Windham County, CT Homes

• 

  Est $307,038 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2 Charles St, Plainfield, CT 06374

  2 Charles St, Plainfield, CT 06374
• 

  

  

  /7

  $49,900

  • Land
  • 1.5 Acres
  • $33,267 per Acre

  0 Center Rd, Woodstock, CT 06281

  Lovely 1.5 wooded acres with spring fed pond with over 200 feet of road frontage. Beautiful area of town. Property was perc'd at one time, but hasn't been done in years. Build your dream house in the Woodstock school district. Buyer and buyers agent to due their due diligence.

  Diane White CR Premier Properties

  0 Center Rd, Woodstock, CT 06281
• 

  $420,000 Sold Jun 06, 2025

  351 Brandy Hill Rd, Thompson, CT 06277

  • 4 Beds
  • 2 Baths
  • 2,136 Sq Ft
  • Built 1982

  Last Sold Summary

  • 1% Below List Price
  • $197/SF
  • 47 Days On Market

  Current Estimated Value $419,421

  Last Listing Agent Matthew Huberdault Byrnes Real Estate Company

  351 Brandy Hill Rd, Thompson, CT 06277
• 

  Est $391,109 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,562 Sq Ft

  233 Dow Rd, Plainfield, CT 06374

  233 Dow Rd, Plainfield, CT 06374
• 

  

  /2

  $115,000

  • Land
  • 8.5 Acres
  • $13,529 per Acre

  85 Mashentuck Rd, Killingly, CT 06239

  Located in a peaceful rural setting near I-395 and Rhode Island, this spacious plot of land offers abundant potential for subdivision or development. Its strategic location provides easy access to major transportation routes, making it an ideal opportunity for creating residential lots. Surrounded by natural beauty and tranquil surroundings, this property presents endless possibilities for

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  85 Mashentuck Rd, Killingly, CT 06239
• 

  $28,500 Sold Jun 17, 2025

  25 Connecticut 197, Woodstock, CT 06281

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1990

  Last Sold Summary

  • 59% Below List Price
  • $31/SF
  • 49 Days On Market

  Last Listing Agent Melanie Taylor Berkshire Hathaway NE Prop.

  25 Connecticut 197, Woodstock, CT 06281
• 

  Est $443,940 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  430 Wauregan Rd, Danielson, CT 06239

  430 Wauregan Rd, Danielson, CT 06239
• 

  

  /32

  $895,000

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  350 Hartford Pike, Dayville, CT 06241

  Come enjoy this wonderful home. All large rooms with mostly tin ceilings. Some hardwood floors. First floor has a Eat-in kitchen, formal dining room, formal living room, den, bedroom, laundry room and a half bath. The second floor you have a primary suite which takes up half of the upstairs...bedroom, with a full bath and sitting area and walk in closet. Two more bedrooms and another full

  Mark Benard Brunet and Company Real Estate

  350 Hartford Pike, Dayville, CT 06241
• 

  $160,000 Sold Dec 24, 2025

  33 MacHine Shop Hill Rd, South Windham, CT 06266

  • 5 Beds
  • 1 Bath
  • 2,548 Sq Ft
  • Built 1850

  Last Sold Summary

  • 33% Below List Price
  • $63/SF
  • 145 Days On Market

  Last Listing Agent Franchesca Pescatello Prue Realty LLC

  33 MacHine Shop Hill Rd, South Windham, CT 06266
• 

  Est $658,702 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,526 Sq Ft

  3 Holmeslea Ct, Woodstock, CT 06281

  3 Holmeslea Ct, Woodstock, CT 06281
• 

  

  /4

  $150,000

  • 3 Beds
  • 2 Baths
  • 4,384 Sq Ft

  438 Hartford Pike, Dayville, CT 06241

  Sale includes property located at 442 Hartford Pike also. Zoned General Commercial. Multi family that need to be completely renovated or torn down. No interior access

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  438 Hartford Pike, Dayville, CT 06241
• 

  $70,000 Sold Jun 30, 2025

  0 Red Bridge Rd, Thompson, CT 06255

  • Land
  • 2 Acres
  • $35,000 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 26 Days On Market

  Last Listing Agent Rachael Johnston Johnston & Associates Real Estate, LLC

  0 Red Bridge Rd, Thompson, CT 06255
• 

  Est $348,176 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  530 Wauregan Rd, Danielson, CT 06239

  530 Wauregan Rd, Danielson, CT 06239
• 

  

