239 Chestnut St, Newton, MA 02465
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Property image
OFF MARKET

239 Chestnut St
Newton, MA 02465

West Newton
  • 7 Beds
  • 3.5 Baths
  • 6,916 sqft (on 0.77 acres)

$4,446,100

Trulia Estimate
as of Jul 6, 2026

$4,446,100

Trulia Estimate
as of Jul 6, 2026
7 Beds
3.5 Baths
6,916 sqft
(on 0.77 acres)

Local Information

  • Map ViewExplore the area around 239 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Available for the first time in 50 years, this iconic sun-filled brick and slate roof Landmark Estate is majestically set on three quarter park-like acres in coveted West Newton Hill location. Built in 1919 with later additions in the 1930's, this home features a large entry hall, magnificent oak paneled library with limestone fireplace, ornamental ceiling and custom tile floor plus spacious living room with fireplace, wood paneled formal dining room, updated kitchen and separate breakfast room. Sprawling second floor with large master bedroom suite and unique billiard room/family room with hand hewn beamed ceiling. Separate four room, two bedroom one bath apartment over three-car garage with separate access. Spectacular grounds offering mature specimen trees from Arnold Arboretum, formal gardens, stone walls and bluestone patios. Updated heating/AC system. Convenient access to major routes, commuter rail and West Newton Hill neighborhood club.
239 Chestnut St, Newton, MA 02465 is a 7 bedroom, 4 bathroom, 6,916 sqft single-family home in West Newton, built in 1919. It last sold for $2,300,000 on Jun 27, 2016. It is currently off market. The Trulia Estimate is $4,446,100, with a rent estimate of $7,678/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 239 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 15
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: BrickGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1919
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.77 acres

Price History for 239 Chestnut St

DatePriceEventSource
06/27/2016$2,300,000Sold
N/A
06/01/2016$2,495,000PendingAgent Provided
04/20/2016$2,495,000Listed For SaleAgent Provided

Market trends in Newton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.51M
$86.67KMoM
Sale-to-List Price
99.3%
0.4%MoM
Price per sq ft
$602
$20MoM
Available listings
344
38MoM
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Property Tax and Assessment

Year2025
Tax$42,769
Assessment$4,364,200
Home facts updated by county records

Comparable Sales for 239 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
222 Prince St, Newton, MA
0.15
Single-Family Home
$4,677,000
12/02/25
6
5
6,445
69 Prince St, Newton, MA
0.16
Single-Family Home
$3,950,000
09/18/25
6
4.5
7,226
249 Highland St, Newton, MA
0.20
Single-Family Home
$2,900,000
11/06/25
4
3.5
3,986
279 Chestnut St, Newton, MA
0.09
Single-Family Home
$3,000,000
11/14/25
4
4.5
4,297
23 Ascenta Ter, Newton, MA
0.17
Single-Family Home
$2,150,000
06/12/26
5
3.5
2,756
26 Sewall St, Newton, MA
0.22
Single-Family Home
$3,210,000
04/24/26
5
4
4,445
141 Prince St, Newton, MA
0.13
Single-Family Home
$5,300,000
07/31/25
6
7
7,978
39 Valentine Park, Newton, MA
0.11
Single-Family Home
$2,800,000
12/12/25
5
4
3,894
33 Colbert Rd E, Newton, MA
0.28
Single-Family Home
$2,522,000
07/17/25
5
4.5
5,042
40 Sewall St, Newton, MA
0.23
Single-Family Home
$4,500,000
05/07/26
6
6.5
6,301

Nearby homes

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Assigned Schools

These are the assigned schools for 239 Chestnut St.
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

West Newton
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about West Newton

At least 81 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 91 % Say there are sidewalks

  • 86 % Say parking is easy

  • 81 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 77 % Say people would walk alone at night

  • 75 % Say car is needed

  • 71 % Say there's holiday spirit

  • 70 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 60 % Say it's walkable to grocery stores

