Winter Springs, FL Homes

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  /27

  Est $137,130 Not Listed For Sale

  30 Sheoah Blvd Unit 23, Winter Springs, FL 32708

  • 1 Bed
  • 1 Bath
  • 710 Sq Ft
  • Built 1973

  30 Sheoah Blvd Unit 23, Winter Springs, FL 32708

  Last Sold Summary

  • 9% Below List Price
  • $211/SF
  • 18 Days On Market

  • Last Sold Price $150,000
  • Feb 15, 2024

  Last Listing Agent Joyce Gary PAINE-ANDERSON PROPERTIES, INC
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  /41

  $728,500 Pending

  • 5 Beds
  • 3 Baths
  • 3,385 Sq Ft

  1553 Cranston St, Winter Springs, FL 32708

  Reduced! Nestled in the heart of Winter Springs, this lovely 5-bedroom, 3-bathroom pool home offers the perfect blend of comfort and convenience. Located in a serene and gated neighborhood with easy access to major roadways, Downtown Orlando, UCF and other top-rated schools, this home is ideal for those looking to experience the best of suburban living in Central Florida. Interior features

  Ari Rokh LEGACY REALTY & BROKERS LLC

  1553 Cranston St, Winter Springs, FL 32708
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  /2

  $519,000 Sold Dec 30, 2025

  112 Redtail Place, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1996

  Last Sold Summary

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

  Current Estimated Value $513,313

  Last Listing Agent Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

  112 Redtail Place, Winter Springs, FL 32708
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  /2

  Not Listed For Sale

  1375 Tarflower Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,476 Sq Ft
  • Built 2023

  1375 Tarflower Dr, Winter Springs, FL 32708

  Last Sold Summary

  • $294/SF
  • 281 Days On Market

  • Last Sold Price $434,682
  • Oct 29, 2024

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  /25

  $379,000 Pending

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

  704 Lancewood Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Don’t miss your opportunity to buy this beautiful FOUR bed POOL home with a detached BONUS OFFICE! This home is perfect for entertaining family and friends. Enjoy the beautiful WELL-LIT VAULTED ceilings. CERAMIC TILE and LAMINATE flooring throughout. The kitchen features tiled BACKSPLASH and STAINLESS STEEL appliances. In the owner’s suite you’ll have

  Amanda Haines PREFERRED REAL ESTATE BROKERS II

  704 Lancewood Dr, Winter Springs, FL 32708
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  /2

  $360,000 Sold Jun 16, 2025

  110 N Alderwood St, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $280/SF
  • 2 Days On Market

  Current Estimated Value $355,398

  Last Listing Agent Stacia Stephenson FLORIDA HOME TEAM REALTY LLC

  110 N Alderwood St, Winter Springs, FL 32708
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  /2

  Not Listed For Sale

  1371 Tarflower Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2023

  1371 Tarflower Dr, Winter Springs, FL 32708

  Last Sold Summary

  • $270/SF
  • 167 Days On Market

  • Last Sold Price $453,545
  • Jul 30, 2024

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  /50

  $79,900

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

  168 Costa Cir, Winter Springs, FL 32708

  BEAUTIFUL RENOVATED HOME with ALL NEW APPLIANCES including a surface gas stove, new hot water heater & HVAC. Beautiful 4 panel doors, vinyl flooring throughout.All new vapor barrier and installation underneath. New homes will be put in next door and this home has beautiful landscaping all around. This is a must see home! Shopping,Restaurants, major highways nearby. Fire Department, hospital,

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  168 Costa Cir, Winter Springs, FL 32708
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  /2

  $470,000 Sold Feb 04, 2026

  380 Michael Blake Blvd, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,868 Sq Ft
  • Built 2012

  Last Sold Summary

  • $252/SF
  • 9 Days On Market

  Current Estimated Value $468,407

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  380 Michael Blake Blvd, Winter Springs, FL 32708
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  /19

  Est $454,636 Not Listed For Sale

  1422 Blumberg Blvd, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,709 Sq Ft
  • Built 2023

  1422 Blumberg Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • 6% Below List Price
  • $282/SF
  • 122 Days On Market

  • Last Sold Price $481,901
  • May 22, 2024

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  /13

  $179,900

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  1091 Cherokee Village Trail, Winter Springs, FL 32708