  /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
• 

  $600,000 Sold Sep 05, 2025

  90 Putnam Pike, Killingly, CT 06241

  • Land
  • 54 Acres
  • $11,111 per Acre

  Last Sold Summary

  • 316 Days On Market

  Current Estimated Value $1,365,000

  Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

  90 Putnam Pike, Killingly, CT 06241
• 

  Est $350,807 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,380 Sq Ft

  59 Broad St, Danielson, CT 06239

  59 Broad St, Danielson, CT 06239
• 

  

  /4

  $60,000

  • Land
  • 0.61 Acre
  • $98,361 per Acre

  81 Deerfield Dr, Sterling, CT 06377

  Discover this beautiful 0.61-acre lot-ready and waiting for your dream build. Tucked away on a private road in Sterling, CT, this property offers the perfect opportunity to create your own peaceful retreat. Whether you're envisioning a custom home or a quiet getaway, this slice of heaven provides the privacy and space you've been looking for.

  Kristopher Tramont Real Broker CT, LLC

  81 Deerfield Dr, Sterling, CT 06377
• 

  $130,000 Sold Oct 28, 2025

  0 Connecticut 169, Woodstock, CT 06281

  • Land
  • 3.96 Acres
  • $32,828 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 22 Days On Market

  Last Listing Agent Richard Loomis RE/MAX Bell Park Realty

  0 Connecticut 169, Woodstock, CT 06281
• 

  Est $688,570 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,277 Sq Ft

  739 Route 171, Woodstock, CT 06281

  739 Route 171, Woodstock, CT 06281
• 

  

  /40

  $399,000 Open Sun 11:30AM - 12:45PM

  • 6 Beds
  • 2 Baths
  • 2,279 Sq Ft

  30 S Walnut St, Plainfield, CT 06387

  Fully renovated, side-by-side duplex offering space, quality, and peace of mind. Each unit features three spacious bedrooms, an open living and dining area, a mud room, and a brand-new kitchen with modern cabinetry and new appliances. Both units include completely renovated bathrooms and fresh paint throughout, creating a true move-in-ready opportunity. The basement offers abundant storage, ideal

  Jake Pereira HERE Realty

  30 S Walnut St, Plainfield, CT 06387
• 

  $650,000 Sold Jul 23, 2025

  128 Spaulding Rd, Brooklyn, CT 06234

  • 3 Beds
  • 2.5 Baths
  • 2,176 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $299/SF
  • 66 Days On Market

  Current Estimated Value $639,248

  Last Listing Agent Kristen Kaskela Berkshire Hathaway NE Prop.

  128 Spaulding Rd, Brooklyn, CT 06234
• 

  Est $286,334 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft

  135 Franklin St, Danielson, CT 06239

  135 Franklin St, Danielson, CT 06239
• 

  

  /15

  $215,000

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

  74 Athol St, Danielson, CT 06239

  Welcome to Townhouse Place! This well-maintained 2-bedroom, 1.5-bath townhouse offers comfortable living in a highly convenient location. Situated at the back of the complex, this unit provides added privacy and a serene setting-step out through your sliders and enjoy a beautiful open yard right outside your door. Inside, the home features an open-concept main level perfect for modern living and

  Kevin Brignole Spaulding Realty Group, LLC

  74 Athol St, Danielson, CT 06239
• 

  $109,001 Sold May 09, 2025

  00 Child Rd, Woodstock, CT 06281

  • Land
  • 2.06 Acres
  • $52,913 per Acre

  Last Sold Summary

  • 9% Above List Price
  • 12 Days On Market

  Last Listing Agent Britt Miglietta Berkshire Hathaway NE Prop.

  00 Child Rd, Woodstock, CT 06281
• 

  Est $539,933 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  184 Tripp Hollow Rd, Brooklyn, CT 06234

  184 Tripp Hollow Rd, Brooklyn, CT 06234
• 

  

  /20

  $164,900

  • Land
  • 3 Acres
  • $54,967 per Acre

  49 Stone Rd, Killingly, CT 06241

  LOCATION LOCATION LOCATION!! 3 acre building lot with over 295' of water frontage on the Five Mile River! Build your dream home on this tranquil park like setting. The pictures don't do it justice! This location is surrounded by high end custom homes, sitting on a quiet country road, yet still close to all major amenities and routes such as I-395, Rte 44, and Rte 101.

