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

27 Winslow Rd
Needham, MA 02492

  • 4 Beds
  • 2.5 Baths
  • 2,827 sqft

$1,856,900

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $11,052/mo*
Refinance Your Home

$1,856,900

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $11,052/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,827 sqft

Home Value

Trulia Estimate
$1.86M
Since last month
Decreased$19K (-1%)
Since last year
Increased$92K (+5.2%)
Since last sale
Increased$706K (+61.3%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$1.86M
July 2026$1.87M
June 2026$1.89M
May 2026$1.9M
April 2026$1.85M
March 2026$1.83M
February 2026$1.77M
January 2026$1.75M
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
0.12
Single-Family Home
$1,305,000
08/14/26
4
2.5
2,345
51 Stockdale Rd, Needham, MA
0.08
Single-Family Home
$1,580,000
05/08/26
4
4
2,375
51 Alden Rd, Needham, MA
0.19
Single-Family Home
$1,125,000
05/01/26
4
2
1,701
78 Whiting Way, Needham, MA
0.22
Single-Family Home
$1,105,000
10/15/25
3
1.5
2,001
21 Brewster Dr, Needham, MA
0.34
Single-Family Home
$1,425,000
05/05/26
4
1.5
1,840
29 Canavan Cir, Needham, MA
0.26
Single-Family Home
$1,700,000
08/13/26
3
2.5
2,496
61 Fuller Brook Ave, Needham, MA
0.40
Single-Family Home
$1,794,000
09/17/25
4
2.5
3,108
37 Standish Rd, Needham, MA
0.28
Single-Family Home
$1,645,000
05/05/26
3
2.5
2,155
15 Mackintosh Ave, Needham, MA
0.30
Single-Family Home
$1,310,000
04/30/26
5
2.5
4,354
122 Great Plain Ave, Wellesley, MA
0.41
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
21 Winslow Rd, Needham, MA 02492
0.01
$3,149,000
5
6.5
6,179
For Sale
51 Pilgrim Rd, Needham, MA 02492
0.02
-
6
5
6,114
Off Market
14 Winslow Rd, Needham, MA 02492
0.04
-
6
6.5
6,200
Off Market
100 Mary Chilton Rd, Needham, MA 02492
0.09
$1,725,700
3
3
3,016
Off Market
51 Stockdale Rd, Needham, MA 02492
0.08
$1,580,000
4
4
2,375
Recently Sold
34 Mary Chilton Rd, Needham, MA 02492
0.08
-
6
6
5,800
Off Market
57 Mayflower Rd, Needham, MA 02492
0.13
-
3
1.5
1,488
Off Market
16 Stockdale Rd, Needham, MA 02492
0.12
$1,305,000
4
2.5
2,345
Recently Sold
6 Mary Chilton Rd, Needham, MA 02492
0.12
$1,240,100
3
2
1,559
Off Market
5 Mayflower Rd, Needham, MA 02492
0.16
$2,315,000
7
5
4,631
Off Market
78 Mayflower Rd, Needham, MA 02492
0.17
$2,595,900
4
3.5
4,825
Off Market
51 Alden Rd, Needham, MA 02492
0.19
$1,125,000
4
2
1,701
Recently Sold

Local Information

  • Map ViewExplore the area around 27 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
1987
Living Area
2,827 sqft
Price/Sqft
$657
Parking
Garage

About this House

Beautifully updated sunshine filled contemporary colonial ready to move in and call home! This home features newly renovated kitchen with white cabinets, granite countertops, stainless appliances. Finishing details include pristine walnut stained hardwood floors, wainscoting, crown molding, recessed lighting throughout, cozy outdoor living space including front porch, back deck and tree lined yard providing canvas for building memories. Features include skylights, 3 zone central heating and AC, CV. Perfectly quiet neighborhood, walking distance to Newman Elementary, downtown Needham, Wellesley, Boston Sports Club and outdoor pool complex, Babson & Olin Colleges, and more!
27 Winslow Rd, Needham, MA 02492 is a 4 bedroom, 3 bathroom, 2,827 sqft single-family home built in 1987. It last sold for $1,150,000 on Sep 8, 2017. More recently, it was listed as a rental in December 2023 with an asking price of $3,500 per month. That rental listing was removed on December 7, 2023. It is currently off market. The Trulia Estimate is $1,856,900, with a rent estimate of $6,684/month.

Home Details for 27 Winslow Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1987Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price and Tax history

DateEventPrice
Dec 7, 2023
Source: Zillow Rentals
ListingRemoved
Dec 4, 2023
Source: Zillow Rentals
Listed For Rent
$3,500
Sep 8, 2017
Source: N/A
Sold
$1,150,000
Jun 22, 2017
Source: Agent Provided
Pending
$1,149,000
Jun 8, 2017
Source: N/A
Listed For Sale
$1,149,000

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
    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

LGBTQ Local Legal Protections

Frequently asked questions about 27 Winslow Rd

  • What is 27 Winslow Rd estimated to be worth?
    Trulia's estimated value for 27 Winslow Rd in Needham, MA is $1,856,900.
  • What is the price history for 27 Winslow Rd?
    27 Winslow Rd in Needham, MA last sold for $1,150,000 in September 2017.
  • 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 27 Winslow Rd?
    The lot at 27 Winslow Rd in Needham, MA is about 0.23 acres (10,018 sq ft).
  • Does 27 Winslow Rd have a garage?
    Yes, 27 Winslow Rd in Needham, MA has a garage.

Explore by feature - Pet Friendly

26 pet-friendly rentals in Needham, MA

Explore by feature - Garage

10 rentals with a garage in Needham, MA

Explore by feature - Air Conditioning

27 rentals with air conditioning in Needham, MA

Explore by feature - Pool

6 rentals with a pool in Needham, MA

Explore by feature - Washer/dryer

33 rentals with a washer/dryer in Needham, MA

Explore by feature - Outdoor Space

6 rentals with an outdoor space in Needham, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 27 Winslow Rd

Skip to last item
Skip to first item

Homes for sale near 27 Winslow Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item