Search Winter Springs Homes for Sale

Winter Springs FL Homes for Sale

1329 Augusta National Boulevard, Winter Springs
$529,900
3 Beds ⋅ 2 Baths ⋅ Country Club Village Unit 3 SubDv. ⋅ 32708 Zip Code
Renovated, remodeled, and reimagined in the highly sought-after Country Club Village at Tuskawilla. This beautifully renovated residence has been thoughtfully transformed with an extraordinary level of quality and attention to detail, delivering a truly turnkey opportunity for today’s discerning buyer - NO EXPENSE SPARED! Extensive recent improvements include a NEW TILE ROOF (July 2025), new gutters, all-new plumbing throughout (2026), fresh interior and exterior paint, and newly textured ceilings throughout, creating a clean, modern aesthetic from top to bottom. Inside, elegance meets functionality with stunning European white oak wood flooring throughout the main living areas, complemented by new carpet in the secondary bedrooms for added comfort. The heart of the home is the beautifully reimagined kitchen, featuring new 42-inch cabinetry, quartz countertops, all-new appliances, and a designer backsplash that adds both sophistication and visual appeal. Entertain effortlessly with a stylish wet bar complete with a beverage refrigerator and matching designer backsplash. Every bathroom has been completely remodeled, showcasing luxurious finishes and quartz surfaces throughout. Additional upgrades include new lighting fixtures inside and out, new door handles and hinges, new plugs and switches, custom roller shades throughout, and a custom closet system in the primary suite. Outside, refreshed landscaping enhances curb appeal and completes this impressive renovation, making this home a rare blend of timeless design, modern luxury, and move-in-ready convenience. The HOA-maintained lawn allows for low-maintenance living, while the location places you just moments from the private Tuscawilla Country Club. Zoned for some of the highest-rated public schools in the state and offers exceptional convenience—just 25 minutes from downtown Orlando, 30 minutes to Orlando International Airport, and less than an hour from Florida’s beautiful beaches and world-renowned theme parks. This property may be under audio/visual surveillance.

1329 Augusta National Boulevard, Winter Springs

216 Tavestock Loop, Winter Springs
$605,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home located in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you’ll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, a whole-house water filtration system, two mini-split air conditioning systems (2025), and an energy-efficient year-round. The backyard is also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don’t miss your opportunity to own this exceptional waterfront home in one of Winter Springs’ most desirable communities!

216 Tavestock Loop, Winter Springs

498 Green Spring Cir, Winter Springs
$244,000
2 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 4 Of SubDv. ⋅ 32708 Zip Code
Welcome to 498 Green Spring Circle in the desirable Mount Greenwood community of Winter Springs! This beautifully maintained 2 bedroom, 1.5 bath end-unit townhome offers peaceful pond views, low-maintenance living, and access to top-rated Seminole County schools. Step inside to an open and inviting floor plan featuring ceramic tile flooring throughout the main living areas and fresh interior paint. The spacious living and dining areas flow seamlessly to the oversized screened patio with paver flooring, creating the perfect space to relax, entertain, or enjoy your morning coffee while overlooking the tranquil water and mature trees. The kitchen opens to the main living space, creating a bright and functional layout ideal for everyday living. Upstairs, you'll find two generously sized bedrooms with large closets and ample storage. An additional exterior storage closet off the patio provides even more convenience. Residents of Mount Greenwood enjoy a low HOA and outstanding community amenities, including a sparkling pool, tennis courts, playground, and scenic walking and biking trails. Ideally located just off SR 434 and minutes from Winter Springs Town Center, shopping, dining, parks, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or searching for the perfect Florida retreat, this move-in-ready townhome offers comfort, convenience, and beautiful waterfront views. Don't miss this opportunity to enjoy the Florida lifestyle in one of Winter Springs' most desirable locations. Schedule your private showing today!

498 Green Spring Cir, Winter Springs

268 Tavestock Loop, Winter Springs
$557,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
New Price **268 Tavestock Loop, Winter Springs, FL 32708** Perfectly situated in the heart of Winter Springs, this stunning 4-bedroom, 2.5-bathroom home offers the ideal location with easy access to shopping, dining, theme parks, major roads, and the airport. Nestled within a desirable gated community, you'll enjoy peace of mind along with fantastic amenities including a community Lake Jess Up, pool, park, and 2 playground walking path, community benches. Step inside this beautiful two-story home and immediately notice the high ceilings that create a bright, open atmosphere throughout. Hard flooring runs seamlessly from room to room, giving the entire 2,883 square feet a clean, modern feel that is both stylish and easy to maintain. The kitchen is equipped with sleek stainless steel appliances, making it the perfect space to prepare meals and gather with family and friends. With four spacious bedrooms, there is plenty of room for everyone. The primary bedroom offers a comfortable retreat after a long day, while the additional bedrooms provide flexible space for family, guests, or a home office. Two full and half bathroom ensure convenience for the entire household. This move-in ready home means no waiting and no hassle. Simply unpack and start enjoying everything this wonderful property and community have for you. Whether you are relaxing by the community pool, taking the family to the playground, walking trails, Lake Jess Up or exploring all that Central Florida has in store, this home puts it all within reach. Don't miss your chance to make 268 Tavestock Loop your new home. Schedule your private showing today!

