1,894

North Windham, CT Homes

Section Image Section Image
  • 16 Pond Way, North Windham, CT 06256
    16 Pond Way, North Windham, CT 06256
    16 Pond Way, North Windham, CT 06256
    /22

    $67,900 Pending

    • 2 Beds
    • 2 Baths
    • 1,218 Sq Ft

    16 Pond Way, North Windham, CT 06256

    3% Interest, $0 Down Financing Available! Welcome home to your spacious 2 bedroom, 2 full bathroom open floor plan at 16 Pond Way, North Windham (Stonegate Manor). First floor laundry, mudroom with backyard access, and 1,218 sqft (rarely found at this affordable price point). This home is perfect for first-time buyers, downsizers, and value-seekers looking for affordable homeownership in a

    Agent Photo

    Stephen Daly

    KW Legacy Partners

    (860) 864-5536

    16 Pond Way, North Windham, CT 06256
  • 26 Jacqueline Ln, North Windham, CT 06256

    $70,000 Sold Aug 18, 2025

    26 Jacqueline Ln, North Windham, CT 06256

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft
    • Built 1987

    Last Sold Summary

    • $76/SF
    • 34 Days On Market

    Last Listing Agent Derek Greene Derek Greene

    26 Jacqueline Ln, North Windham, CT 06256
    • Unlisted Address

      Not Listed For Sale

      Unlisted Address

      • 2 Beds
      • 2 Baths
      • 1,218 Sq Ft
      • Built 1987
      Unlisted Address

      Last Sold Summary

      • $63/SF
      • 29 Days On Market

      Last Sold Price $77,250

      Last Listing Agent Clarence Russ Home Selling Team

  • 69 N Bedlam Rd, Chaplin, CT 06235
    69 N Bedlam Rd, Chaplin, CT 06235
    69 N Bedlam Rd, Chaplin, CT 06235
    /40

    $579,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,979 Sq Ft

    69 N Bedlam Rd, Chaplin, CT 06235

    Opportunity knocking again! Prior buyer's financing fell through. Welcome to your New England Equestrian Trial Riders Dream property! Featuring a lovingly preserved and updated antique Cape Cod home, a 40x50' newer five-stall barn with heated tack room and workshop located on a country road with almost 6 private acres of picturesque fenced pasture land adjacent to over 200 acres of preserved land

    Tammy Lucier eXp Realty

    69 N Bedlam Rd, Chaplin, CT 06235
  • 36 Fairway Dr, Windham, CT 06256

    $50,000 Sold Jul 29, 2025

    36 Fairway Dr, Windham, CT 06256

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft
    • Built 1971

    Last Sold Summary

    • 9% Below List Price
    • $74/SF
    • 81 Days On Market

    Last Listing Agent Erica Molochnick RbRE, LLC

    36 Fairway Dr, Windham, CT 06256
    • 260 Phoenixville Rd, Chaplin, CT 06235

      Est $425,583 Not Listed For Sale

      260 Phoenixville Rd, Chaplin, CT 06235

      • 4 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2024
      260 Phoenixville Rd, Chaplin, CT 06235

      Last Sold Summary

      • 6% Below List Price
      • $171/SF
      • 4 Days On Market

      Last Sold Price $453,000

      Last Listing Agent Cathyann Schulte Countryside Realty

  • 5 Woods Way Unit WOOD005, Windham, CT 06256
    5 Woods Way Unit WOOD005, Windham, CT 06256
    5 Woods Way Unit WOOD005, Windham, CT 06256
    /13

    $134,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,141 Sq Ft

    5 Woods Way Unit WOOD005, Windham, CT 06256

    Welcome to Stonegate Manor, an all-age active and vibrant community, where you can find yourself in your dream home. We have a stunning, brand new, beautiful, 2025 3 bed, 2 bath home for sale featuring 1141.52 sq ft of beautifully designed living space. Located in North Windham. Step inside to find an open-concept floor plan, hardwood floors, high ceilings and natural light. The kitchen boasts

    Nichole Boisvert Stonegate Manor

    5 Woods Way Unit WOOD005, Windham, CT 06256
  • 206 Boston Post Rd, Windham, CT 06256

    $45,000 Sold Jun 23, 2025

    206 Boston Post Rd, Windham, CT 06256

    • Land
    • 0.41 Acre
    • $109,756 per Acre

    Last Sold Summary

    • 32% Below List Price
    • 12 Days On Market

    Last Listing Agent Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    206 Boston Post Rd, Windham, CT 06256
    • 10 Zoldak Dr, North Windham, CT 06256

