Active
21 Days on market
85 High St Winchester — Photo 1 of 38

85 High St Winchester — Photo 1 of 38

$1,999,000

85 High St, Winchester, MA 01890

Winchester, MA 01890

Beds

4

Baths

2.5

SqFt

3,757

Style

Single Family

Built

1931

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$532/sqft
Local Avg (Winchester)$557/sqft
4% BelowMarket Average

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

Property Details

Financials

Original Price$1,999,000
Annual Taxes$15,671

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms12
Fireplaces1
FlooringTile, Hardwood, Flooring - Hardwood, Laminate
BasementFull, Partially Finished, Walk-Out Access, Interior Entry, Bulkhead, Sump Pump, Concrete

Climate & Utilities

HeatingSteam, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
RoofShingle
FoundationStone
ZoningRDB

Property & Lot

Acres0.29
SqFt Lot12,489
Lot FeaturesCorner Lot, Level

Amenities & Appliances

Water Heater • Oven • Dishwasher • Disposal • Range • Refrigerator • Washer • Dryer

Neighborhood

Public Transportation • Tennis Court(s) • Park • Medical Facility • Bike Path • Conservation Area

Geography

Floorplan Breakdown

Structural Layout

Third
Bedroom 5
Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenFamily RoomBathroom 1
Living Room
Lvl First

24 x 14

Closet/Cabinets - Custom Built, Flooring - Hardwood

Dining Room
Lvl First

13 x 14

Flooring - Hardwood

Kitchen
Lvl First

11 x 11

Flooring - Hardwood, Countertops - Stone/Granite/Solid, Recessed Lighting

Family Room
Lvl First

17 x 16

Closet/Cabinets - Custom Built, Flooring - Wood

Master Bedroom
Lvl Second

23 x 12

Bathroom - Full, Walk-In Closet(s), Flooring - Wall to Wall Carpet

Bedroom 2
Lvl Second

15 x 9

Bedroom 3
Lvl Second

14 x 12

Flooring - Hardwood

Bedroom 4
Lvl Second

14 x 10

Flooring - Hardwood

Bedroom 5
Lvl Third

19 x 13

Flooring - Wood

Bathroom 1
Lvl First

8 x 6

Bathroom - Half

Bathroom 2
Lvl Second

8 x 6

Bathroom - Full, Bathroom - Tiled With Tub & Shower

Bathroom 3
Lvl Second

13 x 7

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall

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

2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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 3,757 sq ft principal dwelling). Lot size: 12,489 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: Catherine Albiani

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

MLS® Number: 73565817

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