Winter Springs Real Estate

Winter Springs Real Estate

Welcome to Winter Springs, Florida—a hidden gem nestled in the heart of Seminole County. Known for its picturesque landscapes and friendly community, Winter Springs offers a unique blend of suburban charm and natural beauty, making it an ideal place to call home.

This vibrant city is characterized by its lush parks, scenic trails, and sparkling lakes, providing residents with ample opportunities for outdoor activities. The 600-acre Central Winds Park is a local favorite, featuring sports fields, playgrounds, and walking paths that wind through beautiful greenery. For those who enjoy a leisurely stroll, the Cross Seminole Trail offers miles of paved paths perfect for biking, jogging, or simply enjoying the Florida sunshine.

Winter Springs boasts a strong sense of community, with various annual events that bring residents together, including the popular Winter Springs Festival of the Arts and the Winter Springs Farmers Market. The city's commitment to family-friendly living is evident in its top-rated schools and safe neighborhoods, making it an attractive choice for families and professionals alike.

Centrally located, Winter Springs provides easy access to major highways, allowing for a quick commute to nearby cities like Orlando and Sanford. With a diverse range of housing options—from charming single-family homes to modern townhouses—there’s something for everyone in this welcoming community.

Whether you’re exploring the local dining scene, enjoying the vibrant arts culture, or simply taking in the stunning natural surroundings, Winter Springs offers a quality of life that is hard to beat. Discover the magic of Winter Springs, where your dream home awaits!

Newest Listings in Winter Springs

733 Lakeview Drive, Winter Springs
$365,000
3 Beds ⋅ 2 Baths ⋅ O6450539 MLS
Fresh interior paint and partial new flooring. Well-maintained 3-bedroom, 2-bath single-story home in Winter Springs with 1,597 sq ft of living space. The open layout offers a living room, family room, and separate dining area, plus a private primary suite with walk-in closet. Located on a quiet street near Winter Springs schools, parks, and shopping. Sold as-is. Opendoor Property Trust I. Please submit offers via opendoor.com/makeoffer. Include buyer-executed Opendoor addendum and Affiliated Business Disclosure.

733 Lakeview Drive, Winter Springs
417 Holly Court, Winter Springs
$380,000
3 Beds ⋅ 2 Baths ⋅ O6449688 MLS
It's always so refreshing when all the hard work is already done for you! Tucked away on a quiet cul-de-sac in one of Winter Springs' established communities, this 3-bedroom, 2-bath POOL home offers an inviting blend of comfort, privacy, and Florida living at its finest. And the best part? NO HOA! Step inside to discover a welcoming home with thoughtful updates including luxury vinyl plank flooring in all bedrooms and neutral tile in the spacious main living areas. The updated kitchen features newer stainless steel appliances, an oversized butcher block island with plenty of storage and 42 inch solid wood cabinetry for the discerning buyer. Soaring ceilings in the living room, dining and kitchen accentuate the open feel as soon as you walk through the freshly painted front door. Split bedroom floor plan allows privacy for all family members including the serene Primary bedroom with en-suite bath and walk-in closet featuring custom closet design. Two additional large bedrooms with built in closets allow room for the family to spread out or guests to stay for a visit. But the real showstopper is waiting out back! Step into your own private Florida retreat, where a MASSIVE SCREENED in swimming POOL takes center stage, surrounded by lush landscaping and a spacious backyard designed for enjoying the outdoors. Whether you're cooling off in the pool, hosting weekend barbecues, or gathering around the firepit under the stars, this outdoor space delivers the kind of lifestyle that makes Florida living so special. A solar pool water heater adds to the appeal, while a pool pump replaced in 2022 offers another valuable improvement. The backyard also features a storage shed, freshly painted in 2024 to complement the home's updated exterior and garden boxes with additional dedicated irrigation. And there's plenty more to appreciate! A NEW ROOF IN 2025, FRESH EXTERIOR PAINT in 2024, and a NEW VINYL PRIVACY FENCE installed in 2023 and AC 2022 are just a few of the improvements already completed. In 2026, the ELECTRICAL PANEL was replaced and an EV CHARGER OUTLET added, providing a practical upgrade for today's needs. Need a WASHER AND DRYER....those stay too. Even the irrigation system has its own dedicated water meter, separate from the home's main meter, which can help reduce water costs. Located in this tucked away, desirable area of Winter Springs, this peaceful, updated property offers the freedom of NO HOA restrictions, a quiet cul-de-sac setting, and convenient access to shopping, dining, parks, and major roadways. This is the Florida lifestyle you've been looking for!