      Est $387,631 Not Listed For Sale

      10 Zoldak Dr, North Windham, CT 06256

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2008
      10 Zoldak Dr, North Windham, CT 06256

      Last Sold Summary

      • 19% Above List Price
      • $166/SF
      • 6 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Jonathan King Aspen Realty Group

  • 11 Mountain Laurel Ln, Chaplin, CT 06235
    11 Mountain Laurel Ln, Chaplin, CT 06235
    11 Mountain Laurel Ln, Chaplin, CT 06235
    /40

    $275,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 904 Sq Ft

    11 Mountain Laurel Ln, Chaplin, CT 06235

    What an opportunity with this home. Cape that sits on 3.85 acres sits up on a hill with great views. Great opportunity for expansion, 2nd floor is not finished so home could be 4 bedrooms with 2 full bath. Main level offers two bedrooms with a full bath. Living room with wood stove to help keep the heating costs down. Large kitchen with eat in area that can hold a large table, sliders to back

    Jeanne Crum Home Selling Team

    11 Mountain Laurel Ln, Chaplin, CT 06235
  • Unlisted Address

    $150,000 Sold Jan 14, 2026

    Unlisted Address

    • 3 Beds
    • 1 Bath
    • 1,614 Sq Ft
    • Built 1835

    Last Sold Summary

    • 25% Below List Price
    • $93/SF
    • 10 Days On Market

    Current Estimated Value $163,439

    Last Listing Agent Jeanne Crum Home Selling Team

    Unlisted Address
    • 257 Willimantic Rd, Chaplin, CT 06235

      Est $194,223 Not Listed For Sale

      257 Willimantic Rd, Chaplin, CT 06235

      • 2 Beds
      • 1 Bath
      • 1,050 Sq Ft
      • Built 1952
      257 Willimantic Rd, Chaplin, CT 06235

      Last Sold Summary

      • 16% Above List Price
      • $160/SF
      • 60 Days On Market

      Last Sold Price $168,000

      Last Listing Agent Robert Ferrigno Ferrigno-Willimantic REALTORS

  • 0 Hampton Rd Unit 170523717, Chaplin, CT 06235
    0 Hampton Rd Unit 170523717, Chaplin, CT 06235
    /2

    $139,000

    • Land
    • 12.1 Acres
    • $11,488 per Acre

    0 Hampton Rd Unit 170523717, Chaplin, CT 06235

    12.1 acre lot with frontage on Route 6 and Cross Road. Button Ball Brook runs through property. Could be a great home site, or potential commercial development with zone change. Rolling hills of gravel, mostly wooded.

    David Mieczynski National Realty Advisors LLC

    0 Hampton Rd Unit 170523717, Chaplin, CT 06235
  • 1 Circle Dr, North Windham, CT 06256

    $154,000 Sold Jul 18, 2025

    1 Circle Dr, North Windham, CT 06256

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Below List Price
    • $107/SF
    • 252 Days On Market

    Last Listing Agent Ryan Smithwick eRealty Advisors, Inc.

    1 Circle Dr, North Windham, CT 06256
    • 35 Jordan Ln, North Windham, CT 06256

      Est $329,599 Not Listed For Sale

      35 Jordan Ln, North Windham, CT 06256

      • 3 Beds
      • 1.5 Baths
      • 1,618 Sq Ft
      • Built 2007
      35 Jordan Ln, North Windham, CT 06256

      Last Sold Summary

      • 12% Above List Price
      • $182/SF
      • 97 Days On Market

      Last Sold Price $295,000

      Last Listing Agent Amy Rio Executive Real Estate

  • 6 Skyline Dr, North Windham, CT 06256
    6 Skyline Dr, North Windham, CT 06256
    6 Skyline Dr, North Windham, CT 06256
    /39

    $215,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,158 Sq Ft

    6 Skyline Dr, North Windham, CT 06256

    Welcome to this well-maintained 3-bedroom, 2-bath condominium built in 2002, offering 1,158 square feet of comfortable living space in the heart of Windham, CT. This home features a bright, open layout with generously sized bedrooms and two full bathrooms, providing both functionality and flexibility. The thoughtfully designed floor plan is ideal for everyday living, remote work, or entertaining.