268 Tavestock Loop, Winter Springs

335 Kirkcaldy Drive, Winter Springs
$324,900
3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Seller is offering to contribute towards the buyer's closing cost up to $5,000. Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs

1304 Ortega Street, Winter Springs
$459,900
4 Beds ⋅ 3 Baths ⋅ Sunrise Estates Unit 1 SubDv. ⋅ 32708 Zip Code
NEW PRICE! MAJOR UPDATES & AN AMAZING BACKYARD RETREAT! Discover a home that offers more than just a place to live — Welcome to this 4-bedroom, 2.5-bath home offering 2,152 SqFt of living space on a spacious 10,019-square-foot lot in the desirable Sunrise Estates community of Winter Springs. BIG-TICKET UPDATES ALREADY COMPLETED! Enjoy added peace of mind with a NEW ROOF (2023), A/C (2020), WATER HEATER (2023), and WHOLE-HOME WATER SOFTENER (2024). Additional features include updated bathrooms, fresh interior paint, ceramic tile flooring, soaring vaulted and cathedral ceilings, and an alkaline water filtration system at the kitchen sink. Step inside and discover a unique multi-level layout designed to offer both comfortable gathering spaces and privacy. The main level welcomes you with spacious formal living and dining areas, while the eat-in kitchen features solid wood cabinetry, solid-surface countertops, a pantry, and generous storage. Just a few steps down, the impressive 21x18 family room creates the perfect setting for relaxing or entertaining, complete with a charming stone wood-burning fireplace and French doors leading to the outdoor living area. Upstairs, you’ll find all four bedrooms, including a spacious primary suite with a walk-in closet. YOUR OWN PRIVATE BACKYARD RETREAT AWAITS! Imagine enjoying your morning coffee on the oversized 21x14 covered and screened lanai, hosting weekend gatherings, or unwinding after a long day. The fully fenced backyard offers a gas fire pit, an additional outdoor fire pit, garden space, a dedicated dog run, play area, and storage shed. A private irrigation well helps maintain the landscaping without using metered household water. Additional highlights include an indoor laundry room, two-car garage, extended driveway parking, public water and sewer, and a LOW HOA: $30 PER MONTH! Located in a non-flood zone and NO rental restrictions, this property offers flexibility for homeowners and investors alike. LOCATION, LOCATION, LOCATION! Conveniently situated near Rainbow Elementary School, Winter Springs Town Center, Oviedo, Tuskawilla Road, shopping, dining, parks, and SR-417, providing easy access to Orlando, UCF, and Lake Mary. A FANTASTIC OPPORTUNITY TO ENJOY SPACE, MAJOR UPDATES, AND OUTDOOR LIVING IN WINTER SPRINGS! The property is vacant and ready for its next owner. Seller may consider assistance toward buyer’s closing costs with an acceptable offer. DON’T MISS YOUR OPPORTUNITY — SCHEDULE YOUR PRIVATE SHOWING TODAY!

1304 Ortega Street, Winter Springs

50 Sheoah Boulevard Unit 33, Winter Springs
$154,950
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 1 SubDv. ⋅ 32708 Zip Code
THIS HOME QUALIFIES FOR $0 DOWN WITH OUR PREFERRED LENDER!!! DON'T MISS YOUR OPPORTUNITY TO OWN THIS BEAUTIFUL HOME!! 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

421 Horizon Drive, Winter Springs
$285,000
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
MOTIVATED SELLERS!!! Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3 bedrooms, 2 bathrooms, and 1,069 square feet of living space. Inside, you'll find newer Mohawk laminate flooring in the main living areas and bedrooms, tile in the kitchen and baths, updated light fixtures, newer ceiling fans, upgraded baseboards, and modernized doors and hardware throughout. The primary suite features a fully renovated bathroom with a walk-in shower, glass enclosure, rain shower head, and updated vanity. The guest bathroom has also been extensively renovated. High and vaulted ceilings enhance the open great room and dining space, while the sliding glass doors lead to an extended and stamped concrete patio within a private vinyl fenced yard, ideal for relaxing or entertaining. Located on a quiet cul-de-sac with assigned parking and curb parking available, this home is just a short walk to the community pool and directly across from the park, playground, and tennis courts. The HOA covers lawn maintenance, making for easy, low-maintenance living in a prime Seminole County location zoned for Winter Springs schools.

