Winter Springs, FL Homes

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  $575,000 Sold Jun 06, 2025

  120 W Trade Winds Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 2,382 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $241/SF
  • 14 Days On Market

  Current Estimated Value $575,866

  Last Listing Agent Barbara Mills COLDWELL BANKER REALTY

  120 W Trade Winds Rd, Winter Springs, FL 32708
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  Est $838,914 Not Listed For Sale

  1005 Nancy Cir, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 3,361 Sq Ft
  • Built 1990

  1005 Nancy Cir, Winter Springs, FL 32708

  Last Sold Summary

  • $250/SF
  • 2 Days On Market

  Last Sold Price $841,000

  Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES
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  /66

  $480,000 Pending

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

  697 N Endeavour Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. DO NOT MISS OUT ON THIS WONDERFUL BUY IN GREAT SUBDIVISION!! NEW ROOF AND NEW A/C JUST INSTALLED IN 12/2025. This lovely home is located in one of Winter Springs most desirable neighborhoods. The serene community is outstanding with Oak tree canopies and spacious lots with nice curb appeal and lush landscaping. Welcome to this inviting 4 bedroom, 2 bath

  Nancy Langley PREMIUM PROPERTIES R.E SERVICE

  697 N Endeavour Dr, Winter Springs, FL 32708
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  $559,000 Sold Aug 29, 2025

  433 Woodcrest St Unit 2, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,315 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Below List Price
  • $241/SF
  • 49 Days On Market

  Current Estimated Value $560,070

  Last Listing Agent Keegan Siegfried LPT REALTY, LLC

  433 Woodcrest St Unit 2, Winter Springs, FL 32708
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  /31

  Est $274,945 Not Listed For Sale

  268 San Gabriel St, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,089 Sq Ft
  • Built 1994

  268 San Gabriel St, Winter Springs, FL 32708

  Last Sold Summary

  • 6% Below List Price
  • $270/SF
  • 13 Days On Market

  Last Sold Price $293,900

  Last Listing Agent Raquel Toribio Carela LPT REALTY, LLC
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  /41

  $214,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,434 Sq Ft

  505 Moree Loop, Winter Springs, FL 32708

  Welcome to this charming 2-bedroom, 2 1/2-bath home located in the heart of Winter Springs! This beautifully maintained residence offers an open and functional layout, perfect for both everyday living and entertaining. The bright kitchen features ample cabinet space and a breakfast bar that overlooks the spacious living and dining areas. Step outside to a large wood deck and fenced backyard—ideal

  Matt Magee LPT REALTY LLC

  505 Moree Loop, Winter Springs, FL 32708
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  $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 $1,458,818

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

  699 Bear Paw Ct, Winter Springs, FL 32708
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  /20

  Est $235,876 Not Listed For Sale

  1306 Park Villa Place, Winter Springs, FL 32708

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

  1306 Park Villa Place, Winter Springs, FL 32708

  Last Sold Summary

  • $203/SF
  • 48 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Rick Protheroe RE/MAX
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  /28

  $360,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  502 Lancers Dr, Winter Springs, FL 32708

  Charming 3-bedroom, 2-bath home offering an open split floor plan with vaulted ceilings and abundant natural light. The main living areas feature tile and laminate flooring for a stylish, low-maintenance finish. The primary suite includes a generous walk-in closet with elevated ceilings for added storage. Sliding glass doors open to a private backyard with a concrete patio and easy-care lawn,

  Kayla Williams Realty Pros Commercial

  502 Lancers Dr, Winter Springs, FL 32708
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  $297,000 Sold May 02, 2025

  530 San Gabriel Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $250/SF
  • 66 Days On Market

  Current Estimated Value $287,215

  Last Listing Agent Amy Moline EXP REALTY LLC

  530 San Gabriel Ct, Winter Springs, FL 32708
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  Est $317,390 Not Listed For Sale

  530 Harbor Winds Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft
  • Built 2008

  530 Harbor Winds Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $238/SF
  • 26 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Wally Gilmour UNITED REAL ESTATE PREFERRED
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  /30

