237 High St
Winchester, MA 01890
- 3 Beds
- 1.5 Baths
- 2,113 sqft (on 0.37 acres)
3 Beds
1.5 Baths
2,113 sqft
(on 0.37 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1956
Lot Size
0.37 acres
Living Area
2,113 sqft
Price/Sqft
$988
Parking
Garage
About this House
Welcome to 237 High Street, a nature loverâs dream tucked in a serene location surrounded by beautiful conservation land, hiking trails and pond views. Relax in the living room next to the fireplace or, on a warm day, in the enclosed 3 season sun porch surrounded by sights and sounds of nature. A beautiful family room features dramatic cathedral ceilings, skylight & cozy wood stove, plus sliders to a private deck & sprawling backyard. Contemporary kitchen with stainless steel appliances & granite counters. Formal dining room & half bath complete the 1st floor. Three generously sized bedrooms & 1 full bath on 2nd floor. Lower level features a large entertainment room with dry bar, laundry, storage & exterior access. Additional highlights include Nest thermostats, insulated attic, outdoor motion lights, recessed lighting. 1 car garage & off-street parking for 6 cars. Situated on a large lot in desirable West End neighborhood near VO Elementary.
237 High St, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 2,113 sqft single-family home built in 1956. It last sold for $1,775,000 on Sep 21, 2021. It is currently off market. The Trulia Estimate is $2,086,700, with a rent estimate of $5,425/month.
Home Details for 237 High St
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Interior Details BasementNumber of Rooms: 11 |
Heating & Cooling Heating: Baseboard, OilAir ConditioningHeating Fuel: Baseboard |
Appliances & Utilities DishwasherRefrigerator |
Fireplace & Spa Fireplace |
Levels, Entrance, & Accessibility Floors: Tile, Hardwood, Laminate |
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Exterior Home Features Roof: AsphaltDeckExterior: VinylPorch |
Parking & Garage GarageParking Space: 1Parking: Garage Attached |
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Year Built Year Built: 1956Year Updated: 2020 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 0.37 acres |
Price History for 237 High St
| Date | Price | Event | Source |
|---|---|---|---|
| 06/03/2022 | ListingRemoved | MLS PIN #72801610 | |
| 09/21/2021 | $1,775,000 | Sold | MLS PIN #72862556 |
| 08/17/2021 | $1,899,000 | Pending | MLS PIN #72862556 |
| 08/03/2021 | $1,899,000 | Contingent | MLS PIN #72862556 |
| 07/08/2021 | $1,899,000 | Listed For Sale | MLS PIN #72862556 |
| 04/13/2021 | $1,799,999 | ListingRemoved | MLS PIN #72801610 |
| 04/01/2021 | $1,799,999 | Listed For Sale | MLS PIN #72801610 |
| 02/15/2021 | $1,799,999 | ListingRemoved | MLS PIN #72780142 |
| 01/29/2021 | $1,799,999 | Listed For Sale | MLS PIN #72780142 |
| 09/01/2020 | $920,000 | Sold | N/A |
| 07/16/2020 | $939,000 | Pending | Agent Provided |
| 06/05/2020 | $939,000 | PriceChange | Agent Provided |
| 05/20/2020 | $999,000 | Listed For Sale | Agent Provided |
| 06/01/2012 | $635,000 | Sold | N/A |
| 03/02/2012 | $659,900 | PriceChange | Agent Provided |
| 02/14/2012 | $699,900 | Listed For Sale | Agent Provided |
Market trends in Winchester
Last updated June 2026
Avg. sale price
$1.41M
Sale-to-List Price
101.7%
Price per sq ft
$571
Available listings
77
2MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $21,078 |
| Assessment | $1,900,600 |
Home facts updated by county records
Comparable Sales for 237 High St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Single-Family Home | $1,375,000 | 03/20/26 | 3 | 1.5 | 2,351 | |
0.15 | Single-Family Home | $1,700,000 | 05/01/26 | 3 | 3 | 3,182 | |
0.49 | Single-Family Home | $1,240,000 | 04/27/26 | 3 | 2 | 2,087 | |
0.51 | Single-Family Home | $1,270,000 | 05/01/26 | 3 | 2 | 1,888 | |
0.26 | Single-Family Home | $1,191,000 | 01/13/26 | 4 | 3 | 2,126 | |
0.36 | Single-Family Home | $1,400,000 | 03/06/26 | 3 | 2.5 | 2,316 | |
0.59 | Single-Family Home | $1,345,000 | 06/11/26 | 3 | 2 | 1,986 | |
0.31 | Single-Family Home | $1,899,000 | 07/09/26 | 5 | 2.5 | 3,278 | |
0.52 | Single-Family Home | $955,225 | 01/27/26 | 4 | 1.5 | 2,162 | |
0.51 | Single-Family Home | $1,025,000 | 03/31/26 | 3 | 1.5 | 1,936 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 237 High St.
What Locals Say about Winchester
At least 93 Trulia users voted on each feature.
92 % Say it's dog friendly
88 % Say yards are well-kept
87 % Say people would walk alone at night
85 % Say parking is easy
79 % Say there are sidewalks
79 % Say car is needed
77 % Say it's walkable to restaurants
77 % Say kids play outside
75 % Say streets are well-lit
74 % Say there's holiday spirit
67 % Say they plan to stay for at least 5 years
67 % Say there's wildlife
66 % Say neighbors are friendly
65 % Say it's walkable to grocery stores
64 % Say it's quiet
54 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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