33 Winding River Rd, Needham, MA 02492
Property image
Property image
OFF MARKET

33 Winding River Rd
Needham, MA 02492

  • 4 Beds
  • 3.5 Baths
  • 4,300 sqft (on 1 acre)

$2,258,300

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $13,486/mo*
Refinance Your Home

$2,258,300

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $13,486/mo*
Refinance Your Home
4 Beds
3.5 Baths
4,300 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 33 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
1978
Lot Size
1 acre
Living Area
4,300 sqft
Price/Sqft
$525
Parking
Garage

About this House

Captivating and expansive 4 bedroom New England Classic Cape beautifully nestled on 1.22 private acre with mature plantings in sought after neighborhood setting. This beautiful home offers open, well appointed rooms with large windows capturing the sunlight and scenic views of the natural landscaping. Appreciate the welcoming foyer, elegant sun filled living room with fireplace and custom built ins, gracious dining room, bright eat in kitchen plus first floor family room and study. First floor master suite with private bath. Second floor includes 2 generous bedrooms, 2 bath and 2 large walk in closets and brand new master suite. Enjoy summer evenings relaxing on the screened porch listening to the tranquil sounds of nature. Welcome home.
33 Winding River Rd, Needham, MA 02492 is a 4 bedroom, 4 bathroom, 4,300 sqft single-family home built in 1978. It last sold for $1,200,000 on Jun 8, 2018. It is currently off market. The Trulia Estimate is $2,258,300, with a rent estimate of $7,621/month.

Home Details for 33 Winding River Rd

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation Room, Sun RoomStorageWet Bar
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: Central, SolarHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleDeckExterior: Other, VinylGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1978Year Updated: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 33 Winding River Rd

DatePriceEventSource
06/08/2018$1,200,000Sold
N/A
05/03/2018$1,125,000PendingAgent Provided
05/03/2018$1,125,000Listed For SaleAgent Provided
03/21/2018$1,125,000ListingRemovedAgent Provided
03/20/2018$1,125,000PendingAgent Provided
03/15/2018$1,125,000Listed For SaleAgent Provided
05/31/1991$460,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$21,006
Assessment$1,981,700
Home facts updated by county records

Comparable Sales for 33 Winding River Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Troutbrook Rd, Dover, MA
0.84
Single-Family Home
$1,280,000
05/22/26
4
2.5
2,565
30 Pleasant St, Natick, MA
0.82
Single-Family Home
$1,700,000
08/22/25
4
4.5
4,162
60 Pleasant St, Natick, MA
0.75
Single-Family Home
$1,225,000
10/24/25
4
2
2,758
76 Pleasant St, Natick, MA
0.76
Single-Family Home
$980,000
11/20/25
3
2.5
2,206
6 Meadowbrook Rd, Dover, MA
0.63
Single-Family Home
$2,675,000
08/18/25
5
5
5,900
60 Main St, Dover, MA
0.79
Single-Family Home
$1,650,000
11/13/25
4
3.5
3,233
193 Winding River Rd, Wellesley, MA
0.37
Single-Family Home
$4,375,000
11/17/25
5
5.5
7,000
8 Warren Rd, Natick, MA
0.60
Single-Family Home
$2,210,000
07/30/26
4
4
4,030
11 Parsons Way, Natick, MA
1.16
Single-Family Home
$1,500,000
10/17/25
4
3.5
3,753
25 Longmeadow Rd, Wellesley, MA
0.72
Single-Family Home
$2,795,000
06/30/26
5
4.5
4,582

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 33 Winding River Rd.
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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

25 pet-friendly rentals in Needham, MA

Explore by feature - Garage

7 rentals with a garage in Needham, MA

Explore by feature - Air Conditioning

27 rentals with air conditioning in Needham, MA

Explore by feature - Pool

Explore by feature - Washer/dryer

26 rentals with a washer/dryer in Needham, MA

Explore by feature - Outdoor Space

Homes for sale near 33 Winding River Rd

Skip to last item
Skip to first item

Off Market Homes Near 33 Winding River Rd

Skip to last item
Skip to first item

Frequently asked questions about 33 Winding River Rd

  • What is 33 Winding River Rd estimated to be worth?
    Trulia's estimated value for 33 Winding River Rd in Needham, MA is $2,258,300.
  • What is the price history for 33 Winding River Rd?
    33 Winding River Rd in Needham, MA last sold for $1,200,000 in June 2018.
  • 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.
  • Does 33 Winding River Rd have air conditioning?
    Yes, 33 Winding River Rd in Needham, MA has air conditioning.
  • Does 33 Winding River Rd have laundry facilities?
    Yes, 33 Winding River Rd in Needham, MA has in-unit laundry.