417 Holly Court, Winter Springs
1352 Casa Park Circle, Winter Springs
$245,000
2 Beds ⋅ 3 Baths ⋅ O6449586 MLS ⋅ Na BLDG.
Completely updated and move-in ready townhome in the desirable Casa Park Villas community of Winter Springs! Located directly across from Trotwood Park and zoned for top-rated Seminole County schools, this beautifully maintained 2-bedroom, 2.5-bath home offers extensive upgrades throughout. Major improvements include a new AC (2023), complete whole-house repipe (2023), hurricane-rated double-pane argon gas Low-E windows throughout (2025), and a new double-pane argon gas sliding glass door with built-in blinds (2025). The remodeled kitchen features an oversized white quartz countertop, updated cabinetry, custom backsplash, and new dishwasher, refrigerator, and microwave (2025). The first floor showcases newly updated neutral tile flooring, while the staircase has been enhanced with an updated wrought iron railing. Upstairs features luxury vinyl plank flooring throughout, updated bathroom vanities, new toilets, and a beautifully renovated primary bathroom. Additional upgrades include a new front door with decorative glass, new front landscaping, redesigned backyard with iron fencing, Tesla charging station with outdoor lock box, and fiber internet wiring to the upper level. Enjoy a private patio overlooking green space and access to community amenities including a pool, spa, and sauna. Conveniently located near Winter Springs Town Center, SR-417, shopping, dining, UCF, and recreation. This is a rare opportunity to own one of the most extensively updated homes in Casa Park Villas.

1352 Casa Park Circle, Winter Springs
1519 Woodsglen Drive, Winter Springs
$440,000
3 Beds ⋅ 2 Baths ⋅ O6449065 MLS
Welcome to this charming 3-bedroom, 2-bath home in the sought-after Fox Glen neighborhood at Chelsea Parc in Tuscawilla. With 1,701 square feet, a split floor plan, and low monthly dues that cover lawn maintenance plus access to a community pool, fitness area, and clubhouse, it offers easy living in a well-kept Seminole County setting close to parks, highly regarded schools, and major highways. A paved driveway and walkway lead to a new glass front door. Inside, tile runs through the main living areas, while the bedrooms feature engineered wood floors. High ceilings, a transom window, and views to the backyard keep the living and dining space light, bright, and open. Built-in shelves add practical storage, and French doors with built-in blinds open to a screened, covered porch with a ceiling fan. The updated kitchen includes refreshed cabinets, Corian counters, and stainless steel appliances. A small breakfast bar with pendant lighting sits beside an eat-in area with plantation shutters and windows overlooking the backyard. The primary suite has a large walk-in closet with built-in shelving and an updated en-suite bath with a walk-in shower finished in attractive tile, a dual-sink vanity with a makeup desk area, quartz counters, updated lighting and mirrors, and a separate linen cabinet. Both secondary bedrooms are comfortably sized, with ceiling fans and engineered wood floors. One has a standard closet; the other has French doors and a small walk-in closet and could easily serve as a den. The second full bath offers a tub/shower combination, granite vanity counters, and updated mirror and lighting. The private backyard is enclosed by a white picket fence. An indoor laundry room includes a closet, built-in cabinets, and a washer and dryer. The two-car garage has pull-down stairs to the attic, and the roof was replaced this year. Move-in ready and low-maintenance, this home blends updated finishes with the convenience of a cared-for Tuscawilla community.