  Dale Bunn Riverview Realty, LLC

  49 Stone Rd, Killingly, CT 06241
• 

  $259,900 Sold Sep 12, 2025

  77 Plains Rd, Windham, CT 06280

  • 3 Beds
  • 1.5 Baths
  • 1,624 Sq Ft
  • Built 1984

  Last Sold Summary

  • $160/SF
  • 11 Days On Market

  Current Estimated Value $260,802

  Last Listing Agent Lisa Barstow Simply Sold Real Estate

  77 Plains Rd, Windham, CT 06280
• 

  Est $342,059 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  15 Rachel Dr, North Grosvenordale, CT 06255

  15 Rachel Dr, North Grosvenordale, CT 06255
• 

  

  /12

  $374,900

  • 4 Beds
  • 4.5 Baths
  • 3,029 Sq Ft

  133 Maple St, Danielson, CT 06239

  Incredible investment opportunity is knocking with this 4-family home.

  Rick McCullough R.A. McCullough Homes, LLC

  133 Maple St, Danielson, CT 06239
• 

  $360,000 Sold Apr 14, 2025

  155 Boston Turnpike, Eastford, CT 06259

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $291/SF
  • 80 Days On Market

  Last Listing Agent Debra Burns Real Broker CT, LLC

  155 Boston Turnpike, Eastford, CT 06259
• 

  Est $389,365 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,584 Sq Ft

  210 Mechanic St, Danielson, CT 06239

  210 Mechanic St, Danielson, CT 06239
• 

  

  /37

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,228 Sq Ft

  15 Cracow Ave, Windham, CT 06280

  Welcome to this inviting 3-bedroom, 2-bath ranch featuring a 1-car garage and a fantastic layout perfect for comfortable everyday living. Placed right along side the Natchaug River used for fishing and kayaking! Step inside to find a bright, open floor plan with warm natural light and easy flow throughout. Outside, the property truly shines. Enjoy summer days in your beautiful inground pool (with

  Julienne Jaber KW Legacy Partners

  15 Cracow Ave, Windham, CT 06280
• 

  $620,000 Sold Dec 01, 2025

  26 N Society Rd, Canterbury, CT 06331

  • 3 Beds
  • 2.5 Baths
  • 1,062 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Above List Price
  • $584/SF
  • 4 Days On Market

  Last Listing Agent Heather Bassett Team Bassett Realty LLC

  26 N Society Rd, Canterbury, CT 06331
• 

  Est $406,157 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  329 South St, Willimantic, CT 06226

  329 South St, Willimantic, CT 06226
• 

  

  /40

  $549,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 3,208 Sq Ft

  55 Island Rd, Dayville, CT 06241

  Escape the every day at 55 Island Road - your private lakeside retreat on Alexander's Lake. Estate property, professionally cleaned out - ready to move right in. Built in 1985 with a brand-new oil tank, this Classic Cape needs cosmetic update - new floors, paint, maybe a kitchen refresh - gives 2,120 square feet of cozy without compromise. Two generous bedrooms, with the possibility of a third

  Michelle Richardson Kazantzis Real Estate, LLC

  55 Island Rd, Dayville, CT 06241
• 

  

  /41

  $495,000 Sold Jul 17, 2025

  15 Bunny Ln, Brooklyn, CT 06234

  • 4 Beds
  • 2.5 Baths
  • 2,296 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $216/SF
  • 23 Days On Market

  Last Listing Agent The Rachel Jones Team Rachel Jones

  15 Bunny Ln, Brooklyn, CT 06234
• 

  Est $419,458 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,632 Sq Ft

  196 Main St, Hampton, CT 06247

  196 Main St, Hampton, CT 06247
• 

  

  /18

  $425,000 Pending

  • 7 Beds
  • 4 Baths
  • 2,769 Sq Ft

  61 Oak St, Willimantic, CT 06226

  INVESTORS TAKE NOTICE. 61 Oak St sits on a nice level lot with an open back yard and nice front porches. Located on a desirable street close to Eastern and up in the hills. Brand new roof and Water heater! Both 2 bedroom units have the possibility of a third bedroom with a large front room that is without a closet. So much potential for this property!

  Julienne Jaber KW Legacy Partners

  61 Oak St, Willimantic, CT 06226
• 

  $380,000 Sold Aug 14, 2025

  90 Broad St, Danielson, CT 06239

  • 3 Beds
  • 2 Baths
  • 1,869 Sq Ft
  • Built 1925

  Last Sold Summary

  • $203/SF
  • 15 Days On Market

  Current Estimated Value $381,772

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

  90 Broad St, Danielson, CT 06239
• 

  

  /39

  Est $484,522 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,644 Sq Ft

  1115 Route 169, Woodstock, CT 06281

  1115 Route 169, Woodstock, CT 06281

Showing Results 481 - 520, Page 13 of 18