Winter Springs, FL Homes

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  $324,000 Sold Jul 11, 2025

  415 Old Farm Ln, Winter Springs, FL 32708

  • 3 Beds
  • 3 Baths
  • 1,504 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $215/SF
  • 53 Days On Market

  Current Estimated Value $327,437

  Last Listing Agent Tatyana Clark COLDWELL BANKER REALTY

  415 Old Farm Ln, Winter Springs, FL 32708
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  Est $689,195 Not Listed For Sale

  782 Gainer Way, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 3,094 Sq Ft
  • Built 2012

  782 Gainer Way, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $232/SF
  • 51 Days On Market

  Last Sold Price $717,500

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC
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  /59

  $64,500 Pending

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  448 La Vista Dr, Winter Springs, FL 32708

  Priced to sell-Almost everything has been replaced/redone. Everything has been modernized-home has an attached enclosed porch for multiple uses-Seller is an artist, interior designer and used her creativity in this home. Kitchen, baths, flooring, electrical, plumbing, etc. are up to date. Hacienda Village 55+ is centrally off State Road 434-45 minutes from the Beaches & Parks. There is shopping,

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  448 La Vista Dr, Winter Springs, FL 32708
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  $519,000 Sold May 27, 2025

  659 N Endeavour Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1989

  Last Sold Summary

  • $251/SF
  • 4 Days On Market

  Current Estimated Value $520,307

  Last Listing Agent Dominic Persampiere OPTIMA REAL ESTATE

  659 N Endeavour Dr, Winter Springs, FL 32708
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  Est $103,262 Not Listed For Sale

  1360 Delaney Dr, Winter Springs, FL 32708

  1360 Delaney Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 29% Above List Price
  • 0 Days On Market

  Last Sold Price $80,000

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC
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  $489,995

  • 4 Beds
  • 3.5 Baths
  • 2,353 Sq Ft

  1262 Spotted Sandpiper Loop, Winter Springs, FL 32708

  Imagine a home that doesn't just house your life but elevates every chapter of it. At this stunning tri-level townhouse, the story begins the moment you step across the covered front porch and through the front door.Your day begins on the third level, where light pours through the expansive windows of your primary retreat. You wake up in a sanctuary defined by a sense of total calm. The

  Mark Anthony Buot ROI AVE LLC

  1262 Spotted Sandpiper Loop, Winter Springs, FL 32708
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  $340,000 Sold Aug 18, 2025

  620 Fruitwood Ave, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $282/SF
  • 63 Days On Market

  Current Estimated Value $335,871

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  620 Fruitwood Ave, Winter Springs, FL 32708
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  Est $447,294 Not Listed For Sale

  1141 Orange Ave, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 2,225 Sq Ft
  • Built 2015

  1141 Orange Ave, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $211/SF
  • 32 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Kelly Butterfield RE/MAX
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  $39,900

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft

  272 Ponce de Leon Dr, Winter Springs, FL 32708

  HACIENDA VILLAGE 55+ WELL MAINTAINED HOME! PERFECT FLOOR PLAN. INSIDE UTILITY CENTRAL AIR SYSTEM - FULL SYSTEM 2 HTD AREA 2 BEDROOMS - SPACIOUS MASTE SUITE WITH DRESSING, KITCHEN HAS AN ISLAND TOP COOKING. BEAUTIFUL BACKYARD AND SCREENED INSIDE PORCH. HACIENDA VILLAGE IS A LEGACY COMMUNITY - WITH NEW AMENITIES. MONTHLY Base RENT $1075. COME SEE US TODAY!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  272 Ponce de Leon Dr, Winter Springs, FL 32708
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  $390,000 Sold Aug 31, 2025

  1009 Troon Trace, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 1,681 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $232/SF
  • 136 Days On Market

  Current Estimated Value $390,895

  Last Listing Agent Mark Allen REALTY INTERNATIONAL LLC

  1009 Troon Trace, Winter Springs, FL 32708
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  Est $500,239 Not Listed For Sale

  1488 Connors Ln, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 2,120 Sq Ft
  • Built 1987

  1488 Connors Ln, Winter Springs, FL 32708

  Last Sold Summary

  • 3% Above List Price
  • $230/SF
  • 12 Days On Market

  Last Sold Price $487,000

  Last Listing Agent Danny Pena EXP REALTY LLC
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  /18

  $484,940 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  161 Bear Springs Dr, Winter Springs, FL 32708

  With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural

  Mattamy Homes Builder

  161 Bear Springs Dr, Winter Springs, FL 32708
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  $380,000 Sold Sep 10, 2025

  995 Troon Trace, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,651 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $230/SF
  • 66 Days On Market

  Current Estimated Value $383,830

  Last Listing Agent Karen Ripperger LPT REALTY, LLC

  995 Troon Trace, Winter Springs, FL 32708
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  Est $422,120 Not Listed For Sale

