507

Windsor Estates Homes

Section Image
  • /14

    $49,900 Pending

    • Land
    • 22,651 Sq Ft
    • $95,962 per Acre

    0 Linda Cir Unit Lot 9, Winston-Salem, NC 27106

    Discover a rare opportunity to build your dream home in a beautiful, well-established neighborhood just off Reynolda Rd. This wooded, sloped basement lot offers a serene setting surrounded by mature trees, providing natural privacy and peaceful atmosphere. Gentle slope is ideal for a basement-style home, allowing for creative design possibilities that blend seamlessly into the landscape. Small

    Willette Roper Roper Triad Realty

    0 Linda Cir Unit Lot 9, Winston-Salem, NC 27106
  • /35

    $1,450 - $1,875 per month

    Crowne Park

    1 - 3 Beds

    900 Crowne Park Dr, Winston-Salem, NC 27106

    Established in a preserve, adjacent to the old growth forest that is Sunnynoll, Crowne Park Apartments is well situated at the prime intersection of Silas Creek Parkway and Fairlawn Drive, just one mile west of Wake Forest University in Winston-Salem, North Carolina.

    900 Crowne Park Dr, Winston-Salem, NC 27106
  • /42

    $318,000 Sold Aug 28, 2025

    1151 Cypress Cir, Winston Salem, NC 27106

    • 5 Beds
    • 3 Baths
    • 2,885 Sq Ft
    • Built 1968

    Last Sold Summary

    • 11% Below List Price
    • $110/SF
    • 38 Days On Market

    Current Estimated Value $336,741

    Last Listing Agent Donna Meeker Keller Williams Realty

    1151 Cypress Cir, Winston Salem, NC 27106
    • /28

      Est $285,054 Not Listed For Sale

      1131 Cypress Cir, Winston Salem, NC 27106

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 1961
      1131 Cypress Cir, Winston Salem, NC 27106

      Last Sold Summary

      • $168/SF
      • 7 Days On Market
      • Last Sold Price $285,000
      • May 10, 2024

      Last Listing Agent Sandy Elliott Howard Hanna Allen Tate - Winston Salem

  • /2

    $65,000

    • Land
    • 1.51 Acres
    • $43,046 per Acre

    0 Old Town Rd Unit 1151582, Winston-Salem, NC 27106

    This property is zoned as RS9. Neighboring parcel also available. Potential for rezoning. So many possibilities make this the perfect property for your next investment! Just minutes from Bethabara Park, Wake Forest University, as well as local shopping and dining options. Centrally located near University Pkwy and Reynolda Road. Less than 20 minutes from Wake Forest Baptist Health. Call for more

    Shaunna Overman Howard Hanna Allen Tate Oak Ridge Commons

    0 Old Town Rd Unit 1151582, Winston-Salem, NC 27106
  • /50

    $985 - $1,149 per month

    New Salem Village

    1 - 2 Beds

    1520 Woods Rd, Winston-Salem, NC 27106

    Free heat, hot water, water & sewer, and trash removal. No admin fees and No amenity fees. Inquire about our Preferred Employer Discount program for additional savings. Enjoy our fitness center, swimming pool, dog park, barbeque stations, and arcade game room (Pet Spa coming soon).Placed in a beautiful park-like setting New Salem Village is down the street from Bethabara Park and located

    1520 Woods Rd, Winston-Salem, NC 27106
  • /45

    $501,000 Sold Apr 17, 2026

    35 Edith Ave, Winston Salem, NC 27106

    • 3 Beds
    • 3 Baths
    • 3,374 Sq Ft
    • Built 1959

    Last Sold Summary

    • 5% Above List Price
    • $148/SF
    • 63 Days On Market

    Current Estimated Value $464,504

    Last Listing Agent Dana Scrattish Forsyth Realty Group

    35 Edith Ave, Winston Salem, NC 27106
    • /29

      Est $339,118 Not Listed For Sale

      1403 Polo Rd, Winston Salem, NC 27106

      • 4 Beds
      • 3 Baths
      • 1,500 Sq Ft
      • Built 1930
      1403 Polo Rd, Winston Salem, NC 27106