1519 Woodsglen Drive, Winter Springs
1496 Wescott Loop, Winter Springs
$669,900
4 Beds ⋅ 3 Baths ⋅ TB8558088 MLS
Virtually Staged. Welcome to this stunning 4-bedroom, 3-bathroom home nestled in the gated community of Barrington Estates! A dedicated office or study room greets you at the entrance, perfect for working from home. The kitchen features brand new quartz countertops, a center island, and a breakfast bar that opens seamlessly to the living room — ideal for everyday living and entertaining. The primary suite is a true retreat, complete with a sitting area, separate closets, dual sinks, a garden tub, and a walk-in shower with dual shower heads. Vinyl flooring flows throughout the home. Upstairs, a large bonus room with a closet offers endless possibilities as a second family room, media room, or additional office. Step outside to a covered patio overlooking a spacious, grassy backyard — perfect for relaxing or entertaining. Barrington Estates offers a peaceful, tree-lined setting with a private gated entrance and community playground. Ideally located just off SR-434, this home is less than 20 minutes from UCF, Research Park, and an abundance of shopping and dining options. Don’t miss out on this move-in ready home!

1496 Wescott Loop, Winter Springs
1008 Forest Circle, Winter Springs
$559,000
3 Beds ⋅ 2 Baths ⋅ O6449425 MLS
Beautifully maintained and extensively renovated, this three-bedroom, two-bath home in the desirable Tuscawilla community reflects the pride of ownership of the same owners for over 22 years. A recent renovation and addition enhance the home, while a newer roof and two newer AC units offer added value. The inviting eat-in kitchen features beautiful custom cabinetry and granite countertops, complemented by wood-look plank tile flooring. The primary suite boasts an oversized walk-in closet with a built-in storage system and a spacious walk-in shower. A mature oak tree adds charm to the front yard, while the oversized screened porch and open pool deck in the rear provide plenty of space for relaxing and entertaining. A wonderful opportunity to enjoy a thoughtfully updated home in an established community.

1008 Forest Circle, Winter Springs
609 Viana Court, Winter Springs
$925,000
5 Beds ⋅ 4 Baths ⋅ O6449245 MLS
Space, privacy, and exceptional features define this impressive 5-bedroom, 3.5-bath POOL HOME in the GATED Seville Chase community of Winter Springs! Situated on a generous .67-ACRE CORNER LOT in a quiet CUL-DE-SAC, this estate-style home offers over 3,500 SQUARE FEET of thoughtfully designed living space, a ***FULLY PAID OFF TESLA SOLAR SYSTEM with FOUR POWERWALLS*** - leaving this large home virtually free of any electric bill, and a private backyard retreat. Major improvements include UPDATED A/C’s (2021 & 2026), and a hybrid water heater (2019). The heated SALTWATER POOL & SPA were resurfaced with PebbleTec in 2019, along with a new pool pump. Beautiful curb appeal welcomes you with mature landscaping, ample parking in the paver driveway, and a side-entry 3-CAR GARAGE. Inside, high ceilings, crown molding, decorative ceiling details, abundant natural light, and TILE & WOOD FLOORS create a warm and inviting atmosphere. Designed to live like a single-story home, the versatile floor plan offers formal and family living spaces, a DEDICATED OFFICE, and a second-floor BONUS ROOM above the garage, ideal for a media room, game room, or additional flex space. At the heart of the home, the spacious kitchen features BUILT-IN STAINLESS STEEL APPLIANCES, a GAS COOKTOP, ample cabinetry, and easy access to the surrounding living and dining areas, making everyday living and entertaining effortless. The PRIMARY SUITE is a private retreat with a spacious en-suite bath and THREE CLOSETS, including two walk-ins. Two additional bedrooms share a convenient JACK & JILL BATH, while a fourth bedroom enjoys access to another full bath. Step outside and into your own backyard oasis, where a paver lanai and pool deck surround the heated pool and spa where you can lounge, dine, and entertain. Mature trees and the oversized lot provide exceptional privacy and room to enjoy the outdoors. Additional features include a WATER SOFTENER SYSTEM and energy-efficient solar power with battery storage. Seville Chase offers the privacy of a gated neighborhood in a fantastic Winter Springs location, convenient to shopping, dining, parks, recreation, and TOP-RATED SCHOOLS, including Sterling Park Elementary, South Seminole Middle, and Winter Springs High. With its flexible living spaces, impressive energy features, and private backyard, this is a home that truly has room for it all. Call today to schedule a tour and let us say WELCOME HOME!

