237 Hillside St, Milton, MA 02186
Property image
Property image
OFF MARKET

$1,890,900

Trulia Estimate
  • 5 Beds
  • 2.5 Baths
  • 3,168 sqft (on 1 acre)

237 Hillside St, Milton, MA 02186

Est. Refi. Payment $11,273/mo*
Refinance Your Home
Currently Off Market - Sold Dec 15, 2021 for $1,625,000

Home Value

Trulia Estimate
$1.89M
Since last month
Decreased$42K (-2.2%)
Since last year
Increased$72K (+4%)
Since last sale
Increased$266K (+16.4%)
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 +104% in the last 10 years
MonthEstimated value
2026
August 2026$1.89M
August 2026$1.89M
July 2026$1.93M
June 2026$1.94M
May 2026$1.91M
April 2026$1.89M
March 2026$1.89M
February 2026$1.81M
January 2026$1.79M
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
23 Parkwood Dr, Milton, MA
0.08
Single-Family Home
$2,215,000
05/12/26
4
2.5
3,418
57 Brierbrook St, Milton, MA
0.31
Single-Family Home
$2,100,000
05/12/26
5
3.5
3,329
80 Brierbrook St, Milton, MA
0.29
Single-Family Home
$2,850,000
12/02/25
5
3.5
4,644
5 Mark Ln, Milton, MA
0.58
Single-Family Home
$2,200,000
06/12/26
5
4.5
5,503
63 Sears Rd, Milton, MA
0.55
Single-Family Home
$1,100,000
11/17/25
5
4
4,232
79 Hilltop St, Milton, MA
0.65
Single-Family Home
$1,130,000
08/20/26
3
3
2,257
161 Sassamon Ave, Milton, MA
0.77
Single-Family Home
$1,300,000
05/21/26
5
3.5
4,048
6 Brewster Rd, Milton, MA
0.82
Single-Family Home
$1,815,000
04/30/26
5
4.5
4,788
407 Highland St, Milton, MA
1.17
Single-Family Home
$1,785,000
02/02/26
4
3
2,968
37 Sassamon Ave, Milton, MA
0.71
Single-Family Home
$1,385,000
09/03/26
5
4
3,074

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
23 Parkwood Dr, Milton, MA 02186
0.08
$2,215,000
4
2.5
3,418
Recently Sold
22 Parkwood Dr, Milton, MA 02186
0.09
$4,155,100
5
4.5
7,628
Off Market
287 Hillside St, Milton, MA 02186
0.15
$3,316,100
5
5.5
6,950
Off Market
24 Brierbrook St, Milton, MA 02186
0.27
$2,109,600
5
4.5
4,473
Off Market
80 Brierbrook St, Milton, MA 02186
0.29
$2,850,000
5
3.5
4,644
Recently Sold
57 Brierbrook St, Milton, MA 02186
0.31
$2,100,000
5
3.5
3,329
Recently Sold
52 Ford Ranch Rd, Milton, MA 02186
0.30
$1,863,500
4
2.5
6,212
Off Market
540 Harland St, Milton, MA 02186
0.33
$11,900,000
5
6
10,000
For Sale
97 Brierbrook St, Milton, MA 02186
0.37
$1,795,400
3
3.5
3,180
Off Market
79 Hillside St, Milton, MA 02186
0.37
$1,630,000
-
-
-
Recently Sold
427 Hillside St, Milton, MA 02186
0.43
$3,622,500
6
6
8,032
Off Market
1274 Randolph Ave, Milton, MA 02186
0.50
$1,471,500
4
2.5
3,283
Off Market

Local Information

  • Map ViewExplore the area around 237 Hillside St.
  • Schools2 Preschool Schools4 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1820
1 acre lot
3,168 sqft
$597/sqft