      Last Sold Summary

      • 5% Above List Price
      • $215/SF
      • 3 Days On Market
      • Last Sold Price $323,000
      • Jul 26, 2023

      Last Listing Agent Susan Maier-Colon Berkshire Hathaway HomeServices Carolinas Realty

  • /34

    $375,000

    • 3 Beds
    • 2 Baths
    • 2,503 Sq Ft

    3301 Midkiff Rd, Winston Salem, NC 27106

    Enjoy the space & versatility of this brick ranch on a large fenced lot near Wake Forest University. The main level features 3 bedrooms, w/access to a large back deck from the primary suite & an additional bedroom which creates a seamless indoor-outdoor flow. The kitchen offers lots of cabinet space, bar seating, & eat-in area w/fireplace. The partially finished basement expands your living

    Morgan Reitzel Leonard Ryden Burr Real Estate

    3301 Midkiff Rd, Winston Salem, NC 27106
  • /53

    $975 - $1,095 per month

    Hunt Club Apartments, LLC

    1 - 2 Beds

    103 Echo Glen Dr, Winston-Salem, NC 27106

    Hunt Club Apartments in Winston Salem offers beautiful newly renovated one and two bedroom apartment homes. This resort-style complex has much to offer! Gorgeous grounds, colorful flower beds, sweeping green lawns, and towering trees surround Hunt Club. This apartment community is located next to Bethabara Park, and we are only 5 minutes from Wake Forrest University. Our apartments have the best

    103 Echo Glen Dr, Winston-Salem, NC 27106
  • /33

    $231,000 Sold Dec 15, 2025

    1138 Edgebrook Dr, Winston Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 1984

    Last Sold Summary

    • 36% Above List Price
    • $143/SF
    • 6 Days On Market

    Current Estimated Value $233,333

    Last Listing Agent Paul Gwin Hunter Realty & Property Management, LLC

    1138 Edgebrook Dr, Winston Salem, NC 27106
    • /38

      Est $303,907 Not Listed For Sale

      1116 Edgebrook Dr, Winston Salem, NC 27106

      • 3 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 1974
      1116 Edgebrook Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 2% Above List Price
      • $157/SF
      • 22 Days On Market
      • Last Sold Price $299,000
      • Jul 14, 2023

      Last Listing Agent Alexis Melendez MCA Realty Int & Building Co. LLC

  • /2

    $72,000

    • Land
    • 1.54 Acres
    • $46,753 per Acre

    1406 Old Town Rd, Winston-Salem, NC 27106

    This property is zoned as RS9. Neighboring parcel also available. Potential for rezoning. So many possibilities make this the perfect property for your next investment! Just minutes from Bethabara Park, Wake Forest University, as well as local shopping and dining options. Centrally located near University Pkwy and Reynolda Road. Less than 20 minutes from Wake Forest Baptist Health. Call for more

    Shaunna Overman Howard Hanna Allen Tate Oak Ridge Commons

    1406 Old Town Rd, Winston-Salem, NC 27106
  • /50

    $937 - $1,304 per month

    Trails At Bethabara

    1 - 3 Beds

    1620 Woods Rd, Winston-Salem, NC 27106

    You will find the ultimate in apartment home living at The Trails at Bethabara. This desirable community in Winston Salem, North Carolina reflects a tradition of elegant living and creates an atmosphere of serenity enhanced by lush landscaping and dramatic architecture. Beyond the beautiful residences and landscaping you'll discover a vibrant neighborhood of shops, restaurants, schools, and

    1620 Woods Rd, Winston-Salem, NC 27106
  • /33

    $346,900 Sold Jul 07, 2025

    3306 Midkiff Rd, Winston Salem, NC 27106

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Below List Price
    • $157/SF
    • 2 Days On Market