  $279,990 Open Sun 1PM - 4PM

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

  314 San Gabriel St, Winter Springs, FL 32708

  PRICE REDUCTION: Welcome to your dream home in the highly sought-after Deer Song Community of Winter Springs! This charming 3-bedroom, 2-bath corner single family home is packed with upgrades, including a brand new hot water heater (installed 2/23/2026), a newer roof (2021) and re-plumb (2021), state-of-the-art appliances (2021-2022), a top-of-the-line air conditioning system (2022), a water

  Linda Bain WEICHERT REALTORS HALLMARK PRO

  314 San Gabriel St, Winter Springs, FL 32708
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  $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 $323,106

  Last Listing Agent Destiny Anderson LIVE FLORIDA REALTY

  1515 Braewick St, Winter Springs, FL 32708
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  Est $338,070 Not Listed For Sale

  487 Harbor Winds Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,914 Sq Ft
  • Built 2008

  487 Harbor Winds Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $179/SF
  • 272 Days On Market

  Last Sold Price $342,000

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP
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  /23

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  403 Murphy Rd, Winter Springs, FL 32708

  Welcome home to this beautiful 3 bedrooms, 2 bathrooms house with a pool. Come and enjoy the large pool, modern and updated kitchen with granite countertop and stainless-steel appliances. The spacious interior along with the bonus room will give your family enough space to grow. In the last 4 years the roof, air conditioning unit and water heater have all been replaced. The solar panels will

  Celeste Baez FLORIDA REALTY INVESTMENTS

  403 Murphy Rd, Winter Springs, FL 32708
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  $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 $252,182

  Last Listing Agent Shari Starner CHARLES RUTENBERG REALTY ORLANDO

  602 Casa Park Court F, Winter Springs, FL 32708
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  Est $329,409 Not Listed For Sale

  447 Harbor Winds Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 2008

  447 Harbor Winds Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 2% Below List Price
  • $201/SF
  • 6 Days On Market

  Last Sold Price $337,000

  Last Listing Agent Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO
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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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  $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 $312,989

  Last Listing Agent Uwem Akpan CHARLES RUTENBERG REALTY ORLANDO

  251 Buttonwood Ave, Winter Springs, FL 32708
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  /33

  Est $327,287 Not Listed For Sale

  450 Tradition Ln, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft
  • Built 2005

  450 Tradition Ln, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $233/SF
  • 17 Days On Market

  Last Sold Price $342,000

  Last Listing Agent Gabriella Nystrom UNITED REAL ESTATE PREFERRED
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  /57

  $719,000

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

  1503 Graceful Doe Loop, Winter Springs, FL 32708

  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 main level features an open and versatile

  Gabriel Andrada FLORIDA SPIRIT HOMES

  1503 Graceful Doe Loop, Winter Springs, FL 32708
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  $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 $404,142

  Last Listing Agent Marian Schneider RE/MAX PRIME PROPERTIES

  626 Pearl Rd, Winter Springs, FL 32708
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  /51

  Est $525,905 Not Listed For Sale

  914 Devon Creek Rd, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,996 Sq Ft
  • Built 2004

  914 Devon Creek Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 12% Below List Price
  • $298/SF
  • 0 Days On Market

  Last Sold Price $595,100

  Last Listing Agent Tania Crandall SHORESTONE PROPERTY GROUP
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  /27

  $310,000

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

  600 Northern Way Unit 906, Winter Springs, FL 32708

  Turnkey townhouse and ready for immediate move-in. All sold as-is and with the right to inspect. Exceptional open floor plan with flexibility for multi-generation living. This beautiful home has three en-suites with one of the bedrooms on the ground level, so it’s perfect for a mother-in-law suite. Large sized rooms, updated bathrooms, and all the features you are looking for. The kitchen has

  John Vincent JR REALTY GROUP LLC

  600 Northern Way Unit 906, Winter Springs, FL 32708
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  $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 $285,194

  Last Listing Agent Rafael Salado GREATER ORLANDO REALTY, LLC

  737 Sherwood Dr, Winter Springs, FL 32708
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  Est $729,447 Not Listed For Sale

  410 Park Lake Dr, Winter Springs, FL 32708

  • 5 Beds
  • 4.5 Baths
  • 3,639 Sq Ft
  • Built 2003

  410 Park Lake Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 7% Below List Price
  • $216/SF
  • 24 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Erin Tompkins COLDWELL BANKER REALTY
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  $285,000 Open Sat 2PM - 4PM

