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

271 Chestnut St
Newton, MA 02465

West Newton
  • 6 Beds
  • 5.5 Baths
  • 6,200 sqft (on 0.69 acres)

$3,787,800

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $22,696/mo*
Refinance Your Home

$3,787,800

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $22,696/mo*
Refinance Your Home
6 Beds
5.5 Baths
6,200 sqft
(on 0.69 acres)

Local Information

  • Map ViewExplore the area around 271 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
0.69 acres
Living Area
6,200 sqft
Price/Sqft
$611
Parking
Garage

About this House

Fully restored historically significant home in the heart of West Newton Hill on almost 3/4 of an acre. This property was revived to its original glory through an elaborate and impeccable renovation in 2016/2017.

Starting with its privately gated entry off of chestnut street, this fully fenced in property has a warm and inviting curb appeal, highlighted by its porte cochere and stone pillars. The winding driveway opens up in the back to a large parking area for 5-6 cars and a detached 2 car garage.

The grounds are well segmented with 2 distinct yard areas, a lovely secluded patio with a hot tub, direct piped gas grill, outdoor TV and access to an adjacent 3 season porch.

The home's interior has a well thought out and functional layout that is ideal for today's lifestyle. Walk into a striking foyer with custom millwork and a grand staircase, large coat closet and powder room. The formal living and dining rooms have grand scale, original millwork including leaded windows, and 2 sets of virtually floor to ceiling french doors. A large butler's pantry connects the dining room and kitchen and has a sink, sub zero beverage center and ample storage.

The open concept Kitchen and Family room are magnificent with 3 exposures, custom built ins and a large dining banquette and breakfast bar. The chef's kitchen has a 6 burner/double oven Wolf range, Sub Zero Fridge, pantry cabinet and epic full wall herringbone tile back splash. There is an additional office/den on the main level with custom built in book shelves and glass display cases.

The 2nd level has 4 bedrooms and 3 baths (2 en suite), including a charming bedroom with arched window overlooking the large back yard. The master suite has 2 walk in closets and a 5 piece bath with steam shower and soaking tub. Large laundry room with sink and plenty of storage.

The fully finished lower level has 2 play rooms, an in law suite with kitchenette, full bath, a home fitness room, ample storage, and mudroom with heated floor, and built in benches/storage that has a direct walk out the patio.

The garage has a work bench, adequate storage and can fit 2 cars. There is private entry to a super efficient additional guest suite with 3/4 bath, heated floor, central HVAC, and a kitchenette/wet bar.
271 Chestnut St, Newton, MA 02465 is a 6 bedroom, 6 bathroom, 6,200 sqft single-family home in West Newton, built in 1905. It last sold for $3,175,000 on Jan 6, 2022. It is currently off market. The Trulia Estimate is $3,787,800, with a rent estimate of $7,694/month.

Home Details for 271 Chestnut St

Interior Features

Interior Details
BasementIn-law unitNumber of Rooms: 15Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation RoomWet Bar
Heating & Cooling
Heating: Forced Air, Other, Gas, OtherAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, HardwoodGated Entry
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: Other, SlateExterior: StuccoLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 7Parking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1905Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Craftsman

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Building

Community rooms
Fitness Center

Price History for 271 Chestnut St

DatePriceEventSource
01/06/2022$3,175,000Sold
MLS PIN #72894711
11/03/2021$3,350,000PriceChange
MLS PIN #72894711
09/14/2021$3,399,000Listed For SaleMLS PIN #72894711
07/17/2021ListingRemovedMLS PIN #72832932
06/22/2021$3,399,000PriceChange
MLS PIN #72832932
05/17/2021$3,475,000Listed For SaleMLS PIN #72832932
06/17/2016$1,725,000Sold
N/A
04/01/2016$1,695,000PendingAgent Provided
03/30/2016$1,695,000Listed For SaleAgent Provided

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$30,218
Assessment$3,083,500
Home facts updated by county records

Comparable Sales for 271 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
222 Prince St, Newton, MA
0.09
Single-Family Home
$4,677,000
12/02/25
6
5
6,445
279 Chestnut St, Newton, MA
0.02
Single-Family Home
$3,000,000
11/14/25
4
4.5
4,297
69 Prince St, Newton, MA
0.21
Single-Family Home
$3,950,000
09/18/25
6
4.5
7,226
26 Sewall St, Newton, MA
0.27
Single-Family Home
$3,210,000
04/24/26
5
4
4,445
40 Sewall St, Newton, MA
0.28
Single-Family Home
$4,500,000
05/07/26
6
6.5
6,301
18 Sewall St, Newton, MA
0.26
Single-Family Home
$4,200,000
02/24/26
5
5.5
4,848
39 Valentine Park, Newton, MA
0.11
Single-Family Home
$2,800,000
12/12/25
5
4
3,894
81 Fuller St, Newton, MA
0.33
Single-Family Home
$3,960,000
07/01/26
6
6.5
7,319
249 Highland St, Newton, MA
0.24
Single-Family Home
$2,900,000
11/06/25
4
3.5
3,986
94 Highland St, Newton, MA
0.41
Single-Family Home
$3,125,000
06/18/26
5
5.5
5,280

Nearby homes

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Assigned Schools

These are the assigned schools for 271 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
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  • 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
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  • 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
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  • 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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Explore by feature - Pet Friendly

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Homes for sale near 271 Chestnut St

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Off Market Homes Near 271 Chestnut St

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