Winter Springs, FL Homes

• 

  

  

  /68

  $590,000

  $110K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 2,474 Sq Ft

  214 Chestnut Ridge St, Winter Springs, FL 32708

  Under contract-accepting backup offers. WOW, BEST PRICE IN Winter Springs! Executive TUSCAWILLA Golf Course and Country Club living! Incredible opportunity. Here is your future DREAM HOME! Best price DIRECT GOLF FRONT HOME IN ORLANDO! Why wait to build on a 50 ft lot when you can live in a custom home Did you ever dream of drinking your Coffee daily while looking at a pristine GOLF course and

  

  Laurie Cain

  CHARLES RUTENBERG REALTY ORLANDO

  214 Chestnut Ridge St, Winter Springs, FL 32708
• Explore Winter Springs

• 

  

  

  /33

  $1,795 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft
  • Townhouse for Rent

  604 Casa Park A Ct, Winter Springs, FL 32708

  Welcome to the Casa Park Villas community. This two story townhome features 2 bedrooms and 2.5 bathrooms, offering both privacy and comfort. The main living area, kitchen, dinette and kitchen showcase tile flooring, for added durability and style. Upstairs, both bedrooms are comfortably carpeted. The unit also includes two dedicated parking spaces and a convenient outdoor utility storage room.

  

  Azim Manji

  WEICHERT REALTORS HALLMARK PRO

  604 Casa Park A Ct, Winter Springs, FL 32708
• 

  

  /2

  $482,500

  Sold Nov 05, 2025

  1322 Swift Creek Way, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $270/SF
  • 18 Days On Market

  Current Estimated Value $486,978

  Last Listing Agent Jason Eckmann JECK ENTERPRISES LLC

  1322 Swift Creek Way, Winter Springs, FL 32708
• 

  

  /2

  Est $413,388

  Not Listed For Sale

  1287 Tarflower Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,476 Sq Ft
  • Built 2024

  1287 Tarflower Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 71 Days On Market
• 

  

  

  /45

  $499,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,222 Sq Ft

  472 Dewars Ct, Winter Springs, FL 32708

  Under contract-accepting backup offers. Welcome to 472 Dewars Court, a beautifully maintained 4-bedroom, 2.5-bath pool home offering over 2,200 square feet of living space in one of Winter Springs' most desirable communities. Tucked away at the end of a quiet cul-de-sac, this exceptional property provides the perfect combination of privacy, comfort, and convenience with a serene wooded backdrop

  

  David Coker

  KELLER WILLIAMS WINTER PARK

  472 Dewars Ct, Winter Springs, FL 32708
• 

  

  /116

  Starting at $1,264 Per Month

  • 1 - 3 Beds

  1 Laurel Oaks Dr, Winter Springs, FL 32708

  Experience resort-style living at The Avenues at Winter Springs! Our pet-friendly community offers spacious 1, 2, and 3-bedroom apartment homes with modern finishes and everyday conveniences.Enjoy amenities like a resort-style pool with sundeck, 24-hour fitness and wellness center, tennis court, playground, and leash-free pet park. Stay connected with 400 Mbps internet, and take advantage

  The Avenues at Winter Springs

  

  1 Laurel Oaks Dr, Winter Springs, FL 32708
• 

  /2

  $630,000

  Sold Oct 24, 2025

  1118 Winter Springs Blvd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft
  • Built 1979

  Last Sold Summary

  • $269/SF
  • 3 Days On Market

  Current Estimated Value $602,691

  Last Listing Agent Rick Cole KELLER WILLIAMS WINTER PARK

  1118 Winter Springs Blvd, Winter Springs, FL 32708
• 

  /2

  Est $522,212

  Not Listed For Sale

  1121 Trotwood Blvd, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,293 Sq Ft
  • Built 1992

  1121 Trotwood Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • 295 Days On Market
• 

  

