4 Bedroom Homes for Sale in Winchester Town, CT

14 Homes for Sale

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Photo 3 of Single family home for sale at 469 Platt Hl Rd, Winchester, CT 06098 | MLS# 24172121 | Listing updated on 2026-08-31

Photo 1 of Single family home for sale at 469 Platt Hl Rd, Winchester, CT 06098 | MLS# 24172121 | Listing updated on 2026-08-31

Photo 2 of Single family home for sale at 469 Platt Hl Rd, Winchester, CT 06098 | MLS# 24172121 | Listing updated on 2026-08-31

$895,000

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4Bds

2Ba

3,088sqft

Single family home for sale

469 Platt Hl Rd, Winchester, CT 06098

Cohen Agency

Price Drop: $10K

Photo 3 of Single family home for sale at 122 Standard Ave, Winsted, CT 06098 | MLS# 24196702 | Listing updated on 2026-10-01

Photo 1 of Single family home for sale at 122 Standard Ave, Winsted, CT 06098 | MLS# 24196702 | Listing updated on 2026-10-01

Photo 2 of Single family home for sale at 122 Standard Ave, Winsted, CT 06098 | MLS# 24196702 | Listing updated on 2026-10-01

$389,900

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4Bds

2Ba

1,944sqft

Single family home for sale

122 Standard Ave, Winsted, CT 06098

Northwest Ct Realty

Photo 1 of Single family home for sale at 205 Perch Rock Trl, Winsted, CT 06098 | MLS# 24210637 | Listing updated on 2026-10-01

$300,000

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4Bds

3Ba

2,407sqft

Single family home for sale

205 Perch Rock Trl, Winsted, CT 06098

Find Real Estate Llc

Open House

Photo 3 of Single family home for sale at 173 Gilbert Ave, Winsted, CT 06098 | MLS# 24210073 | Listing updated on 2026-10-07

Photo 1 of Single family home for sale at 173 Gilbert Ave, Winsted, CT 06098 | MLS# 24210073 | Listing updated on 2026-10-07

Photo 2 of Single family home for sale at 173 Gilbert Ave, Winsted, CT 06098 | MLS# 24210073 | Listing updated on 2026-10-07

$289,900

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4Bds

2Ba

1,664sqft

Single family home for sale

173 Gilbert Ave, Winsted, CT 06098

Tier 1 Real Estate

Photo 3 of Single family home for sale at 136 Losaw Rd, Winsted, CT 06098 | MLS# 24202969 | Listing updated on 2026-09-19

Photo 1 of Single family home for sale at 136 Losaw Rd, Winsted, CT 06098 | MLS# 24202969 | Listing updated on 2026-09-19

Photo 2 of Single family home for sale at 136 Losaw Rd, Winsted, CT 06098 | MLS# 24202969 | Listing updated on 2026-09-19

$439,900

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4Bds

2Ba

1,977sqft

Single family home for sale

136 Losaw Rd, Winsted, CT 06098

Northwest Ct Realty

Hot

Price Drop: $50K

Photo 3 of Multi family home for sale at 752 Lake Dr, Winsted, CT 06098 | MLS# 24190733 | Listing updated on 2026-10-07

Photo 1 of Multi family home for sale at 752 Lake Dr, Winsted, CT 06098 | MLS# 24190733 | Listing updated on 2026-10-07

Photo 2 of Multi family home for sale at 752 Lake Dr, Winsted, CT 06098 | MLS# 24190733 | Listing updated on 2026-10-07

$1,550,000

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4Bds

3Ba

2,129sqft

Multi family home for sale

752 Lake Dr, Winsted, CT 06098

William Raveis Real Estate

Photo 3 of Single family home for sale at 100 Norfolk Rd, Winsted, CT 06098 | MLS# 24207462 | Listing updated on 2026-09-28

Photo 1 of Single family home for sale at 100 Norfolk Rd, Winsted, CT 06098 | MLS# 24207462 | Listing updated on 2026-09-28

Photo 2 of Single family home for sale at 100 Norfolk Rd, Winsted, CT 06098 | MLS# 24207462 | Listing updated on 2026-09-28

$350,000

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4Bds

2Ba

2,914sqft

Single family home for sale

100 Norfolk Rd, Winsted, CT 06098

Northwest Ct Realty

Photo 3 of Single family home for sale at 293 Torringford St, Winsted, CT 06098 | MLS# 24185819 | Listing updated on 2026-09-15

Photo 1 of Single family home for sale at 293 Torringford St, Winsted, CT 06098 | MLS# 24185819 | Listing updated on 2026-09-15