  1426 Blumberg Blvd, Winter Springs, FL 32708

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

  1426 Blumberg Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $298/SF
  • 113 Days On Market

  Last Sold Price $439,647

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $268,990

  • 3 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  4467 Brook Hollow Cir, Winter Springs, FL 32708

  Imagine coming home to a space where comfort, privacy, and peace of mind come together effortlessly. Welcome to 4467 Brook Hollow Cir, the beautifully maintained and updated 3-bedroom, 2.5-bath townhome, offering 1,344 sq ft, invites you to slow down and truly enjoy everyday living. The ceramic tile flooring throughout the first floor creates a bright and welcoming atmosphere.At upstairs, new

  Miriam Hernandez Gonzalez LA ROSA REALTY ORLANDO LLC

  4467 Brook Hollow Cir, Winter Springs, FL 32708
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  $275,000 Sold Jun 13, 2025

  720 Lakeside Dr, Winter Springs, FL 32708

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Below List Price
  • $236/SF
  • 8 Days On Market

  Current Estimated Value $268,736

  Last Listing Agent Melissa Flores PREMIER SOTHEBYS INT'L REALTY

  720 Lakeside Dr, Winter Springs, FL 32708
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  Est $459,169 Not Listed For Sale

  1438 Blumberg Blvd, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft
  • Built 2024

  1438 Blumberg Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $282/SF
  • 36 Days On Market

  Last Sold Price $480,964

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $325,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,886 Sq Ft

  307 Freedoms Ring Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Facade Grass is photoshopped green, due to Winter. This beautifully designed 3 bedroom, 2.5-bath townhome offers the perfect balance of space, comfort, and style. With over 1,800 square feet of living space, the open and airy floor plan features distinct living and dining areas, along with a versatile flex space upstairs—ideal for today’s modern lifestyle.

  Gale Milgrim KELLER WILLIAMS WINTER PARK

  307 Freedoms Ring Dr, Winter Springs, FL 32708
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  $510,000 Sold Apr 28, 2025

  600 Tuskawilla Point Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,038 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Below List Price
  • $250/SF
  • 13 Days On Market

  Current Estimated Value $494,811

  Last Listing Agent Lois Vonderbecke COLDWELL BANKER REALTY

  600 Tuskawilla Point Ln, Winter Springs, FL 32708
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  Est $396,083 Not Listed For Sale

  1177 Orange Ave, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft
  • Built 2015

  1177 Orange Ave, Winter Springs, FL 32708

  Last Sold Summary

  • 3% Below List Price
  • $212/SF
  • 40 Days On Market

  Last Sold Price $409,000

  Last Listing Agent Michael Post FOLIO REALTY LLC
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  $33,900

  • 1 Bed
  • 2 Baths
  • 1,008 Sq Ft

  421 Costa Rica Dr, Winter Springs, FL 32708

  Located in the wonderful Hacienda Village 55 plus community in Winter Springs, this 1 Bed, 2 Bath home has been beautifully renovated and is truly a must-see to believe. Pictures simply do not do it justice! Whether you are looking for the perfect winter retreat or a full-time residence, this home offers comfort, style, and an amazing location close to everything you need. Move-in ready,

  Isabel Dalgleish Four Star Homes, Inc.

  421 Costa Rica Dr, Winter Springs, FL 32708
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  $400,000 Sold Feb 26, 2026

  1427 Whitehall Blvd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1993

  Last Sold Summary

  • 16% Below List Price
  • $246/SF
  • 49 Days On Market

  Current Estimated Value $448,932

  Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

  1427 Whitehall Blvd, Winter Springs, FL 32708
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  Not Listed For Sale

  1410 Blumberg Blvd, Winter Springs, FL 32708

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

  1410 Blumberg Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • $255/SF
  • 19 Days On Market

  Last Sold Price $427,955

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $550,000 Pending

  • Land
  • 3.44 Acres
  • $159,884 per Acre

  705 E State Road 434, Winter Springs, FL 32708

  FRESH COMMERCIAL DEVELOPMENT SITE with C-1 ZONING. 400' street frontage on E State Road 434 in Winter Springs Development area. (see attached City list of approved retail businesses). Two adjacent lots sold together making 3.4 acres. Find the Perkins restaurant on the corner of Hayes Rd & 434, go East on 434. See sign on the right side of the road. If you reach the Church at Shore Rd, you've gone

  Thomas Namey APPLE REALTY

  705 E State Road 434, Winter Springs, FL 32708
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  $715,000 Sold Apr 24, 2025

  443 Dancing Water Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Above List Price
  • $255/SF
  • 103 Days On Market

  Current Estimated Value $698,791

  Last Listing Agent Kerry Westmeyer PALMANO GROUP RE BROKERAGE LLC

  443 Dancing Water Dr, Winter Springs, FL 32708
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  /19

  Est $459,323 Not Listed For Sale

  1395 Tarflower Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,709 Sq Ft
  • Built 2024

  1395 Tarflower Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 8% Below List Price
  • $292/SF
  • 122 Days On Market

  Last Sold Price $498,877

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $169,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft

