29 Pilgrim Dr Winchester, MA ^$ 1,749,000

29 Pilgrim Dr

^$ 1,749,000

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Open House 3/27 5pm - 6:30pm

29 Pilgrim Dr

Winchester, MA, 01890

^$ 1,749,000

Bedrooms5 Baths3.0 Sq 3,271

Monthly Estimate*

^$ 10,769

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Single Family Home for sale in Winchester, MA

for $1,749,000 with 5 bedrooms and 3 full baths. This 3,271 square foot home was built in 1963 on a lot size of 0.47.

Beautifully updated home offers generous living spaces and a seamless, open flow. Sun-filled living and dining areas feature hardwood floors, elegant detailing, and a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, and large island that opens to the dining area, which flows into the family room with direct access outdoors - ideal for yard access and entertaining. French doors between the kitchen, dining, and family room help to create a quieter, more private setting for the bedroom and formal living areas. The primary suite provides a private retreat with a full bath, while three additional bedrooms and full bath complete this level. A finished walk-out lower level adds versatility with a fireplace playroom, 5th bedroom, full bath, and laundry. Enjoy professionally landscaped grounds and inviting outdoor areas, complemented by an attached garage and ample parking.

Open House

3/27/2026 5:00 PM - 6:30 PM

3/28/2026 1:00 PM - 2:30 PM

3/29/2026 1:00 PM - 2:30 PM

29 Pilgrim Dr Winchester, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

^$ 1,749,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 17,564

Style

Raised Ranch

Lot Size

0.47

Year Built

1963

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73491480

List By

Anne Spry

Listing Agent

Barrett Sotheby's International Realty

Broker

Affordability Calculator

$12,233

Per Month

Monthly Principal & Interest: $10,769
Monthly Property Taxes: $1,464
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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Trends

Single family listings in Winchester, MA

Average List Price ^$2,588,890

Percent of Sale Price 48%

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.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
3/25/2026	$1,749,000		Listed Price

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29 Pilgrim Dr, Winchester, MA, 01890 is a Single Family Home for sale at $1,749,000 with 3,271 sqft and a lot size of 0.47. 29 Pilgrim Dr has 5 bedrooms, 3.0 baths, and was built in 1963. 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 3/27/2026.

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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29 Pilgrim Dr

Single Family Home for sale in Winchester, MA

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