Winter Springs, FL Homes

• 

  

  /2

  $380,000 Sold Aug 05, 2025

  • 1,872 Sq Ft
  • $203/SF
  • 259 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2007

  535 Crimson Ln, Winter Springs, FL 32708

  Don’t miss this spacious and stylish 3-bedroom, 3.5-bath townhouse with a 2-car garage in the heart of Winter Springs! Thoughtfully designed across three levels, this home offers a private first-floor bedroom with full bath—ideal for guests or multi-generational living. The open-concept second floor features a modern kitchen, dining area, cozy living space, half bath, and balcony. Upstairs, enjoy

  Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

  535 Crimson Ln, Winter Springs, FL 32708
• 

  

  

  /31

  Est $375,958 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,519 Sq Ft

  1345 Mill Stream Ln, Winter Springs, FL 32708

  1345 Mill Stream Ln, Winter Springs, FL 32708
• 

  

  

  /22

  $459,900

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft

  1111 Ermine Ave, Winter Springs, FL 32708

  Looking for your dream home in Winter Springs for under $500,000? You just found it! This great 3 bedroom split plan home has a private plunge pool/spa, lake frontage and NO HOA!! You will love the space this home offers with its 3/4 of an acre and spacious rooms. Spend groovy family time in the sunken family room with wood burning fireplace or enjoy the evenings by the lake on your large

  Christy Fauquher PERFECT FIT PROPERTIES

  1111 Ermine Ave, Winter Springs, FL 32708
• 

  

  

  /12

  Sold Aug 04, 2025

  • 1,678 Sq Ft

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  1318 Tarflower Dr, Winter Springs, FL 32708

  The Catalina I is a harmonious blend of style, functionality, and comfort, offering a lifestyle that caters to your every need. As you step inside you are greeted by an open-concept design that seamlessly integrates the gathering room, dining room, and kitchen, creating an inviting space for both everyday living and entertaining. This townhome features 3 bedrooms, providing flexible living

  Mattamy Homes

  1318 Tarflower Dr, Winter Springs, FL 32708
• 

  

  

  /49

  Est $515,063 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,986 Sq Ft

  218 Wooded Vine Dr, Winter Springs, FL 32708

  218 Wooded Vine Dr, Winter Springs, FL 32708
• 

  

  /21

  $31,999

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  42 La Vista Dr, Winter Springs, FL 32708

  If you've been waiting for the perfect investment in a thriving, active 55+ community, this is it! 42 La Vista Drive offers 2 bedrooms, 2 baths, and a prime location on a quiet street with a babbling creek right behind the home. Big-ticket upgrades are already in place: NEW roof (2025) with 3-year transferable warranty, AC (2023), refrigerator (2023), range (2021), and microwave (2024). In 2019,

  Veronica Zerpa Partners Dealership LLC

  42 La Vista Dr, Winter Springs, FL 32708
• 

  /2

  $440,000 Sold Aug 04, 2025

  • 1,628 Sq Ft
  • $270/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  748 Andover Cir, Winter Springs, FL 32708

  Welcome home to the highly desirable and beautiful Tuscawilla community and discover this inviting 3-bedroom, 2-bathroom home that effortlessly blends modern upgrades with classic comfort. A well-manicured, shaded front yard, along with a paver driveway and walkway, sets the tone for what lies ahead.Step through the front door into a light-filled, fluid layout that immediately feels both

  Ron Howell, II EXP REALTY LLC

  748 Andover Cir, Winter Springs, FL 32708
• 

  

  /26

  Est $489,293 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,324 Sq Ft

  461 Diamond Dove Cove, Winter Springs, FL 32708

  461 Diamond Dove Cove, Winter Springs, FL 32708
• 

  

  /22

  $64,800

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  Welcome to your ideal Florida retreat! This beautifully updated 2-bedroom, 2-bath home is nestled in a highly sought-after 55+ community in Winter Springs, just minutes from shopping, dining, and entertainment. Step inside to find luxury plank flooring throughout and a fully remodeled kitchen-perfect for cooking and entertaining. The semi-furnished interior offers both comfort and convenience,

