Winter Springs, FL Homes

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  /64

  $822,800 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,512 Sq Ft

  422 Sandringham Ct, Winter Springs, FL 32708

  Under contract-accepting backup offers. Nestled at the end of a peaceful cul-de-sac within an exclusive gated community, this exceptional lakefront residence offers breathtaking water views and direct access from your own private dock. Just a short walk from the community pool, playgrounds, and tennis courts, this home perfectly blends tranquility with convenience.Boasting 5 bedrooms and 3.5

  Yujie Jiang INTOP REALTY LLC

  422 Sandringham Ct, Winter Springs, FL 32708
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  /2

  $1,500,000 Sold Jan 30, 2026

  699 Bear Paw Ct, Winter Springs, FL 32708

  • 7 Beds
  • 5 Baths
  • 4,260 Sq Ft
  • Built 1984

  Last Sold Summary

  • $352/SF
  • 18 Days On Market

  Current Estimated Value $1,469,814

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

  699 Bear Paw Ct, Winter Springs, FL 32708
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  /28

  Est $462,467 Not Listed For Sale

  1732 Fox Glen Ct, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 1,939 Sq Ft
  • Built 2000

  1732 Fox Glen Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Above List Price
  • $227/SF
  • 41 Days On Market

  • Last Sold Price $440,000
  • Jan 06, 2024

  Last Listing Agent Rebecca Heatherington CHARLES RUTENBERG REALTY ORLANDO
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  /57

  $719,000 Pending

  • 5 Beds
  • 3 Baths
  • 3,287 Sq Ft

  1503 Graceful Doe Loop, Winter Springs, FL 32708

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This stunning 5-bedroom, 3-bathroom home with a three-car garage offers a perfect blend of style, comfort, and functionality. As you step inside, you are greeted by a spacious floor plan. One bedroom and a full bathroom are conveniently located downstairs, providing privacy and flexibility for guests.The

  Gabriel Andrada FLORIDA SPIRIT HOMES

  1503 Graceful Doe Loop, Winter Springs, FL 32708
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  /2

  $325,000 Sold Sep 29, 2025

  1515 Braewick St, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $253/SF
  • 33 Days On Market

  Current Estimated Value $326,696

  Last Listing Agent Destiny Anderson LIVE FLORIDA REALTY

  1515 Braewick St, Winter Springs, FL 32708
• 

  /2

  Est $818,273 Not Listed For Sale

  1105 Superior Ct, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,875 Sq Ft
  • Built 1986

  1105 Superior Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $288/SF
  • 13 Days On Market

  • Last Sold Price $829,000
  • Mar 27, 2025

  Last Listing Agent Hannah Evans FLORIDA REALTY INVESTMENTS
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  /15

  $424,900

  • 3 Beds
  • 2.5 Baths
  • 1,658 Sq Ft

  820 Wakulla Ln, Winter Springs, FL 32708

  Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfortable living with fresh interior paint, new carpet, and new light fixtures throughout. The open main living area flows easily into the kitchen, where new quartz countertops, a new range, microwave, and dishwasher add style and everyday functionality. A new roof provides valuable peace of mind, while the

  Robert Jones OFFERPAD BROKERAGE FL, LLC

  820 Wakulla Ln, Winter Springs, FL 32708
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  /2

  $256,000 Sold Oct 15, 2025

  602 Casa Park Court F, Winter Springs, FL 32708

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

  Last Sold Summary

  • $221/SF
  • 4 Days On Market

  Current Estimated Value $252,416

  Last Listing Agent Shari Starner CHARLES RUTENBERG REALTY ORLANDO

  602 Casa Park Court F, Winter Springs, FL 32708
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  /46

  Est $723,405 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

  • $288/SF
  • 5 Days On Market

  • Last Sold Price $720,000
  • Sep 28, 2023

  Last Listing Agent Evelyn Pilchick RE/MAX
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  /12

  $389,990 New Construction

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

  1262 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 Builder

  1262 Tarflower Dr, Winter Springs, FL 32708
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  /2

  $324,900 Sold Nov 10, 2025

  251 Buttonwood Ave, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1972

  Last Sold Summary

  • $295/SF
  • 3 Days On Market

  Current Estimated Value $313,132

  Last Listing Agent Uwem Akpan CHARLES RUTENBERG REALTY ORLANDO

  251 Buttonwood Ave, Winter Springs, FL 32708
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  /33

  Est $453,602 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

  • 5% Below List Price
  • $268/SF
  • 0 Days On Market

  • Last Sold Price $480,000
  • Nov 02, 2023

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP
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  /25

  $310,000

  • 3 Beds
  • 3 Baths
  • 1,609 Sq Ft

  600 Northern Way Unit 906, Winter Springs, FL 32708

  Turnkey townhouse in Tuscany Place located in beautiful Winter Springs. The townhouse style is limited to only a few homes found in the new phase of this great community. Excellent layout—all bedrooms have their own private full bathroom—one of the bedrooms with an en-suite full bath is on the ground level so it’s perfect for an office or a mother-in-law suite. The natural focal point of this

