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1 Overlook Way, Winchester MA 01890

$1,750,000

Estimated $12,254/month Calculator

Single Family

4 Bedrooms

Baths

3604

Total Parking: 8 (2 Garage)

15,680 (0.36)

Built in 1941

NEW Photos! Welcome to One Overlook Way in Winchester. This home is located on a 1/3 acre corner lot on a short cul-de-sac off High Street- a premier location close to Ambrose Elementary School and the Winchester Country Club. Don't miss this spacious 4+ bedroom center-entrance Colonial. with a thoughtfully designed circular flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen with room to add an island or large table also opens naturally into the comfortable family room - with gas fireplace, custom built-ins, a new split AC and access to the back and side yard! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a split AC, private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a second home office, hangout zone or storage. The finished lower level adds another playroom, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished storage space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

This home has been viewed 13 times

Last Checked: October 31st, 2026 at 8:58am (Source: MLS PIN #73581571)

Garage Parking

Air Conditioning

Waterview

Lead Paint Free

General Information for 1 Overlook Way, Winchester MA 01890

Listing ID73581571

Property TypeSingle Family / Detached

Price$1,750,000 ($485.57/SqFt)

StyleColonial

CityWinchester

CountyMiddlesex

MLS AreaWedgemere

Neighborhood(s)

Garage Parking2

ZoningRDA

Year Built1941

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 1 Overlook Way, Winchester MA 01890

Approximate Living Area Total3604

Living Area Includes BasementYes

Rooms11

Bedrooms4

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric220 Volts

Exterior Features for 1 Overlook Way, Winchester MA 01890

Approximate Lot Size (Acres)0.36

Approximate Lot Size (Square Feet)15680

Total Parking8 (2 Garage)

Garage Parking2

WaterPublic

SewerPublic Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Approximate Street Frontage127.00

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections

Water ViewsNo

Water Views Features

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 1 Overlook Way, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourceMeasured

Special Listing Conditions

ExclusionsWall Mounted Tv's-Brackets To Remain

Compensation Based On

Financial Information for 1 Overlook Way, Winchester MA 01890

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax17650

Tax Year2026

Assessed Value$1,593,000

Location Information for 1 Overlook Way, Winchester MA 01890

Elementary SchoolAmbrose

Middle SchoolMccall

High SchoolWhs

Neighborhood(s)

MLS AreaWedgemere

Area AmenitiesWalk/jog Trails

Contact Information for 1 Overlook Way, Winchester MA 01890

Agent

Name: Lynne Russo

Office

Name: Better Homes and Gardens Real Estate - The Shanahan Group

Phone: 781-729-9030

Payment Calculator

, Interest

Property Taxes 1470.83

Principal & Interest 10782.94

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Better Homes and Gardens Real Estate - The Shanahan Group

Lynne Russo

Agent Phone

Office Phone

(781) 729-9030

Text Agent Call Agent Call Office

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EXIT

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