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  338 Casa Grande Dr, Winter Springs, FL 32708
• 

  /2

  $865,000 Sold Aug 01, 2025

  • 3,181 Sq Ft
  • $272/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1990

  1689 Wingspan Way, Winter Springs, FL 32708

  Elegant Pool Home in Glen Eagle in Winter Springs. Situated on a large CORNER LOT with lush landscaping and mature trees, this beautifully kept 4-bedroom, 3-bathroom home offers comfort, privacy, charm, and elegant living throughout. From the moment you step through the front door, you're welcomed by a spacious foyer, soaring ceilings with crown molding, and rich wood flooring throughout the

  Jessica Estrada KELLER WILLIAMS ADVANTAGE III

  1689 Wingspan Way, Winter Springs, FL 32708
• 

  

  /47

  Est $573,938 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,470 Sq Ft

  170 Wooded Vine Dr, Casselberry, FL 32708

  170 Wooded Vine Dr, Casselberry, FL 32708
• 

  

  /34

  $310,000

  • 4 Beds
  • 2 Baths
  • 1,322 Sq Ft

  551 Laurel Ct Unit 3, Winter Springs, FL 32708

  Priced well below recent appraisal! Investor special in the sought-after Highlands of Winter Springs! This home is in a desirable community of Winter Springs. Sitting on a large cul-de-sac lot, this property needs some TLC, but offers strong flip or rental potential. Features a split floor plan, open living/dining area, and access to community amenities including pool, tennis, and walking

  Miraya Lane KELLER WILLIAMS ADVANTAGE III

  551 Laurel Ct Unit 3, Winter Springs, FL 32708
• 

  /2

  $235,000 Sold Aug 01, 2025

  • 960 Sq Ft
  • $245/SF
  • 22 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1982

  600 Northern Way Unit 103, Winter Springs, FL 32708

  Welcome to 600 Northern Way #103, a beautifully recently updated 1-bedroom, 1.5-bathroom move-in-ready condo nestled in the desirable Tuscany Place community of Winter Springs. This nearly 1,000 sq ft ground-floor condo offers modern upgrades and a prime location, making it an ideal choice for first-time buyers, downsizers, or investors. Step inside to discover a bright and open living space

  Nick Gustafson FLORIDA REALTY INVESTMENTS

  600 Northern Way Unit 103, Winter Springs, FL 32708
• 

  /2

  Est $606,881 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,531 Sq Ft

  203 Wise Owl Way, Casselberry, FL 32708

  203 Wise Owl Way, Casselberry, FL 32708
• 

  

  /73

  $685,000

  • 4 Beds
  • 2.5 Baths
  • 3,119 Sq Ft

  201 Burgess Dr, Winter Springs, FL 32708

  Welcome to 201 Burgess Drive, an elegant colonial-style home in the gated Avery Park community of Winter Springs. This spacious 4-bedroom, 2.5-bath residence offers a warm and inviting atmosphere perfect for families and entertaining alike. Step inside to find beautifully updated interiors featuring plantation shutters, fresh paint, new light fixtures, and brand-new flooring on the entire first

  Virginia Bellhorn WATSON REALTY CORP

  201 Burgess Dr, Winter Springs, FL 32708
• 

  /2

  $325,000 Sold Aug 01, 2025

  • 1,085 Sq Ft
  • $300/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2011

  338 Roberts Family Ln, Winter Springs, FL 32708

  Welcome to the perfect blend of comfort and convenience in the heart of highly sought-after Winter Springs! This immaculate townhouse boast 2 bedrooms both of which include ensuites and split level providing ultimate privacy and functionality. As you step inside you will discover a fully renovated, spacious open-concept layout filled with natural light, high ceilings and modern touches. Elegant

