20 Winslow Rd, Needham, MA 02492
Property image
Property image
OFF MARKET

20 Winslow Rd
Needham, MA 02492

  • 4 Beds
  • 3 Baths
  • 2,496 sqft

$1,441,900

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $8,653/mo*
Refinance Your Home

$1,441,900

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $8,653/mo*
Refinance Your Home
4 Beds
3 Baths
2,496 sqft

Home Value

Trulia Estimate
$1.44M
Since last month
Decreased$5K (-0.4%)
Since last year
Increased$93K (+6.9%)
Since last sale
Increased$492K (+51.8%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$1.44M
July 2026$1.45M
June 2026$1.48M
May 2026$1.48M
April 2026$1.44M
March 2026$1.43M
February 2026$1.39M
January 2026$1.38M
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
16 Stockdale Rd, Needham, MA
0.13
Single-Family Home
$1,305,000
08/14/26
4
2.5
2,345
51 Stockdale Rd, Needham, MA
0.10
Single-Family Home
$1,580,000
05/08/26
4
4
2,375
51 Alden Rd, Needham, MA
0.22
Single-Family Home
$1,125,000
05/01/26
4
2
1,701
78 Whiting Way, Needham, MA
0.24
Single-Family Home
$1,105,000
10/15/25
3
1.5
2,001
29 Canavan Cir, Needham, MA
0.29
Single-Family Home
$1,700,000
08/13/26
3
2.5
2,496
37 Standish Rd, Needham, MA
0.30
Single-Family Home
$1,645,000
05/05/26
3
2.5
2,155
61 Fuller Brook Ave, Needham, MA
0.42
Single-Family Home
$1,794,000
09/17/25
4
2.5
3,108
21 Brewster Dr, Needham, MA
0.36
Single-Family Home
$1,425,000
05/05/26
4
1.5
1,840
15 Mackintosh Ave, Needham, MA
0.31
Single-Family Home
$1,310,000
04/30/26
5
2.5
4,354
122 Great Plain Ave, Wellesley, MA
0.38
Single-Family Home
$2,050,000
08/07/26
4
3.5
3,122

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
34 Mary Chilton Rd, Needham, MA 02492
0.06
-
6
6
5,800
Off Market
14 Winslow Rd, Needham, MA 02492
0.02
-
6
6.5
6,200
Off Market
21 Winslow Rd, Needham, MA 02492
0.02
$3,149,000
5
6.5
6,179
For Sale
6 Mary Chilton Rd, Needham, MA 02492
0.10
$1,240,100
3
2
1,559
Off Market
51 Pilgrim Rd, Needham, MA 02492
0.05
-
6
5
6,114
Off Market
51 Stockdale Rd, Needham, MA 02492
0.10
$1,580,000
4
4
2,375
Recently Sold
16 Stockdale Rd, Needham, MA 02492
0.13
$1,305,000
4
2.5
2,345
Recently Sold
100 Mary Chilton Rd, Needham, MA 02492
0.11
$1,715,700
3
3
3,016
Off Market
5 Mayflower Rd, Needham, MA 02492
0.17
$2,315,000
7
5
4,631
Off Market
57 Mayflower Rd, Needham, MA 02492
0.15
-
3
1.5
1,488
Off Market
17 Whiting Way, Needham, MA 02492
0.22
$2,750,000
5
5.5
5,400
Recently Sold
78 Mayflower Rd, Needham, MA 02492
0.20
$2,603,800
4
3.5
4,825
Off Market

Local Information

  • Map ViewExplore the area around 20 Winslow Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1983
Living Area
2,496 sqft
Price/Sqft
$578
Parking
Garage

About this House

Meticulously maintained home in Winslow Estates on the Wellesley line! Great Opportunity to live in desireable neighborhood close to Babson, Wellesley and Olin College of Engineering. Nine (9) generous rooms include 3 bedrooms & 2 full baths on the first floor. Lower level consists of a fireplaced family room, office/4th bdrm. & laundry area. Recent updates include eterior walkway & front strair, landscaping, new hardwood floors. Central Air & Vacuumn and underground sprinkler systems make this home an excellent investment!
20 Winslow Rd, Needham, MA 02492 is a 4 bedroom, 3 bathroom, 2,496 sqft single-family home built in 1983. It last sold for $950,000 on Dec 22, 2021. It is currently off market. The Trulia Estimate is $1,441,900, with a rent estimate of $6,755/month.

Home Details for 20 Winslow Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1983Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price and Tax history

DateEventPrice
Dec 22, 2021
Source: MLS PIN #72912760
Sold
$950,000
Oct 26, 2021
Source: MLS PIN #72912760
Listed For Sale
$950,000
Feb 18, 2012
Source: Agent Provided
ListingRemoved
$689,900
Oct 27, 2011
Source: Agent Provided
Listed For Sale
$689,900
Apr 8, 2002
Source: N/A
Sold
$577,500

Market trends in Needham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.57M
$76.33KMoM
Sale-to-List Price
101.7%
0.5%MoM
Price per sq ft
$602
$9MoM
Available listings
82
25MoM

Around this home

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
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  • 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
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  • 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
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  • Ellen W. D.
    "I live in the neighborhood and it's close to everything and really friendly!"
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 20 Winslow Rd

  • What is 20 Winslow Rd estimated to be worth?
    Trulia's estimated value for 20 Winslow Rd in Needham, MA is $1,441,900.
  • What is the price history for 20 Winslow Rd?
    20 Winslow Rd in Needham, MA last sold for $950,000 in December 2021.
  • 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 $1.57M. That is up $76.33K from the prior month.
  • How big is the lot at 20 Winslow Rd?
    The lot at 20 Winslow Rd in Needham, MA is about 0.23 acres (10,018 sq ft).
  • Does 20 Winslow Rd have a garage?
    Yes, 20 Winslow Rd in Needham, MA has a garage.

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 20 Winslow Rd

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