  • 60 % Say it's quiet

  • 59 % Say neighbors are friendly

  • 55 % Say there's wildlife

  • 51 % Say they plan to stay for at least 5 years

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Soniamgregory
    "Suburban with walkable stores and activities. Easy access to commuter rail into Boston. Great public schools "
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  • Pmellios
    "I grew up in newton. Lots to do! Crystal lake, 4th of July at Fessenden, farmers markets. Nice sense of community and very safe! Now feels more urban but still come back from downtown Boston to visit family on the weekends."
    1
    Flag
  • Trulia User
    "Friendly dog walkers are out and about at all hours. Traffic is pretty slow - no fast speeding vehicles. "
    0
    Flag
  • Trulia User
    "Safe area to live with a family, close to everything and schools are great. Commute to Boston by commuter rail that is quite expensive"
    0
    Flag
  • Rebecca
    "My neighborhood is quiet, safe and close to the commuter rail and some restaurants. It’s a very pleasant area."
    1
    Flag
  • Rebecca
    "Many people in the neighborhood have dogs and there are some nice places to walk them. A few parks and trails easy to find."
    0
    Flag
  • Claire S.
    "Farmers market, moody street, cook restaurant, west newton pizza market, nice neighborhood, safe feeling, cute houses"
    0
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  • Claire S.
    "Nothing comes to mind! They would probably like it. Flat surfaces to walk dogs and friendly neighbors."
    0
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  • Samantha F.
    "Family friendly, great area for walking and exercising. Schools are fantastic. Night life within walking distance."
    0
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  • Rulla T.
    "There are lots of dogs. People are friendly easy to walk dogs. For those with little dogs should be aware of coyotes "
    0
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  • Alexa.shabecoff
    "Very dog friendly , dog owners would like, you so have to drive to the nearest dog park though . That should be enough info"
    0
    Flag
  • Cameron C.
    "all kids will be safe and protected, well educated and self defense based . I serve both kids and parents will respect and honor "
    0
    Flag
  • Kathy S.
    "Accessible via express bus or trolley. There is also train service but other than rush hour service is infrequent."
    0
    Flag
  • Kathy S.
    "Many friendships are made socializing with our dogs. Dog owner met in parks and conservation areas become life long friends. Having a dog in Newton is a great way for new comers to find friends."
    0
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  • Alyson W.
    "Many nearby parks / trails to walk your pup. Sidewalks are everywhere so you don't have to worry about walking in the street. One con is the size of yards. Unless you purchase an expensive home you are unlikely to have a decent space for your dog to use."
    0
    Flag
  • Alyson W.
    "West Newton offers a diverse shopping selection. There are numerous shops, many of which are small and owned by locals, where you can find just about anything you're looking for. If you're hungry, you can find just about any food, whether it's Mediterranean, Chinese, BBQ, home style diners, and I could go on!"
    0
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  • Alyson W.
    "I live conveniently close to the Turnpike, making it easy to commute to work each day. Depending on the time of day, there may be traffic but that's common in this location."
    0
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  • Alyson W.
    "It's very safe. I can leave my door unlocked when I'm not home and trust that nothing bad will happen. There's many schools and it's a diverse community."
    0
    Flag
  • Rachel S.
    "Lots of dogs, lots of sidewalks and parks."
    0
    Flag
  • Rachel S.
    "Convenient to everything, friendly neighborhood, great local restaurants."
    0
    Flag
  • Rachel S.
    "Light traffic. Driving to Boston during rush hour is heavy traffic. South down 95 in the morning is easy."
    0
    Flag
  • Rachel S.
    "Great schools! Lots of kids around, very kid friendly area."
    0
    Flag
  • Christian R.
    "Diversity of backgrounds, commonality of values. We raise our kids together in this neighborhood, we celebrate each other’s wins and losses. We come out to catch up in the middle of the street on weeknight evenings and weekend afternoons, and we plan events like July 4th together, since the city fireworks show is part of an evening stroll around our block. "
    3
    Flag
  • Jane L.
    "It is a lovely community with friendly people. A very family-oriented location."
    0
    Flag
  • Jane L.
    "Accessible to all major highways: rte. 9, rte. 128/95, Mass Pike."
    0
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  • Jane L.
    "This a very family oriented community with great schools."
    0
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  • Aaron S.
    "We have some of the best schools. We are also able to commute to Boston quickly."
    0
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  • Aaron S.
    "Busy, the streets are not well-paved. So the commute is bumpy and dangerous."
    0
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  • Aaron S.
    "That it is expensive to live here. It is a liberal bubble politically."
    0
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  • liv
    "I have lived in Newton my entire life I love it , people are friendly and I love going to The Fessenden School Campus to watch the fireworks on the 4th of July"
    2
    Flag
  • Rebecca M. B.
    "Iv lived here for 4 years it’s super safe friendly accessible with lots to do the only thing I’d say it’s lacking is clothing stores but there’s plenty or supermarkets and restaurants and bars and everything els I walk my dog sometimes at 2am because I’m a bartender and get home late and never have felt scared or in danger I meet lots of neighbors outside cause everyone seems to have a dog and has to walk them cause there’s no fences in yards so it’s nice cause you get to know people I love it "
    2
    Flag
  • Artod
    "Great safe neighborhood. Easily walk to west newton square and best school systems. Quiet neighborhood yet lots of families with kids playing outdoors. We usually leave our cars unlocked and feel safe doing so. "
    1
    Flag
  • Jack a.
    "Shopping. Schools. Tennis courts. Public swimming pool. Movie theater shops and restaurants. Public transportation (communter train and busses) are all within walking distance."
    0
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  • Bdar66
    "We love our neighborhood! Lots of families, a good mix of different types of people. I have kids in Franklin and we are pleased with our experience with this school. We love being walking distance to Gath Pool and the fireworks on the fourth. West Newton Square is great place to walk for a date night or a Saturday morning movie with the kids. It is a good blend of city and town feel, with a lot of intellectuals, academics, and just super interesting people for neighbors."
    0
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  • lola
    " very safe - great schools - walk to grocery stores - pharmacies - restaurants - parks "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

112 pet-friendly rentals in Newton, MA

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Homes for sale near 239 Chestnut St

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Off Market Homes Near 239 Chestnut St

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