Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out at $499,900!! OVERSIZED 2 car DETACHED garage with CONCRETE PAD on side for your camper or boat and a ATTACHED 2 car garage for the car enthusiast or someone who loves to work on vehicles! 24 X 32 ENORMOUS family room(already sheet rocked) w/ FRENCH DOORS leading outside. You could make a 1 st floor bedroom, dining, kitchen and bathroom on main level with 2 bedrooms on upper level that has a slider would lead to a balcony. Set back off the road with stone boundary in the front sitting on 2 ACRES! Whether your an investor, builder or homeowner this property has A TON of POTENTIAL and awaits your finishing touches!! * * * CASH

$289,900

3 beds1.5 baths2,236 sq ft

360 N Society Rd, Canterbury, CT 06331

Stone boundary • Concrete pad • French doors

ABOUT THIS HOME
Windham County, CT Homes for Sale
Come see this move-in ready 3-bedroom, 1.5 bath Cape set on a beautiful 1 acre lot in Brooklyn. The home features a brand new roof, brand new septic, updated kitchen, bathrooms and a bright, open living area with exposed beams and a cathedral ceiling. Enjoy the peaceful country setting with plenty of space for outdoor activities, or relaxing in the yard. If you're looking for a home that's been nicely updated but still has that classic New England charm, this one's worth a look!

$369,000

3 beds1.5 baths1,528 sq ft

68 Allen Hill Rd, Brooklyn, CT 06234

Move-in ready • Updated kitchen • Exposed beams

ABOUT THIS HOME
Windham County, CT Homes for Sale
A beautifully maintained colonial nestled in one of Woodstock's most picturesque settings with many recent updates. Offering the perfect blend of traditional New England charm and modern comfort, featuring 4 bedrooms, 2.5-baths and spanning nearly 3,000 square feet. (Additional 664 sq ft in basement) Upon arrival you are greeted with a front farmers porch, step inside to discover 9' ceilings throughout a sun filled open floor plan. The heart of the home, a chef's kitchen with high-end appliances, granite countertops, and a spacious island-perfect for entertaining or casual family meals. The kitchen flows seamlessly into a large dining area and a warm, welcoming living room anchored by a coz

$799,900

4 beds2.5 baths3,662 sq ft

189 Center Rd, Woodstock, CT 06281

Front farmers porch • Dedicated offices • Granite countertops

3D WALKTHROUGH

ABOUT THIS HOME
Windham County, CT Homes for Sale
Move right into comfort and style with this beautifully updated 4/5 bedroom, 2-bath Colonial set on a rare two-acre lot in a suburban area of Connecticut. This move-in-ready home blends the best of both worlds-modern living and expansive outdoor space. Inside, enjoy fresh updates throughout including newly refreshed bathrooms, fresh paint, new flooring and carperts! The spacious first floor primary suite features generous closet space, a large mud room. Perfect for entertaining, the main level offers a seamless flow from living and dining areas to a large yard over looking the serene, tree-lined property-ideal for outdoor gatherings or quiet evenings. With plenty of room for gardening, play

$365,000

4 beds2.5 baths2,220 sq ft

106 Tripp Hollow Rd, Brooklyn, CT 06234

Fresh paint • New flooring • Large yard

ABOUT THIS HOME
Windham County, CT Homes for Sale
Great 2 Family with plenty of parking. Both units have been tastefully upgraded. The larger unit has 3 bedrooms and 1 bath with an extra room for an office. The second unit has 2 bedrooms and 1 bath. All separate utilities. Each unit has their own laundry hookup as well.

