Casselberrry/Winter Springs / Tuscawilla Homes under $750,000

Casselberrry/Winter Springs / Tuscawilla Homes under $750,000

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 lush landscapes, friendly neighborhoods, and an abundance of recreational opportunities, making it the perfect place to call home.

Winter Springs is a charming city that boasts a rich blend of suburban tranquility and urban convenience. With its picturesque parks, scenic trails, and a strong sense of community, residents enjoy an enviable lifestyle that prioritizes outdoor activities and family-friendly events. The nearby Tuscawilla community is particularly appealing, offering a golf course, serene lakes, and beautiful tree-lined streets, ideal for leisurely strolls or bike rides.

For those seeking their dream home, you'll be delighted to discover a variety of options available under $750,000. From modern single-family homes to cozy townhouses, the real estate market in this region caters to diverse tastes and budgets. Many of these homes feature spacious layouts, updated kitchens, and inviting backyards perfect for entertaining or simply unwinding after a long day.

Living in Casselberry, Winter Springs, and Tuscawilla means you’ll have access to top-rated schools, shopping centers, and dining options, all while being just a short drive from the vibrant attractions of Orlando. With its unique blend of natural beauty and suburban charm, this area is a hidden gem waiting for you to explore. Discover the perfect home for you and your family in this thriving community today!

Newest Casselberrry/Winter Springs / Tuscawilla Homes under $750,000

408 Lancers Drive, Winter Springs
$349,000
3 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 5 Of SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to this charming home in the Mount Greenwood community of desirable Winter Springs! Offering comfortable one-story living, this home combines a versatile layout with a fantastic Seminole County location surrounded by established neighborhoods, parks and recreation. Vaulted ceilings give the main living spaces an open, airy feel, while the split bedroom plan provides separation between the primary suite and secondary bedrooms. The living and dining area features French doors opening directly to the fenced backyard. The kitchen features a closet pantry and pendant lighting, with an adjacent dining area that keeps meals and gatherings conveniently close. Just off the kitchen, an indoor laundry room leads to a flex area that can be used as a breakfast nook, home office or sitting area. Prefer your breakfast nook toward the front of the home? The area to the left of the front door provides another option, leaving the flex space available for whatever best suits your needs. The primary suite includes a generously sized walk-in closet and its own bathroom with a tub and shower combination. The secondary bathroom also offers a tub and shower combination, and the additional bedrooms provide space for guests, a home office or hobbies. The Winter Springs location is another major plus, offering access to Seminole County public schools and plenty of ways to enjoy the outdoors. Spend time at Central Winds Park, explore the Cross Seminole Trail on foot or by bike, or enjoy the shopping and dining options throughout Winter Springs and neighboring communities. Access to State Road 434 and the 417 makes it convenient to connect with the greater Orlando area while enjoying an established residential setting. A two-car garage provides parking and storage, and the fenced backyard offers room to create your own outdoor gathering space, add a garden or simply relax at the end of the day. With flexible living spaces and so much to enjoy in the surrounding area, this home is ready for your personal touch. Come check out your future home today!!

408 Lancers Drive, Winter Springs
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
632 Tuskawilla Point Lane, Winter Springs
$574,900
4 Beds ⋅ 3 Baths ⋅ Tuskawilla Point SubDv. ⋅ 32708 Zip Code
BEAUTIFULLY RENOVATED POOL HOME IN TUSKAWILLA POINT! Welcome to 632 Tuskawilla Point Ln, a stunning 4-bedroom, 2.5-bath home offering approximately 1,917 square feet of thoughtfully updated living space in the heart of Winter Springs. Step inside to a bright, open-concept layout enhanced by soaring vaulted ceilings, an updated fireplace with warm wood accents, and a seamless connection between the kitchen, family room, and main living areas. The beautifully redesigned kitchen is the heart of the home, featuring a sophisticated mix of white and natural wood cabinetry, quartz countertops, modern black hardware and fixtures, stainless steel appliances, updated lighting, and a spacious peninsula perfect for everyday living and entertaining. The bathrooms have been refreshed with modern tile, updated vanities, contemporary fixtures, and cohesive finishes throughout. A conveniently located half bath near the pool area makes entertaining even easier while helping keep wet feet out of the main living spaces. Step outside and discover your own private Florida retreat. The screened in-ground pool, covered outdoor living area, and fenced backyard provide the perfect setting for weekend gatherings, morning coffee, or relaxing poolside while enjoying Florida's year-round sunshine. Additional improvements include professionally cleaned A/C ductwork, adding to the attention given to both the visible finishes and the home's everyday comfort. Located in established Tuskawilla Point, this home offers convenient access to shopping, dining, recreation, schools, and major roadways while maintaining the feel of an established residential neighborhood. More than a cosmetic remodel, this is a beautifully updated, move-in-ready pool home where style, functionality, and Florida living come together. The renovation is complete. The pool is ready. All that's missing is you. Schedule your private showing and experience 632 Tuskawilla Point Ln for yourself!

