56 Winding River Rd, Needham, MA 02492
OFF MARKET

56 Winding River Rd
Needham, MA 02492

  • 4 Beds
  • 3.5 Baths
  • 3,851 sqft (on 1.01 acres)

$2,445,800

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $14,624/mo*
Refinance Your Home

$2,445,800

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $14,624/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,851 sqft
(on 1.01 acres)

Home Value

Trulia Estimate
$2.45M
Since last month
Decreased$6K (-0.2%)
Since last year
Increased$167K (+7.3%)
Since last sale
Increased$1M (+81.9%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$2.45M
July 2026$2.45M
June 2026$2.48M
May 2026$2.49M
April 2026$2.43M
March 2026$2.43M
February 2026$2.35M
January 2026$2.32M
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
30 Pleasant St, Natick, MA
0.84
Single-Family Home
$1,700,000
08/22/25
4
4.5
4,162
42 Troutbrook Rd, Dover, MA
0.90
Single-Family Home
$1,280,000
05/22/26
4
2.5
2,565
60 Pleasant St, Natick, MA
0.79
Single-Family Home
$1,225,000
10/24/25
4
2
2,758
193 Winding River Rd, Wellesley, MA
0.31
Single-Family Home
$4,375,000
11/17/25
5
5.5
7,000
60 Main St, Dover, MA
0.86
Single-Family Home
$1,650,000
11/13/25
4
3.5
3,233
76 Pleasant St, Natick, MA
0.81
Single-Family Home
$980,000
11/20/25
3
2.5
2,206
8 Warren Rd, Natick, MA
0.64
Single-Family Home
$2,210,000
07/30/26
4
4
4,030
17 Eliot St, Natick, MA
0.90
Single-Family Home
$1,665,000
05/18/26
4
2.5
3,422
11 Parsons Way, Natick, MA
1.17
Single-Family Home
$1,500,000
10/17/25
4
3.5
3,753
25 Longmeadow Rd, Wellesley, MA
0.66
Single-Family Home
$2,795,000
06/30/26
5
4.5
4,582

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
869 Charles River St, Needham, MA 02492
0.12
$1,758,600
4
2.5
3,879
Off Market
68 Locust Ln, Needham, MA 02492
0.26
$4,388,888
6
7
9,825
For Sale
80 Locust Ln, Needham, MA 02492
0.27
$3,385,000
7
5
5,969
For Sale
97 Main St, Dover, MA 02030
0.34
$2,567,100
3
3
3,410
Off Market
198 Winding River Rd, Wellesley, MA 02482
0.30
$3,864,900
5
3.5
4,669
Off Market
27 Locust Ln, Needham, MA 02492
0.32
$1,622,700
3
3
2,141
Off Market
12 Winding River Cir, Wellesley, MA 02482
0.31
$4,999,000
6
7
8,729
For Sale
193 Winding River Rd, Wellesley, MA 02482
0.31
$4,375,000
5
5.5
7,000
Recently Sold
9 Buttercup Ln, Dover, MA 02030
0.37
$2,450,000
5
7
6,800
For Sale
11 Winding River Cir, Wellesley, MA 02482
0.36
$3,405,200
5
4
4,125
Off Market
25 Meadowbrook Rd, Dover, MA 02030
0.54
$1,958,700
4
3
4,456
Off Market
121 Livingston Rd, Wellesley, MA 02482
0.49
$6,660,000
6
8.5
10,090
Recently Sold

Local Information

  • Map ViewExplore the area around 56 Winding River 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
1959
Lot Size
1.01 acres
Living Area
3,851 sqft
Price/Sqft
$635
Parking
Garage

About this House

In a park-like tranquil setting this 10 room 5 bedroom Royal Barry Wills Colonial has direct waterfront access to the Charles River! Enjoy canoeing in the summer and skating in the winter. The level grounds include fruit trees, a vegetable garden, and beds of brightly colored annuals. Truly a gardener's paradise. This very fine riverfront home offers exquisite views and is truly a home for all seasons. Expansion possibilities.
56 Winding River Rd, Needham, MA 02492 is a 4 bedroom, 4 bathroom, 3,851 sqft single-family home built in 1959. It last sold for $1,344,200 on May 3, 2013. It is currently off market. The Trulia Estimate is $2,445,800, with a rent estimate of $7,503/month.

Home Details for 56 Winding River Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Recreation Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1959Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1.01 acres

Price and Tax history

DateEventPrice
May 3, 2013
Source: N/A
Sold
$1,344,200
May 25, 2012
Source: N/A
Sold
$900,000
Mar 1, 2012
Source: Agent Provided
Listed For Sale
$992,000

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 56 Winding River Rd

  • What is 56 Winding River Rd estimated to be worth?
    Trulia's estimated value for 56 Winding River Rd in Needham, MA is $2,445,800.
  • What is the price history for 56 Winding River Rd?
    56 Winding River Rd in Needham, MA last sold for $1,344,200 in May 2013.
  • 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 56 Winding River Rd?
    The lot at 56 Winding River Rd in Needham, MA is about 1 acre.
  • Does 56 Winding River Rd have a garage?
    Yes, 56 Winding River Rd in Needham, MA has a garage.

Explore by feature - Pet Friendly

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Off Market Homes Near 56 Winding River Rd

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