  Located on large corner lot, this well built Palm Harbor Home has many upgrades. Along with so much storage space in Kitchen, large closets, a one car garage. Carpet new in Living room and beautiful tile in Kitchen and Baths. This Village area of Tuskawilla Trails has all brick paver driveways and is on City Water and Sewer. The monthly Lot rent of $835.00 also includes Lawn Service-Mowing, Weed

  Todd Newby NEWBY REALTY INC

  1091 Cherokee Village Trail, Winter Springs, FL 32708
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  /2

  $220,000 Sold Jan 19, 2026

  431 S Alderwood St, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,558 Sq Ft
  • Built 1973

  Last Sold Summary

  • 31% Below List Price
  • $141/SF
  • 19 Days On Market

  Current Estimated Value $276,638

  Last Listing Agent Julie Bailey HOME SOLD NETWORK LLC

  431 S Alderwood St, Winter Springs, FL 32708
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  /88

  Est $732,384 Not Listed For Sale

  1443 Rushing Rapids Way, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 2,841 Sq Ft
  • Built 2020

  1443 Rushing Rapids Way, Winter Springs, FL 32708

  Last Sold Summary

  • $257/SF
  • 3 Days On Market

  • Last Sold Price $730,000
  • Jan 05, 2024

  Last Listing Agent David Gallup RE/MAX
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  /62

  $849,900 Pending

  • 5 Beds
  • 4 Baths
  • 2,832 Sq Ft

  684 Olean Ct, Winter Springs, FL 32708

  Walk on it and call it home! This amazingly cared for POOL home with 3 Car Garage in Chelsea Woods, Tuscawilla is ready for its new owner! With nearly 3,000 square feet, this spacious 5-bedroom, 4-bathroom home sits on over one-third of an acre and offers the perfect blend of comfort, functionality, and Florida living. As you step inside, you’re greeted by an open and inviting family room with

  Lindsay Kaye Voss VOSS REALTY INC

  684 Olean Ct, Winter Springs, FL 32708
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  /2

  $450,000 Sold Oct 07, 2025

  111 Lido Rd, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,849 Sq Ft
  • Built 1979

  Last Sold Summary

  • $243/SF
  • 11 Days On Market

  Current Estimated Value $446,370

  Last Listing Agent Mikael Khaldi HOMESMART

  111 Lido Rd, Winter Springs, FL 32708
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  Not Listed For Sale

  611 Casa Park Ct E Unit J, Winter Springs, FL 32708

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1985

  611 Casa Park Ct E Unit J, Winter Springs, FL 32708

  Last Sold Summary

  • $230/SF
  • 48 Days On Market

  • Last Sold Price $225,000
  • Jan 10, 2024

  Last Listing Agent Austin Cummings NEXTDWELL
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  /45

  $815,000 Pre-Foreclosure

  • 6 Beds
  • 4 Baths
  • 3,100 Sq Ft

  135 W Trade Winds Rd, Winter Springs, FL 32708

  Discover this stunning home nestled on over an acre in the highly sought-after Ranch Lands, where you can enjoy the freedom of no HOA—offering ample space and proximity to Orlando, shopping, theme parks, beaches, and both Orlando and Sanford airports; pull into the oversized roundabout driveway and step into a bright living room, with access to the kitchen or a right turn to the second level

  Joshua Crittendon EXP REALTY LLC

  135 W Trade Winds Rd, Winter Springs, FL 32708
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  /2

  $500,000 Sold Oct 24, 2025

  221 Morton Ln, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Above List Price
  • $242/SF
  • 5 Days On Market

  Current Estimated Value $491,640

  Last Listing Agent Beth Hobart MAINFRAME REAL ESTATE

  221 Morton Ln, Winter Springs, FL 32708
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  /16

  Not Listed For Sale

  0 E 434 State Rd Unit MFRO6086069, Winter Springs, FL 32708

  0 E 434 State Rd Unit MFRO6086069, Winter Springs, FL 32708

  Last Sold Summary

  • 196 Days On Market

  • Last Sold Price $270,000
  • Oct 13, 2023

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC
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  /35

  $454,900

  • 4 Beds
  • 2 Baths
  • 1,632 Sq Ft

  859 Benchwood Dr, Winter Springs, FL 32708

  Welcome to this beautifully updated 4-bedroom, 2-bath home nestled in one of Winter Springs’ most sought-after neighborhoods! Perfectly positioned next to a quiet dead-end street, this move-in ready property offers both privacy and convenience—ideal for hosting guests with extra parking or enjoying peaceful, low-traffic surroundings. Step inside to discover a thoughtfully upgraded interior

