161 Winter St, Ashland, MA 01721
OFF MARKET

$676,500

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,344 sqft (on 1.24 acres)

161 Winter St, Ashland, MA 01721

Est. Refi. Payment $4,075/mo*
Refinance Your Home
Currently Off Market - Sold Aug 28, 2015 for $344,000

Home Value

Trulia Estimate
$677K
Since last month
Decreased$14K (-2%)
Since last year
Increased$1K (+0.2%)
Since last sale
Increased$333K (+96.9%)
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 +87% in the last 10 years
MonthEstimated value
2026
August 2026$677K
August 2026$677K
July 2026$691K
June 2026$694K
May 2026$705K
April 2026$689K
March 2026$684K
February 2026$659K
January 2026$645K
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
95 Pine Hill Rd, Ashland, MA
0.17
Single-Family Home
$741,000
05/07/26
3
2
1,662
58 Cedar Hill Rd, Ashland, MA
0.21
Single-Family Home
$640,000
07/15/26
3
2
1,823
94 Myrtle St, Ashland, MA
0.47
Single-Family Home
$600,000
04/14/26
3
2
1,442
46 Pine Hill Rd, Ashland, MA
0.32
Single-Family Home
$665,000
02/24/26
4
2
1,912
66 Cedar Hill Rd, Ashland, MA
0.23
Single-Family Home
$630,000
03/18/26
3
1
1,272
33 Birch Hill Rd, Ashland, MA
0.28
Single-Family Home
$730,000
07/23/26
3
2
2,032
55 Sudbury Rd, Ashland, MA
0.37
Single-Family Home
$995,000
10/20/25
4
2.5
2,258
30 Birch Hill Rd, Ashland, MA
0.30
Single-Family Home
$560,000
05/21/26
3
1
1,086
37-37 Park Rd #R, Ashland, MA
0.83
Single-Family Home
$600,000
11/04/25
3
2
1,344
12 Alfred Rd, Ashland, MA
0.66
Single-Family Home
$625,000
02/06/26
4
1.5
1,456

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
101 Pine Hill Rd, Ashland, MA 01721
0.15
$615,300
3
1
1,178
Off Market
84 Pine Hill Rd, Ashland, MA 01721
0.15
$639,700
3
2
1,744
Off Market
95 Pine Hill Rd, Ashland, MA 01721
0.17
$741,000
3
2
1,662
Recently Sold
43 Cedar Hill Rd, Ashland, MA 01721
0.14
$1,266,900
6
4
4,058
Off Market
201 Winter St, Ashland, MA 01721
0.20
$686,600
4
1.5
2,016
Off Market
4 Woodridge Ln, Ashland, MA 01721
0.21
$942,600
4
2.5
2,052
Off Market
63 Cedar Hill Rd, Ashland, MA 01721
0.21
$1,249,200
3
1.5
1,592
Off Market
58 Cedar Hill Rd, Ashland, MA 01721
0.21
$640,000
3
2
1,823
Recently Sold
62 Cedar Hill Rd, Ashland, MA 01721
0.22
$657,200
4
2
1,567
Off Market
66 Cedar Hill Rd, Ashland, MA 01721
0.23
$630,000
3
1
1,272
Recently Sold
33 Birch Hill Rd, Ashland, MA 01721
0.28
$730,000
3
2
2,032
Recently Sold
43 Shadow Creek Ln #43, Ashland, MA 01721
0.30
$697,800
2
2.5
1,799
Off Market

Local Information

  • Map ViewExplore the area around 161 Winter St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
1.24 acre lot
1,344 sqft
$503/sqft
Garage

About this House

This single-family home is located at 161 Winter St, Ashland, MA. 161 Winter St is in Ashland, MA and in ZIP code 01721. This property has 4 bedrooms, 2 bathrooms and approximately 1,344 sqft of floor space. This property has a lot size of 1.24 acres and was built in 1960.
161 Winter St, Ashland, MA 01721 is a 4 bedroom, 2 bathroom, 1,344 sqft single-family home built in 1960. It last sold for $344,000 on Aug 28, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $676,500, with a rent estimate of $3,908/month.

