Winter Springs, FL Homes

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  $645,000 Sold May 14, 2025

  1104 Dyson Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Above List Price
  • $326/SF
  • 6 Days On Market

  Current Estimated Value $638,176

  Last Listing Agent Chris Sheedy COLDWELL BANKER REALTY

  1104 Dyson Dr, Winter Springs, FL 32708
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  Est $435,819 Not Listed For Sale

  1145 Orange Ave, Winter Springs, FL 32708

  • 3 Beds
  • 3.5 Baths
  • 2,294 Sq Ft
  • Built 2015

  1145 Orange Ave, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $199/SF
  • 121 Days On Market

  • Last Sold Price $457,500
  • Jun 28, 2024

  Last Listing Agent Denise McKinley RE/MAX
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  $573,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,566 Sq Ft

  203 Herrell Rd, Winter Springs, FL 32708

  Under contract-accepting backup offers. **Seller will contribute towards buyer closing costs that buyer can use towards renovations. This number is negotiable.** Incredible opportunity to own this fantastic 5 bedroom, 3.5 bathroom home with OVER 3,500 square feet of living space and NO HOA in the highly sought after Ranchlands community. This home has a beautiful covered front porch, circular

  Margeaux Eddy MAINFRAME REAL ESTATE

  203 Herrell Rd, Winter Springs, FL 32708
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  $625,000 Sold Feb 19, 2026

  1621 White Dove Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft
  • Built 1985

  Last Sold Summary

  • $293/SF
  • 4 Days On Market

  Current Estimated Value $628,980

  Last Listing Agent Ryan Minadie COLDWELL BANKER REALTY

  1621 White Dove Dr, Winter Springs, FL 32708
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  Est $511,100 Not Listed For Sale

  1328 Swift Creek Way, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,986 Sq Ft
  • Built 2020

  1328 Swift Creek Way, Winter Springs, FL 32708

  Last Sold Summary

  • 3% Below List Price
  • $264/SF
  • 6 Days On Market

  • Last Sold Price $525,000
  • Mar 29, 2024

  Last Listing Agent Jennifer Christ RE/MAX
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  $750,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  124 Blue Creek Dr, Winter Springs, FL 32708

  Welcome to this 5 bedroom, 3 bathroom pool home in the highly desirable Tuskawilla neighborhood of Chestnut Estates. This home offers open-concept living with pool access from the primary bedroom, living room, and family room. As you walk through the front door, the dining room and spacious living room open to the lanai and screened-in pool area. The master bedroom and 5th bedroom are located on

  Ryan Langley FLORIDA REALTY INVESTMENTS

  124 Blue Creek Dr, Winter Springs, FL 32708
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  $790,000 Sold May 28, 2025

  859 Windcrest Place, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Above List Price
  • $274/SF
  • 5 Days On Market

  Current Estimated Value $784,682

  Last Listing Agent Lori Hoover EXP REALTY LLC

  859 Windcrest Place, Winter Springs, FL 32708
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  Est $414,892 Not Listed For Sale

  1170 Spotted Sandpiper Loop, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,521 Sq Ft
  • Built 2023

  1170 Spotted Sandpiper Loop, Winter Springs, FL 32708

  Last Sold Summary

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

  • Last Sold Price $432,803
  • Jan 19, 2024

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $25,000

  • 2 Beds
  • 2 Baths
  • 966 Sq Ft

  242 Aztec Dr, Winter Springs, FL 32708

  Bank Owned-repainted-2-bedroom, 2 bath newer HVAC about 2023. Hacienda Village has recently been renovated with an added pickle ball court, putt putt, Doggy Park, Tiki Huts, Barbecue's, and More. Hacienda is located near major highways with only about 45 minutes to Beaches & Parks, Restaurants, Shopping, Doctors, Fire & Police Departments close by. Monthly base rent is $1075.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  242 Aztec Dr, Winter Springs, FL 32708
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  $775,000 Sold Dec 02, 2025

  108 Seville Chase Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,917 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $266/SF
  • 5 Days On Market

  Current Estimated Value $773,078

  Last Listing Agent Bud Williams THE WILLIAMS REAL ESTATE CO

  108 Seville Chase Dr, Winter Springs, FL 32708
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  Est $664,250 Not Listed For Sale