    Current Estimated Value $350,612

    Last Listing Agent Marlana Riley Keller Williams Realty Elite

    3306 Midkiff Rd, Winston Salem, NC 27106
    • /35

      Est $427,885 Not Listed For Sale

      1173 Edgebrook Dr, Winston Salem, NC 27106

      • 4 Beds
      • 3 Baths
      • 3,500 Sq Ft
      • Built 1972
      1173 Edgebrook Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 10% Above List Price
      • $111/SF
      • 15 Days On Market
      • Last Sold Price $390,000
      • Jun 30, 2023

      Last Listing Agent Lynn Ray RE/MAX

  • /40

    $375,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,206 Sq Ft

    3239 Linda Cir, Winston Salem, NC 27106

    This well-maintained home in an established neighborhood. The functional layout offers comfortable living spaces ideal for everyday living and entertaining. The partially finished basement provides flexible space for a bonus room, office, or recreation area, along with abundant storage and additional space in the basement garage. Enjoy outdoor living on the large deck overlooking the backyard,

    Steven Montgomery Berkshire Hathaway HomeServices Carolinas Realty

    3239 Linda Cir, Winston Salem, NC 27106
  • /27

    $1,090 - $1,365 per month

    The Pines at Bethabara

    1 - 2 Beds

    511 Bethabara Hills Ct, Winston-Salem, NC 27106

    Apply today & take advantage of our MOVE-IN SPECIAL: 1/2 Month FREE on First Month’s Rent!Welcome home to The Pines at Bethabara. With easy access to delicious local restaurants, plentiful shopping, fun entertainment, historic Bethabara Park, and Wake Forest University, everything you need is nearby. If location and convenience are important factors in your lifestyle, you've come to the

    511 Bethabara Hills Ct, Winston-Salem, NC 27106
  • /50

    $319,900 Sold Jul 08, 2025

    1160 Edgebrook Dr, Winston Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 2,051 Sq Ft
    • Built 1961

    Last Sold Summary

    • 2% Below List Price
    • $156/SF
    • 28 Days On Market

    Current Estimated Value $312,620

    Last Listing Agent Kristie Wright Innovate Real Estate

    1160 Edgebrook Dr, Winston Salem, NC 27106
    • /44

      Est $333,181 Not Listed For Sale

      1447 Old Town Rd, Winston Salem, NC 27106

      • 4 Beds
      • 3 Baths
      • 2,802 Sq Ft
      • Built 1939
      1447 Old Town Rd, Winston Salem, NC 27106

      Last Sold Summary

      • $118/SF
      • 18 Days On Market
      • Last Sold Price $332,000
      • Feb 21, 2025

      Last Listing Agent Carol Milligan Howard Hanna Allen Tate High Point

  • /8

    $1,200 per month

    • 2 Beds
    • 2 Baths
    • 991 Sq Ft
    • ****** HALF OFF FIRST FULL MONTH OF RENT!! ******

    133 Columbine Dr, Winston-Salem, NC 27106

    Welcome to 133 Columbine Drive, Unit #113, a well-maintained 2-bedroom, 2-bath apartment located in the desirable 27106 area of Winston-Salem. This inviting unit features a bright and comfortable living space with plenty of natural light and a functional layout perfect for everyday living.The kitchen comes equipped with a refrigerator, stove, and dishwasher, offering convenience for meal

    133 Columbine Dr, Winston-Salem, NC 27106
  • /45

    $470,000 Sold Oct 08, 2025

    2106 Bethabara Rd, Winston Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 2,126 Sq Ft
    • Built 1940

    Last Sold Summary

    • 24% Below List Price
    • $221/SF
    • 189 Days On Market

    Current Estimated Value $455,921

    Last Listing Agent Stephen Lawing Leonard Ryden Burr Real Estate

    2106 Bethabara Rd, Winston Salem, NC 27106
    • /36

      Est $334,165 Not Listed For Sale

      2621 Greencrest Dr, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 2,100 Sq Ft
      • Built 1963
      2621 Greencrest Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 8% Above List Price
      • $148/SF
      • 1 Day On Market
      • Last Sold Price $310,000
      • May 30, 2023

