29 Jackson Rd, Somerville, MA 02145
Property image
Property image
OFF MARKET

$1,238,500

Trulia Estimate
  • 9 Beds
  • 3 Baths
  • 4,136 sqft

29 Jackson Rd, Somerville, MA 02145

Winter Hill
Est. Refi. Payment $7,425/mo*
Refinance Your Home
Currently Off Market - Sold Mar 7, 2017 for $625,000

Home Value

Trulia Estimate
$1.24M
Since last month
Decreased$36K (-2.8%)
Since last year
Decreased$52K (-4%)
Since last sale
Increased$614K (+98.2%)
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 +21% in the last 10 years
MonthEstimated value
2026
August 2026$1.24M
July 2026$1.27M
June 2026$1.29M
May 2026$1.31M
April 2026$1.3M
March 2026$1.32M
February 2026$1.27M
January 2026$1.25M
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
10 Mortimer Pl, Somerville, MA
0.05
Multi-Family Home
$1,465,000
01/30/26
7
3
2,850
6 Mortimer Pl, Somerville, MA
0.06
Multi-Family Home
$1,515,000
08/29/25
6
3
2,850
71 Thurston St, Somerville, MA
0.26
Multi-Family Home
$925,000
12/18/25
7
3
3,716
39 Bradley St, Somerville, MA
0.04
Multi-Family Home
$1,650,000
07/17/26
8
3
3,111
400 Medford St, Somerville, MA
0.33
Multi-Family Home
$1,080,000
07/31/26
7
3
2,864
10 Stickney Ave, Somerville, MA
0.16
Multi-Family Home
$1,690,000
09/03/25
9
3
5,686
81 Wheatland St, Somerville, MA
0.35
Multi-Family Home
$1,025,000
11/12/25
6
3
3,426
18 Otis St, Somerville, MA
0.31
Multi-Family Home
$1,500,000
12/12/25
12
3
4,707
21 Cross St, Somerville, MA
0.35
Multi-Family Home
$1,250,000
07/24/26
8
3
2,774
147-149 Pearl St, Somerville, MA
0.34
Multi-Family Home
$1,780,000
12/11/25
11
4
4,491

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
41-41A Sargent Ave #2, Somerville, MA 02145
0.02
$1,040,000
3
2.5
1,806
Recently Sold
41 Sargent Ave #B, Somerville, MA 02145
0.02
-
3
2.5
1,899
Off Market
45 Sargent Ave, Somerville, MA 02145
0.02
$1,720,900
5
4.5
3,280
Off Market
42 Sargent Ave, Somerville, MA 02145
0.04
$1,599,200
4
2.5
2,826
Off Market
35 Sargent Ave #1, Somerville, MA 02145
0.03
$946,000
3
3
1,621
Off Market
35 Sargent Ave #2, Somerville, MA 02145
0.03
$934,700
3
2
1,550
Off Market
36 Sargent Ave, Somerville, MA 02145
0.04
-
3
1.5
1,217
Off Market
50 Sargent Ave, Somerville, MA 02145
0.04
$1,144,800
4
2.5
2,410
Off Market
32 Jackson Rd #A, Somerville, MA 02145
0.02
$1,217,000
3
2.5
2,308
Off Market
53 Sargent Ave, Somerville, MA 02145
0.03
$1,396,600
5
4
3,644
Off Market
22 Sargent Ave, Somerville, MA 02145
0.05
$1,314,900
6
3
2,987
Off Market
24 Jackson Rd #2, Somerville, MA 02145
0.03
$964,900
3
2
1,620
Off Market

Local Information

  • Map ViewExplore the area around 29 Jackson Rd.
  • Schools7 Preschool Schools8 Elementary Schools6 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1890
Living Area
4,136 sqft
Price/Sqft
$299

