5 Bedroom Homes in Winchester, MA

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3 beds New construction With a pool

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11 Listings

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5 Bedroom Homes in Winchester, MA

11 Listings

42

11 listings

5 Bedroom Homes in Winchester, MA

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11 Listings

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5 Bedroom Homes in Winchester, MA

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

42

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Active

$1,599,000

5 bd · 3 ba · 2,944 sqft

143 Arlington Street, Winchester, MA

38Active

$4,299,000

5 bd · 6 ba · 6,526 sqft

4 Dartmouth, Winchester, MA

42Active

$1,650,000

5 bd · 4 ba · 3,722 sqft

117 Highland, Winchester, MA

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

35Active

$2,995,000

5 bd · 6 ba · 6,500 sqft

8 Priscilla Lane, Winchester, MA

37Active

$1,749,000

5 bd · 4 ba · 3,508 sqft

17 Churchill Rd, Winchester, MA

40Active

$1,050,000

5 bd · 3 ba · 2,801 sqft

257 Cross Street, Winchester, MA

42Active

$3,199,000

5 bd · 5 ba · 5,406 sqft

10 Rangeley Road, Winchester, MA

4Active

$3,200,000

5 bd · 6 ba · 5,295 sqft

18 Ridge St, Winchester, MA

Price Reduced42Active

$1,870,000

5 bd · 4 ba · 3,210 sqft

79 Grove St, Winchester, MA

Price Reduced37Active

$2,400,000

5 bd · 3 ba · 4,071 sqft

9 Plymouth Rd, Winchester, MA

Price Reduced36Active

$2,195,000

5 bd · 4 ba · 5,006 sqft

276 High Street, Winchester, MA

Listing data & MLS disclosures

MLS Property Information Network (MLS PIN): The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-09-19 00:06:00 UTC

Explore Winchester homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Listing data & MLS disclosures

MLS Property Information Network (MLS PIN): The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-09-19 00:06:00 UTC

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Explore Winchester homes

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