Windham County CT FSBO Homes (250)

Sort By

List
Map

We have 250 homes for sale by owner in Windham County, CT. The median list price in Windham County, CT is $367,631 and the average price per square foot is $1,816.

Homes For Sale

$299,900

2 Bed
1 Bath
1,344 Sqft
0.72 Acre(Lot)

43 Douglas Drive, Windham County, CT

Welcome to this sprawling ranch located at the end of a non thru street! super private and spacious yard!... Read More

Homes For Sale

$375,000

3 Bed
1 Bath
1,248 Sqft
0.46 Acre(Lot)

226 Labby Road, Windham County, CT

Amazing ranch just over the ma line. this well-maintained home offers three bedrooms & a full bath. the country... Read More

Homes For Sale

$995,000

3 Bed
2 Bath
2,502 Sqft
3.48 Acres(Lot)

187 Chaplin Road, Windham County, CT

Rustic luxury in connecticut's quiet corner nestled in the hills of connecticut's "quiet corner," this stunning... Read More

Homes For Sale

$435,000

3 Bed
3 Bath
1,728 Sqft
3.7 Acres(Lot)

2325 Waterfall Road, Windham County, CT

Welcome to 23-25 waterfall road! this oversized ranch, nestled on a 3.7 acre lot, boasts three bedrooms, three... Read More

Homes For Sale

$860,000

4 Bed
3 Bath
2,220 Sqft
16.19 Acres(Lot)

106a Tripp Hollow Road, Windham County, CT

Attention investors - huge opportunity! 106a tripp hollow rd, brooklyn, ct rare investment with cash flow +... Read More

Homes For Sale

$450,000

4 Bed
3 Bath
1,800 Sqft
0.8 Acre(Lot)

105 Reilly Road, Windham County, CT

Gorgeous 2025 raised ranch with open floor plan has living/ dining area and stainless appliances in kitchen w/... Read More

Homes For Sale

$325,000

3 Bed
2 Bath
1,654 Sqft
2 Acres(Lot)

297 Main Street, Windham County, CT

Adventure awaits in this 1850 hampton gem! step back in time with this solidly built 1850 home featuring... Read More

Homes For Sale

$175,000

3 Bed
2 Bath
1,296 Sqft
1.95 Acres(Lot)

116 Paradise Drive, Windham County, CT

This listing includes 6 lots, totaling 1.95 acres. the mobile home is a 2003, with 1296sqft of living space. the... Read More

Pending

Homes For Sale

$450,000

4 Bed
3 Bath
1,800 Sqft
0.8 Acre(Lot)

103 Reilly Road, Windham County, CT

Gorgeous 2025 raised ranch with open floor plan has living/ dining area and stainless appliances in kitchen w/... Read More

Homes For Sale

$500,000

4 Bed
3 Bath
2,503 Sqft
0.74 Acre(Lot)

63 Parent Hill Road, Windham County, CT

A stunning kitchen, massive spa-style primary bath, and a barn with serious potential make this... Read More

Homes For Sale

$338,900

3 Bed
2 Bath
1,624 Sqft
0.44 Acre(Lot)

373 Woodstock Avenue, Windham County, CT

Charming bungalow-style ranch featuring 3 bedrooms and 2 full bathrooms. home offers over 1600 sq. ft. of living... Read More

Homes For Sale

$424,900

4 Bed
2 Bath
1,694 Sqft
0.56 Acre(Lot)

3 Plainview Drive, Windham County, CT

Welcome to your next chapter in this beautifully maintained 4-bedroom, 2-bath raised ranch in plainfield, ct!... Read More

Homes For Sale

$424,900

4 Bed
2 Bath
2,111 Sqft
0.56 Acre(Lot)

3 Plainview Dr, Windham County, CT

Welcome to your next chapter in this beautifully maintained 4-bedroom, 2-bath raised ranch in plainfield! the... Read More

Homes For Sale

$345,000

3 Bed
1 Bath
1,102 Sqft
0.18 Acre(Lot)

172 Sabin Street, Windham County, CT

Completely fresh and clean! the kitchen has been updated with brand new appliances, granite counter, and vinyl... Read More

Homes For Sale

$789,000

2 Bed
2 Bath
1,918 Sqft
0.4 Acre(Lot)

43 Hiawatha Heights, Windham County, CT

Welcome to the home where sunsets paint the sky, the water whispers just steps from your door, and every day... Read More

Homes For Sale

$219,900

3 Bed
1 Bath
1,003 Sqft
0.06 Acre(Lot)

21 Chassey Street, Windham County, CT

Adorable putnam cape- 3 bedrooms and an additional office or 4 bedrooms, large living room and kitchen. home was... Read More