421 Horizon Drive, Winter Springs

1112 Orange Avenue, Winter Springs
$3,700,000
5 Beds ⋅ 7 Baths ⋅ Lake Jessup SubDv. ⋅ 32708 Zip Code
Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its breathtaking setting, grand architecture, and resort-style amenities, the property offers a level of versatility rarely available in today's market. Inspired by the elegance of the Italian countryside, the residence makes a lasting first impression with a dramatic front waterscape, lush gardens, and timeless architectural details. Inside, guests are welcomed by a grand foyer featuring exquisite marble finishes and a spectacular custom-painted 24-karat gold dome. Designed for both entertaining and everyday luxury, the expansive living spaces showcase panoramic views of beautiful Lake Jessup, soaring ceilings, stunning chandeliers, and a grand marble fireplace. The thoughtfully designed "H" floor plan encompasses more than 8,000 square feet of air-conditioned living space, offering five spacious bedrooms and six-and-a-half bathrooms, all conveniently situated on a single level. The primary suite is a true private retreat, featuring eight sets of French doors opening directly to the pool and lakefront, a custom-designed closet that doubles as a safe room, and a spa-inspired bathroom complete with a tranquil garden retreat. The gourmet chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and an oversized walk-in butler's pantry designed to accommodate large-scale entertaining. Additional luxury amenities include a temperature-controlled wine cellar, private movie theater, dedicated nanny or guest quarters, and a six-car garage with extensive attic storage. Outside, the estate transforms into a private resort. A spectacular sports pool with multiple water features serves as the centerpiece, complemented by a summer kitchen, wet bar, outdoor fireplace, and expansive covered veranda overlooking the serene waters of Lake Jessup. Whether hosting elegant weddings, unforgettable events, corporate gatherings, or private family celebrations, the setting is simply unmatched. Combining custom craftsmanship, Tuscan and Greek-inspired design elements, commercial zoning flexibility, and an irreplaceable waterfront location, this remarkable estate offers a truly rare opportunity to own one of Central Florida's most unique properties. Schedule your private tour today to experience the endless possibilities and extraordinary lifestyle this one-of-a-kind property provides.

1112 Orange Avenue, Winter Springs

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Winter Springs FL Homes for Sale

There are 119 homes for sale in Winter Springs, Florida as of 2026-11-05, at a median list price of $389,900 and a median of 57 days on market. Every active Winter Springs listing is above, newest first. What follows is what those listings add up to.

Winter Springs market at a glance

Active listings119
Median list price$389,900
Median price per square foot$237
Median size1,616 square feet
Median year built1987
Median days on market57
On market 60+ days55 (46.22%)
Priced below original asking69 (57.98%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-11-05. Updated weekly.

What the numbers say for Winter Springs buyers

69 of the 119 Winter Springs homes on the market (58%) are asking less than they did on day one, and 55 (46%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 60 or more days in who has already cut once is a different negotiation than one of the 64 listings still inside its first 60 days.

Across the 69 Winter Springs listings that have already come down, the typical reduction is 4.0% off the original asking price. That is the size of a first concession, not a final one.

Winter Springs homes by price range

Under $250,0002117.6%
$250,000 to $400,0004235.3%
$400,000 to $600,0003932.8%
$600,000 and up1714.3%

Winter Springs homes by feature

FeatureActiveShareMedian list price
Private pool2722.7%$550,000
No HOA2722.7%$389,900
New construction32.5%$799,900*
Waterfront54.2%$650,000
In a 55+ community10.8%$234,000*

Features as the listing agent entered them in Stellar MLS, as of 2026-11-05. No HOA means no association fee is required and the listing shows no monthly HOA or condo fee. 55+ leaves out manufactured, mobile, modular and condo-hotel listings. A home can carry more than one feature. Each feature opens the live listings. The No HOA search shows houses with no association, so it can run a little under the count above. * Medians on rows with fewer than 4 listings are indicative only.

Property types in Winter Springs

Single Family Residence79
Townhouse32
Condominium7
1/2 Duplex1

Neighborhoods and subdivisions in Winter Springs

Every Winter Springs subdivision with an active listing or its own page here, ranked by inventory. A subdivision showing 0 still appears: this is a live MLS feed and inventory changes daily. Every one of the 119 Winter Springs listings carries a subdivision name.

