538 Chestnut St, Newton, MA 02468
OFF MARKET

538 Chestnut St
Newton, MA 02468

Newton Highlands
  • 6 Beds
  • 8 Baths
  • 6,156 sqft (on 0.34 acres)

$3,356,300

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $19,836/mo*
Refinance Your Home

$3,356,300

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $19,836/mo*
Refinance Your Home
6 Beds
8 Baths
6,156 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 538 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1905
Lot Size
0.34 acres
Living Area
6,156 sqft
Price/Sqft
$545
Parking
Garage

Description

2004 expansion and restoration of this grand shingle style "cottage" in Waban. Cedar shake exterior, faux slate roof, gardens, & patio make this property architecturally distinguished. Main house has 5 bedrooms each w/en suite bathrooms, large eat-in kitchen (Wolf, Sub-Zero, Fisher&Paykel appliances) gives access to family room with fireplace, decks & grounds. Basement offers media room, game room, play room and full bathroom. Off of kitchen is mudroom and garage with au pair suite overhead.
538 Chestnut St, Newton, MA 02468 is a 6 bedroom, 8 bathroom, 6,156 sqft single-family home in Newton Highlands, built in 1905. It last sold for $1,600,000 on Jun 1, 2010. It is currently off market. The Trulia Estimate is $3,356,300, with a rent estimate of $6,983/month.

Home Details for 538 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateDeckExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1905
Property Type / Style
Property Type: Single Family HomeArchitecture: Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price History for 538 Chestnut St

DatePriceEventSource
06/01/2010$1,600,000Sold
N/A
10/03/2009$1,799,000Listed For SaleAgent Provided
04/12/2002$845,000Sold
N/A

Market trends in Newton

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.53M
$17.5KMoM
Sale-to-List Price
100.0%
0.7%MoM
Price per sq ft
$619
$17MoM
Available listings
321
23MoM
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Property Tax and Assessment

Year2025
Tax$28,726
Assessment$2,931,200
Home facts updated by county records

Comparable Sales for 538 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
151 Pine Ridge Rd, Newton, MA
0.29
Single-Family Home
$1,325,000
01/20/26
6
7.5
7,000
479 Chestnut St, Newton, MA
0.15
Single-Family Home
$2,330,000
11/20/25
6
5
5,200
110 Avalon Rd, Newton, MA
0.20
Single-Family Home
$2,499,000
06/22/26
5
5.5
4,607
19 Gordon Rd, Newton, MA
0.18
Single-Family Home
$3,800,000
04/16/26
5
5
6,255
29 Montclair Rd, Newton, MA
0.23
Single-Family Home
$5,225,000
03/10/26
6
6.5
7,274
513 Chestnut St, Newton, MA
0.07
Single-Family Home
$1,975,000
12/02/25
5
3.5
2,821
1438 Beacon St, Newton, MA
0.13
Single-Family Home
$1,725,000
04/23/26
6
3.5
3,691
81 Fuller St, Newton, MA
0.32
Single-Family Home
$3,960,000
07/01/26
6
6.5
7,319
80 Pine Ridge Rd, Newton, MA
0.25
Single-Family Home
$2,445,000
01/02/26
5
4.5
4,183
180 Allen Ave, Newton, MA
0.49
Single-Family Home
$4,485,450
05/07/26
6
7
6,343

Nearby homes

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Assigned Schools

These are the assigned schools for 538 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

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

What Locals Say about Newton Highlands

At least 32 Trulia users voted on each feature.

