Winter Springs, FL Homes

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  /46

  Est $719,139

  Not Listed For Sale

  1771 Owasco St, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,503 Sq Ft
  • Built 1987

  1771 Owasco St, Winter Springs, FL 32708

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY
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  /25

  $605,000

  $35K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,355 Sq Ft

  216 Tavestock Loop, Winter Springs, FL 32708

  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

  Jessica Gallant CREEGAN GROUP

  216 Tavestock Loop, Winter Springs, FL 32708
• 

  

  /2

  $395,000

  Sold Aug 24, 2026

  560 Pleasant Grove Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • Built 1996

  Last Sold Summary

  • 11% Below List Price
  • $239/SF
  • 93 Days On Market

  Current Estimated Value $416,088

  Last Listing Agent David Fraser KELLER WILLIAMS ADVANTAGE III

  560 Pleasant Grove Dr, Winter Springs, FL 32708
• 

  

  

  /33

  Est $454,009

  Not Listed For Sale

  929 Old White Way, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 1998

  929 Old White Way, Winter Springs, FL 32708

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP
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  /2

  $386,990

  New Construction Pending

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

  1407 Tarflower Dr, Winter Springs, FL 32708

  As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a

  Melissa Flores PREMIER SOTHEBYS INT'L REALTY

  1407 Tarflower Dr, Winter Springs, FL 32708
• 

  /2

  $425,000

  Sold Apr 21, 2026

  791 Andover Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $261/SF
  • 12 Days On Market

  Current Estimated Value $424,901

  Last Listing Agent Phil Herman SHORES REAL ESTATE

  791 Andover Cir, Winter Springs, FL 32708
• 

  

  /43

  Est $431,205

  Not Listed For Sale

  1054 Chokecherry Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,979 Sq Ft
  • Built 1986

  1054 Chokecherry Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Jena Caldwell CAPITAL HOMES INC
• 

  

  /25

  $359,000

  $31K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,425 Sq Ft

  142 Bayberry Ct, Winter Springs, FL 32708

  PRICE IMPROVEMENT: This 4 bedroom 2 bath home located on a quiet cul de sac is perfect for Family Living. Upgraded kitchen features pass through window to the large rear screened patio. Open floorplan is perfect for entertaining. The original garage has been converted to a large space offering additional square footage to be utilized as a bedroom, game room, home office, theatre or a gym. Fenced

  Roxanne Rose ROSE PROPERTY MANAGEMENT INC

  142 Bayberry Ct, Winter Springs, FL 32708
• 

  /2

  $255,500

  Sold Mar 25, 2026

  606 Casa Park A Ct, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft
  • Built 1984

  Last Sold Summary

  • 5% Below List Price
  • $221/SF
  • 25 Days On Market

  Current Estimated Value $254,564

  Last Listing Agent Tamara Kerr PA SAND DOLLAR REALTY GROUP INC

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

  /2

  Est $390,816

  Not Listed For Sale

  628 Sailfish Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1978

  628 Sailfish Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Chelsea Feinberg EXP REALTY LLC
• 

  

  /28

  $35,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  284 La Vista Dr, Winter Springs, FL 32708

  This clean and move-in ready 2 bedroom, 2 bath home is located in a quiet and well maintained senior community, offering comfort, convenience, and a relaxed lifestyle. Featuring a spacious floor plan with large bedrooms, a bright living room, dedicated dining area, and an oversized kitchen with plenty of cabinet space, this home is perfect for everyday living and entertaining. Recent updates

  Corali Fuentes Four Star Homes, Inc.

  284 La Vista Dr, Winter Springs, FL 32708
• 

  /2

  $335,000

  Sold Oct 31, 2025

  221 N Devon Ave, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 1959

  Last Sold Summary

  • 7% Below List Price
  • $209/SF
  • 37 Days On Market

  Current Estimated Value $338,556

  Last Listing Agent Sara Nicholas, PA CHARLES RUTENBERG REALTY ORLANDO

  221 N Devon Ave, Winter Springs, FL 32708
• 

  

  /25

  Est $451,353

  Not Listed For Sale

  999 El Lago Terrace, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,846 Sq Ft
  • Built 1989

  999 El Lago Terrace, Winter Springs, FL 32708

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
• 

  

  /26

  $385,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  200 W Panama Rd, Winter Springs, FL 32708

  Welcome to this beautifully updated 3-bedroom, 2-bath home situated on a spacious 0.27-acre lot with NO HOA in Winter Springs! This inviting home features a bright and functional layout, a beautifully kitchen, modern bathrooms, and a cozy living area with a wood-burning fireplace. The home also features a roof installed in 2021, along with newer windows and sliding doors throughout.The

  Maria Santana EXP REALTY LLC

  200 W Panama Rd, Winter Springs, FL 32708
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  /2

  $222,500

  Sold May 12, 2026

  604 Casa Park A Ct, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $192/SF
  • 56 Days On Market

  Current Estimated Value $226,900

  Last Listing Agent Victoria Myers RE/MAX TOWN & COUNTRY REALTY

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

  

  /40

  Est $451,968

  Not Listed For Sale

  3955 Biscayne Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,092 Sq Ft
  • Built 1988

  3955 Biscayne Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Yolanda Floyd COLDWELL BANKER REALTY
• 

  

  /28

  $335,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  518 Harbor Winds Ct, Winter Springs, FL 32708

  Welcome to 518 Harbor Winds Ct! A beautifully maintained and move-in-ready townhome nestled within a very desirable gated community. Featuring 3 bedrooms, 2.5 bathrooms, an attached 2-car garage, primary suite on the first floor, and backs up to a GORGEOUS POND VIEW! The home features soaring ceilings and a bright open-concept! The kitchen features granite countertops, 42-inch wood cabinets,

  Michelle Richardson KELLER WILLIAMS CLASSIC

  518 Harbor Winds Ct, Winter Springs, FL 32708
• 

  /2

  $537,500

  Sold Dec 22, 2025

  1103 Marcus Ct, Winter Springs, FL 32708

  • 3 Beds
  • 3 Baths
  • 2,463 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $218/SF
  • 40 Days On Market

  Current Estimated Value $561,614

  Last Listing Agent Ralph Harvey LISTWITHFREEDOM.COM

  1103 Marcus Ct, Winter Springs, FL 32708
• 

  /2

  Est $449,927

  Not Listed For Sale

  1022 E Pebble Beach Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1994

  1022 E Pebble Beach Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Elizabeth Larsen JULIE B REALTY, INC
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  /44

  $392,500

  $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft

  227 Mcleods Way, Winter Springs, FL 32708

  Experience maintenance-free living in the heart of Winter Springs at Jesup's Reserve, where charming streetscapes, walkability, and everyday convenience come together. Perfectly positioned with peaceful pond views from the front porch and both upper-level balconies, this three-story townhome offers over three levels of thoughtfully designed living space just steps from Winter Springs Town

  Linda Jokbengboon COMPASS FLORIDA LLC

  227 Mcleods Way, Winter Springs, FL 32708

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