  /16

  $543,888

  $74K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  1421 Happy Bird Ln, Winter Springs, FL 32708

  Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step

  

  Brent DeHoop

  RE/MAX ASSURED

  1421 Happy Bird Ln, Winter Springs, FL 32708
• 

  

  /24

  $1,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Condo for Rent

  80 Moree Loop Unit 9, Winter Springs, FL 32708

  Dreams Do Come True CABLE INCLUDED!! All new Stainless Steel style Appliances and this Gem is ready for you! Welcome home to this stunning 3-bedroom, 2-bath First-floor condo offering nearly 1,200 sq ft of wide-open living space designed for effortless entertaining and everyday comfort. From the moment you step inside, you’ll appreciate the no-wasted-space floorplan, stylish tile flooring, Open

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  80 Moree Loop Unit 9, Winter Springs, FL 32708
• 

  /2

  $360,000

  Sold Sep 05, 2025

  171 Mcleods Way, Winter Springs, FL 32708

  • 3 Beds
  • 3.5 Baths
  • 1,854 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $194/SF
  • 89 Days On Market

  Current Estimated Value $370,416

  Last Listing Agent Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

  171 Mcleods Way, Winter Springs, FL 32708
• 

  /2

  Est $232,591

  Not Listed For Sale

  1523 Casa Park Cir, Winter Springs, FL 32708

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft
  • Built 1986

  1523 Casa Park Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 14 Days On Market
• 

  

  /52

  $525,000

  $24K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  440 Buckskin Ct, Winter Springs, FL 32708

  **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.** PAID-OFF 15kW SOLAR + 10Gb whole-home Ethernet — corner lot in the heart of Winter Springs! This 4BR/2.5BA Deer Run home blends colonial charm and fresh curb appeal with smart upgrades new construction can't touch.

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  440 Buckskin Ct, Winter Springs, FL 32708
• 

  

  /31

  Starting at $1,497

  Total Monthly Price

  • 1 - 3 Beds

  440 Courtney Springs Cir, Winter Springs, FL 32708

  Legends Winter Springs effortlessly combines exceptional service with outstanding features to provide the ultimate living experience. Located near upscale shopping and entertainment, your home is minutes to Lake Jessup and the excitement of downtown Orlando. Enjoy the peaceful, relaxing atmosphere of Legends Winter Springs. Please call for an appointment today.

  Legends Winter Springs

  

  440 Courtney Springs Cir, Winter Springs, FL 32708
• 

  

  /12

  Sold Aug 04, 2025

  1318 Tarflower Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • 137 Days On Market

  Mattamy Homes Hickory Grove

  1318 Tarflower Dr, Winter Springs, FL 32708
• 

  /2

  Est $866,938

  Not Listed For Sale

  1745 Seneca Blvd, Winter Springs, FL 32708

  • 5 Beds
  • 3 Baths
  • 2,811 Sq Ft
  • Built 1987

  1745 Seneca Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • 4 Days On Market
• 

  

  /33

  $313,700

  $4K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,878 Sq Ft

  702 Glasgow Ct, Winter Springs, FL 32708

  Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  702 Glasgow Ct, Winter Springs, FL 32708
• 

  

  /29

  $2,250 Per Month

  • 4 Beds
  • 2 Baths
  • 1,571 Sq Ft
  • House for Rent

  1311 Alfonzo Cir, Winter Springs, FL 32708

  Dreams Do Come True! Spacious 4 bedroom, 2 bathroom 1571 sqft ranch-style home available for rent in the desirable Sunrise community of Winter Springs. This well-maintained property features an open floor plan with neutral colors, tile, wood, and carpet flooring throughout. The master bedroom includes a walk-in closet and direct access to the screened-in patio, which overlooks a peaceful

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  1311 Alfonzo Cir, Winter Springs, FL 32708
• 

  