  940 Talon Place, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,696 Sq Ft
  • Built 2021

  940 Talon Place, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $249/SF
  • 126 Days On Market

  • Last Sold Price $670,000
  • Jun 29, 2023

  Last Listing Agent Justin Core EXP REALTY LLC
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  $29,900

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

  125 Las Almas Ln, Winter Springs, FL 32708

  Very Modern-open-Newer Windows, New Rood 2021, Newer Appliances, Replumbed. A beautiful setting. Hacienda Village is a Legacy 55+ Community with newer Amenities, Pickle Ball, Putt Putt, Doggie Park, 2 pools, one which is heated. Always something going on- Never a dull moment. Base mo. rent is $1075. (Pictures coming soon) Great buy for this large home!!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  125 Las Almas Ln, Winter Springs, FL 32708
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  $600,000 Sold Apr 30, 2026

  689 Seven Oaks Blvd, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 2,541 Sq Ft
  • Built 2017

  Last Sold Summary

  • $236/SF
  • 4 Days On Market

  Current Estimated Value $580,531

  Last Listing Agent Dan Teston EXP REALTY LLC

  689 Seven Oaks Blvd, Winter Springs, FL 32708
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  Est $448,221 Not Listed For Sale

  1364 Congressional Ct, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,854 Sq Ft
  • Built 2014

  1364 Congressional Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $252/SF
  • 87 Days On Market

  • Last Sold Price $467,500
  • Apr 11, 2024

  Last Listing Agent Barbara Friedman FANNIE HILLMAN & ASSOCIATES
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  $339,900

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft

  335 Kirkcaldy Dr, Winter Springs, FL 32708

  Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new

  Irina Carp MILLENIUM REALTY GROUP

  335 Kirkcaldy Dr, Winter Springs, FL 32708
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  $700,000 Sold Jul 31, 2025

  694 Tuscora Dr, Winter Springs, FL 32708

  • 5 Beds
  • 3 Baths
  • 2,480 Sq Ft
  • Built 1983

  Last Sold Summary

  • 14% Below List Price
  • $282/SF
  • 67 Days On Market

  Current Estimated Value $692,919

  Last Listing Agent Randy Fontanez, II CHARLES RUTENBERG REALTY ORLANDO

  694 Tuscora Dr, Winter Springs, FL 32708
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  Est $383,729 Not Listed For Sale

  1291 Mill Pond Ln, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft
  • Built 2015

  1291 Mill Pond Ln, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Below List Price
  • $237/SF
  • 59 Days On Market

  • Last Sold Price $398,733
  • Nov 15, 2023

  Last Listing Agent Daniel Hart HEROES REAL ESTATE GROUP LLC
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  $625,000 Pending

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

  1106 Superior Ct, Winter Springs, FL 32708

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to the highly sought-after Tuscawilla community, a neighborhood known for its tree-lined streets, strong sense of community, and access to some of the top-rated Seminole County schools. From the moment you walk through the front door, you’re greeted with an abundance of natural light that fills the

  David Miller KELLER WILLIAMS HERITAGE REALTY

  1106 Superior Ct, Winter Springs, FL 32708
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  $420,000 Sold Dec 31, 2025

  630 Sailfish Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1978

  Last Sold Summary

  • $250/SF
  • 0 Days On Market

  Current Estimated Value $416,445

  Last Listing Agent Non-Member Non-Member Out Of Area Non-MLS or Out of Area

  630 Sailfish Rd, Winter Springs, FL 32708
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  Est $277,276 Not Listed For Sale

  Unlisted Address

  Unlisted Address

  Last Sold Summary

  • 3% Below List Price
  • 5 Days On Market

  • Last Sold Price $285,000
  • Aug 30, 2023

  Last Listing Agent Juan Maldonado A PLUS REALTY LLC
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  $135,500

  • 2 Beds
  • 2 Baths

  154 Hacienda Dr, Winter Springs, FL 32708

  This brand-new 2026 model home offers modern comfort and style throughout, featuring recessed lighting, elegant crown molding, and durable luxury plank flooring. The thoughtfully designed layout includes spacious walk-in closets and a versatile den-perfect for a home office or study space. The kitchen is equipped with sleek stainless steel appliances, and the property also includes a shed with