Photo 2 of Single family home for sale at 293 Torringford St, Winsted, CT 06098 | MLS# 24185819 | Listing updated on 2026-09-15

$495,000

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4Bds

3Ba

3,834sqft

Single family home for sale

293 Torringford St, Winsted, CT 06098

Coldwell Banker Realty

Photo 3 of Single family home for sale at 205 Wallens St, Winsted, CT 06098 | MLS# 24200204 | Listing updated on 2026-09-13

Photo 1 of Single family home for sale at 205 Wallens St, Winsted, CT 06098 | MLS# 24200204 | Listing updated on 2026-09-13

Photo 2 of Single family home for sale at 205 Wallens St, Winsted, CT 06098 | MLS# 24200204 | Listing updated on 2026-09-13

$600,000

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4Bds

3Ba

3,486sqft

Single family home for sale

205 Wallens St, Winsted, CT 06098

Sullivan Real Estate Inc

Photo 3 of Multi family home for sale at 77 Hubbard St, Winsted, CT 06098 | MLS# 24206509 | Listing updated on 2026-10-07

Photo 1 of Multi family home for sale at 77 Hubbard St, Winsted, CT 06098 | MLS# 24206509 | Listing updated on 2026-10-07

Photo 2 of Multi family home for sale at 77 Hubbard St, Winsted, CT 06098 | MLS# 24206509 | Listing updated on 2026-10-07

$359,900

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4Bds

2Ba

2,699sqft

Multi family home for sale

77 Hubbard St, Winsted, CT 06098

Better Homes And Gardens Real Estate Executive Real Estate

Photo 3 of Single family home for sale at 237 Wallens Hl Rd, Winsted, CT 06098 | MLS# 24185645 | Listing updated on 2026-09-02

Photo 1 of Single family home for sale at 237 Wallens Hl Rd, Winsted, CT 06098 | MLS# 24185645 | Listing updated on 2026-09-02

Photo 2 of Single family home for sale at 237 Wallens Hl Rd, Winsted, CT 06098 | MLS# 24185645 | Listing updated on 2026-09-02

$579,900

4Bds

3Ba

2,628sqft

Single family home for sale

237 Wallens Hl Rd, Winsted, CT 06098

Northwest Ct Realty

Photo 3 of Multi family home for sale at 48 Center St, Winchester, CT 06098 | MLS# 24199882 | Listing updated on 2026-08-31

Photo 1 of Multi family home for sale at 48 Center St, Winchester, CT 06098 | MLS# 24199882 | Listing updated on 2026-08-31

Photo 2 of Multi family home for sale at 48 Center St, Winchester, CT 06098 | MLS# 24199882 | Listing updated on 2026-08-31

$325,000

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4Bds

3Ba

2,257sqft

Multi family home for sale

48 Center St, Winchester, CT 06098

Northwest Ct Realty

Photo 3 of Multi family home for sale at 119 W Wakefield Blvd, Winsted, CT 06098 | MLS# 24191163 | Listing updated on 2026-08-31

Photo 1 of Multi family home for sale at 119 W Wakefield Blvd, Winsted, CT 06098 | MLS# 24191163 | Listing updated on 2026-08-31

Photo 2 of Multi family home for sale at 119 W Wakefield Blvd, Winsted, CT 06098 | MLS# 24191163 | Listing updated on 2026-08-31

$849,900

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4Bds

2Ba

1,781sqft

Multi family home for sale

119 W Wakefield Blvd, Winsted, CT 06098

Kw Legacy Partners

Price Drop: $19.9K

Photo 3 of Single family home for sale at 70 Walnut St, Winsted, CT 06098 | MLS# 24189288 | Listing updated on 2026-10-02

Photo 1 of Single family home for sale at 70 Walnut St, Winsted, CT 06098 | MLS# 24189288 | Listing updated on 2026-10-02

Photo 2 of Single family home for sale at 70 Walnut St, Winsted, CT 06098 | MLS# 24189288 | Listing updated on 2026-10-02

$305,000

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4Bds

2Ba

2,722sqft

Single family home for sale

70 Walnut St, Winsted, CT 06098

Northwest Ct Realty

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Historic Homes for Sale Winchester Town

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Single Family Homes for Sale in Winchester Town

Land for Sale in Winchester Town

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2 Bedroom Homes for Sale in Winchester Town, CT

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Houses for Sale in Winchester Town Under $100K

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Based on information provided to and compiled by the SMART MLS, Inc. through Oct 7, 2026, 11:30 AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.