  Christina Perez CHAMBERLAIN REALTY LLC

  338 Roberts Family Ln, Winter Springs, FL 32708
• 

  

  /33

  Est $246,469 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft

  610 Casa Park Ct E, Winter Springs, FL 32708

  610 Casa Park Ct E, Winter Springs, FL 32708
• 

  

  /23

  $304,900

  • 2 Beds
  • 2.5 Baths
  • 1,275 Sq Ft

  421 Tradition Ln, Winter Springs, FL 32708

  Welcome to 421 Tradition Lane in Winter Springs! This beautiful TownHouse with 2 bedrooms and 2.5 bathrooms is perfect for those looking for a comfortable and well-located home. There is no carpet anywhere, as the house features wood flooring throughout and ceramic tile in the wet areas, making it easy to clean and maintain.Featuring double pane windows for enhanced energy efficiency and comfort.

  Georgette Pinango THE REALTY COLLECTION

  421 Tradition Ln, Winter Springs, FL 32708
• 

  /2

  $319,000 Sold Aug 01, 2025

  • 1,466 Sq Ft
  • $218/SF
  • 85 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2005

  558 Pinebranch Cir, Winter Springs, FL 32708

  AMAZING OPPORTUNITY TO OWN A MOVE-IN READY TOWNHOME IN WINTER SPRINGS IN THE GATED COMMUNITY OF BARCLAY RESERVE! This pristine, small, quiet community sits on the Oviedo-Winter Springs line. Top-rated local Oviedo public schools. Oviedo & Winter Springs are known for their many parks and recreation facilities: The Black Hammock Trailhead is 1/2 mile away to access the Cross Seminole Trail – 23

  Sidney Galloway GALLOWAY REAL ESTATE

  558 Pinebranch Cir, Winter Springs, FL 32708
• 

  

  /48

  Est $680,162 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,094 Sq Ft

  997 Eagle Bay St, Winter Springs, FL 32708

  997 Eagle Bay St, Winter Springs, FL 32708
• 

  

  /60

  $265,000

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft

  611 Casa Park Ct N Unit G, Winter Springs, FL 32708

  **Prime Location! Exquisite 2-Bed, 2.5-Bath Renovated Townhome** NEW Windows plumbing, flooring, kitchen,bathrooms, stairs, closets, and painted.Step into your dream home! This stunning, fully updated townhome is nestled in a highly sought-after neighborhood, offering the perfect blend of modern elegance and comfort. The chef's kitchen dazzles with gorgeous countertops, sleek new

  William Grim, III RE/MAX ASSURED

  611 Casa Park Ct N Unit G, Winter Springs, FL 32708
• 

  /2

  $1,325,000 Sold Aug 01, 2025

  • 3,902 Sq Ft
  • $340/SF
  • 86 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2003

  205 Torcaso Ct, Winter Springs, FL 32708

  Presenting a truly exceptional 5-bedroom, 4.5-bath residence where luxury and sophistication converge. This magnificent estate, nestled in the intimate gated community of St. John’s Landing, where only 31 homes reside, has been meticulously crafted for an unparalleled living experience. No expense has been spared in creating a home that radiates elegance and refinement at every turn. Upon entry,

  Cristina Hutchek LPT REALTY, LLC

  205 Torcaso Ct, Winter Springs, FL 32708
• 

  

  /4

  Est $186,395 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 945 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /50

  $298,990

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft

  718 Lakeside Dr, Winter Springs, FL 32708

  Welcome to 718 LAKESIDE Drive in the heart of Winter Springs! This beautifully move in ready 2-bedroom, 2-bath Home perfectly blends style, comfort, and convenience. As you step inside, you are greeted by a BRIGHT OPEN LIVING SPACE with VAULTED CEILINGS, UPDATED FIXTURE, STYLIST NEWER LAMINATE FLOORING, and a COZY FIREPLACE that instantly makes the home feel warm and inviting. The spacious