The Highlands12 active$202,000
North Orlando Ranches7 active$425,000
Oak Forest7 active$449,900
Casa Park Villas7 active$234,900
Parkstone6 active$558,900
Wildwood6 active$284,900
Tuscawilla4 active$420,950
Hickory Grove4 active$472,000
Seasons3 active$299,900*
Foxmoor3 active$335,000*
Heritage Park3 active$289,000*
North Orlando 2nd3 active$345,000*
Country Club Village3 active$525,000*
Tuscany Place2 active$243,500*
Harbor Winds2 active$332,000*
Barclay Reserve Townhomes2 active$332,450*
Wedgewood2 active$429,950*
Mount Greenwood2 active$296,500*
Moss Cove2 active$205,749*
Barrington Estates2 active$679,900*
Sunrise Estates2 active$454,900*
Sunrise Village2 active$374,949*
Hollowbrook2 active$482,000*
Jesups Landing2 active$402,000*
North Orlando Terrace2 active$304,999*
Lake Jessup1 active$3,700,000*
Deersong1 active$242,000*
Heritage Commons1 active$276,200*
Chestnut Estates1 active$665,000*
Georgetowne1 active$550,000*
Moss Place1 active$220,000*
Eagles Watch1 active$475,000*
Seville Chase1 active$925,000*
Bentley Green1 active$679,000*
Avery Park1 active$635,000*
Northern Oaks1 active$749,000*
Greens At Tuscawilla1 active$474,900*
Tuskawilla Point1 active$574,900*
Huntridge1 active$589,900*
The Highlands Sec Four Tracts A & B Rep1 active$469,000*
North Orlando1 active$310,000*
Talis Crossing1 active$2,495,000*
Highland Patio Homes1 active$299,990*
Deer Run1 active$439,900*
Glen Eagle1 active$835,000*
Forrest Creek Estates1 active$655,000*
Seven Oaks1 active$515,000*
Winding Hollow1 active$650,000*

Subdivision names come from the MLS as agents entered them. Active count and median list price as of 2026-11-05. * Medians on rows with fewer than 4 listings are indicative only. Open a subdivision for days on market, price per square foot and sales history.

More Winter Springs subdivisions

No active listing today. Each page keeps its sales history and refills as inventory changes.

About Winter Springs

Winter Springs is a city of 38,342 at the 2020 census, in the central southwest part of Seminole County.

It has been renamed twice. It was settled around 1865 as the community of Tuskawilla, incorporated in 1959 as the City of North Orlando, and renamed the City of Winter Springs in 1972 because it is not adjacent to Orlando and the old name caused confusion.

Its growth is recent and steep: 609 residents in 1960, 10,475 by 1980, 38,342 by 2020.

Winter Springs zip codes

32708 (119 listings)

More Seminole County searches

Frequently asked questions

How many homes are for sale in Winter Springs, FL?

There were 119 active residential listings in Winter Springs as of 2026-11-05, at a median list price of $389,900. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median home price in Winter Springs, FL?

The median list price in Winter Springs was $389,900 as of 2026-11-05, or about $237 per square foot. The median home on the market is 1,616 square feet and was built in 1987.

How long do homes take to sell in Winter Springs?

Median days on market was 57 as of 2026-11-05. 55 of the 119 listings, 46% of the Winter Springs market, have been listed 60 days or longer, and that is where most of the negotiating room sits.

Are Winter Springs sellers reducing their prices?

69 Winter Springs listings, 57.98% of the market, are now asking less than they did originally, at a median reduction of 4.0%. That is the size of a typical first concession here, and it is usually not the last one.

What neighborhoods are in Winter Springs, FL?

50 named subdivisions had at least one active listing in Winter Springs as of 2026-11-05, and every one is listed above with its active count and median list price. The Highlands led with 12 active listings at a median of $202,000.

How many homes for sale in Winter Springs are under $250,000?

21 of the 119 active listings in Winter Springs, 18%, were listed under $250,000 as of 2026-11-05. Another 42 (35%) were listed between $250,000 and $400,000. Each price range above opens its listings.

How many Winter Springs homes for sale have a pool or no HOA?

Of the 119 active listings in Winter Springs as of 2026-11-05, 27 listings (23%) have a private pool at a median list price of $550,000; 27 listings (23%) have no HOA at a median list price of $389,900; 3 listings (3%) are new construction at a median list price of $799,900. The counts are the listing agents' own MLS entries.

Is Winter Springs a buyer's or seller's market?

By our local two-factor read, Winter Springs is a seller's market as of November 2026: 2.6 months of supply against 4.3 across the four counties, and sellers closing at 96.5 percent of original asking price against 96.0 percent regionally.

The Homes In Orlando Team at NextHome Neighborhood Realty works with buyers and sellers across six Central Florida counties and publishes market data for Orange, Seminole, Lake, and Volusia. Call or text 407-616-9019 to see any Winter Springs listing on this page.

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