      Last Listing Agent Sage Tuttle Team RDE LLC

  • /18

    $1,195 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Two Bedroom Condo Convenient To WFU

    2711 Reynolda Rd, Winston-Salem, NC 27106

    Welcome to the Two Bedroom Condo Convenient To WFU in Winston-Salem, NC! This cozy condo features 2 bedrooms and 2 bathrooms, perfect for those looking for a comfortable living space. The unit boasts luxury vinyl plank flooring throughout, along with a stove, refrigerator, microwave, and disposal in the kitchen. Enjoy the convenience of a pantry for extra storage, as well as a patio for

    2711 Reynolda Rd, Winston-Salem, NC 27106
  • /38

    $662,500 Sold Apr 15, 2026

    910 Idlewilde Heath Ct, Winston Salem, NC 27106

    • 3 Beds
    • 3.5 Baths
    • 4,031 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $164/SF
    • 47 Days On Market

    Current Estimated Value $671,976

    Last Listing Agent Toni Phillips Leonard Ryden Burr Real Estate

    910 Idlewilde Heath Ct, Winston Salem, NC 27106
    • /39

      Est $337,907 Not Listed For Sale

      2680 Greencrest Dr, Winston Salem, NC 27106

      • 3 Beds
      • 3.5 Baths
      • 1,700 Sq Ft
      • Built 1976
      2680 Greencrest Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 9% Above List Price
      • $182/SF
      • 1 Day On Market
      • Last Sold Price $309,500
      • Jul 12, 2023

      Last Listing Agent Wendy Taylor Keller Williams Realty Elite

  • /10

    $1,300 per month

    • 2 Beds
    • 2 Baths
    • "Charming 2-Bed, 2-Bath Condo Retreat in Prime Winston-Salem Location"

    135 Columbine Dr Unit 223, Winston-Salem, NC 27106

    Synonymous with comfort and convenience, 135 Columbine Dr, Unit 223 in Winston-Salem, NC, is a delightful two-bedroom condo that promises a harmonious living experience. Step inside to discover an inviting atmosphere where every corner is designed for relaxation and functionality. With two full bathrooms, morning routines and evening unwinding are effortlessly streamlined for both residents and

    135 Columbine Dr Unit 223, Winston-Salem, NC 27106
  • /22

    $140,000 Sold Dec 01, 2025

    1074 Hickory Glen Rd, Winston Salem, NC 27106

    • 2 Beds
    • 2.5 Baths
    • 1,121 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $125/SF
    • 9 Days On Market

    Current Estimated Value $141,617

    Last Listing Agent Donna Tickle Hillcrest Realty Group

    1074 Hickory Glen Rd, Winston Salem, NC 27106
    • /40

      Est $195,068 Not Listed For Sale

      2651 Reynolda Rd Unit A2, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1975
      2651 Reynolda Rd Unit A2, Winston Salem, NC 27106

      Last Sold Summary

      • 5% Above List Price
      • $155/SF
      • 5 Days On Market
      • Last Sold Price $186,377
      • Jun 08, 2023

      Last Listing Agent Vicki Fleming Mays Realty

  • /25

    $252,500 Sold May 15, 2025

    4523 Old Town Dr, Winston Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 1,360 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $186/SF
    • 33 Days On Market

    Current Estimated Value $247,821

    Last Listing Agent Blake Ginther Keller Williams Realty Elite

    4523 Old Town Dr, Winston Salem, NC 27106
    • /21

      Est $196,727 Not Listed For Sale

      2651 Reynolda Rd Unit A1, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1975
      2651 Reynolda Rd Unit A1, Winston Salem, NC 27106

      Last Sold Summary

      • 27% Above List Price
      • $129/SF
      • 11 Days On Market
      • Last Sold Price $155,000
      • Jun 08, 2023