About this House

This Massive 2 Family in Gilman Square is a MUST SEE. The First Unit is a 2 Bed 1 Bath with an Office Space, Living Room, Dining Room and an Eat in Kitchen. The Second Unit, spread over two levels, is a 6 Bed 2 Bath with a Living Room, Dining Room, Eat in Kitchen and Walk in Closet. Both Units have Hardwood Floors, Soaring Ceilings and are Flooded with Natural Light. Huge Finished Basement with High Ceilings adds two bonus rooms and a full bathroom as well as a laundry room. There is Driveway Parking and a yard. .
29 Jackson Rd, Somerville, MA 02145 is a 9 bedroom, 3 bathroom, 4,136 sqft multi-family in Winter Hill, built in 1890. It last sold for $625,000 on Mar 7, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,238,500, with a rent estimate of $3,618/month.

Home Details for 29 Jackson Rd

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 15

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other

Property Information

Year Built
Year Built: 1890
Property Type / Style
Property Type: Multi Family

Community

Units in Building: 2

Lot Information

Lot Area: 3049 sqft

Price and Tax history

DateEventPrice
Mar 7, 2017
Source: N/A
Sold
$625,000
Jul 29, 2016
Source: Agent Provided
ListingRemoved
$1,000,000
Jul 19, 2016
Source: Agent Provided
Pending
$1,000,000
Jul 12, 2016
Source: Agent Provided
Listed For Sale
$1,000,000
Jun 15, 1995
Source: N/A
Sold
$150,000

Market trends in Somerville

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$958K
$73.33KMoM
Sale-to-List Price
100.0%
Price per sq ft
$738
$4MoM
Available listings
177
28MoM

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.

Neighborhood Overview

Winter Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Winter Hill

At least 165 Trulia users voted on each feature.

