Homes with a Pool in Winchester, MA

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3 beds New construction With a pool

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11 Listings

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Homes with a Pool in Winchester, MA

11 Listings

16Active

11 listings

Homes with a Pool in Winchester, MA

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11 Listings

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Homes with a Pool in Winchester, MA

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

16Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

$399,000

1 bd · 1 ba · 613 sqft

200 Swanton St #727, Winchester, MA

24Active

$495,000

2 bd · 1 ba · 822 sqft

200 Swanton St #303, Winchester, MA

41Active

$769,000

2 bd · 2 ba · 1,170 sqft

666 Main St #310, Winchester, MA

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

42Active

$1,650,000

5 bd · 4 ba · 3,722 sqft

117 Highland, Winchester, MA

42Active

$3,149,000

7 bd · 8 ba · 8,540 sqft

37 Mayflower Road, Winchester, MA

Price Reduced34Active

$1,329,000

3 bd · 3 ba · 2,459 sqft

110 Thornberry Road, Winchester, MA

Price Reduced42Active

$685,000

2 bd · 2 ba · 1,170 sqft

666 Main Street #211, Winchester, MA

28Active

$288,750

1 bd · 1 ba · 388 sqft

200 Swanton #L8, Winchester, MA

37Active

$649,900

2 bd · 2 ba · 1,025 sqft

666 Main Street #315, Winchester, MA

Price Reduced32Active

$2,695,000

4 bd · 5 ba · 5,233 sqft

18 Middlesex St, Winchester, MA

Price Reduced30Active

$349,900

1 bd · 1 ba · 613 sqft

200 Swanton St #717, 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: 2026-09-20 08:05:00 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: 2026-09-20 08:05:00 UTC

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Listing data & MLS disclosures

Explore Winchester homes

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Listing data & MLS disclosures