    Brianne Carrington William Raveis Real Estate

    6 Skyline Dr, North Windham, CT 06256
  • 4 Jackson Ln, Mansfield, CT 06250

    $700,000 Sold Jun 27, 2025

    4 Jackson Ln, Mansfield, CT 06250

    • 4 Beds
    • 2.5 Baths
    • 2,518 Sq Ft
    • Built 2025

    Last Sold Summary

    • $278/SF
    • 54 Days On Market

    Last Listing Agent Sheri Shvonski List N Show LLC

    4 Jackson Ln, Mansfield, CT 06250
    • 73 Bolduc Ln, Chaplin, CT 06235

      Est $336,641 Not Listed For Sale

      73 Bolduc Ln, Chaplin, CT 06235

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1969
      73 Bolduc Ln, Chaplin, CT 06235

      Last Sold Summary

      • 5% Above List Price
      • $333/SF
      • 4 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Stephen Daly KW Legacy Partners

  • 13 Bates Rd, Chaplin, CT 06235
    13 Bates Rd, Chaplin, CT 06235
    13 Bates Rd, Chaplin, CT 06235
    /40

    $499,900

    • 5 Beds
    • 2.5 Baths
    • 2,887 Sq Ft

    13 Bates Rd, Chaplin, CT 06235

    Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

    Kristen Merrill Countryside Realty

    13 Bates Rd, Chaplin, CT 06235
  • 27 Haley Ln, North Windham, CT 06256

    $81,400 Sold Feb 20, 2026

    27 Haley Ln, North Windham, CT 06256

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Above List Price
    • $88/SF
    • 17 Days On Market

    Last Listing Agent Katherine Hernandez Lantigua KW Legacy Partners

    27 Haley Ln, North Windham, CT 06256
    • 285 Willimantic Rd, Chaplin, CT 06235

      Est $466,685 Not Listed For Sale

      285 Willimantic Rd, Chaplin, CT 06235

      • 7 Beds
      • 5 Baths
      • 1,800 Sq Ft
      • Built 1980
      285 Willimantic Rd, Chaplin, CT 06235

      Last Sold Summary

      • 2% Below List Price
      • $264/SF
      • 14 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Amy Brunet Brunet and Company Real Estate

  • 0 Scotland Rd Unit 24160798, Chaplin, CT 06235
    0 Scotland Rd Unit 24160798, Chaplin, CT 06235
    /2

    $335,000

    • Land
    • 62.27 Acres
    • $5,380 per Acre

    0 Scotland Rd Unit 24160798, Chaplin, CT 06235

    **Builders Take Notice** This is a beautiful 62.273 acres with subdivision opportunities. A-2 Survey is available. Owner financing is available.

    Sherry Borgeson Berkshire Hathaway NE Prop.

    0 Scotland Rd Unit 24160798, Chaplin, CT 06235
  • 5 Chappell St, Chaplin, CT 06235

    $355,000 Sold Jan 14, 2026

    5 Chappell St, Chaplin, CT 06235

    • 3 Beds
    • 2.5 Baths
    • 1,748 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $203/SF
    • 53 Days On Market

    Current Estimated Value $344,419

    Last Listing Agent Gregory Hanner Garden Realty

    5 Chappell St, Chaplin, CT 06235
    • 26 Baker Rd, North Windham, CT 06256

      Est $289,176 Not Listed For Sale

      26 Baker Rd, North Windham, CT 06256

      • 3 Beds
      • 1.5 Baths
      • 1,350 Sq Ft
      • Built 1970
      26 Baker Rd, North Windham, CT 06256

      Last Sold Summary

      • 1% Above List Price
      • $211/SF
      • 72 Days On Market

      Last Sold Price $285,000

      Last Listing Agent Diane Kendrick Coldwell Banker Realty

  • 28 Circle Dr, Windham, CT 06256
    28 Circle Dr, Windham, CT 06256
    28 Circle Dr, Windham, CT 06256
    /35

    $168,500

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    28 Circle Dr, Windham, CT 06256

    As little or no down, 3 fixed (3.15 APR). Completely remodeled three bedroom, two full bathroom home in Stonegate Manor. Yes completely remodeled floor to ceiling home, new kitchen cabinets, new appliances gas range, dishwasher, microwave hood vent, washer and washer, garnet counter tops, everything new, walls flooring new rear steps, and full size deck. Have your agent provide list of upgrades.

