20 Winslow Rd, Needham, MA 02492
OFF MARKET

20 Winslow Rd
Needham, MA 02492

  • 4 Beds
  • 3 Baths
  • 2,496 sqft

$1,443,900

Trulia Estimate
as of May 21, 2026
Est. Refi. Payment $8,634/mo*
Refinance Your Home

$1,443,900

Trulia Estimate
as of May 21, 2026
Est. Refi. Payment $8,634/mo*
Refinance Your Home
4 Beds
3 Baths
2,496 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 20 Winslow Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
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 History for 20 Winslow Rd

DatePriceEventSource
12/22/2021$950,000Sold
MLS PIN #72912760
10/26/2021$950,000Listed For SaleMLS PIN #72912760
02/18/2012$689,900ListingRemovedAgent Provided
10/27/2011$689,900Listed For SaleAgent Provided
04/08/2002$577,500Sold
N/A
12/16/1992$287,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$12,818
Assessment$1,209,200
Home facts updated by county records

Comparable Sales for 20 Winslow Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
6 Mary Chilton Rd, Needham, MA
0.10
Single-Family Home
$1,200,000
08/15/25
3
2
1,559
37 Standish Rd, Needham, MA
0.30
Single-Family Home
$1,645,000
05/05/26
3
2.5
2,155
31 Standish Rd, Needham, MA
0.30
Single-Family Home
$1,525,000
06/30/25
3
3.5
2,336
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
40 Brewster Dr, Needham, MA
0.39
Single-Family Home
$1,629,000
07/10/25
5
3
3,612
15 Mackintosh Ave, Needham, MA
0.31
Single-Family Home
$1,310,000
04/30/26
5
2.5
4,354

Assigned Schools

These are the assigned schools for 20 Winslow Rd.
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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

  • 61 % 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.
  • 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
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  • 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
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  • Phillip m.
    "The three train stations and close proximity to 95/128, along with a charming, quaint town center make this an ideal location. A caring community with services for all ages, Needham offers a safe and open atmosphere for families with kids."
    0
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20 Winslow Rd, Needham, MA 02492 is a 4 bedroom, 3 bathroom, 2,496 sqft single-family home built in 1983. This property is not currently available for sale. 20 Winslow Rd was last sold on Dec 22, 2021 for $950,000. The current Trulia Estimate for 20 Winslow Rd is $1,443,900.