  • 94 % Say there are sidewalks

  • 89 % Say it's dog friendly

  • 89 % Say it's walkable to restaurants

  • 75 % Say it's walkable to grocery stores

  • 74 % Say streets are well-lit

  • 74 % Say people would walk alone at night

  • 63 % Say parking is easy

  • 60 % Say there's holiday spirit

  • 56 % Say kids play outside

  • 53 % Say yards are well-kept

  • 48 % Say neighbors are friendly

  • 48 % Say car is needed

  • 45 % Say it's quiet

  • 44 % Say they plan to stay for at least 5 years

  • 36 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Jayjoshua0913
    "Beautiful parks and supermarkets are very close wherever you live in the area. Also great schools and safe environment. "
    0
    Flag
  • Trulia User
    "I work from home so the commute is great! There is a lot of traffic but that is anywhere in the city. It’s a pretty place you should enjoy it! "
    1
    Flag
  • Jake W.
    "Somerville recently has prioritized building great new parks with playgrounds and currently is upgrading schoolyards, making this a great city for families with young kids."
    1
    Flag
  • Chuck G.
    "Lots of places to walk nearby, parks, paths, etc. People do drive fast however so make sure to keep your dog on the leash "
    1
    Flag
  • Jayjoshua0913
    "People walk around with their dogs all the time and it feels good to go out in a friendly neighborhood "
    1
    Flag
  • Jean B.
    "i have lived here for almost 2 years and my child goes to school in the neighborhood, it's a quiet and secure place."
    1
    Flag
  • Nachiket L.
    "I have been living here for the past 7 years and I love it. Though buying in this neighborhood might not be ideal due to prices, renting is definitely worth it "
    0
    Flag
  • Jean B.
    "Winter Hill is a secure and very peaceful area, MTBA service is good, it's great for family to live. "
    0
    Flag
  • Thomas O.
    "City life with old school character Everything is walkable but you’re also only moments from the highway"
    4
    Flag
  • Jean B.
    "is a safe place to live. Children can go to the park, recently i lost my purse and guest what? Someone sent it back to me in my mail box."
    0
    Flag
  • Mikayjr
    "There is an elementary school with a fantastic 3 level playground. A park with a community pool nearby. Somerville High is in walking distance."
    0
    Flag
  • Vanessa E.
    "It’s not unique. Winter Hill is the least developed neighborhood in Somerville. There are a couple of pizza places, a liquor store, Walgreens and a couple of banks. After 7pm, no one is out. "
    5
    Flag
  • Natalie M.
    "I do not use public transportation. I drive or take uber's because the public transportation is not convenient for my commute or access to areas of the city I go after work"
    0
    Flag
  • Casey D.
    "Fluff festival, Porchfest, assembly row movie nights and other random things throughout the year. That’s it for now. Enjoy your search."
    0
    Flag
  • SB
    "There are lots of playgrounds all within walking distance and a lot of them have been newly renovated."
    0
    Flag
  • Richard M.
    "Easy access to I-93, but can be a wait to merge into on-ramp in morning. It’s a short bus ride to Davis Square or Sullivan Square T stations to go into Boston. Green line will be nearby soon, but not soon enough. "
    0
    Flag
  • Brian D.
    "Nice mix of longtime residents and new families and students. Safe, friendly and new restaurants, cafes."
    0
    Flag
  • Linda C.
    "There are many parks to walk to for children and an MDC pool park for children and teens/adults. Is a pretty safe neighborhood. "
    0
    Flag
  • Kathleen O.
    "There are lots of dog parks around the area."
    0
    Flag
  • Kathleen O.
    "There are several bus lines which make commuting easy."
    0
    Flag
  • Kathleen O.
    "Winter Hill has been in movies. It is a safe place for children. The parks are nice."
    0
    Flag
  • Kathleen O.
    "The schools are great. Parks are all nice. Safe place to raise kids."
    0
    Flag
  • Ihstern
    "This neighborhood is up and coming, with a lot of character and diversity. You can get anywhere in Boston or out from here super easily."
    0
    Flag
  • Arlene V.
    "They would love the neighborhood -- very dog friendly."
    0
    Flag
  • Arlene V.
    "Very easy commute. Everything is within walking distance."
    0
    Flag
  • Arlene V.
    "Great atmosphere. And the people are diverse. You really feel together with everyone."
    0
    Flag
  • Donald T.
    "A lot of cats. A lot of cars. Many other like-minded dog owners to talk to when walking canine companions."
    0
    Flag
  • Donald T.
    "Historic houses lovingly renovated by owners. Combination of ethnic groups: Latinos, Brazilians, Asian, Americans. Small and large parks. Great schools. Interesting restaurants."
    0
    Flag
  • Liv S.
    "They can walk their dogs and there is a park."
    0
    Flag
  • Liv S.
    "Train and bus are a good commute in this area, especially if you don't have a car."
    0
    Flag
  • Liv S.
    "The stores, the cars, the people -- everything about this place called Winter Hill is amazing."
    0
    Flag
  • Dick S.
    "Too hilly but some level places for dog walking."
    0
    Flag
  • Dick S.
    "Easy, but some traffic. It's not too bad."
    0
    Flag
  • Dick S.
    "It's a great place to live. Handy to all major routes. Great walking too."
    0
    Flag
  • ShaneW
    "Friendly neighbors, with a mix of young professionals and families. Walking and biking distance to many locations, including restaurants, library, city hall, and grocery stores. "
    1
    Flag
  • E s.
    "People are friendly and for the most part mind their business and respect personal space. It’s diverse with no violence. Close access to anything i need (conv store, grocery, gas, park, etc."
    1
    Flag
  • Rudy L.
    "I am looking forward to live in the neighborhood in the future, I would love to live in a great place with great neighbors, where the beach is close by and also nightlife."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 29 Jackson Rd

  • What is 29 Jackson Rd estimated to be worth?
    Trulia's estimated value for 29 Jackson Rd in Somerville, MA is $1,238,500.
  • What is the price history for 29 Jackson Rd?
    29 Jackson Rd in Somerville, MA last sold for $625,000 in March 2017.
  • Is Somerville a buyer's or seller's market?
    Somerville is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Somerville?
    The median sale price in Somerville is $958K. That is up $73.33K from the prior month.

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