159 Cross St, Winchester, MA 01890
Property image
Property image
OFF MARKET

$924,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,266 sqft (on 0.26 acres)

159 Cross St, Winchester, MA 01890

Est. Refi. Payment $5,785/mo*
Refinance Your Home
Currently Off Market - Sold Jun 21, 2002 for $350,000

Home Value

Trulia Estimate
$925K
Since last month
Decreased$19K (-2%)
Since last year
Increased$600 (+0.1%)
Since last sale
Increased$567K (+162%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +50% in the last 10 years
MonthEstimated value
2026
September 2026$917K
August 2026$920K
July 2026$936K
June 2026$954K
May 2026$963K
April 2026$936K
March 2026$926K
February 2026$891K
January 2026$873K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
17 Baldwin St, Winchester, MA
0.08
Single-Family Home
$878,000
09/26/25
3
1.5
1,672
15 East St, Winchester, MA
0.13
Single-Family Home
$1,060,000
05/28/26
3
1.5
1,973
55 Brookside Ave, Winchester, MA
0.21
Single-Family Home
$657,500
07/17/26
3
1
1,245
11 Williams Cir, Winchester, MA
0.04
Single-Family Home
$1,350,000
09/02/26
4
2.5
2,392
9 James Ter, Woburn, MA
0.62
Single-Family Home
$775,000
08/28/26
3
2
1,424
39 Blueberry Hill Rd, Woburn, MA
0.55
Single-Family Home
$804,000
06/15/26
3
1.5
1,800
1 Orient St, Winchester, MA
0.35
Single-Family Home
$1,330,000
05/28/26
3
1.5
2,222
8 James Ter, Woburn, MA
0.63
Single-Family Home
$650,000
10/28/25
4
2
1,469
41 Englewood Rd, Winchester, MA
0.55
Single-Family Home
$1,038,500
12/01/25
3
1.5
1,683
571 Washington St, Winchester, MA
0.36
Single-Family Home
$900,000
01/05/26
3
1
1,425

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
11 Williams Cir, Winchester, MA 01890
0.04
$1,350,000
4
2.5
2,392
Recently Sold
17 Baldwin St, Winchester, MA 01890
0.08
$901,900
3
1.5
1,672
Off Market
18 Forest St, Winchester, MA 01890
0.12
$1,310,100
3
2.5
2,365
Off Market
15 East St, Winchester, MA 01890
0.13
$1,060,000
3
1.5
1,973
Recently Sold
28 Garfield Ave, Winchester, MA 01890
0.19
$1,318,300
4
1.5
1,696
Off Market
26 Adams Rd #26, Winchester, MA 01890
0.19
-
4
3.5
3,105
Off Market
44 Forest St, Winchester, MA 01890
0.21
$1,203,800
3
1.5
1,906
Off Market
55 Brookside Ave, Winchester, MA 01890
0.21
$657,500
3
1
1,245
Recently Sold
7 Conant Rd #24, Winchester, MA 01890
0.20
$689,600
2
2
1,196
Off Market
5 Highland View Ave, Winchester, MA 01890
0.21
$1,090,000
4
2
1,913
Off Market
235 Cross St, Winchester, MA 01890
0.22
$889,200
3
1.5
1,931
Off Market
7 Conant Rd #53, Winchester, MA 01890
0.23
$745,000
2
2
1,588
Recently Sold

Local Information

  • Map ViewExplore the area around 159 Cross St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1950
0.26 acre lot
1,266 sqft
$730/sqft

About this House

Enjoy easy access to Boston, and Rtes. 93 and 95 when you rent this beautifully maintained 3 bedroom 1.5 bath single family home in Winchester, MA ! Level one features a kitchen, open dining room/living room, and half bath. Level two boasts three bedrooms and an oversized full bath with a jetted tub. Other features include: Central AC, attached garage and off street parking for four cars. Basement storage available. Updated windows, heating system and hot water. No pets. No smoking. Available immediately.
159 Cross St, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 1,266 sqft single-family home built in 1950. It last sold for $350,000 on Jun 21, 2002. More recently, it was listed as a rental in August 2015 with an asking price of $2,600 per month. That rental listing was removed on October 1, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $924,800, with a rent estimate of $3,784/month.

Home Details for 159 Cross St

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherPatioSprinkler System

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Oct 1, 2015
Source: Agent Provided
ListingRemoved
$2,600
Aug 14, 2015
Source: Agent Provided
Listed For Rent
$2,600
Jun 21, 2002
Source: N/A
Sold
$350,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

Around this home

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.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 159 Cross St

  • What is 159 Cross St estimated to be worth?
    Trulia's estimated value for 159 Cross St in Winchester, MA is $924,800.
  • What is the price history for 159 Cross St?
    159 Cross St in Winchester, MA last sold for $350,000 in June 2002.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • How big is the lot at 159 Cross St?
    The lot at 159 Cross St in Winchester, MA is about 0.26 acres (11,325 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 159 Cross St

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