517

Windsor Estates Homes

Section Image
  • /14

    $49,900

    Under Contract
    • 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
  • /53

    Starting at $975 Per Month

    • 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

    Hunt Club Apartments, LLC

    103 Echo Glen 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 $343,477

    Last Listing Agent Donna Meeker Keller Williams Realty

    1151 Cypress Cir, Winston Salem, NC 27106
    • /37

      Est $480,141

      Not Listed For Sale

      1224 Idlewilde Heath Dr, Winston Salem, NC 27106

      • 3 Beds
      • 3 Baths
      • 3,003 Sq Ft
      • Built 1989
      1224 Idlewilde Heath Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Jackson Faude Keller Williams Realty Elite

  • /38

    $425,000

    • 4 Beds
    • 3 Baths
    • 3,135 Sq Ft

    1131 Barclay Terrace, Winston Salem, NC 27106

    Just minutes from Wake Forest University, this timeless brick ranch offers space, privacy, and exceptional convenience. Situated on nearly half an acre just three homes from the cul-de-sac at the end of the street, the home features 4 bedrooms, 3 full baths, and approximately 3,135 heated square feet. Multiple living areas provide inviting spaces to gather, complemented by two wood-burning

    Keith Martin Southern Luxe Realty

    1131 Barclay Terrace, Winston Salem, NC 27106
  • /50

    Starting at $946 Per Month

    • 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

    Trails At Bethabara

    1620 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 $460,934

    Last Listing Agent Dana Scrattish Forsyth Realty Group

    35 Edith Ave, Winston Salem, NC 27106
    • /50

      Est $314,768

      Not Listed For Sale

      1160 Edgebrook Dr, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 2,051 Sq Ft
      • Built 1961
      1160 Edgebrook Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kristie Wright Innovate Real Estate

  • /45

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft

    1131 Cypress Cir, Winston Salem, NC 27106

    Location, space, and income potential—this home has it all! Walk to the Wake Forest campus and the future site of The Grounds, or take a quick drive to downtown Winston-Salem. This spacious split-level home features gorgeous hardwood floors, formal living and dining spaces, and an updated kitchen with granite counters that opens directly to a private backyard and deck. The upper level offers

    Kristin Ranson Leonard Ryden Burr Real Estate

    1131 Cypress Cir, Winston Salem, NC 27106
  • /50

    Starting at $900 Per Month

    • 1 - 3 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

    New Salem Village

    1520 Woods Rd, 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 $259,105

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

    1138 Edgebrook Dr, Winston Salem, NC 27106
    • /44

      Est $357,692

      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

      • 18 Days On Market

      Last Listing Agent Carol Milligan Howard Hanna Allen Tate High Point

  • /11

    $269,000

    • 3 Beds
    • 2 Baths
    • 2,080 Sq Ft

    2651 Greencrest Dr, Winston Salem, NC 27106

    Handy man Special Or Investors....... Inside pics coming soon!! Come check out this charming home. She is just waiting for someone to love her. This home is ABSOLUTLEY livable as is. But needs some repairs. Hall sinks need to be hooked up, a few tile repaired in the primary Bath.... some new floors and some paint would make this home GORGEOUS!!!!!!! Roof about a year old. HVAC about a year old...

    Michelle Epley Southern Key Realty

    2651 Greencrest Dr, Winston Salem, NC 27106
  • /29

    Starting at $1,530 Per Month

    • 1 - 3 Beds

    875 Crowne Forest Ct, Winston-Salem, NC 27106

    Discover distinctive living at Crowne Polo Apartments in the prestigious Sunnynoll area of Winston-Salem, North Carolina. We are located just minutes from Wake Forest University.