  John Vincent JR REALTY GROUP LLC

  600 Northern Way Unit 906, Winter Springs, FL 32708
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  /2

  $394,000 Sold Jun 30, 2025

  626 Pearl Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • Built 2001

  Last Sold Summary

  • $265/SF
  • 3 Days On Market

  Current Estimated Value $397,713

  Last Listing Agent Marian Schneider RE/MAX PRIME PROPERTIES

  626 Pearl Rd, Winter Springs, FL 32708
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  /43

  Est $416,731 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

  • 2% Above List Price
  • $207/SF
  • 14 Days On Market

  • Last Sold Price $410,000
  • Nov 20, 2023

  Last Listing Agent Jena Caldwell CAPITAL HOMES INC
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  /27

  $265,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,077 Sq Ft

  649 David St, Winter Springs, FL 32708

  Welcome home! This 3-bedroom, 1-bathroom single-family Winter Springs home is move-in ready with tons of upgrades! All the mechanicals have been updated or replaced: Roof replacement in 2024, new plumbing (complete repipe) 2023, AC unit replaced in 2023, and a new electrical panel in 2026. The Kitchen and Bathroom have both been updated, with all-new kitchen appliances. All this with no HOA and a

  Chad Busby BUSBY REALTY LLC

  649 David St, Winter Springs, FL 32708
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  /2

  $299,500 Sold Jan 28, 2026

  737 Sherwood Dr, Winter Springs, FL 32708

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1984

  Last Sold Summary

  • $240/SF
  • 39 Days On Market

  Current Estimated Value $292,322

  Last Listing Agent Rafael Salado GREATER ORLANDO REALTY, LLC

  737 Sherwood Dr, Winter Springs, FL 32708
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  /2

  Est $390,741 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

  • 2% Below List Price
  • $260/SF
  • 7 Days On Market

  • Last Sold Price $400,000
  • Sep 10, 2024

  Last Listing Agent Chelsea Feinberg EXP REALTY LLC
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  /39

  $755,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,218 Sq Ft

  1570 Myrtle Oaks Trail, Oviedo, FL 32765

  Under contract-accepting backup offers. Welcome to this pristine, 2020-built home located in the desirable Southern Oaks community of Oviedo. Offering 4 bedrooms, 3.5 bathrooms, a private Office/study with glass french doors, a MASSIVE BONUS ROOM, and a 3-car garage, this home combines modern design, thoughtful upgrades, and everyday functionality. From the moment you enter, you’ll notice the

  Colleen Kahl RE/MAX TOWN & COUNTRY REALTY

  1570 Myrtle Oaks Trail, Oviedo, FL 32765
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  /2

  $750,000 Sold Apr 02, 2026

  1542 Wescott Loop, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 3,242 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $231/SF
  • 129 Days On Market

  Current Estimated Value $757,800

  Last Listing Agent Lalta Sanichar LIBERTY HOME SALES INC

  1542 Wescott Loop, Winter Springs, FL 32708
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  /25

  Est $450,072 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

  • 4% Below List Price
  • $255/SF
  • 53 Days On Market

  • Last Sold Price $470,000
  • Nov 30, 2023

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
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  /62

  $275,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  476 Club Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy

  Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

  476 Club Dr, Winter Springs, FL 32708
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  /2

  $430,000 Sold Jan 05, 2026

  821 Sheoah Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 2,185 Sq Ft
  • Built 1978

  Last Sold Summary

  • 18% Below List Price
  • $197/SF
  • 113 Days On Market

  Current Estimated Value $421,271

  Last Listing Agent Sean Calegan CFRP REALTY LLC

  821 Sheoah Cir, Winter Springs, FL 32708
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  /40

  Est $457,150 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% Below List Price
  • $229/SF
  • 5 Days On Market

  • Last Sold Price $479,900
  • Apr 22, 2024

  Last Listing Agent Yolanda Floyd LA ROSA REALTY PRESTIGE
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  /58

  $450,000

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft

  758 N Gretna Ct, Winter Springs, FL 32708

  Welcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both comfort and opportunity. From the moment you step inside, you’re greeted by a warm, inviting atmosphere that instantly feels like home. The rich vinyl flooring stretches seamlessly throughout, adding both elegance and durability, while the light-colored walls reflect natural light to create a bright, airy

  Nicholas Kovats KELLER WILLIAMS ADVANTAGE REALTY

  758 N Gretna Ct, Winter Springs, FL 32708
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  /2

  $425,000 Sold Nov 03, 2025

  861 Big Buck Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $232/SF
  • 46 Days On Market

  Current Estimated Value $420,849

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  861 Big Buck Cir, Winter Springs, FL 32708
• 

  /2

  Est $441,966 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

  • 4% Below List Price
  • $247/SF
  • 12 Days On Market

  • Last Sold Price $459,000
  • Dec 12, 2024

  Last Listing Agent Elizabeth Larsen JULIE B REALTY, INC
• 

  

