Active
1 Days on market
1 Overlook Way Winchester — Photo 1 of 39

1 Overlook Way Winchester — Photo 1 of 39

$1,850,000

1 Overlook Way, Winchester, MA 01890

Winchester, MA 01890 — Wedgemere

Investor Analysis

Beds

4

Baths

2.5

SqFt

3,092

Style

Single Family

Built

1941

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful 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 also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! 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 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 home office or storage. The finished lower level adds even more usable space, 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 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.

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$598/sqft
Local Avg (Winchester)$544/sqft
10% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$1,850,000
Annual Taxes$17,650

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms11
Fireplaces3
FlooringTile, Hardwood, Engineered Hardwood, Flooring - Wood, Flooring - Wall to Wall Carpet, Laminate
BasementFull, Partially Finished, Interior Entry, Bulkhead, Sump Pump, Concrete

Climate & Utilities

HeatingCentral, Baseboard, Natural Gas, Electric, Ductless, Fireplace
CoolingDuctless
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA

Property & Lot

Acres0.36
SqFt Lot15,705
Lot FeaturesCorner Lot, Wooded, Level

Amenities & Appliances

Gas Water Heater • Range • Dishwasher • Trash Compactor • Microwave • Refrigerator • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Conservation Area

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
Family Room
Main,First
Living RoomDining RoomKitchenBathroom 1
Living Room
Lvl Main,First

18 x 13

Flooring - Hardwood, Window(s) - Bay/Bow/Box

Dining Room
Lvl Main,First

13 x 12

Closet/Cabinets - Custom Built, Flooring - Hardwood, Chair Rail

Kitchen
Lvl Main,First

17 x 13

Flooring - Stone/Ceramic Tile, Window(s) - Bay/Bow/Box, Dining Area, Countertops - Stone/Granite/Solid, Open Floorplan, Recessed Lighting, Stainless Steel Appliances

Family Room
Lvl First

20 x 15

Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Exterior Access, Open Floorplan, Recessed Lighting, Slider

Primary Bedroom
Lvl Second

19 x 13

Bathroom - Full, Bathroom - Double Vanity/Sink, Ceiling Fan(s), Flooring - Hardwood, Double Vanity, Closet - Double

Bedroom 2
Lvl Second

16 x 13

Bedroom 3
Lvl Second

19 x 12

Flooring - Hardwood, Attic Access, Closet - Double

Bedroom 4
Lvl Second

12 x 12

Closet, Flooring - Hardwood

Bathroom 1
Lvl Main,First

6 x 4

Bathroom - Half, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl Second

13 x 5

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile

Bathroom 3
Lvl Second

9 x 5

Bathroom - Full, Bathroom - Tiled With Tub & Shower

Population

23,406

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$230K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

18.3%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Middlesex County

2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,092 sq ft principal dwelling). Lot size: 15,705 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Lynne Russo

Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group

MLS® Number: 73581571

Browse More Homes in Winchester

Explore other active listings in the area.