  40 Sheoah Blvd Unit 27, Winter Springs, FL 32708

  Under contract-accepting backup offers. Experience the perfect blend of comfort, convenience, and community with this beautifully maintained 2/2, 1187 sqft, first-floor condo located in the highly desirable Highlands neighborhood in Winter Springs. Set within the top-rated Seminole County School District, this ground-level residence offers true ease of living—no stairs, no hassle, just effortless

  Travis Cepregi KELLER WILLIAMS WINTER PARK

  40 Sheoah Blvd Unit 27, Winter Springs, FL 32708
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  $335,000 Sold Jun 20, 2025

  561 Pinebranch Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,564 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $214/SF
  • 12 Days On Market

  Current Estimated Value $331,200

  Last Listing Agent Zardiah Shipman EXP REALTY LLC

  561 Pinebranch Cir, Winter Springs, FL 32708
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  Est $422,507 Not Listed For Sale

  1434 Blumberg Blvd, Winter Springs, FL 32708

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

  1434 Blumberg Blvd, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $299/SF
  • 154 Days On Market

  Last Sold Price $440,647

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $399,900 Open Fri 12PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  724 Barrington Cir, Winter Springs, FL 32708

  Very well maintained home in Tuskawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature trail are walking distance from the home. Walk to Trotwood Park

  Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

  724 Barrington Cir, Winter Springs, FL 32708
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  $420,000 Sold Mar 31, 2025

  1197 Orange Ave, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 2,164 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Below List Price
  • $194/SF
  • 30 Days On Market

  Current Estimated Value $419,200

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1197 Orange Ave, Winter Springs, FL 32708
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  Est $464,996 Not Listed For Sale

  1605 Sapphire Star Dr, Oviedo, FL 32765

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 2013

  1605 Sapphire Star Dr, Oviedo, FL 32765

  Last Sold Summary

  • 1% Above List Price
  • $233/SF
  • 33 Days On Market

  Last Sold Price $460,000

  Last Listing Agent James Clark CENTURY 21 ALTON CLARK
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  $485,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,854 Sq Ft

  1360 Congressional Ct, Winter Springs, FL 32708

  Under contract-accepting backup offers. Welcome to your dream home nestled within the prestigious Tuscawilla gated community of The Greens at Tuscawilla! This meticulously designed two-bedroom townhome offers a perfect blend of sophistication and comfort, promising a lifestyle of convenience and luxury. Step inside and be greeted by an expansive open floor plan that exudes warmth and elegance.

  Lou DiBerardino KELLER WILLIAMS WINTER PARK

  1360 Congressional Ct, Winter Springs, FL 32708
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  $412,000 Sold Nov 14, 2025

  915 Cypresswood Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,412 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $292/SF
  • 8 Days On Market

  Current Estimated Value $409,705

  Last Listing Agent Millie Brockmeyer RE/MAX INNOVATION

  915 Cypresswood Ct, Winter Springs, FL 32708
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  Est $143,357 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

  • 4% Below List Price
  • $211/SF
  • 18 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Joyce Gary PAINE-ANDERSON PROPERTIES, INC
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  /25

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  116 Philadelphia Way, Winter Springs, FL 32708

  Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated community, offering a great combination of functionality, privacy, and location. Designed for comfortable living, this home includes energy-efficient double-pane windows that enhance interior comfort and help reduce outside noise. The primary suite features a spacious walk-in closet with natural light, creating a bright and welcoming

  Isabel Sirizzotti SUNNY 365 REALTY GROUP

  116 Philadelphia Way, Winter Springs, FL 32708
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  $442,000 Sold Mar 12, 2026

  1328 Congressional Ct, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,854 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Below List Price
  • $238/SF
  • 14 Days On Market

  Current Estimated Value $467,112

  Last Listing Agent Barbara Friedman FANNIE HILLMAN & ASSOCIATES

  1328 Congressional Ct, Winter Springs, FL 32708
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  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

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $415,000

  • 2 Beds
  • 2 Baths
  • 1,831 Sq Ft

  1352 Augusta National Blvd, Winter Springs, FL 32708

  Welcome to your new home in the highly sought after community of Tuscawilla, nestled in beautiful Winter Springs! This move-in ready residence offers comfort, convenience and exceptional value-one of the best prices in the entire community! Featuring a newer (2020) barrel tile roof, brand new plumbing though out (2025), and a spacious double garage, this home is perfect for buyers seeking low

  Andrea Rusch URBAN PALM REAL ESTATE COMPANY

  1352 Augusta National Blvd, Winter Springs, FL 32708
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  $380,000 Sold May 16, 2025

  1349 Mill Stream Ln, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,435 Sq Ft
  • Built 2015

  Last Sold Summary

  • 1% Below List Price
  • $265/SF
  • 183 Days On Market

  Current Estimated Value $374,895

  Last Listing Agent Tim Veigle WATSON REALTY CORP

  1349 Mill Stream Ln, Winter Springs, FL 32708

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