632 Tuskawilla Point 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
4038 Biscayne Drive, Winter Springs
$525,000
4 Beds ⋅ 3 Baths ⋅ Hollowbrook SubDv. ⋅ 32708 Zip Code
Welcome to 4038 Biscayne Drive, a warm and inviting pool home on a corner lot spanning more than a quarter acre in the heart of Winter Springs. Thoughtfully cared for and filled with character, this home offers a comfortable layout with inviting spaces designed for both everyday living and entertaining. Step through the foyer, where a beadboard accent wall and built-in credenza immediately set the tone for the home's thoughtful details. To the left, the cozy living room flows naturally into the dining room. At the center of the home, the spacious kitchen features updated stainless steel appliances and a layout that places it perfectly at the heart of the action. Just beyond, the family room welcomes you with vaulted ceilings, an electric fireplace, built-in bench seating perfect for settling in with a book, and sliding doors overlooking the pool and backyard. A convenient half bath is located just off the foyer, while a nearby nook offers the opportunity to bring the washer and dryer inside from their current location along the opposite wall of the garage. The primary suite is a peaceful retreat with high ceilings and abundant natural light. A split-bedroom layout provides privacy from the additional bedrooms upstairs. Through a barn door, the updated primary bath blends timeless details with practical comfort, featuring a vintage dresser-style vanity, large walk-in shower with subway tile and built-in bench, brass fixtures, large-format floor tile, a generous walk-in closet, and a private water closet. Upstairs, three additional bedrooms share a full bathroom, with two bedrooms offering walk-in closets. Additional attic storage is easily accessible, providing valuable space for the things you don't need every day. Throughout the home, shiplap, board-and-batten and beadboard accent walls, updated lighting and decorative sconces add warmth and character. Outside, the oversized backyard is where this property truly comes to life. The screened pool enclosure creates a private outdoor retreat with a covered awning for dining, a separate seating area, plenty of room for kids to play and dogs to run, and space for gardening and landscaping projects. The corner-lot setting adds to the sense of space and privacy. Located in Winter Springs, this home offers convenient access to Red Bug Lake Road, SR 434, 417, Tuskawilla Road, parks, restaurants, shopping, and highly regarded Seminole County schools. The neighborhood setting provides a comfortable residential feel while keeping everyday conveniences and major roadways close at hand. The oversized garage comfortably accommodates two vehicles while leaving ample room for additional storage. Major updates include a 2020 roof, 2025 HVAC system, 2025 water heater, and PEX plumbing allowing you to enjoy the home's character with some of the big-ticket items already addressed. This is a home that has been genuinely loved and thoughtfully cared for. Now, it is ready for its next stewards to make it their own and begin the next chapter in a wonderful Winter Springs setting.

4038 Biscayne Drive, 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
734 Seneca Meadows Road, Winter Springs
$520,000
4 Beds ⋅ 2 Baths ⋅ Parkstone Unit 3 SubDv. ⋅ 32708 Zip Code
Beautifully updated, thoughtfully designed, and surrounded by mature landscaping, this single-story home offers the space, flexibility, and finishes that make everyday living feel effortless. From the welcoming front porch and sitting area to the private, fenced backyard, this gorgeous updated home has been designed to enjoy both indoors and out. Inside, the 4-bedroom, 2-bath floor plan features a desirable three-way split, providing wonderful separation between the large primary suite and 3 additional bedrooms. An additional large office with French doors adds even more versatility and could easily serve as an additional guest room, den, fitness space, or creative retreat. At the heart of the home is a completely remodeled kitchen that feels fresh, current, and ready to be enjoyed. Quartz countertops pair beautifully with a stylish new backsplash, newer appliances, updated finishes, and new luxury vinyl flooring that continues throughout most of the home, creating a cohesive and polished look. The open layout allows the kitchen to remain connected to the main living spaces, making it equally suited for quiet evenings at home or a house full of guests. The primary suite is a true retreat, complete with a spacious walk-in closet and glass sliding doors that provide direct access to the enclosed porch. Take in the recently remodeled en-suite bath that's been transformed into a spa-inspired space featuring dual vanities, a separate soaking tub, and a glass-enclosed tiled shower with two shower heads. The enclosed porch expands the home’s living space even further and has been updated with its own mini-split A/C system, creating a comfortable spot to relax throughout the year. Step outside to a fully fenced backyard with a generous pavered sitting area—the perfect setting for weekend grilling, outdoor dining, evening cocktails, or gathering with friends under the Florida sky. Many updates to this home will give you ease including, H/W HEATER 2019, ROOF 2021, CARPETS 2021, EXTERIOR PAINT 2023, UPDATED PRIMARY BATH 2025, LUXURY VINYL FLOORING 2025, REMODELED KITCHEN 2026, NEW GARAGE DOOR MOTOR Beautiful landscaping enhances both the front and backyard, while the front porch offers its own inviting sitting area for enjoying a morning cup of coffee or winding down at the end of the day. Located within a gated community, the HOA includes lawn maintenance, giving you more time to enjoy the neighborhood amenities, including a community pool and tennis courts. Walking trails are easily accessible, and nearby Central Winds Park provides an exceptional setting for recreation and many of Winter Springs’ favorite community events. With its remodeled kitchen and primary bath, flexible three-way split floor plan, dedicated office, multiple indoor and outdoor living spaces, and convenient location, 734 Seneca Meadows Road offers a home that has already been thoughtfully updated—leaving more time to simply move in and enjoy it.

734 Seneca Meadows 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
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