About this House

Before you come into this beauty take a drive by and see for yourself how magical the Hillside Neighborhood also known as Scott's Woods is. Tucked at the bottom of the Blue Hills Reservation is one of Milton's oldest settlements with historic houses, cellars and landmarks. A taste of Vermont only 8 miles south of the city makes this location an absolute treasure. Inside will charm you with character, wide pine floors, high ceilings, 2 working fireplaces and generous size rooms. Front and back staircases lead to five bedrooms, two full bathrooms and a laundry closet. An updated kitchen functional for todays needs along with a new gas heating system, new roof and updated electrical give you the opportunity to move in and enjoy the scenery. Set on a mature landscaped acre lot thoughtfully lined with a combination of a stone wall and rail fence. Stop by one of the three open houses so we can tell you more about one of our favorite neighborhoods in Milton.
237 Hillside St, Milton, MA 02186 is a 5 bedroom, 3 bathroom, 3,168 sqft single-family home built in 1820. It last sold for $1,625,000 on Dec 15, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,890,900, with a rent estimate of $6,765/month.

Home Details for 237 Hillside St

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
Parking Spaces: 6Parking: Off Street

Property Information

Year Built
Year Built: 1820
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Dec 15, 2021
Source: MLS PIN #72910883
Sold
$1,625,000
Oct 20, 2021
Source: MLS PIN #72910883
Listed For Sale
$1,395,000
Apr 25, 2019
Source: N/A
Sold
$1,050,000
Mar 20, 2019
Source: Agent Provided
Pending
$1,149,000
Nov 23, 2018
Source: Agent Provided
PriceChange
$1,149,000
Price decreased by 4%

Market trends in Milton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
3MoM

Around this home

What Locals Say about Milton

At least 214 Trulia users voted on each feature.