609 Viana Court, Winter Springs
1361 San Diego Court, Winter Springs
$349,900
3 Beds ⋅ 2 Baths ⋅ TB8557602 MLS
Welcome home to this freshly updated 3-bedroom, 2-bath single-story block home in the Sunrise Village neighborhood of Winter Springs. Featuring a two-car garage, this home has been refreshed throughout with new luxury vinyl plank flooring in the main living areas and bathrooms, new carpet in all three bedrooms, fresh two-tone interior paint, and modern black hardware, lighting, and ceiling fans. The updated kitchen features new Carrara quartz countertops, an undermount sink with a pull-down faucet, and new stainless steel appliances, including a range and dishwasher. The living room features a cozy fireplace and sliding glass doors leading to the rear porch, creating a welcoming space to relax or entertain. With convenient access to Red Bug Lake Road, SR-417, and nearby shopping and dining, this move-in-ready home offers comfort and convenience in Winter Springs.

1361 San Diego Court, Winter Springs
499 Club Drive, Winter Springs
$205,000
2 Beds ⋅ 2 Baths ⋅ O6447987 MLS ⋅ 499 BLDG.
Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities -- including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by -- groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!

499 Club Drive, Winter Springs
135 Cortez Court, Winter Springs
$314,900
3 Beds ⋅ 2 Baths ⋅ O6449016 MLS
Welcome home to this charming 3-bed/2-bath with an oversized 1-car garage, ideally situated on nearly a 1/4 acre on a quiet cul-de-sac in desirable Seminole County! Featuring durable concrete block construction, this property offers peace of mind with several significant improvements already completed, including a NEW ROOF (2020), A/C (2018), and ELECTRICAL REWIRE (2024)! Enjoy a spacious fenced backyard with plenty of room for outdoor entertaining, gardening, pets, or creating your own private Florida oasis. The cul-de-sac location provides added privacy and minimal through traffic. Whether you're a first-time homebuyer, investor, or looking for your next primary residence, this property presents an outstanding opportunity to own a solid home with major capital improvements already in place. PRIME SEMINOLE COUNTY LOCATION! Conveniently located near shopping, dining, parks, schools, and major roadways such as US Hwy 17-92 and the 417 Expressway; downtown Winter Springs; near Oviedo on the Park; 7 miles to Sanford Orlando Airport; 15 miles to Downtown Orlando; and 30 miles to Orlando International Airport. Easy access to everything Central Florida offers. Don't miss this opportunity to make this home your own!

135 Cortez Court, Winter Springs
491 Harbor Winds Court, Winter Springs
$335,000
3 Beds ⋅ 3 Baths ⋅ S5159212 MLS ⋅ Na BLDG.
Enjoy extra savings with up to $10,000 in seller concessions, and breathe easy knowing the big expenses are already handled for you with a newer Roof (2023), AC (2022), and Water Heater (2023)! Welcome to your beautiful new chapter at 491 Harbor Winds Ct! Nestled in a highly desirable gated community, this bright, move-in-ready townhome is designed for effortless living. Retreat to your private 1st-floor primary sanctuary, complete with dual closets, a walk-in shower, and a relaxing jacuzzi. The cheerful layout offers 3 spacious bedrooms, 2.5 baths, convenient laundry, and a 2-car garage. Reclaim your weekends! Your low monthly HOA fee covers exterior maintenance and grounds care, giving you more time to enjoy the resort-style community pool, nearby nature trails, and top-rated Seminole County schools. Everything you have been looking for is right here. Schedule your tour today!

491 Harbor Winds Court, Winter Springs
3600 Biscayne Drive, Winter Springs
$449,000
4 Beds ⋅ 2 Baths ⋅ V4951714 MLS
Welcome to 3600 Biscayne Drive in the delightful Hollowbrook neighborhood of Winter Springs. This roomy corner-lot home offers 4 bedrooms, 2 full baths, a versatile den/flex space, and an enclosed Florida room. The kitchen opens to the living room, perfect for entertaining, with extra bar seating for guests. The spacious living room features a cozy fireplace for chilly evenings. The primary bedroom has direct access to the Florida room, and the renovated primary bathroom adds a touch of elegance with a large walk-in closet. The den/flex space is ideal for working from home, while the fenced backyard off the Florida room provides privacy. The roof was installed in 2013. Zoned for Lake Howell High—Go Silver Hawks!

3600 Biscayne Drive, Winter Springs
Start Your Search