  Mariana Cisneros PREMIUM PROPERTIES R.E SERVICE

  718 Lakeside Dr, Winter Springs, FL 32708
• 

  /2

  $337,000 Sold Jul 31, 2025

  • 1,131 Sq Ft
  • $298/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  610 Huntly Ln, Winter Springs, FL 32708

  Welcome to your beautifully updated home in the highly desirable Highlands community of Winter Springs! This charming 3-bedroom, 2-bath home is truly move-in ready, with thoughtful upgrades throughout. Step inside to discover 9-inch porcelain tile floors, elegant 6-inch craftsman-style baseboards, and recessed LED lighting with a nightlight function that creates a warm ambiance. The brand-new

  Alicia Kerns KORR REALTY CORP

  610 Huntly Ln, Winter Springs, FL 32708
• 

  

  /9

  Est $490,206 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,846 Sq Ft

  1505 Corkery Ct, Winter Springs, FL 32708

  1505 Corkery Ct, Winter Springs, FL 32708
• 

  

  /25

  $444,000

  • 4 Beds
  • 2 Baths
  • 2,064 Sq Ft

  1073 Chesterfield Cir, Winter Springs, FL 32708

  Welcome to 1073 Chesterfield Circle: a well-maintained 4 bedroom, 2 bathroom home located in a quiet, established neighborhood in the desirable Winter Springs/Tuskawilla area.This spacious residence boasts a split floor plan, spacious bedrooms, and a cozy fireplace creating the perfect balance of comfort and functionality. Recent upgrades include a new AC (2024), new roof (2025), and fresh

  Summer Hornburg BELMONT REALTY

  1073 Chesterfield Cir, Winter Springs, FL 32708
• 

  /2

  $1,275,000 Sold Jul 31, 2025

  • 3,442 Sq Ft
  • $370/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  740 Bear Creek Cir, Winter Springs, FL 32708

  Nestled within the exclusive, gated community of Bear Creek Estates, this timeless Von Jacobs-built estate offers the perfect blend of elegance, comfort, and privacy along with ample storage. Set on a spacious .79-acre wooded lot, this meticulously maintained home has been cherished by the same owners for 30 years and is ready for its next chapter.Step through the grand entry into a

  Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

  740 Bear Creek Cir, Winter Springs, FL 32708
• 

  

  /59

  Est $885,850 Not Listed For Sale

  • 7 Beds
  • 4 Baths
  • 4,182 Sq Ft

  720 Fanning Dr, Winter Springs, FL 32708

  720 Fanning Dr, Winter Springs, FL 32708
• 

  

  /27

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  498 Club Dr, Winter Springs, FL 32708

  Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs

  Joyce Gary PAINE-ANDERSON PROPERTIES, INC

  498 Club Dr, Winter Springs, FL 32708
• 

  /2

  $508,000 Sold Jul 31, 2025

  • 2,466 Sq Ft
  • $206/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1990

  849 Bentley Green Cir, Winter Springs, FL 32708

  Welcome to this beautifully updated 4-bedroom, 2-bathroom home perfectly situated on a corner lot in Tuscawilla’s desirable Bentley Green. From the moment you step inside, you’ll appreciate the thoughtfully designed layout and refined finishes throughout. The formal living and dining rooms are elegantly divided by a striking double-sided fireplace—an ideal setting for entertaining or relaxing

  Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  849 Bentley Green Cir, Winter Springs, FL 32708
• 

  

  /34

  Est $536,231 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,986 Sq Ft

  1367 Brave Wolf Point, Winter Springs, FL 32708

  1367 Brave Wolf Point, Winter Springs, FL 32708
• 

  

  /76

  $429,000

  • 3 Beds
  • 3.5 Baths
  • 2,288 Sq Ft

  1354 Mill Stream Ln, Winter Springs, FL 32708

  Welcome to your beautiful new home in the heart of Winter Springs! This spacious and low-maintenance townhome in the highly desirable Jesup’s Landing community is 100% move-in ready and filled with modern updates and smart features. This three-story home offers 3 bedrooms, 3.5 bathrooms, and plenty of space to spread out. On the ground level, you’ve got a roomy two-car garage with overhead