      Last Listing Agent Vicki Fleming Mays Realty

  • /19

    $132,000 Sold Apr 17, 2026

    133 Columbine Dr Unit 118, Winston Salem, NC 27106

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Built 1986

    Last Sold Summary

    • $126/SF
    • 12 Days On Market

    Current Estimated Value $115,453

    Last Listing Agent Ty Cannon Berkshire Hathaway HomeServices Yost & Little Realty

    133 Columbine Dr Unit 118, Winston Salem, NC 27106
    • /10

      Est $200,719 Not Listed For Sale

      2707 Reynolda Rd Unit C3, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1975
      2707 Reynolda Rd Unit C3, Winston Salem, NC 27106

      Last Sold Summary

      • 26% Above List Price
      • $132/SF
      • 2 Days On Market
      • Last Sold Price $159,000
      • May 23, 2023

      Last Listing Agent Donna Hendrickson Keller Williams Realty

  • /28

    $144,000 Sold Dec 10, 2025

    133 Columbine Dr, Winston Salem, NC 27106

    • 2 Beds
    • 2 Baths
    • 991 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Above List Price
    • $145/SF
    • 15 Days On Market

    Last Listing Agent Deborah Overbey Empyrean Realty

    133 Columbine Dr, Winston Salem, NC 27106
    • /34

      Est $203,800 Not Listed For Sale

      4505 Old Town Dr, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1972
      4505 Old Town Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 2% Above List Price
      • $182/SF
      • 0 Days On Market
      • Last Sold Price $200,000
      • Mar 26, 2024

      Last Listing Agent Joey Miller R&B Legacy Group

  • /39

    $330,000 Sold Mar 17, 2026

    3051 Minart Dr, Winston Salem, NC 27106

    • 4 Beds
    • 2.5 Baths
    • 2,560 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Above List Price
    • $129/SF
    • 4 Days On Market

    Current Estimated Value $328,395

    Last Listing Agent Brent Moser Real Broker LLC

    3051 Minart Dr, Winston Salem, NC 27106
    • /36

      Est $258,299 Not Listed For Sale

      4411 Old Town Dr, Winston Salem, NC 27106

      • 3 Beds
      • 1 Bath
      • 1,200 Sq Ft
      • Built 1929
      4411 Old Town Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 11% Below List Price
      • $242/SF
      • 18 Days On Market
      • Last Sold Price $290,000
      • Jul 26, 2024

      Last Listing Agent John Southard Your Home Team

  • /20

    $263,355 Sold Nov 06, 2025

    1467 Woods Rd, Winston-Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 1,383 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $190/SF
    • 17 Days On Market

    Current Estimated Value $216,427

    Last Listing Agent Hannah Bean Glenwood Homes

    1467 Woods Rd, Winston-Salem, NC 27106
    • /14

      Est $124,673 Not Listed For Sale

      135 Columbine Dr Unit 228, Winston Salem, NC 27106

      • 2 Beds
      • 2 Baths
      • 800 Sq Ft
      • Built 1985
      135 Columbine Dr Unit 228, Winston Salem, NC 27106

      Last Sold Summary

      • 5% Above List Price
      • $149/SF
      • 5 Days On Market
      • Last Sold Price $119,000
      • May 12, 2023

      Last Listing Agent Bonnie Owens Mantle LLC

  • /50

    $382,000 Sold Apr 09, 2026

    1443 Old Town Rd, Winston Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft
    • Built 1940

    Last Sold Summary

    • 8% Below List Price
    • $179/SF
    • 10 Days On Market

    Current Estimated Value $408,170

    Last Listing Agent Blair Schmidt Smart Move Group

    1443 Old Town Rd, Winston Salem, NC 27106

Showing Results 1 - 40, Page 1 of 13

Home Trends in Windsor Estates, NC

Housing Trends

Median Sale Price
$322,400
Median Single Family Sale Price
$338,450
Average Price Per Sq Ft
$154
Number of Homes for Sale
1
Last 12 months Home Sales
18
Months of Supply
0.70
Median List Price
$359,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
18%
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