4 Dartmouth St Winchester, MA ^$ 4,699,000

4 Dartmouth St

^$ 4,699,000

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4 Dartmouth St

Winchester, MA, 01890

^$ 4,699,000

Bedrooms5 Baths5.1 Sq 6,526

Monthly Estimate*

^$ 28,933

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Single Family Home for sale in Winchester, MA

for $4,699,000 with 5 bedrooms and 5 full baths, 1 half bath. This 6,526 square foot home was built in 1935 on a lot size of 0.67.

Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully maintained and updated, blending classic architecture with modern comfort. This 5 bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the kitchen, family room and study, while several curated outdoor dining and gathering areas invite entertaining overlooking the pond. The expansive living and dining rooms complete the first floor. A generous primary suite is a private retreat with a spacious bath and ample closets. 4 other ample bedrooms and a second floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Kayak, skate, go fishing and enjoy life on the water!

Single Family Active

Price

^$ 4,699,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 51,006

Style

Tudor

Lot Size

0.67

Year Built

1935

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73482952

List By

The Pallotta Group

Listing Agent

Gibson Sotheby's International Realty

Broker

Affordability Calculator

$33,183

Per Month

Monthly Principal & Interest: $28,933
Monthly Property Taxes: $4,251
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Winchester, MA

Average List Price ^$2,497,774

Percent of Sale Price 47%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
3/5/2026	$4,699,000		Listed Price

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4 Dartmouth St, Winchester, MA, 01890 is a Single Family Home for sale at $4,699,000 with 6,526 sqft and a lot size of 0.67. 4 Dartmouth St has 5 bedrooms, 5.1 baths, and was built in 1935. The property's zip code is 01890 which is in Winchester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 3/7/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, 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, and the Images, 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, or as to the accuracy of any of the Images, set forth herein.

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4 Dartmouth St

Single Family Home for sale in Winchester, MA

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