  Todd Vagts Hacienda Village

  154 Hacienda Dr, Winter Springs, FL 32708
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  $275,000 Sold Apr 03, 2026

  100 Silver Sea Rd, Winter Springs, FL 32708

  • 2 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Below List Price
  • $222/SF
  • 30 Days On Market

  Current Estimated Value $288,066

  Last Listing Agent Carla Cabrera MODERN WORLD REALTY LLC

  100 Silver Sea Rd, Winter Springs, FL 32708
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  Not Listed For Sale

  0 E 434 State Rd Unit O6066271, Winter Springs, FL 32708

  0 E 434 State Rd Unit O6066271, Winter Springs, FL 32708

  Last Sold Summary

  • 60 Days On Market

  • Last Sold Price $330,000
  • Apr 19, 2024

  Last Listing Agent Kat Harden GRACE REALTY, INC.
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  $94,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  1090 Apache Trail, Winter Springs, FL 32708

  This 1056 sq. ft. home remodeled home has many extra features that makes it so unique. Private Back Yard with screen porch is so inviting, Has extra large added garage with workshop attached. Good size bedrooms and totally upgraded Bathrooms. Lot rent is $755.00 per month. Home is on septic and drainfield that Park maintains.

  Todd Newby NEWBY REALTY INC

  1090 Apache Trail, Winter Springs, FL 32708
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  $545,000 Sold Aug 07, 2025

  687 N Endeavour Dr, Winter Springs, FL 32708

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

  Last Sold Summary

  • 1% Below List Price
  • $264/SF
  • 27 Days On Market

  Current Estimated Value $552,499

  Last Listing Agent Joe Sayers KELLER WILLIAMS ADVANTAGE REALTY

  687 N Endeavour Dr, Winter Springs, FL 32708
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  Est $460,016 Not Listed For Sale

  1471 Connors Ln, Winter Springs, FL 32708

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

  1471 Connors Ln, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $235/SF
  • 41 Days On Market

  • Last Sold Price $485,000
  • Apr 26, 2024

  Last Listing Agent Julia Jordan KELLER WILLIAMS WINTER PARK
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  $455,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,934 Sq Ft

  905 Torrey Pine Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Greenbriar of Tuscawilla offers a spacious, Light & Bright, open-concept 3-bedroom, 2-bath layout with peaceful views and an easy, connected flow for everyday living and entertaining. The kitchen opens directly to the living area, so you’re always part of the conversation—whether it’s morning coffee or game day. Gas fireplace in the living room for those

  Laura Leigh Wood RE/MAX TOWN & COUNTRY REALTY

  905 Torrey Pine Dr, Winter Springs, FL 32708
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  $525,000 Sold Jul 31, 2025

  370 Brushwood Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,272 Sq Ft
  • Built 1986

  Last Sold Summary

  • $231/SF
  • 3 Days On Market

  Current Estimated Value $525,526

  Last Listing Agent Gretchen Carlson REAL ESTATE HOUSE FL INC

  370 Brushwood Ln, Winter Springs, FL 32708
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  Est $393,739 Not Listed For Sale

  1174 Spotted Sandpiper Loop, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,521 Sq Ft
  • Built 2022

  1174 Spotted Sandpiper Loop, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $273/SF
  • 316 Days On Market

  • Last Sold Price $415,000
  • Jan 18, 2024

  Last Listing Agent Ping Song SUNSHINE GROUP USA, INC
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  $395,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,314 Sq Ft

  1029 E Pebble Beach Cir, Winter Springs, FL 32708

  Welcome home to this charming 3-bedroom, 2-bath residence in the desirable community of Country Club Village. This home features a split bedroom floor plan and a kitchen large enough for a breakfast nook. Enjoy your morning coffee on either of the TWO screened porch areas.Located in the heart of Winter Springs, you are minutes from top-rated Seminole County Schools, parks, shopping, and the

  Stephanie Kovats KELLER WILLIAMS ADVANTAGE REALTY

  1029 E Pebble Beach Cir, Winter Springs, FL 32708
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  $1,250,000 Sold Aug 22, 2025