Home Details for 161 Winter St

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1.24 acres

Price and Tax history

DateEventPrice
Aug 28, 2015
Source: N/A
Sold
$344,000
Jul 1, 1994
Source: N/A
Sold
$120,000

Market trends in Ashland

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$615K
$51.67KMoM
Sale-to-List Price
—
Price per sq ft
$340
$17MoM
Available listings
47
3MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Ashland

At least 91 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 77 % Say people would walk alone at night

  • 75 % Say there's wildlife

  • 74 % Say there are sidewalks

  • 73 % Say there's holiday spirit

  • 73 % Say it's quiet

  • 71 % Say kids play outside

  • 66 % Say neighbors are friendly

  • 62 % Say yards are well-kept

  • 56 % Say it's walkable to restaurants

  • 53 % Say they plan to stay for at least 5 years

  • 43 % Say streets are well-lit

  • 38 % Say it's walkable to grocery stores

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Christine.f.graham
    "Kids playing outside every day! Great walkable neighborhoods and outdoor spaces. Farmer's market, The Corner Spot, School & Halloween events. "
    2
    Flag
  • Stephanie
    "There are a lot of irresponsible dog owners that don’t pick up their dogs poop. Some people think they’re dog is friendly and think it’s ok to let them come up to your dog with no control. "
    3
    Flag
  • Kellia E.
    "Quiet friendly community. Close enough to major shopping but just far enough to feel like a getaway from city life. "
    0
    Flag
  • Misssueshair
    "None that I know of It’s a very quiet area Great for walking or running or even riding your bike I think if we had a community pool it would make this area perfect "
    0
    Flag
  • Krisna
    "I’m finding it’s a wonderful little community, here. People look you in the eyes here, are patient and listen and are welcoming. It’s the kind of place where if you’re carrying groceries to your door, but start to your drop bags, someone will offer to help carry them inside for you... and then leave afterwards without hurting you. "
    0
    Flag
  • Christinaandrade100
    "I live in this neighborhood for two years and I loved it. Here is safe, quiet and good for children. The schools are great, because they're a good place and excellent staff. We have too amazing water, square and green spaces to go out."
    0
    Flag
  • Sontay
    "The town is very safe and diverse. Plenty of parks for your pet or children. Great schools and plenty of activities to do with your children during warmer months. It’s also fairly close to major highways for a speedy way to get to the city or other locations. Overall great and friendly town. "
    0
    Flag
  • yancen li
    "The ashland mbta and framingham mbta is not far. Bus is nearby also. Generally speaking commute is not a problem. But a car is strongly recommended."
    2
    Flag
  • Nadia
    "Safe, familiar and very good area for children. Schools are very good also. "
    0
    Flag
  • Ducktapedebbie
    " lived here for 25 years the neighborhood is nice and clean people follow the rules and lots of dogs and kids and lots of different ethnic groups and we cohabitate very well. "
    1
    Flag
  • Davis0569 s.
    "I just moved to this area. I really enjoy the life here in Ashland and the people. I have seen some wild Turkey's in the area. "
    1
    Flag
  • Amy
    "It's a lovely neighborhood that's we'll maintained by the condo association. there are beautiful perrenials everywhere. The little avenues and cul de sacs make it feel like a little cape cod village. It is quiet and safe."
    2
    Flag
  • Marabout79
    "Love Ashland, community is tight knit, friendly neighbors quiet neighborhoods. Great school system. "
    0
    Flag
  • Tim M.
    "Ashland is only 25 west of Boston, very easy to get there by car or commuter rail. You also get the feel of a small town that is very easy to get around, plus the schools are rated in the top 50 in Massachusetts. The Ashland Reservior is a gem - swimming, sailing, fishing, and a very nice public beach. Very safe town that is investing in itself even more in the coming years with the Pond Street Project."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 161 Winter St

  • What is 161 Winter St estimated to be worth?
    Trulia's estimated value for 161 Winter St in Ashland, MA is $676,500.
  • What is the price history for 161 Winter St?
    161 Winter St in Ashland, MA last sold for $344,000 in August 2015.
  • Is Ashland a buyer's or seller's market?
    Ashland is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Ashland?
    The median sale price in Ashland is $615K. That is up $51.67K from the prior month.
  • How big is the lot at 161 Winter St?
    The lot at 161 Winter St in Ashland, MA is about 1.2 acres.
  • Does 161 Winter St have a garage?
    Yes, 161 Winter St in Ashland, MA has a garage.

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