$350,000

5 beds2 baths2,672 sq ft

420 Putnam Pike, Dayville, CT 06241

0.38 acre lot • Built 1900 • Listed 16 days

Property at 277 Moosup Pond Rd, Moosup, CT 06354, 4 beds, 2.5 baths

$675,000

4 beds2.5 baths2,204 sq ft

277 Moosup Pond Rd, Moosup, CT 06354

Property at 84 Perry St #220, Putnam, CT 06260, 2 beds, 2.5 baths

$319,900

2 beds2.5 baths1,848 sq ft

84 Perry St #220, Putnam, CT 06260

Property at 93 E Putnam Rd, Putnam, CT 06260, 3 beds, 2.5 baths

$585,000

3 beds2.5 baths2,324 sq ft

93 E Putnam Rd, Putnam, CT 06260

Property at 94 Mechanic St, Killingly, CT 06239, 2 beds, 1 bath

$290,000

2 beds1 bath864 sq ft

94 Mechanic St, Killingly, CT 06239

Property at 10 Conrad Park, Dayville, CT 06241, 2 beds, 1 bath

$79,900

2 beds1 bath560 sq ft

10 Conrad Park, Dayville, CT 06241

Property at 19 A Rte, Woodstock, CT 06281, 2 beds, 1 bath

$299,999

2 beds1 bath708 sq ft

19 A Rte, Woodstock, CT 06281

Property at 15 Oakwood Dr, Thompson, CT 06277, 3 beds, 2 baths

$389,900

3 beds2 baths1,518 sq ft

15 Oakwood Dr, Thompson, CT 06277

Property at Undisclosed address, Chaplin, CT 06235, 3 beds, 1 bath

$329,000

3 beds1 bath2,931 sq ft

Undisclosed address, Chaplin, CT 06235

Property at 5 Nahaco Hill Ln #5, Eastford, CT 06242, 1 bed, 1.5 baths

$299,900

1 bed1.5 baths1,167 sq ft

5 Nahaco Hill Ln #5, Eastford, CT 06242

Property at 140 Ragged Hill Rd, Pomfret Center, CT 06259, 3 beds, 2 baths

$529,000

3 beds2 baths1,102 sq ft

140 Ragged Hill Rd, Pomfret Center, CT 06259

Property at 478 Wauregan Rd, Killingly, CT 06239, 3 beds, 1 bath

$439,900

3 beds1 bath1,452 sq ft

478 Wauregan Rd, Killingly, CT 06239

Property at 16 Valley View Dr, Dayville, CT 06241, 4 beds, 3 baths

$499,900

4 beds3 baths2,100 sq ft

16 Valley View Dr, Dayville, CT 06241

Property at 6 Harrisville Rd, Putnam, CT 06260, 3 beds, 2 baths

$339,900

3 beds2 baths1,144 sq ft

6 Harrisville Rd, Putnam, CT 06260

Property at 17 Liberty Ln, Thompson, CT 06277, 3 beds, 2 baths

$499,900

3 beds2 baths2,944 sq ft

17 Liberty Ln, Thompson, CT 06277

Property at 279 Moosup Pond Rd, Moosup, CT 06354, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,204 sq ft

279 Moosup Pond Rd, Moosup, CT 06354

Property at 14 Valley View Dr, Dayville, CT 06241, 4 beds, 3 baths

$499,900

4 beds3 baths2,100 sq ft

14 Valley View Dr, Dayville, CT 06241

Property at 67 North Rd, Windham, CT 06280, 4 beds, 1.5 baths

$200,000

4 beds1.5 baths1,621 sq ft

67 North Rd, Windham, CT 06280

Property at 5 Nahaco Hill Ln, Eastford, CT 06242, 1 bed, 1.5 baths

$299,900

1 bed1.5 baths1,167 sq ft

5 Nahaco Hill Ln, Eastford, CT 06242

Property at 81 Parkway Dr, Thompson, CT 06277, 1 bed, 1 bath

$110,000

1 bed1 bath720 sq ft

81 Parkway Dr, Thompson, CT 06277

Property at 165 Old Tatnic Hill Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$496,999