  723 Calico Ct, Winter Springs, FL 32708

  • 6 Beds
  • 5.5 Baths
  • 4,055 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $308/SF
  • 5 Days On Market

  Current Estimated Value $1,214,006

  Last Listing Agent Bradley Merrell COLDWELL BANKER REALTY

  723 Calico Ct, Winter Springs, FL 32708
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  Est $500,841 Not Listed For Sale

  1270 Spotted Sandpiper Loop, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 2,359 Sq Ft
  • Built 2023

  1270 Spotted Sandpiper Loop, Winter Springs, FL 32708

  Last Sold Summary

  • 3% Below List Price
  • $219/SF
  • 444 Days On Market

  • Last Sold Price $517,057
  • Oct 30, 2023

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $230,000

  • 3 Beds
  • 2 Baths
  • 1,367 Sq Ft

  4431 Brook Hollow Cir, Winter Springs, FL 32708

  Welcome home to 4431 Brook Hollow Circle, where clean design meets comfortable living. This light-filled residence offers an open, airy layoutthat feels both spacious and welcoming, with neutral finishes that create a fresh, move-in-ready atmosphere. The living and dining areas flowseamlessly, making everyday living and entertaining effortless. One of the home’s standout features is the

  Nicolas Merino EXP REALTY LLC

  4431 Brook Hollow Cir, Winter Springs, FL 32708
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  $625,000 Sold Nov 10, 2025

  1178 Black Walnut Ct, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • Built 1997

  Last Sold Summary

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

  Current Estimated Value $625,159

  Last Listing Agent Jody Deabenderfer CHARLES RUTENBERG REALTY ORLANDO

  1178 Black Walnut Ct, Winter Springs, FL 32708
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  Est $414,473 Not Listed For Sale

  1152 Spotted Sandpiper Loop, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,521 Sq Ft
  • Built 2024

  1152 Spotted Sandpiper Loop, Winter Springs, FL 32708

  Last Sold Summary

  • 5% Below List Price
  • $287/SF
  • 271 Days On Market

  • Last Sold Price $436,848
  • Jan 16, 2024

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $397,990 Pending

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

  1272 Crab Apple Ln, 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

  Amanda Warren MATTAMY REAL ESTATE SERVICES

  1272 Crab Apple Ln, Winter Springs, FL 32708
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  $872,000 Sold Jun 23, 2025

  1745 Seneca Blvd, Winter Springs, FL 32708

  • 5 Beds
  • 3 Baths
  • 2,811 Sq Ft
  • Built 1987

  Last Sold Summary

  • $310/SF
  • 4 Days On Market

  Current Estimated Value $866,107

  Last Listing Agent Lindsay Kaye Voss VOSS REALTY INC

  1745 Seneca Blvd, Winter Springs, FL 32708
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  Est $413,802 Not Listed For Sale

  1148 Spotted Sandpiper Loop, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,509 Sq Ft
  • Built 2023

  1148 Spotted Sandpiper Loop, Winter Springs, FL 32708

  Last Sold Summary

  • 6% Below List Price
  • $292/SF
  • 559 Days On Market

  • Last Sold Price $441,000
  • Feb 27, 2024

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $310,000

  • 3 Beds
  • 2 Baths
  • 1,105 Sq Ft

  130 Deer Song Dr, Winter Springs, FL 32708

  Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to own one of the most beautifully updated homes in the community! Positioned on a desirable corner lot with ample parking, this fully renovated 3-bedroom, 2-bathroom home stands out as a rare find offering both style and convenience. From the moment you step inside, you’ll notice the thoughtful upgrades

  Yosseff Roman KELLER WILLIAMS ADVANTAGE III

  130 Deer Song Dr, Winter Springs, FL 32708
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  $346,500 Sold Nov 13, 2025

  1341 Mill Stream Ln, Winter Springs, FL 32708

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

  Last Sold Summary

  • 9% Below List Price
  • $241/SF
  • 217 Days On Market

  Current Estimated Value $347,880

  Last Listing Agent Maribel Ramos VESTI LLC

  1341 Mill Stream Ln, Winter Springs, FL 32708

Showing Results 441 - 480, Page 12 of 18