  /26

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,477 Sq Ft

  448 Macgregor Rd, Winter Springs, FL 32708

  Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily

  Karen Albright OPENDOOR BROKERAGE LLC

  448 Macgregor Rd, Winter Springs, FL 32708
• 

  /2

  $369,999 Sold Jun 13, 2025

  382 Panama Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  Last Sold Summary

  • $330/SF
  • 7 Days On Market

  Current Estimated Value $365,229

  Last Listing Agent Jack Luiz LANDSHARK REALTY

  382 Panama Cir, Winter Springs, FL 32708
• 

  

  /26

  Est $405,907 Not Listed For Sale

  523 Shane Cir, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft
  • Built 1979

  523 Shane Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 2% Above List Price
  • $210/SF
  • 9 Days On Market

  • Last Sold Price $399,900
  • Oct 11, 2023

  Last Listing Agent Kimberlee Frank SELL FAST REALTY, LLC
• 

  

  /21

  $309,777 Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft

  1053 W Pebble Beach Cir, Winter Springs, FL 32708

  Under contract-accepting backup offers. This property has significant potential and is located in the highly desirable Tuscawilla Country Club area. This home features three bedrooms, two bathrooms, and a practical two-car garage. It's important to note that this property needs some tender loving care, and it may need a new roof. The current asking price has been strategically set to acknowledge

  Maria Gonzalez Ortiz INT'L PROFESSIONAL REALTY INC

  1053 W Pebble Beach Cir, Winter Springs, FL 32708
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  /2

  $437,000 Sold Dec 19, 2025

  1010 Chokecherry Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 34 Days On Market

  Current Estimated Value $439,033

  Last Listing Agent Suzanne Crudo COLDWELL BANKER REALTY

  1010 Chokecherry Dr, Winter Springs, FL 32708
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  /37

  Est $602,155 Not Listed For Sale

  1192 Falling Pine Ct, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,568 Sq Ft
  • Built 1998

  1192 Falling Pine Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 12 Days On Market

  • Last Sold Price $630,000
  • Jan 12, 2024

  Last Listing Agent Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY
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  /36

  $404,900

  • 3 Beds
  • 3.5 Baths
  • 1,932 Sq Ft

  1384 Mill Stream Ln, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Do not miss out on this opportunity for a spacious, tastefully updated, move-in ready townhome in the heart of Winter Springs! This is a low maintenance 3-bed, 3.5 bath end unit with quaint landscaping leading you up the stairs to your classy entry. The interior boasts recent vinyl flooring and no carpet anywhere, perfect for all season in FL. The

  Joshua Nogowski TAH FLORIDA LLC

  1384 Mill Stream Ln, Winter Springs, FL 32708
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  /2

  $360,000 Sold Dec 16, 2025

  3876 White Birch Run, Winter Springs, FL 32708

  • 5 Beds
  • 3.5 Baths
  • 1,966 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Below List Price
  • $183/SF
  • 17 Days On Market

  Current Estimated Value $360,447

  Last Listing Agent Elaine Masood HEARTFELT REALTY HOMETEAM

  3876 White Birch Run, Winter Springs, FL 32708
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  /31

  Est $693,862 Not Listed For Sale

  674 Vistawilla Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • Built 1987

  674 Vistawilla Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $289/SF
  • 9 Days On Market

  • Last Sold Price $699,000
  • Feb 29, 2024

  Last Listing Agent Denise McKinley RE/MAX
• 

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  38 La Vista Dr, Winter Springs, FL 32708

  Brand-new 2026 Home - The Laguna - offering modern design and quality craftsmanship throughout. This beautifully appointed residence features recessed lighting, elegant crown molding, and luxury plank flooring that flows seamlessly through the home. The stylish kitchen is equipped with stainless steel appliances, creating a sleek and functional space for everyday living and entertaining. A

  Todd Vagts Hacienda Village

  38 La Vista Dr, Winter Springs, FL 32708
• 

  /2

  $740,000 Sold Apr 22, 2026

  1777 Seneca Blvd, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $316/SF
  • 50 Days On Market

  Current Estimated Value $737,990

  Last Listing Agent Chandler Williams EXIT REALTY PREMIER LEGACY

  1777 Seneca Blvd, Winter Springs, FL 32708
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  /38

  Est $1,074,155 Not Listed For Sale

  150 E Bahama Rd, Winter Springs, FL 32708

  • 3 Beds
  • 3.5 Baths
  • 2,956 Sq Ft
  • Built 2018

  150 E Bahama Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 2% Below List Price
  • $372/SF
  • 3 Days On Market

  • Last Sold Price $1,100,000
  • Jan 08, 2024

  Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY
• 

  

  /29

  $381,990 Pending

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

  1276 Crab Apple Ln, 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

  Amanda Warren MATTAMY REAL ESTATE SERVICES

  1276 Crab Apple Ln, Winter Springs, FL 32708

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