29 Jackson Rd, Somerville, MA 02145
OFF MARKET

29 Jackson Rd
Somerville, MA 02145

Winter Hill
  • 9 Beds
  • 3 Baths
  • 4,136 sqft

$1,320,800

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $7,748/mo*
Refinance Your Home

$1,320,800

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $7,748/mo*
Refinance Your Home
9 Beds
3 Baths
4,136 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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. .
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 29 Jackson Rd

Interior Features

Heating & Cooling
Heating: Other, GasHeating Fuel: Other
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 History for 29 Jackson Rd

DatePriceEventSource
03/07/2017$625,000Sold
N/A
07/29/2016$1,000,000ListingRemovedAgent Provided
07/19/2016$1,000,000PendingAgent Provided
07/12/2016$1,000,000Listed For SaleAgent Provided
06/15/1995$150,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$10,678
Assessment$978,700
Home facts updated by county records

Comparable Sales for 29 Jackson Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
43 Bradley St, Somerville, MA
0.03
Multi-Family Home
$1,275,000
05/30/25
8
3
3,749
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
192 Pearl St, Somerville, MA
0.22
Multi-Family Home
$1,180,000
08/25/25
7
3
2,602
61-63 Grant St, Somerville, MA
0.31
Multi-Family Home
$1,350,000
07/28/25
6
3
4,130
10 Stickney Ave, Somerville, MA
0.16
Multi-Family Home
$1,690,000
09/03/25
9
3
5,686
139 Sycamore St, Somerville, MA
0.33
Multi-Family Home
$935,000
07/07/25
7
4
3,525
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

Nearby homes

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Assigned Schools

These are the assigned schools for 29 Jackson Rd.
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

  • 37 % 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
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  • 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
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  • 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

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29 Jackson Rd, Somerville, MA 02145 is a 9 bedroom, 3 bathroom, 4,136 sqft multi-family built in 1890. 29 Jackson Rd is located in Winter Hill, Somerville. This property is not currently available for sale. 29 Jackson Rd was last sold on Mar 7, 2017 for $625,000. The current Trulia Estimate for 29 Jackson Rd is $1,320,800.