Homes For Sale

$69,900

2 Bed
1 Bath
920 Sqft

25 Ct Route 197 Lot 42, Windham County, CT

First time on the market in years! located in the sought-after meadowside community, this spacious lot offers... Read More

Homes For Sale

$389,000

3 Bed
3 Bath
1,312 Sqft
2.57 Acres(Lot)

46 Perry Hill Road, Windham County, CT

Enjoy peace and privacy at 46 perry hill road, ashford! set on a picturesque 2.57-acre lot, this 3-bedroom,... Read More

Homes For Sale

$275,000

3 Bed
1 Bath
1,290 Sqft
1.15 Acres(Lot)

534 Margaret Henry Road, Windham County, CT

This beauty needs some cosmetic tlc such as paint, carpets and other personal touches. the house offers solid... Read More

Pending

Homes For Sale

$450,000

4 Bed
3 Bath
1,800 Sqft
0.8 Acre(Lot)

113 Reilly Road, Windham County, CT

Gorgeous 2025 raised ranch with open floor plan has living/ dining area and stainless appliances in kitchen w/... Read More

First
1
2
3
4
5
6
7
8
9
10
Last

Windham County - Statistics and Home Trends

Actives Activity Chart

Homes For Sale Buy Owner in Windham County 111

	Average Price
1 Bed Homes For Sale in Windham County (1)	$ 875,000
2 Bed Homes For Sale in Windham County (13)	$ 359,931
3 Bed Homes For Sale in Windham County (69)	$ 461,476
4 Bed Homes For Sale in Windham County (24)	$ 505,321
5+ Bed Homes For Sale in Windham County (4)	$ 866,225

AVERAGE PRICE

$ 613,590

NEW LISTINGS THIS WEEK

102

PRICE PER SQUARE FOOT

$ 239

Condos For Sale Buy Owner in Windham County 6

	Average Price
1 Bed Condos For Sale in Windham County (1)	$ 324,900
2 Bed Condos For Sale in Windham County (5)	$ 359,980

AVERAGE PRICE

$ 536,119

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 257

Townhomes For Sale Buy Owner in Windham County 1

	Average Price
3 Bed Townhomes For Sale in Windham County (1)	$ 200,000

AVERAGE PRICE

$ 494,104

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 4,000

Land For Sale Buy Owner in Windham County 57

	Average Price
Land For Sale in Windham County (57)	$ 468,727

AVERAGE PRICE

$ 468,727

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

Statistics Bottom Ads 1

Learn More About Windham County, Connecticut

Currently there are 111 homes for sale, 6 condos and apartments for sale, 57 vacant land for sale and 1 townhomes for sale in Windham County

Currently Windham County has 175 properties on the market for sale. The inventory was last updated 04/25/2025. Of these properties, 111 single family homes are for sale by their owners in Windham County, and 6 condos are for sale by their owners in Windham County. The average price of the single family homes for sale in Windham County, is $613,590, the average condo price in Windham County, is $536,119. The average price per square foot of the active inventory is $125. This is based the living area square footage.

Over the last year, there have been 17 of properties sold in Windham County. Of these properties, 13 single family homes have sold by their owners in Windham County, and 0 condos have sold by their owners in Windham County. The average sales price of the single family homes sold in Windham County, is $337,100. Single family homes have been selling for 199 per square foot of living area. The average sales price of the condos for sale in Windham County, is $304,425. Condos have been selling for N/A per square foot of living area.

If you are thinking of selling your Windham County home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 04/25/2025

Windham County CT FSBO Homes (250)

43 Douglas Drive, Windham County, CT

226 Labby Road, Windham County, CT

187 Chaplin Road, Windham County, CT

2325 Waterfall Road, Windham County, CT

106a Tripp Hollow Road, Windham County, CT

105 Reilly Road, Windham County, CT

297 Main Street, Windham County, CT

116 Paradise Drive, Windham County, CT

103 Reilly Road, Windham County, CT

63 Parent Hill Road, Windham County, CT

373 Woodstock Avenue, Windham County, CT

3 Plainview Drive, Windham County, CT

3 Plainview Dr, Windham County, CT

172 Sabin Street, Windham County, CT

43 Hiawatha Heights, Windham County, CT

21 Chassey Street, Windham County, CT

25 Ct Route 197 Lot 42, Windham County, CT

46 Perry Hill Road, Windham County, CT

534 Margaret Henry Road, Windham County, CT

113 Reilly Road, Windham County, CT

Nearby Cities

Popular Cities

Nearby Counties

Property Types

Windham County - Statistics and Home Trends

Actives Activity Chart

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

Statistics Bottom Ads 1

Learn More About Windham County, Connecticut

For Sale By Owner Massachusetts

Statistics Bottom Ads 2

For Sale By Owner Rhode Island

Statistics Bottom Ads 3

For Sale By Owner Connecticut

Statistics Bottom Ads 4

YouTube Video