    Crowne Polo

    875 Crowne Forest Ct, 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 $459,641

    Last Listing Agent Stephen Lawing Leonard Ryden Burr Real Estate

    2106 Bethabara Rd, Winston Salem, NC 27106
    • /25

      Est $248,109

      Not Listed For Sale

      4523 Old Town Dr, Winston Salem, NC 27106

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1972
      4523 Old Town Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Blake Ginther Keller Williams Realty Elite

  • /50

    $830,000

    • 5 Beds
    • 4.5 Baths
    • 3,818 Sq Ft

    347 Friendship Cir, Winston Salem, NC 27106

    Space, flexibility, and thoughtful updates come together in this expansive 5 bedroom, 4 bathroom home just minutes from Wake Forest University. With over multiple levels of functional living, this home offers room for everyone, whether you're working from home, entertaining guests, or simply looking for space to spread out. The main level features a spacious primary suite complete with dual

    Katie Trenerowski Berkshire Hathaway HomeServices Carolinas Realty

    347 Friendship Cir, Winston Salem, NC 27106
  • /35

    Starting at $1,380 Per Month

    • 1 - 3 Beds

    1000 Crowne Oaks Cir, Winston-Salem, NC 27106

    Crowne Oaks Apartments is surrounded by lush wooded splendor at the intersection of Silas Creek and Bethabara in Winston-Salem, North Carolina. You’ll appreciate the spacious floor plans and superior interior details that make Crowne Oaks’ peaceful and secluded apartment community second to none in the Winston-Salem area.

    Crowne Oaks Apartments

    1000 Crowne Oaks Cir, 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 $661,053

    Last Listing Agent Toni Phillips Leonard Ryden Burr Real Estate

    910 Idlewilde Heath Ct, Winston Salem, NC 27106
    • /34

      Est $215,208

      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

      • 0 Days On Market

      Last Listing Agent Joey Miller R&B Legacy Group

  • /35

    Starting at $1,200 Per Month

    • 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

    The Pines at Bethabara

    511 Bethabara Hills Ct, 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 $140,132

    Last Listing Agent Donna Tickle Hillcrest Realty Group

    1074 Hickory Glen Rd, Winston Salem, NC 27106
    • /36

      Est $287,340

      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

      • 18 Days On Market

      Last Listing Agent John Southard Your Home Team

  • /35

    Starting at $1,455 Per Month

    • 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.

    Crowne Park

    900 Crowne Park Dr, Winston-Salem, NC 27106
  • /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 $132,222

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

    133 Columbine Dr Unit 118, Winston Salem, NC 27106
    • /25

      Est $139,195

      Not Listed For Sale

      135 Columbine Dr Unit 225, Winston Salem, NC 27106

      • 2 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1985
      135 Columbine Dr Unit 225, Winston Salem, NC 27106

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Ramilya Seigel KELLER WILLIAMS REALTY

  • /25

    $1,350

    Total Monthly Price

    • Studio
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    3280 Midkiff Rd Unit 1, Winston-Salem, NC 27106

    Completely furnished studio apartment in quiet residential neighborhood. Wi-Fi, cable and utilities included. Garage parking and private entrance. Washer and dryer. Walk-in closet. Full bath. 32 inch flatscreen TV. Toaster oven and microwave but no full stove. Dishes and linens provided. 2 miles to Wake Forest university. 4 miles to Atrium/Baptist Hospital. Ideal for single professional. No pets,

    3280 Midkiff Rd Unit 1, Winston-Salem, NC 27106
  • /28

    $144,000

    Sold Dec 10, 2025

    133 Columbine Dr Unit 1198839, 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 Unit 1198839, Winston Salem, NC 27106
    • /39

      Est $134,008

      Not Listed For Sale

      135 Columbine Dr Unit 212, Winston Salem, NC 27106

      • 2 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1985
      135 Columbine Dr Unit 212, Winston Salem, NC 27106

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Rebecca Lynch Lynch Realty & Associates

  • /25

    $1,350

    Total Monthly Price

    • Studio
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    3280 Midkiff Rd Unit 1, Winston-Salem, NC 27106