    Clarence Russ Home Selling Team

    28 Circle Dr, Windham, CT 06256
  • 52 Singleton Rd, Chaplin, CT 06235

    $365,000 Sold Oct 08, 2025

    52 Singleton Rd, Chaplin, CT 06235

    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Above List Price
    • $150/SF
    • 67 Days On Market

    Current Estimated Value $356,216

    Last Listing Agent Alexis John RE/MAX One

    52 Singleton Rd, Chaplin, CT 06235
    • 20 Park Dr, Chaplin, CT 06235

      Est $397,555 Not Listed For Sale

      20 Park Dr, Chaplin, CT 06235

      • 3 Beds
      • 2 Baths
      • 1,638 Sq Ft
      • Built 2003
      20 Park Dr, Chaplin, CT 06235

      Last Sold Summary

      • 1% Above List Price
      • $239/SF
      • 20 Days On Market

      Last Sold Price $392,000

      Last Listing Agent Skyla Gagnon RE/MAX

  • 64 Circle Dr, North Windham, CT 06256
    64 Circle Dr, North Windham, CT 06256
    64 Circle Dr, North Windham, CT 06256
    /40

    $150,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    64 Circle Dr, North Windham, CT 06256

    Move-in ready double wide mobile home in the heart of North Windham, offering comfortable single-level living with modern updates and a serene setting. This 3 bedroom, 2 bath layout spans just under 1,200 sqft of thoughtfully renovated space. Enjoy a bright living area with fresh new paint throughout and new flooring that flows seamlessly from room to room. The kitchen features stainless steel

    Britany Goyen BB Realty CT

    64 Circle Dr, North Windham, CT 06256
  • 385 Hampton Rd, Chaplin, CT 06235

    $340,000 Sold Mar 13, 2026

    385 Hampton Rd, Chaplin, CT 06235

    • 5 Beds
    • 3.5 Baths
    • 2,496 Sq Ft
    • Built 1965

    Last Sold Summary

    • 8% Below List Price
    • $136/SF
    • 126 Days On Market

    Current Estimated Value $354,783

    Last Listing Agent Jolanta Rojek eXp Realty

    385 Hampton Rd, Chaplin, CT 06235
    • 242 Tower Hill Rd, Chaplin, CT 06235
      242 Tower Hill Rd, Chaplin, CT 06235
      242 Tower Hill Rd, Chaplin, CT 06235
      /30

      Est $339,610 Not Listed For Sale

      242 Tower Hill Rd, Chaplin, CT 06235

      • 3 Beds
      • 1 Bath
      • 1,584 Sq Ft
      • Built 1992
      242 Tower Hill Rd, Chaplin, CT 06235

      Last Sold Summary

      • $215/SF
      • 6 Days On Market

      Last Sold Price $340,000

      Last Listing Agent Valerie MacNeil Kazantzis Real Estate, LLC

  • 60 Lions Way, North Windham, CT 06256
    60 Lions Way, North Windham, CT 06256
    60 Lions Way, North Windham, CT 06256
    /18

    $85,000 Pending

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    60 Lions Way, North Windham, CT 06256

    Move right into this beautifully maintained 2 bedroom, 2 bath mobile home! Nearby to shopping and the Mansfield Hollow Walking Path and Dam. Filled with natural light, the inviting living room features a ceiling fan and plenty of sunshine, creating a warm and welcoming space. The large eat-in kitchen offers abundant cabinet storage, and convenient access to a laundry room just off the kitchen.