  /12

  $436,494

  Sold Jan 21, 2026

  1308 Crab Apple Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $260/SF
  • 282 Days On Market

  Current Estimated Value $400,538

  Mattamy Homes Hickory Grove

  1308 Crab Apple Ln, Winter Springs, FL 32708
• 

  /2

  Est $423,139

  Not Listed For Sale

  817 Big Buck Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft
  • Built 1984

  817 Big Buck Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 11 Days On Market
• 

  

  /48

  $838,500

  $412K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,350 Sq Ft

  1444 Bird Rd, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. ONE OF A KIND! Stunning Renovated Lakefront Home on Private Peninsula – Welcome to your fully reimagined lakefront retreat at 1444 Bird Road in the heart of Winter Springs. Nestled along the serene shores of Lake Tony, this highly detailed, professionally rehabbed home blends modern luxury with timeless Florida charm. From the moment you arrive,

  

  Bobby Keen

  KEEN REALTY GROUP, INC.

  1444 Bird Rd, Winter Springs, FL 32708
• 

  

  /55

  Starting at $1,650 Per Month

  • 1 - 3 Beds

  150 Bear Springs Dr, Winter Springs, FL 32708

  RiZE at Winter Springs is located in Winter Springs, Florida. We offer sixteen floor plans with one, two, and three bedroom apartment homes for rent. Apartment features include 9-foot ceilings, ceiling fans, central air and heating, a coat closet, vinyl plank flooring, walk-in closets, washer and dryer in home, an all-electric kitchen with a breakfast bar, a refrigerator, and a pantry.All

  RIZE at Winter Springs

  

  150 Bear Springs Dr, Winter Springs, FL 32708
• 

  /2

  $890,000

  Sold Jul 25, 2025

  1141 Waldorf Ct, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,680 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Above List Price
  • $332/SF
  • 6 Days On Market

  Current Estimated Value $874,663

  Last Listing Agent Sarah Darbor DJ & LINDSEY REAL ESTATE

  1141 Waldorf Ct, Winter Springs, FL 32708
• 

  /2

  Est $739,642

  Not Listed For Sale

  647 Saranac Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,512 Sq Ft
  • Built 1987

  647 Saranac Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 28 Days On Market
• 

  

  /43

  $249,990

  Pending

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  294 San Gabriel St, Winter Springs, FL 32708

  Under contract-accepting backup offers. Beautifully maintained 2-bedroom, 2-bath single-family home located in the desirable Deersong community of Winter Springs! Built in 1994 and offering 1,105 heated square feet, this move-in-ready home features numerous major updates for peace of mind. Recent improvements include interior paint (2025), waterproof laminate flooring in the living room and both

  

  Jay Patterson

  KELLER WILLIAMS ADVANTAGE REALTY

  294 San Gabriel St, Winter Springs, FL 32708
• 

  

  /48

  Starting at $1,609 Per Month

  • 1 - 3 Beds

  990 English Town Ln, Winter Springs, FL 32708

  Indulge in the luxury of living where others vacation at The Eli Winter Springs! Our community offers resort-class amenities and exceptional service to pamper residents. With a rich array of amenities, picturesque landscapes featuring swaying palm trees and tranquil waters, you can enjoy a paradise lifestyle. Conveniently located with easy access to 417, the Oviedo Marketplace, and major

  The Eli Winter Springs

  

  990 English Town Ln, Winter Springs, FL 32708
• 

  /2

  $285,000

  Sold Sep 05, 2025

  435 Tradition Ln, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,275 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Below List Price
  • $224/SF
  • 129 Days On Market

  Current Estimated Value $285,346

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  435 Tradition Ln, Winter Springs, FL 32708
• 

  /2

  Est $605,373

  Not Listed For Sale

  226 Ringwood Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 2,304 Sq Ft
  • Built 1985

  226 Ringwood Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 3 Days On Market
• 

  

  /73

  $384,900

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,721 Sq Ft

  622 Anhinga Rd, Winter Springs, FL 32708

  NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026, providing

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  622 Anhinga Rd, Winter Springs, FL 32708
• 