  Chuck Valence VALENCE REALTY GROUP

  859 Benchwood Dr, Winter Springs, FL 32708
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  /2

  $515,000 Sold Apr 01, 2026

  1425 Happy Bird Ln, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 2020

  Last Sold Summary

  • $254/SF
  • 39 Days On Market

  Current Estimated Value $511,316

  Last Listing Agent Jacky Liu YORK MILLS REALTY LLC

  1425 Happy Bird Ln, Winter Springs, FL 32708
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  /20

  Est $179,211 Not Listed For Sale

  411 Sheoah Blvd Unit 43, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft
  • Built 1973

  411 Sheoah Blvd Unit 43, Winter Springs, FL 32708

  Last Sold Summary

  • 6% Below List Price
  • $136/SF
  • 6 Days On Market

  • Last Sold Price $190,000
  • Oct 16, 2023

  Last Listing Agent Chase Morton Tate COMPASS FLORIDA LLC
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  /25

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,044 Sq Ft

  222 W Panama Rd, Winter Springs, FL 32708

  POOL HOME + NEW ROOF! Welcome to this beautifully upgraded 3-bedroom, 2-bath residence with a 2-car garage, perfectly positioned in one of Winter Springs’ most sought-after, established neighborhoods with NO HOA. This home features a private, fully fenced backyard oasis with a sparkling pool—ideal for entertaining, relaxing, and enjoying Florida living year-round. A brand-new roof will be

  Melissa Maldonado CENTURY 21 MCBRIDE REALTY GROUP

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

  $410,000 Sold May 16, 2025

  702 Barrington Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1989

  Last Sold Summary

  • $277/SF
  • 7 Days On Market

  Current Estimated Value $414,993

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

  702 Barrington Cir, Winter Springs, FL 32708
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  /72

  Est $758,072 Not Listed For Sale

  740 Fanning Dr, Winter Springs, FL 32708

  • 5 Beds
  • 4 Baths
  • 3,718 Sq Ft
  • Built 2012

  740 Fanning Dr, Winter Springs, FL 32708

  Last Sold Summary

  • $203/SF
  • 2 Days On Market

  • Last Sold Price $755,000
  • Dec 27, 2023

  Last Listing Agent Jenn Carlisle LPT REALTY, LLC
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  /41

  $799,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  426 Dancing Water Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Welcome to this exceptional 5-bedroom, 3.5-bath pool home with a 3-car garage, perfectly designed for both luxurious living and everyday comfort in the sought-after community of Tuskawilla Crossings. From the moment you step inside, you’ll appreciate the thoughtful layout and spacious design. The heart of the home is a stunning open-concept kitchen and

  Melissa Vance MAINFRAME REAL ESTATE

  426 Dancing Water Dr, Winter Springs, FL 32708
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  /2

  $435,990 Sold May 23, 2025

  1267 Tarflower Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2024

  Last Sold Summary

  • 10% Below List Price
  • $260/SF
  • 158 Days On Market

  Current Estimated Value $441,919

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES

  1267 Tarflower Dr, Winter Springs, FL 32708
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  /42

  Not Listed For Sale

  640 Macduff Ln, Winter Springs, FL 32708

  • 6 Beds
  • 5 Baths
  • 2,500 Sq Ft
  • Built 1979

  640 Macduff Ln, Winter Springs, FL 32708

  Last Sold Summary

  • $260/SF
  • 6 Days On Market

  • Last Sold Price $650,000
  • Jan 23, 2024

  Last Listing Agent Jaime Leizan EXP REALTY LLC
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  /32

  $49,900

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  382 La Vista Dr, Winter Springs, FL 32708

  NEWLY RENOVATED- 2 BEDROOM/2 BATH- 1 MONTH FREE LOT RENT!!! Totally Renovated home with new drywall, paint, & baseboards. Bathrooms have been beautifully renovated with new vanities, showers, and fixtures. Flooring and sub flooring has been installed with waterproof vinyl laminate. All new stainless-steel appliances. The A/C is a 3-new A/C mini split installed, 1 in each bedroom and 1 in the main

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  382 La Vista Dr, Winter Springs, FL 32708
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  /2