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

  476 Club Dr, Winter Springs, FL 32708

  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 the benefits of a 2020 A/C system, a full

  Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

  476 Club Dr, Winter Springs, FL 32708
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  $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 $427,328

  Last Listing Agent Sean Calegan CFRP REALTY LLC

  821 Sheoah Cir, Winter Springs, FL 32708
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  Est $713,624 Not Listed For Sale

  337 Twelve Oaks Dr, Winter Springs, FL 32708

  • 5 Beds
  • 3.5 Baths
  • 3,660 Sq Ft
  • Built 2000

  337 Twelve Oaks Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Above List Price
  • $194/SF
  • 9 Days On Market

  Last Sold Price $709,900

  Last Listing Agent Allison Day RE/MAX
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  /13

  $29,900

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

  31 La Vista Dr, Winter Springs, FL 32708

  A must-see home that has been totally renovated with new luxury vinyl flooring, Kitchen has quartz counter tops and all new stainless-steel appliances. New baseboards freshly painted throughout. New A/C ductwork. Master bathroom has been totally remodeled. a GREAT 55+ COMMUNITY offering lots of amenities. Restaurants & major roads nearby. Vacant & ready for a new owner!!!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  31 La Vista Dr, Winter Springs, FL 32708
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  $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 $420,107

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  861 Big Buck Cir, Winter Springs, FL 32708
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  /27

  Est $455,428 Not Listed For Sale

  125 Stone Gable Cir, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1999

  125 Stone Gable Cir, Winter Springs, FL 32708

  Last Sold Summary

  • $233/SF
  • 2 Days On Market

  Last Sold Price $455,000

  Last Listing Agent Kim Carthen CARTHEN REALTY INC
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  /68

  $93,500

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

  411 La Vista Dr, Winter Springs, FL 32708

  Hacienda Village 55+-Double Wide 1536 sq. ft. 3 bedrooms, 2 bath, split plan with a lot of upgrades. Family Room, screened in area, lots of storage-water purifier, nice size lot to enjoy. Neighborhood is close to all major highways, shopping, doctors, restaurants. All the latest and greatest amenities. Hacienda Village is a legacy Community. Monthly rent is $1025.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES

  411 La Vista Dr, Winter Springs, FL 32708
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  $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 $356,285

  Last Listing Agent Jack Luiz LANDSHARK REALTY

  382 Panama Cir, Winter Springs, FL 32708
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  Est $175,061 Not Listed For Sale

  415 Sheoah Blvd Unit 11, Winter Springs, FL 32708

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft
  • Built 1973

  415 Sheoah Blvd Unit 11, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $197/SF
  • 73 Days On Market

  Last Sold Price $184,500

  Last Listing Agent Cami Coupland KELLER WILLIAMS ADVANTAGE REALTY
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  /27

  $495,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,345 Sq Ft

  223 Tavestock Loop, Winter Springs, FL 32708

  Under contract-accepting backup offers. NEW PRICE REDIUCTION!** Great Opportunity in Winter Springs! This spacious 4-bedroom, 2.5-bath two-story home is located in the gated community of Parkstone and features an oversized backyard, perfect for future upgrades. The floor plan includes a formal living and dining area, as well as a family room with high ceilings and windows that bring in a ton

  Mary Walason MEP REALTY INVESTMENTS LLC

  223 Tavestock Loop, Winter Springs, FL 32708
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  $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 $434,394

  Last Listing Agent Suzanne Crudo COLDWELL BANKER REALTY

  1010 Chokecherry Dr, Winter Springs, FL 32708
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  /26

  Est $286,397 Not Listed For Sale

  227 Albert St, Winter Springs, FL 32708

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1971

  227 Albert St, Winter Springs, FL 32708

  Last Sold Summary

  • 8% Below List Price
  • $285/SF
  • 4 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY
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  $309,777 Pending

  • 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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  $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 $358,431

  Last Listing Agent Elaine Masood HEARTFELT REALTY HOMETEAM

  3876 White Birch Run, Winter Springs, FL 32708

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