558 Chestnut St, Needham, MA 02492
OFF MARKET

558 Chestnut St
Needham, MA 02492

  • 3 Beds
  • 2 Baths
  • 1,581 sqft

$1,123,300

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,746/mo*
Refinance Your Home

$1,123,300

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,746/mo*
Refinance Your Home
3 Beds
2 Baths
1,581 sqft

Local Information

  • Map ViewExplore the area around 558 Chestnut St.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1938
Living Area
1,581 sqft
Price/Sqft
$710
Parking
Garage

About this House

This charming 3 bedroom 1930's Village Colonial is in a desirable location. Walking distance to town/train and in the NEWMAN school district. This very special home features an inviting foyer, beautiful LR with fireplace, gracious DR with built-in China cabinet.The spacious kitchen with breakfastnook overlooks a large deck and backyard for entertaining. Appreciate this lovingly cared for period home w/many special details. A distictive home graced by tradition is waiting for your personal touch
558 Chestnut St, Needham, MA 02492 is a 3 bedroom, 2 bathroom, 1,581 sqft single-family home built in 1938. It last sold for $530,000 on Dec 24, 2008. It is currently off market. The Trulia Estimate is $1,123,300, with a rent estimate of $5,085/month.

Home Details for 558 Chestnut St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1938Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 7841 sqft

Price History for 558 Chestnut St

DatePriceEventSource
12/24/2008$530,000Sold
N/A
10/25/2008$549,900PriceChange
Agent Provided
09/12/2008$579,900Listed For SaleAgent Provided
06/15/2005$560,000Sold
N/A
12/17/1997$275,000Sold
N/A
07/01/1992$200,000Sold
N/A
10/31/1991$190,000Sold
N/A

Market trends in Needham

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.49M
$63.33KMoM
Sale-to-List Price
101.2%
2.1%MoM
Price per sq ft
$592
$37MoM
Available listings
107
4MoM
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Property Tax and Assessment

Year2025
Tax$9,357
Assessment$882,700
Home facts updated by county records

Comparable Sales for 558 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
569 Chestnut St, Needham, MA
0.04
Single-Family Home
$1,220,000
05/12/26
3
1.5
2,190
64 Gayland Rd, Needham, MA
0.25
Single-Family Home
$1,075,000
07/15/26
3
1.5
1,886
150 Laurel Dr, Needham, MA
0.30
Single-Family Home
$890,000
04/29/26
4
2
1,550
50 Gayland Rd, Needham, MA
0.26
Single-Family Home
$1,165,000
07/10/26
3
2
2,065
31 Laurel Dr, Needham, MA
0.33
Single-Family Home
$1,195,000
10/27/25
3
1.5
2,001
1034 Webster St, Needham, MA
0.52
Single-Family Home
$1,079,000
05/04/26
3
1.5
1,670
132 Lincoln St, Needham, MA
0.51
Single-Family Home
$1,091,000
10/17/25
3
2
1,665
971 Webster St, Needham, MA
0.56
Single-Family Home
$835,000
06/17/26
3
2
1,404
95 Marked Tree Rd, Needham, MA
0.75
Single-Family Home
$900,000
09/19/25
3
1.5
1,520
72 Marked Tree Rd, Needham, MA
0.77
Single-Family Home
$650,000
07/10/26
3
2
1,087

Nearby homes

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Assigned Schools

These are the assigned schools for 558 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.

What Locals Say about Needham

At least 138 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 88 % Say there are sidewalks