  • 92 % Say there are sidewalks

  • 87 % Say it's dog friendly

  • 86 % Say car is needed

  • 81 % Say people would walk alone at night

  • 79 % Say it's walkable to restaurants

  • 77 % Say parking is easy

  • 70 % Say there's holiday spirit

  • 66 % Say yards are well-kept

  • 64 % Say it's quiet

  • 63 % Say it's walkable to grocery stores

  • 61 % Say they plan to stay for at least 5 years

  • 60 % Say streets are well-lit

  • 60 % Say kids play outside

  • 57 % Say neighbors are friendly

  • 53 % Say there are community events

  • 51 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Jaime S.
    "Lots of places for walking and several dog parks."
    2
    Flag
  • Jaime S.
    "Busy during rush hour in morning and evening"
    1
    Flag
  • Jaime S.
    "A lot of culture, arts, and good school systems."
    1
    Flag
  • Jaime S.
    "Great education that challenges the students."
    2
    Flag
  • Kara P.
    "I can't really think of anything negative to say about being a dog owner in Newton. There are many dog parks in areas for dogs to play and walk, as well as a multitude of people who are dog owners."
    1
    Flag
  • Kaylyn A.
    "Everything! Tons of dog parks and special paths."
    0
    Flag
  • Kaylyn A.
    "It's not a smoothe ride. This town is right outside of Boston so traffic is inevitable. It's not difficult to navigate through as the roads are pretty straight-forward."
    0
    Flag
  • Kara P.
    "Directly down the street from my house is the MBTA green line, a central spot easily accessed by all in Newton. So much convenience for people who are able to walk there, hop on the train, and go to Boston or just about anywhere else they want to go."
    0
    Flag
  • Kara P.
    "It is a small village of Newton. Everyone here knows one another and it's very similar to a family atmosphere. All our little shops and businesses make for an even tighter bond amoungst us."
    0
    Flag
  • Kaylyn A.
    "I have recently moved here from Virginia with my husband. It's a really nice area but a bit pricey. People seem nice here and the food selection is pretty great as well!"
    0
    Flag
  • Kara P.
    "Newton Highlands is a very kid orientated town. There are many playgrounds, schools, and community events to take your children to and meet other parents."
    0
    Flag
  • Brandy L.
    "There isn't too many dog parks in the area for dogs. There is Crystal Lake close by where they hold children events."
    0
    Flag
  • Brandy L.
    "The commute time to Boston is 30 min without traffic. There is also a major interstate highway close by, I-95."
    0
    Flag
  • Brandy L.
    "Newton Highlands has ton of family owned restaurants and specialty shops."
    0
    Flag
  • Brandy L.
    "It's a safe neighborhood to raise children and has an excellent school system."
    0
    Flag
  • Brandy L.
    "There are not too many dog parks in the area. There is Crystal Lake which is nice to bring dogs to."
    1
    Flag
  • Brandy L.
    "Beautiful houses and trees. Traffic is not that bad, although currently there is a lot of construction going on."
    0
    Flag
  • Brandy L.
    "The area is very close to major highways like I-95. There are also several roads and it's less than a 45 min trip into Boston."
    0
    Flag
  • Brandy L.
    "Excellent school systems. A great neighborhood to raise kids."
    0
    Flag
  • Brandy L.
    "Crystal Lake is close by for walking dogs."
    1
    Flag
  • Brandy L.
    "Beautiful houses, tons of little shops, everything you need is close by."
    0
    Flag
  • Brandy L.
    "It's very close to I-95 and major roads to Boston. Traffic is not that bad. The neighbors are very friendly."
    0
    Flag
  • Brandy L.
    "It's a great neighborhood to raise children."
    0
    Flag
  • Rochelle R.
    "Many walking paths and dog parks. There are a number of groomers and pet stores."
    0
    Flag
  • Rochelle R.
    "Lots of traffic lately but relatively easy to get around. Many stores and restaurants nearby."
    1
    Flag
  • Rochelle R.
    "We are located within 5 min of all major highways. We are surrounded by stores making it easy to get what you need. It is very pretty here."
    0
    Flag
  • Rochelle R.
    "Great school. Lovely community. Eclectic and diverse people."
    0
    Flag
  • Derek K.
    "Dog owners would like Cold Spring Park, where there is a fenced in dog park. The trail is also nice to walk, but the dogs must be on leashes."
    0
    Flag
  • Derek K.
    "Most people either drive to their jobs or take the T. I live about a 10-minute walk from the T, and there is also the 59 bus."
    0
    Flag
  • Derek K.
    "Newton Highlands is fairly small, and I know my neighbors pretty well. We have a small business district with some great stores. We also have a nice park and are pretty well centered in Newton."
    0
    Flag
  • Derek K.
    "Newton Highlands is very safe to live in. We have lots of green space and unless you are on the main streets, it is pretty quiet. We have plenty of green spaces."
    0
    Flag
  • Emilygelbert
    "It’s a gorgeous suburb but close to transit anywhere and close to stores without living on top of them"
    1
    Flag
  • Jeremy M.
    "Green Line T access, walkable to Wholefoods, multiple shops and parks, Newton center, Crystal Lake. Great schools. Easy access to Downtown via the Pike or Route 9. "
    2
    Flag
  • Mgjurilla
    "Great neighbors. Great schools. I love that we are close to the T and stores. Public transportation is very accessible. We are closed to all major highways and access ways."
    1
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 538 Chestnut St

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Off Market Homes Near 538 Chestnut St

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