  Debbie Bergeron PREMIUM PROPERTIES R.E SERVICE

  1354 Mill Stream Ln, Winter Springs, FL 32708
• 

  /2

  $525,000 Sold Jul 31, 2025

  • 2,272 Sq Ft
  • $231/SF
  • 3 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1986

  370 Brushwood Ln, Winter Springs, FL 32708

  Welcome to 370 Brushwood Ln – Your Private Retreat in the Heart of Winter Springs! Nestled in a quiet, established neighborhood, this beautifully maintained 4-bedroom, 2-bathroom home offers the perfect blend of comfort, charm, and modern upgrades. Whether you're looking to entertain or unwind, this home delivers with a spacious fenced backyard, sparkling pool, and spacious outdoor entertaining

  Gretchen Carlson REAL BROKER, LLC

  370 Brushwood Ln, Winter Springs, FL 32708
• 

  

  /5

  Not Listed For Sale

  0 Florida Ave, Winter Springs, FL 32708

  0 Florida Ave, Winter Springs, FL 32708
• 

  

  /16

  $169,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  130 Columbus Cir, Winter Springs, FL 32708

  Looking for your dream home? This stunning 3-bedroom, 2-bathroom property is ready for you! From the moment you arrive, you'll appreciate the curb appeal, with a generous 3-car driveway and a 1-car garage. Step inside and discover an open-concept living space with vaulted ceilings, modern light fixtures, and a walk-in food pantry for all your storage needs. The kitchen is a chef's delight,

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  130 Columbus Cir, Winter Springs, FL 32708
• 

  /2

  $441,000 Sold Jul 31, 2025

  • 2,255 Sq Ft
  • $196/SF
  • 16 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1978

  220 Morton Ln, Winter Springs, FL 32708

  *Highest and Best is due Sunday 6/29 at 12 PM. No showings Sunday.* Welcome to your own peaceful haven in the heart of convenience, North Orlando Ranches, Winter Springs! This spacious 4-bedroom, 3-bath home sits on just over half an acre, surrounded by mature trees that offer shade, privacy, and a natural, tranquil vibe—while still being minutes from shopping, dining, and major roadways

  Mariana Wartella LPT REALTY, LLC

  220 Morton Ln, Winter Springs, FL 32708
• 

  

  /36

  Est $453,250 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,294 Sq Ft

  1145 Orange Ave, Winter Springs, FL 32708

  1145 Orange Ave, Winter Springs, FL 32708
• 

  

  /23

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft

  409 Murphy Rd, Winter Springs, FL 32708

  In the heart of Winter Springs lies your next model home or your next short-term cash-flowing business!! This warm, cozy yet spacious home will make you fall in love from the start and that's not just the homestyle screened in front porch w/ rocking chairs! Step inside & discover a wide-open layout w/ spacious bedrooms, gleaming wood-look flooring, & abundant natural light. The primary suite

  Brandon Ford TOWER TEAM REALTY, LLC

  409 Murphy Rd, Winter Springs, FL 32708
• 

  /2

  $405,000 Sold Jul 31, 2025

  • 1,766 Sq Ft
  • $229/SF
  • 51 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1989

  984 Dinero Dr, Winter Springs, FL 32708

  Welcome to your new sanctuary! This stunning 4-bedroom, 2-bath home is just what you've been searching for.This home boasts a gorgeous new Kitchen with a new stove, dishwasher, and garbage disposal. The house just received new interior and exterior paint, adding charm and vibrancy to every corner. Relax in warmth and comfort by the fireplace during those cool evenings.New double vanity

  Joyce Sanders FLORIDA REAL ESTATE PROPERTIES LLC

  984 Dinero Dr, Winter Springs, FL 32708

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