    Completely furnished studio apartment in quiet residential neighborhood. Wi-Fi, cable and utilities included. Garage parking and private entrance. Washer and dryer. Walk-in closet. Full bath. 32 inch flatscreen TV. Toaster oven and microwave but no full stove. Dishes and linens provided. 2 miles to Wake Forest university. 4 miles to Atrium/Baptist Hospital. Ideal for single professional. No pets,

    3280 Midkiff Rd Unit 1, Winston-Salem, NC 27106
  • /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 $333,942

    Last Listing Agent Brent Moser Real Broker LLC

    3051 Minart Dr, Winston Salem, NC 27106
    • /30

      Est $258,685

      Not Listed For Sale

      4618 Old Town Dr, Winston Salem, NC 27106

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 2001
      4618 Old Town Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Naomi Cooke Berkshire Hathaway HomeServices Carolinas Realty

  • /16

    $1,400 Per Month

    • 3 Beds
    • 2 Baths
    • Condo for Rent

    2711 Reynolda Rd Unit 2D, Winston Salem, NC 27106

    Lovely 3 bed/ 2 bath first floor condo with lots of space! 3 great sized bedrooms, Spacious and open living room/dining room combo and mudroom. Located conveniently near Wake Forest University, shopping, restaurants and more.

    Bailie Guggeis Hunter Realty & Property Management, LLC

    2711 Reynolda Rd Unit 2D, Winston Salem, NC 27106
  • /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 $291,556

    Last Listing Agent Hannah Bean Glenwood Homes

    1467 Woods Rd, Winston-Salem, NC 27106
    • /27

      Est $210,108

      Not Listed For Sale

      4339 Old Town Dr, Winston Salem, NC 27106

      • 2 Beds
      • 1.5 Baths
      • 1,400 Sq Ft
      • Built 1956
      4339 Old Town Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Carla Hoots Fader Real Estate at ERA Live Moore

  • /16

    $1,400 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    2711 Reynolda Rd, Winston-Salem, NC 27106

    3 Bedroom2 Bath$1,400 Monthly Rent$1,400 Security DepositNo SmokingPets conditional (small dogs under 15 lbs) with pet screening and non-refundable pet feeElementary: SpeasMiddle: PaisleyHigh: Mt TaborHeating: Heat PumpHeating Fuel: ElectricCooling: Heat PumpWater Heater: ElectricWater: PublicSewer: PublicDescription:

    2711 Reynolda Rd, Winston-Salem, NC 27106
  • /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 $384,040

    Last Listing Agent Blair Schmidt Smart Move Group

    1443 Old Town Rd, Winston Salem, NC 27106
    • /10

      Est $138,677

      Not Listed For Sale

      4406 Old Town Dr, Winston Salem, NC 27106

      • 2 Beds
      • 1 Bath
      • 732 Sq Ft
      • Built 1940
      4406 Old Town Dr, Winston Salem, NC 27106

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Steven Ross Premier Real Estate Team, Inc

  • /14

    $1,100 Per Month

    • 2 Beds
    • 2 Baths
    • 991 Sq Ft
    • House for 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
  • /34

    $367,500

    Sold Jun 15, 2026

    3301 Midkiff Rd, Winston Salem, NC 27106

    • 3 Beds
    • 2 Baths
    • 2,503 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $147/SF
    • 30 Days On Market

    Current Estimated Value $364,399

    Last Listing Agent Morgan Reitzel Leonard Ryden Burr Real Estate

    3301 Midkiff Rd, Winston Salem, NC 27106

Showing Results 1 - 40, Page 1 of 13

Home Price Trends

Median Sale Price
$324,900
Median Single Family Sale Price
$360,000
Median 2 Bedroom Sale Price
$140,000
Average Price Per Sq Ft
$155
Number of Homes for Sale
4
Last 12 months Home Sales
15
Months of Supply
3.20
Median List Price
$360,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
2%
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