Winter Springs Homes under $750,000

Winter Springs Homes under $750,000

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 perfect blend of suburban tranquility and vibrant city life. With its lush parks, scenic lakes, and winding trails, this charming city is an outdoor enthusiast's paradise, perfect for family outings, morning jogs, or leisurely strolls with your furry friends.

Winter Springs boasts a variety of amenities, including top-rated schools, diverse dining options, and boutique shopping experiences, making it an ideal location for families and professionals alike. The city is also conveniently located near major highways, providing easy access to the bustling cities of Orlando and Sanford, where you can enjoy world-class entertainment, dining, and shopping.

For those looking to call Winter Springs home, the real estate market is thriving, with an impressive selection of homes available for under $750,000. Whether you're searching for a cozy single-family home, a modern townhouse, or a spacious property with ample yard space, Winter Springs has something to suit every taste and budget. Many of these homes feature beautiful designs, contemporary finishes, and access to community amenities like pools, parks, and walking trails.

Embrace the charm of Winter Springs, where you can enjoy a relaxed lifestyle without sacrificing the conveniences of city living. With its affordable housing options and welcoming atmosphere, now is the perfect time to discover your dream home in this delightful community!

Newest Winter Springs Homes under $750,000

161 Bear Springs Drive, Winter Springs
$500,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully designed, newly constructed 2026 END-UNIT townhome in the desirable Hickory Grove community of Winter Springs, Florida. Offering 3 bedrooms, 2.5 bathrooms, and approximately 1,704 square feet of living space, this two-story residence combines modern style, functionality, and low-maintenance living. Step inside the 8’ entryway door to find a bright and airy living space featuring a contemporary kitchen equipped with stainless steel appliances, recessed lighting, 18” tile, and a large breakfast bar, making it ideal for entertaining and everyday living. This Sofia Model by Mattamy Homes features a thoughtfully designed floor plan with a FIRST FLOOR PRIMARY SUITE abundant with natural light, a generous walk-in closet, and a private en suite bathroom complete with dual vanity sinks and a spacious walk-in shower. Upstairs, you will find two additional bedrooms, a guest bathroom, and a versatile loft providing a flexible space that would be ideal for a home office or media room. Additional highlights include high ceilings, an in-home laundry room (located on the first floor), custom plantation shutters, a smart thermostat, a rear entry 2-car garage complete with shark floor coating, a covered screened-in lanai, and a covered front porch with views of Veterans Memorial Park. Residents of Hickory Grove also enjoy community amenities, including a community resort-style swimming pool, playground, and dog park. The HOA also covers exterior maintenance, internet, and landscaping. This home is conveniently located near Winter Springs Town Center and offers access to SR-434 and SR-417, as well as shopping, dining, parks, walking trails, and the Seminole County Public School District, which is widely ranked #1 in Central Florida. Don’t miss this opportunity to enjoy maintenance-free living and make this beautiful townhome your new home!

161 Bear Springs Drive, Winter Springs
1105 Shadowbrook Trail, Winter Springs
$650,000
4 Beds ⋅ 3 Baths ⋅ Winding Hollow Unit 4 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 4-bedroom, 3-bathroom pool home in Winding Hollow, offering over 2,500 square feet of living space, a split-bedroom floor plan, and a 3-car garage! A double-door entry welcomes you inside, where fresh paint throughout and new flooring create an inviting setting. Two separate living spaces—a formal living room and a spacious family room—provide flexibility for entertaining and everyday living, while a formal dining room and a casual breakfast area provides space for every occasion. The updated kitchen features new cabinetry, granite countertops, stainless steel appliances, an island, breakfast bar seating, an updated backsplash, and a dedicated coffee and wine bar. Whether preparing a meal or hosting a gathering, there is plenty of room to cook, serve, and connect. Privately situated on the opposite side of the home from the guest bedrooms, the spacious primary suite features its own sitting area with French doors—an ideal space for a nursery, home office, or quiet retreat—along with access to the lanai. The primary bathroom includes dual vanities with updated countertops, a soaking tub, a separate shower, and a private water closet. Spacious secondary bedrooms share an updated Jack-and-Jill bathroom with a tiled tub/shower combination, while the fourth bedroom enjoys convenient access to the updated third full bathroom, complete with a shower and direct pool access. Step outside to an expansive covered lanai beneath the home’s shingled roof, providing generous sheltered space for outdoor dining and relaxing. The screened-in pool features a waterfall sprayer, while mature landscaping and a partially fenced backyard provide an inviting backdrop with green space beyond the pool enclosure. Additional highlights include an interior laundry room, extra attic storage, south-facing front exposure, and a roof and Trane A/C system installed in 2018. Conveniently located near shopping, dining, schools, Winter Springs Town Center, and area recreation, this home combines thoughtful updates, spacious gathering areas, and inviting outdoor living. Schedule your private showing today! Buyer and buyer’s agent to independently verify all property information, including measurements, square footage, room dimensions, schools, permits, and any other details deemed important to the buyer.

1105 Shadowbrook Trail, Winter Springs
425 S Hawthorn Circle, Winter Springs
$260,000
3 Beds ⋅ 2 Baths ⋅ North Orlando Terrace Unit 2 Sec 8 SubDv. ⋅ 32708 Zip Code
Three bedrooms, a corner lot and NO HOA in the heart of Winter Springs! This concrete block home sits in the established North Orlando Terrace neighborhood, and the roof was replaced in 2023, so one of the biggest-ticket items is already taken care of. Step inside to a spacious 14x16 family room that flows into the dining area and kitchen, which includes a pantry, plus a separate indoor laundry room. The primary bedroom has its own half bath, and two additional bedrooms share the full hall bath. Out back, a 17x12 screened patio overlooks the fenced yard, ready for morning coffee or evening cookouts. A one-car attached garage and driveway parking complete the package. Moss Park is about a 13-minute walk away, and you are minutes from SR-434, SR-417, Winter Springs Town Center, shopping and dining. Zoned for Winter Springs Elementary, Indian Trails Middle and Winter Springs High. Whether you are a first-time buyer, downsizing or adding to your portfolio, this home is ready for its next chapter.

425 S Hawthorn Circle, Winter Springs
733 Lakeview Drive, Winter Springs
$365,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
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 ⋅ Foxmoor Unit 1 SubDv. ⋅ 32708 Zip Code
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
1519 Woodsglen Drive, Winter Springs
$440,000
3 Beds ⋅ 2 Baths ⋅ Fox Glen At Chelsea Parc Tuscawilla SubDv. ⋅ 32708 Zip Code
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 ⋅ Barrington Estates SubDv. ⋅ 32708 Zip Code
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 ⋅ Oak Forest Unit 2a SubDv. ⋅ 32708 Zip Code
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
1361 San Diego Court, Winter Springs
$349,900
3 Beds ⋅ 2 Baths ⋅ Sunrise Village Unit 1 SubDv. ⋅ 32708 Zip Code
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 ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
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 ⋅ North Orlando Terrace Unit 1 Sec 6 SubDv. ⋅ 32708 Zip Code
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 ⋅ Harbor Winds SubDv. ⋅ 32708 Zip Code
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
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