  

  /38

  Starting at $1,223 Per Month

  • 1 - 3 Beds

  300 Sheoah Blvd, Winter Springs, FL 32708

  Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature

  Seville on the Green

  

  300 Sheoah Blvd, Winter Springs, FL 32708
• 

  /2

  $845,000

  Sold Jul 02, 2025

  1525 Eagle Nest Cir, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,853 Sq Ft
  • Built 1993

  Last Sold Summary

  • $296/SF
  • 1 Day On Market

  Current Estimated Value $844,807

  Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY

  1525 Eagle Nest Cir, Winter Springs, FL 32708
• 

  /2

  Est $494,491

  Not Listed For Sale

  1233 Andes Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1989

  1233 Andes Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 41 Days On Market
• 

  

  /30

  $279,990

  Open Sat 11AM - 1PM $6K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,091 Sq Ft

  314 San Gabriel St, Winter Springs, FL 32708

  **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** Seller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome to your dream home, perfectly positioned for easy commuting in Central Florida. This 3 bedroom, 2 full baths, split bedroom plan and

  

  Linda Bain

  WEICHERT REALTORS HALLMARK PRO

  314 San Gabriel St, Winter Springs, FL 32708
• 

  

  /24

  Starting at $1,482

  Total Monthly Price

  • 1 - 3 Beds

  4545 Willa Creek Dr, Winter Springs, FL 32708

  We are now welcoming in-person, virtual and self-guided tours by appointment only. Please contact us today to schedule your appointment.Tuskawilla, Winter Springs, FL Apartments boast premier location great for both business and leisure. Located just minutes from SR417 and SR408, the Tuskawilla Apartments in Winter Springs are perfect for commuters all across Florida. Choose from a variety of

  Tuskawilla at Winter Springs

  

  4545 Willa Creek Dr, Winter Springs, FL 32708
• 

  /2

  $622,000

  Sold Oct 15, 2025

  659 Cayuga Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,492 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $250/SF
  • 4 Days On Market

  Current Estimated Value $631,952

  Last Listing Agent Laura Leigh Wood RE/MAX TOWN & COUNTRY REALTY

  659 Cayuga Dr, Winter Springs, FL 32708
• 

  /2

  Est $221,986

  Not Listed For Sale

  120 Rhoden Ln, Winter Springs, FL 32708

  • 2 Beds
  • 1.5 Baths
  • 898 Sq Ft
  • Built 1986

  120 Rhoden Ln, Winter Springs, FL 32708

  Last Sold Summary

  • 30 Days On Market
• 

  

  /29

  $215,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,134 Sq Ft

  71 Bombay Ave, Winter Springs, FL 32708

  Set in the heart of Winter Springs, 71 Bombay Ave offers the kind of opportunity buyers are always looking for: an established location, a functional footprint, and the chance to create a home that reflects their own style. This property is ready for its next chapter, making it an ideal choice for those who appreciate potential, value, and the ability to personalize a space over time. Life here

  

  Heather Unger, PA

  ACME REAL ESTATE FLORIDA LLC

  71 Bombay Ave, Winter Springs, FL 32708
• 

  

  /21

  Starting at $1,273 Per Month

  • 1 - 4 Beds

  170 N Gardenridge Ct, Winter Springs, FL 32708

  Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located

  Moss Park

  

  170 N Gardenridge Ct, Winter Springs, FL 32708
• 

  

  /12

  $433,244

  Sold Dec 30, 2025

  1284 Crab Apple Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $258/SF
  • 208 Days On Market

  Current Estimated Value $412,239

  Mattamy Homes Hickory Grove

  1284 Crab Apple Ln, Winter Springs, FL 32708
• 

  /2

  Est $495,079

  Not Listed For Sale

  782 Seneca Meadows Rd, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,947 Sq Ft
  • Built 2003

  782 Seneca Meadows Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 59 Days On Market

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