    Brandon Cramer KW Legacy Partners

    60 Lions Way, North Windham, CT 06256
  • 164 Tower Hill Rd, Chaplin, CT 06235

    $265,000 Sold Dec 31, 2025

    164 Tower Hill Rd, Chaplin, CT 06235

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 2000

    Last Sold Summary

    • $263/SF
    • 14 Days On Market

    Current Estimated Value $268,002

    Last Listing Agent Franchesca Pescatello Prue Realty LLC

    164 Tower Hill Rd, Chaplin, CT 06235
    • 90 N Bedlam Rd, Chaplin, CT 06235

      Est $498,946 Not Listed For Sale

      90 N Bedlam Rd, Chaplin, CT 06235

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1726
      90 N Bedlam Rd, Chaplin, CT 06235

      Last Sold Summary

      • 4% Below List Price
      • $260/SF
      • 19 Days On Market

      Last Sold Price $519,000

      Last Listing Agent Michael Hvizdo Coldwell Banker Realty

  • 7 Circle Dr, North Windham, CT 06256
    7 Circle Dr, North Windham, CT 06256
    7 Circle Dr, North Windham, CT 06256
    /36

    $145,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    7 Circle Dr, North Windham, CT 06256

    Open Floor plan, 1152 SF, 3 bedrooms, 2 full baths. Vaulted ceilings, Kitchen offers plenty of cabinet and counter spaces, breakfast bar, dining area, Primary bedroom with full bath and walk in closet, 2 additional bedrooms both with walk in closets, Living room with vaulted ceiling, propane fireplace and is open to dining area and kitchen. Covered deck/porch, large private yard, storage shed.

    Karen Martin Century 21 AllPoints Realty

    7 Circle Dr, North Windham, CT 06256
  • 184 Phoenixville Rd, Chaplin, CT 06235

    $375,000 Sold Oct 15, 2025

    184 Phoenixville Rd, Chaplin, CT 06235

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1790

    Last Sold Summary

    • 3% Below List Price
    • $203/SF
    • 20 Days On Market

    Current Estimated Value $381,627

    Last Listing Agent Derek Greene Derek Greene

    184 Phoenixville Rd, Chaplin, CT 06235
    • 89 Chewink Rd, Chaplin, CT 06235

      Est $276,515 Not Listed For Sale

      89 Chewink Rd, Chaplin, CT 06235

      • 2 Beds
      • 1.5 Baths
      • 1,280 Sq Ft
      • Built 1967
      89 Chewink Rd, Chaplin, CT 06235

      Last Sold Summary

      • 22% Above List Price
      • $177/SF
      • 6 Days On Market

      Last Sold Price $226,000

      Last Listing Agent Michelle Garabedian Home Selling Team

  • 23 James Dr, Windham, CT 06256
    23 James Dr, Windham, CT 06256
    23 James Dr, Windham, CT 06256
    /16

    $130,000

    • 3 Beds
    • 2 Baths
    • 996 Sq Ft

    23 James Dr, Windham, CT 06256

    Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living space. With recent upgrades throughout, this

    Arielle Ruffin Choice Realty

    23 James Dr, Windham, CT 06256
  • 284 Willimantic Rd, Chaplin, CT 06235

    $38,000 Sold Oct 17, 2025

    284 Willimantic Rd, Chaplin, CT 06235

    • Land
    • 1.5 Acres
    • $25,333 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 66 Days On Market

    Current Estimated Value $39,333

    Last Listing Agent Lisa Sader-Goede Aspen Realty Group

    284 Willimantic Rd, Chaplin, CT 06235
    • 4 Jordan Ln, North Windham, CT 06256

      Est $314,606 Not Listed For Sale

      4 Jordan Ln, North Windham, CT 06256

      • 4 Beds
      • 1 Bath
      • 1,412 Sq Ft
      • Built 1936
      4 Jordan Ln, North Windham, CT 06256

      Last Sold Summary

      • 1% Above List Price
      • $220/SF
      • 7 Days On Market

      Last Sold Price $310,000

      Last Listing Agent Stephen Daly KW Legacy Partners

  • 16 Circle Dr, North Windham, CT 06256
    16 Circle Dr, North Windham, CT 06256
    16 Circle Dr, North Windham, CT 06256
    /40

    $159,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    16 Circle Dr, North Windham, CT 06256

    Welcome to this beautifully updated and impeccably maintained double-wide home offering 1,620 square feet of modern, comfortable living. With about $35,000 in thoughtful upgrades since purchase, this home is truly move-in ready and designed for both style and convenience. Step inside to a spacious, open layout that feels airy, welcoming, and immaculate throughout. The updated kitchen features

    Danielle Fortier Coldwell Banker Realty

    16 Circle Dr, North Windham, CT 06256

Showing Results 1 - 40, Page 1 of 18

Connecticut Windham County North Windham

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group