  • 87 % Say it's dog friendly

  • 86 % Say there are sidewalks

  • 82 % Say parking is easy

  • 77 % Say yards are well-kept

  • 76 % Say car is needed

  • 74 % Say streets are well-lit

  • 71 % Say people would walk alone at night

  • 70 % Say there's holiday spirit

  • 69 % Say they plan to stay for at least 5 years

  • 67 % Say kids play outside

  • 65 % Say there's wildlife

  • 59 % Say it's quiet

  • 57 % Say neighbors are friendly

  • 54 % Say it's walkable to grocery stores

  • 53 % Say it's walkable to restaurants

  • 42 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Nancyhicks1962
    "I’ve lived in Milton for over 20 years and enjoy local businesses, walking around the neighborhood and chatting with my neighbors. "
    0
    Flag
  • Nancyhicks1962
    "A great sense of community in the school system and in town .Many online sites in the town to find out about current events, community programs, free items and other valuable resources. Many families are very connected to each other and majors it a great town/community."
    0
    Flag
  • Trulia User
    "Not the best, I live in a low-income area because of the number of people & transportation options, it's not an ideal convenient experience."
    1
    Flag
  • Trulia User
    "Everything, it’s an amazing neighborhood. Tons of families, quiet, clean safe and walking distance to all the schools "
    1
    Flag
  • Trulia User
    "It’s a very quiet and friendly neighborhood, nothing negative to say. During my years living here I’ve had a experience "
    0
    Flag
  • Trulia User
    "The neighborhood is family friendly and they will have the best interests for the neighborhood all around kids and parents seem friendly "
    0
    Flag
  • Trulia User
    "Great neighborhood. I’ve lived here for over 10 years, the people are friendly and I feel safe living here"
    0
    Flag
  • Rena K. S.
    "I’m not sure about the community events held in Milton, however the local grocery store: Fruitcenter Marketplace is fantastic and has the best produce I’ve ever had. Also there are fantastic restaurants. I also really enjoy the plant nurseries in the area. Milton is a great place if you are looking for a pretty diverse community right outside of the city. The school district here is pretty decent, however they do need to update their policies and cultural responsive teaching approach. The schools should also consider hiring more black/ teachers of color. In addition to that they should hold more direct conversations about race, and the way systemic racism manifests and several realms. Tip toeing around racism begets more racism. To that point, there needs to be more conversations about class, sexuality, religion, race and the intersectionality of those things. Other than that Milton is a cute town. I love living here and wish to raise my children here- especially if they can exists being who they truly are."
    10
    Flag
  • Stephanie.fallon
    "Lived in this neighborhood for 20 years , town for 40. Great town, great people, green space, schools, conveniences, etc "
    0
    Flag
  • Charmon8
    "Milton has an explicit commitment to being a diverse and inclusive community. It has excellent schools and a strong sense of caring for the quality of town. "
    1
    Flag
  • Rashawn
    "Elementary schools have a great French immersion program here. Excellent public schools overall. Your child can easily grow up speaking a 2nd or 3rd language. I did thanks to these schools."
    1
    Flag
  • L. D. J.
    "It is convenient to downtown Boston, the regional train system (Amtrak), inter and Intra-state highways, shopping, open space, large housing lots and recreational open space (7,000 acre Blue Hills Reservation). It hosts one of the finest independent schools in the country and is extremely safe."
    1
    Flag
  • Rosalie A.
    "Great schools, beautifully kept neighborhoods. Lower crime rates, amazingly clean and well kept parks, public areas, lots of dogs/pet friendly communities and multiple town events year round. "
    1
    Flag
  • Charmon8
    "Lots of grassy knolls, open parks, bike path with green space surrounding it. People pick up after dogs and many families with young children have pets. "
    0
    Flag
  • Vesper G. B.
    "I don't attend any neighborhood events n Milton. It's basically a bedroom community for my family I do love the privacy and large lot my home is on. Al's it's very close to my office in Boston "
    0
    Flag
  • Milton homeowner
    "Great access to major highways and well maintained, safe community. Neighbors are friendly and there seem to be many dog owners. Dog walking park nearby as well as blue hills "
    0
    Flag
  • Ycajca
    "Good neighborhood, great school system, quit, no crime, lack on food stores we need to go over to next town over for any food shopping. We need a pharmacy."
    0
    Flag
  • David T.
    "There are a lot of sidewalks and side streets and a dog park down the street. Most houses have big backyards "
    1
    Flag
  • Cindy N.
    "Public transit is pretty easy to navigate. It’s not the best, but I can easily take a bus and then a train into Boston."
    0
    Flag
  • Trulia User
    "I have lived in this neighborhood for the last nine years. The schools in the area are excellent and the neighborhoods are safe! Shopping and stores are easily accessible and children activities are plentiful."
    1
    Flag
  • Bme344259
    "Walking distance to public transportation, river view bike path, restaurants, super markets, coffee shops, pizza shop, wine and beer store, liquor store, dry cleaner...."
    3
    Flag
  • Jrosscpa g. c.
    "Yes, lots of dogs in the area and parks with dog friendly play times. Great neighborhood to walk a dog in."
    1
    Flag
  • Jrosscpa g. c.
    "Lots of dogs around and at the parks. Seems to be a Pet friendly neighborhood although we do not currently have a dog."
    0
    Flag
  • Joana D. M.
    "I see people walking dogs frequently. The local coffee shop has a water bowl outside. I believe there is a dog park nearby. "
    0
    Flag
  • Kdemas s.
    "Lots of other dogs and friendly neighbors and owners. Right around the corner from a great park - Kelly Field. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 237 Hillside St

  • What is 237 Hillside St estimated to be worth?
    Trulia's estimated value for 237 Hillside St in Milton, MA is $1,890,900.
  • What is the price history for 237 Hillside St?
    237 Hillside St in Milton, MA last sold for $1,625,000 in December 2021.
  • Is Milton a buyer's or seller's market?
    Milton is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Milton?
    Residents describe Milton, MA as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Milton, MA.
  • How big is the lot at 237 Hillside St?
    The lot at 237 Hillside St in Milton, MA is about 1 acre.
  • Does 237 Hillside St have parking?
    Yes, 237 Hillside St in Milton, MA has on-site parking.

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Off Market Homes Near 237 Hillside St

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