  $494,000 Sold Apr 27, 2026

  1163 Baltic Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $239/SF
  • 0 Days On Market

  Current Estimated Value $504,893

  Last Listing Agent Asia Kendall LPT REALTY, LLC

  1163 Baltic Ln, Winter Springs, FL 32708
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  /65

  Est $896,815 Not Listed For Sale

  664 Fanning Dr, Winter Springs, FL 32708

  • 6 Beds
  • 4 Baths
  • 4,172 Sq Ft
  • Built 2013

  664 Fanning Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 7% Below List Price
  • $231/SF
  • 27 Days On Market

  • Last Sold Price $965,000
  • Apr 26, 2024

  Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY
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  /31

  $275,000

  • 2 Beds
  • 2.5 Baths
  • 1,330 Sq Ft

  4113 Hedge Maple Place, Winter Springs, FL 32708

  If you are looking for a Gated Community with the most desirable location in the community you know you have found it! This home boosts an open floorplan that includes a breakfast bar and open to the family and dining area on the main floor, with high ceilings and lots of natural light. Upgraded appliances, kitchen countertops, and flooring. This floor plan offers two spacious master suites

  Susan Pinnock A+ REALTY PROFESSIONALS, INC

  4113 Hedge Maple Place, Winter Springs, FL 32708
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  /2

  $415,000 Sold May 22, 2025

  605 Marni Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $292/SF
  • 82 Days On Market

  Current Estimated Value $406,946

  Last Listing Agent Maria Shreve RE/MAX TOWN CENTRE

  605 Marni Dr, Winter Springs, FL 32708
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  /97

  Est $766,633 Not Listed For Sale

  467 Dancing Water Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft
  • Built 2019

  467 Dancing Water Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $229/SF
  • 8 Days On Market

  • Last Sold Price $777,000
  • Sep 15, 2023

  Last Listing Agent David Gallup RE/MAX
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  /28

  $284,900

  • 2 Beds
  • 2 Baths
  • 974 Sq Ft

  337 Kirkcaldy Dr, Winter Springs, FL 32708

  Warm and inviting home located in the highly sought-after Highland Village community of Winter Springs—where residents love to live and rarely want to leave. This 2-bedroom, 2-bath home features an open floor plan, abundant natural light, and no carpet throughout. The spacious living and dining areas open a comfortable layout, perfect for everyday living or entertaining. The primary bedroom is

  Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO

  337 Kirkcaldy Dr, Winter Springs, FL 32708
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  /2

  $569,000 Sold Sep 11, 2025

  696 Venture Ct, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1988

  Last Sold Summary

  • $275/SF
  • 6 Days On Market

  Current Estimated Value $566,416

  Last Listing Agent Fran Zvaigzne COLDWELL BANKER REALTY

  696 Venture Ct, Winter Springs, FL 32708
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  /2

  Est $896,223 Not Listed For Sale

  1552 Myrtle Oaks Trail, Oviedo, FL 32765

  • 6 Beds
  • 3.5 Baths
  • 4,210 Sq Ft
  • Built 2020

  1552 Myrtle Oaks Trail, Oviedo, FL 32765

  Last Sold Summary

  • 6% Below List Price
  • $226/SF
  • 12 Days On Market

  • Last Sold Price $952,000
  • Dec 27, 2024

  Last Listing Agent Victoria Myers RE/MAX
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  /3

  $110,000

  • Land
  • 12,632 Sq Ft
  • $379,310 per Acre

  Unlisted Address

  Incredible opportunity to build your dream home on this fantastic vacant land! Great location,situated near Highway 17-92, and SR 434, this property has many conveniences only a few minutesaway from popular spots like Winter Springs town center, Target, Publix, Lowes, Home Depot, and thebeautiful Lake Concord Park. Enjoy life in a well established neighborhood with quick access

  R Webb REALTY PROFESSIONALS USA LLC

  Unlisted Address
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  /57

  $897,000 Sold May 15, 2025

  231 Chestnut Ridge St, Winter Springs, FL 32708

  • 5 Beds
  • 3.5 Baths
  • 2,908 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $308/SF
  • 46 Days On Market

  Current Estimated Value $875,577

  Last Listing Agent Vasiliki Rollas YOUNG REAL ESTATE

  231 Chestnut Ridge St, Winter Springs, FL 32708
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  /25

  Est $371,833 Not Listed For Sale

  1479 Connors Ln, Winter Springs, FL 32708

  • 2 Beds
  • 2 Baths
  • 1,247 Sq Ft
  • Built 1985

  1479 Connors Ln, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Above List Price
  • $288/SF
  • 9 Days On Market

  • Last Sold Price $359,000
  • Aug 04, 2023

  Last Listing Agent Kelli Martin FLORIDA ONE REAL ESTATE LLC

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