  • 87 % Say parking is easy

  • 83 % Say yards are well-kept

  • 82 % Say people would walk alone at night

  • 79 % Say car is needed

  • 76 % Say there's holiday spirit

  • 75 % Say kids play outside

  • 70 % Say streets are well-lit

  • 67 % Say it's quiet

  • 65 % Say it's walkable to restaurants

  • 63 % Say they plan to stay for at least 5 years

  • 62 % Say neighbors are friendly

  • 61 % Say there's wildlife

  • 55 % Say there are community events

  • 54 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Timothy Connolly
    "I have raised six children in Needham. Best place to live "
    0
    Flag
  • Adrian Durbin
    "It is a great place for families or anyone with dogs. Extremely friendly and welcoming. I grew up here and it’s even better than it was 30 years ago. "
    0
    Flag
  • Lschneidermd1
    "People walk their dogs on leash and are good about picking up after them. There are dog friendly hiking trails. "
    0
    Flag
  • Louwf
    "There are Lots of dogs around. Good sidewalks and parks. Great dog facilities in town for dog watching and pet friendly ice cream and coffee shops"
    0
    Flag
  • Trulia User
    "Seems great for dog owners, an excellent spot. Love it! Unsure if there’s a dog park but good sidewalks etc"
    1
    Flag
  • Dikla
    "Most important is school and the Education system. Safety of the streets Family neighborhood. Nice neighborhoods. Friendly. Nice restaurants and coffee shops. "
    2
    Flag
  • Apcollins
    "My commute is easy based on simple access to the highway system and commuter rail. Most of the time I find it is a reverse commute."
    0
    Flag
  • Claire B.
    "There are lots of dogs around and most people are friendly about them. There is a dog park in town as well. Though there are some who are annoying about dogs doing their business on their lawns. I have been yelled at before which is frustrating. "
    3
    Flag
  • Jaugat
    "Respectful, caring neighbors. Kids who play together, new school, proximity to everything. Would not change a thing!"
    0
    Flag
  • Claire B.
    "There are amazing schools and lots of other families with children! There are also great parks and places to go hike."
    0
    Flag
  • Andrew M.
    "Family friendly safe neighborhood. Convenient to the town center, restaurants, stores, medical and dental service providers, etc."
    0
    Flag
  • Claire H
    "The schools in the area are too notch. Join the local parents group! Parenttalk is a wonderful way to connect with other parents "
    0
    Flag
  • Acsmith33
    "Our neighborhood has block parties twice per year. The town has events for all major holidays like NYE and 4th of July "
    0
    Flag
  • Eklayman
    "The area has nice sidewalks and is well lit at night. There are many other dog walkers so you’ll meet other dog fans. "
    1
    Flag
  • Maiken.duelund
    "A lot of good restaurants, cafés and shopping within walking distance supports a lively city center. Many physical activities for children and their parents."
    0
    Flag
  • Chelly2566
    "I really do love my area that I live then I do walk my dog I do clean up after myself but sometimes there be some people who do not and they will leave feces but I've just learned to just pay attention to my surroundings and pay attention to the individuals that don't walk with bags"
    0
    Flag
  • Jjmitchell85
    "Living n Needham and commuting to the city is very straight forward. The rail line is dedicated to the Needham commuter rail, the line ends/originated in Needham, and there are 4 stops in the small town. I walk 5min from my house to the train and get off at back Bay to walk just another 5min to my office. Delays are limited due to the fact that this rail line only serves the Needham line."
    0
    Flag
  • Bobsled
    "Block parties, kids outside, dad/mom nights, walk to school, general sense of security, community, and care. "
    0
    Flag
  • Andrew M.
    "July 4th fireworks, Memorial Day parade, neighborhood/block parties, and other events. Farmers Market. "
    0
    Flag
  • Ray S.
    "I have lived here for twelve years and neighbors are the best, looking out for everyone, friendly and taking interest in the well being of the community."
    0
    Flag
  • JAS
    "There’s a lot of dogs and friendly dog owners. Everyone loves dogs here. Everyone walks their dogs and we all have yards. "
    0
    Flag
  • Gsoldato26
    "I lived in this neighborhood for 9 years. The k-12 schools are great. Very friendly, safe and supportive community. "
    0
    Flag
  • Charlotte S.
    "Amazing school system. A safe town, never any problems. Most of the town is turning into mcmansions, but some of the charm has remained. The population is growing rapidly. The commuter rail runs right into south station in Boston "
    0
    Flag
  • Peter B.
    "It’s nice. Good access to trains and highway. Close to Boston. Very safe. Many families. Some business too across the highway."
    0
    Flag
  • Kumar P.
    "great neighborhood for raising a family. probably the best in the states. very friendly folks. good schools. brilliant library. "
    1
    Flag
  • Bradleycharleswhite
    "My wife and I have lived in Needham for 2 years now and love the community. All of our neighbors are very friendly."
    0
    Flag
  • Ellen W. D.
    "I live in the neighborhood and it's close to everything and really friendly!"
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

26 pet-friendly rentals in Needham, MA

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7 rentals with a garage in Needham, MA

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Explore by feature - Outdoor Space

6 rentals with an outdoor space in Needham, MA

Homes for sale near 558 Chestnut St

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Off Market Homes Near 558 Chestnut St

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Frequently asked questions about 558 Chestnut St

  • What is 558 Chestnut St estimated to be worth?
    Trulia's estimated value for 558 Chestnut St in Needham, MA is $1,123,300.
  • What is the price history for 558 Chestnut St?
    558 Chestnut St in Needham, MA last sold for $530,000 in December 2008.
  • Is Needham a buyer's or seller's market?
    Needham is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Needham?
    The median sale price in Needham is $1.49M. That is up $63.33K from the prior month.
  • How big is the lot at 558 Chestnut St?
    The lot at 558 Chestnut St in Needham, MA is about 0.18 acres (7,841 sq ft).
  • Does 558 Chestnut St have a garage?
    Yes, 558 Chestnut St in Needham, MA has a garage.