3 beds2 baths1,434 sq ft

165 Old Tatnic Hill Rd, Brooklyn, CT 06234

Property at 29 Crooked Trail Ext, Woodstock, CT 06281, 4 beds, 2 baths

$725,000

4 beds2 baths2,630 sq ft

29 Crooked Trail Ext, Woodstock, CT 06281

Property at 23 Birchwood Dr, Dayville, CT 06241, 3 beds, 3.5 baths

$469,000

3 beds3.5 baths2,646 sq ft

23 Birchwood Dr, Dayville, CT 06241

Property at 00 Brook Rd, Hampton, CT 06247, 3 beds, 2.5 baths

$719,000

3 beds2.5 baths2,534 sq ft

00 Brook Rd, Hampton, CT 06247

Property at 177 Barrett Hill Rd, Brooklyn, CT 06234, 4 beds, 3.5 baths

$687,900

4 beds3.5 baths3,779 sq ft

177 Barrett Hill Rd, Brooklyn, CT 06234

Property at 159 Old Tatnic Hill Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$449,999

3 beds2 baths1,350 sq ft

159 Old Tatnic Hill Rd, Brooklyn, CT 06234

Property at 10 North Rd, Windham, CT 06280, 2 beds, 1.5 baths

$249,000

2 beds1.5 baths1,380 sq ft

10 North Rd, Windham, CT 06280

Property at 309 East Putnam Rd, Putnam, CT 06260, 3 beds, 3 baths

$819,000

3 beds3 baths2,338 sq ft

309 East Putnam Rd, Putnam, CT 06260

Property at 133 PRINCE HILL Rd, Brooklyn, CT 06234, 4 beds, 3 baths

$569,900

4 beds3 baths2,250 sq ft

133 PRINCE HILL Rd, Brooklyn, CT 06234

Property at 942 Riverside Dr, North Grosvenordale, CT 06255, 2 beds, 1.5 baths

$265,000

2 beds1.5 baths1,212 sq ft

942 Riverside Dr, North Grosvenordale, CT 06255

Property at 215 Sand Dam Rd, Thompson, CT 06277, 3 beds, 1.5 baths

$414,900

3 beds1.5 baths1,516 sq ft

215 Sand Dam Rd, Thompson, CT 06277

Property at 815 Mashamoquet Rd, Pomfret Center, CT 06259, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths1,656 sq ft

815 Mashamoquet Rd, Pomfret Center, CT 06259

Property at 860 N Main St, Killingly, CT 06239, 3 beds, 2 baths

$399,999

3 beds2 baths1,900 sq ft

860 N Main St, Killingly, CT 06239

Property at 983 Riverside Dr, North Grosvenordale, CT 06255, 6 beds, 2 baths

$299,900

6 beds2 baths2,040 sq ft

983 Riverside Dr, North Grosvenordale, CT 06255

Property at 101 Child Hill Rd, Woodstock, CT 06281, 4 beds, 3 baths

$549,000

4 beds3 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

Property at 359 South St, Brooklyn, CT 06234, 3 beds, 2 baths

$399,999

3 beds2 baths1,236 sq ft

359 South St, Brooklyn, CT 06234

Property at 75 Academy Hill Rd, Plainfield, CT 06374, 3 beds, 2 baths

$349,900

3 beds2 baths1,008 sq ft

75 Academy Hill Rd, Plainfield, CT 06374

Viewing page 2 of 7

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$289,000
North Grosvenor Dale homes for sale
$282,450
Lake Bungee homes for sale
$522,000
Willimantic homes for sale
$269,000
Quinebaug homes for sale
$137,500
Brooklyn homes for sale
$407,500
East Brooklyn homes for sale
$369,000
Danielson homes for sale
$312,500
South Woodstock homes for sale
$549,000
Putnam homes for sale
$332,450
Moosup homes for sale
$457,450
Mansfield Center homes for sale
$385,000
Dayville homes for sale
$499,900

Counties

Hartford County homes for sale
$394,000
New Haven County homes for sale
$419,000
New London County homes for sale
$439,950

Windham County, CT real estate trends

All Home Types trends in Windham County, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$363,500

+3.9% YoY | Sep 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2025

Growth

% YoY

Windham County, CT

$363,500

+3.9%

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