive. At its heart is a beautifully renovated kitchen, designed for slow Sunday breakfasts, weeknight dinners that turn into long conversations, and gatherings that naturally drift toward the counter. All three bedrooms are upstairs, apart from the main living areas, so evenings downstairs stay lively while rest upstairs stays peaceful. Some of the most valuable upgrades are the ones you never have to think about. The roof was replaced in 2023, so you can settle in with confidence. The oversized two-car garage has room for vehicles, storage, a workshop, or the home gym you've been planning. Outside, the generous lot is a rare find in this area. There's room for a garden, play, a future pool, or simply quiet mornings with nothing but the sound of the trees. Everyday conveniences, top-rated Seminole County living, and easy access to the greater Orlando area are all close at hand.This is the kind of home that doesn't just fit your life. It makes room for the one you're building. Connect with us to learn about our preferred lender incentives, and let us help make your move to Winter Springs both elevated and effortless.

45 Hayes Road, Winter Springs
728 Ridgewood Way, Winter Springs
$275,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Set within the established Wildwood community of Winter Springs, this near 1,400-square-foot townhome offers two features that are especially hard to find, a single-story layout and a two-car garage. Add in recent updates that bring real peace of mind, and the result is easy, comfortable living from the moment of arrival. Luxury vinyl plank flooring flows throughout the home, with tile in the kitchen, creating a clean, cohesive look from room to room. At the heart of the living room, a wood-burning fireplace with a natural coquina surround adds warmth and a distinctly Florida sense of character, making the space as inviting on a cool winter evening as it is for everyday gatherings. The dining area opens to the kitchen for a natural, connected flow, and extends outdoors to a covered, screened patio well suited to morning coffee, casual meals or simply enjoying the fresh air without the bugs. The oversized primary bedroom serves as a retreat, featuring a walk-in closet, an en-suite bath and direct access to a rear open patio for a quiet moment outside. Two additional bedrooms and a second full bath provide flexibility for family, guests, a home office or hobby space. The attached two-car garage adds everyday convenience along with valuable room for storage, a workshop area or simply keeping vehicles protected from the Florida sun and rain. Residents of Wildwood enjoy access to a community park, playground, swimming pool and tennis courts, offering plenty of opportunities for recreation close to home. Important recent updates include a 2019 HVAC system and a 2023 roof, two of the most significant investments in any home already taken care of. With the ease of single-story living, the rare advantage of a two-car garage and major systems recently addressed, this townhome is an easy choice in a well-located Seminole County neighborhood.

728 Ridgewood Way, Winter Springs
700 Castlewood Drive, Winter Springs
$275,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Set within the established Wildwood community of Winter Springs, this nearly 1,400-square-foot townhome offers two features that are especially hard to find, a single-story layout and a two-car garage. Tile flooring flows throughout the home, creating a clean, cohesive look from room to room that is durable and easy to maintain. The living room offers a comfortable, welcoming space for relaxing or gathering with friends. The dining area opens to the kitchen for a natural, connected flow, and extends outdoors to a covered, screened patio well suited to morning coffee, casual meals or simply enjoying fresh air without bugs. The oversized primary bedroom serves as a retreat, featuring a walk-in closet, an en-suite bath and direct access to a private covered lanai for a quiet moment outside. Two additional bedrooms and a second full bath provide flexibility for family, guests, a home office or hobby space. The attached two-car garage adds everyday convenience along with valuable room for storage, a workshop area or simply keeping vehicles protected from the Florida sun and rain. Residents of Wildwood enjoy access to a community park, playground, swimming pool and tennis courts, offering plenty of opportunities for recreation close to home. A newer HVAC system adds to the home's appeal. With the ease of single-story living and the rare advantage of a two-car garage, this townhome is an easy choice in a well-located Seminole County neighborhood.

700 Castlewood Drive, Winter Springs
Start Your Search