20 Windsor Rd, Needham, MA 02492
OFF MARKET

20 Windsor Rd
Needham, MA 02492

  • 4 Beds
  • 3.5 Baths
  • 4,552 sqft (on 1.05 acres)

$2,367,500

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $14,133/mo*
Refinance Your Home

$2,367,500

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $14,133/mo*
Refinance Your Home
4 Beds
3.5 Baths
4,552 sqft
(on 1.05 acres)

Local Information

  • Map ViewExplore the area around 20 Windsor 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
1962
Lot Size
1.05 acres
Living Area
4,552 sqft
Price/Sqft
$520
Parking
2 Car Garage

About this House

20 Windsor Road is a charming home situated on an acre of land in Needham’s desirable estate neighborhood. As you enter, you'll be welcomed by the spacious entryway, the bright and oversized living and dining rooms, and an eat-in kitchen offering views of the spacious yard and new deck leading to the patio and backyard. The first floor also features a home office with its own deck and separate entrance. A few steps down, the large family room offers a bar, billiard area, and ample space for entertaining. This level also connects to the patio, yard, mudroom, and 2-car garage. Upstairs, enjoy new wood floors and three spacious bedrooms, one en suite and the other two sharing a renovated bathroom. Up a level, the oversized primary suite offers views of the yard, new California Closets, and a luxurious spa-like bathroom. The private, sprawling backyard is perfect for a pool, sports court, or any custom addition you desire.
20 Windsor Rd, Needham, MA 02492 is a 4 bedroom, 4 bathroom, 4,552 sqft single-family home built in 1962. It last sold for $2,289,000 on May 2, 2025 (9% above the $2,099,000 asking price). It is currently off market. The Trulia Estimate is $2,367,500, with a rent estimate of $7,028/month.

Home Details for 20 Windsor Rd

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4552 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker ConnectionAppliances: Oven, Dishwasher, Range, Refrigerator, Washer, Dryer, Wine Refrigerator, Range Hood, Plumbed For Ice MakerDishwasherDryerLaundry: Electric Dryer Hookup,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Oil,DuctlessHas CoolingAir Conditioning: Central Air,DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 3Fireplace: Family Room, Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Flooring: Tile, Vinyl, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Vinyl
Levels, Entrance, & Accessibility
Levels: Multi/SplitFloors: Tile, Vinyl, Carpet, Hardwood, Flooring Wall To Wall Carpet, Flooring Vinyl

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck - Exterior, Porch, Deck, PatioFencing: Fenced/Enclosed, FencedExterior: Porch, Deck, Patio, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Fenced YardFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Attached,Paved Drive
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadNot on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 3729Finished Area (below surface): 823

Property Information

Year Built
Year Built: 1962
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Garrison
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: 146055

Price & Status

Price
List Price: $2,099,000
Status Change & Dates
Off Market Date: Mon Mar 03 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Needham
School Information
Elementary School: NewmanJr High / Middle School: NpsHigh School: Nps

Building

Building Area
Building Area: 4552 Square Feet

Community

Community Features: Public Transportation, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, UniversityNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.05 Acres

Miscellaneous

BasementMls Number: 73338878Above Grade Unfinished Area: 3729

Additional Information

Public TransportationPoolTennis Court(s)ParkWalk/Jog TrailsStable(s)GolfMedical FacilityBike PathConservation AreaHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationUniversity
Last check for updates: about 20 hours ago
Listed by The Samantha Eisenberg Group, (917) 952-9966
Compass, (617) 752-6845
Bought with: The Samantha Eisenberg Group, (917) 952-9966, Compass, (617) 752-6845
Source: MLS PIN, MLS#73338878

Price History for 20 Windsor Rd

DatePriceEventSource
05/02/2025$2,289,000Sold
MLS PIN #73338878
02/26/2025$2,099,000Listed For SaleMLS PIN #73338878
07/30/2021$1,800,000Sold
N/A
06/22/2021$1,699,000PendingMLS PIN #72846007
06/15/2021$1,699,000ContingentMLS PIN #72846007
06/09/2021$1,699,000Listed For SaleMLS PIN #72846007
09/19/2013$1,399,000ListingRemovedAgent Provided
09/17/2013$1,399,000Listed For SaleAgent Provided
08/15/2013$1,399,000ListingRemovedAgent Provided
05/23/2013$1,399,000Listed For SaleAgent Provided

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
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Property Tax and Assessment

Year2025
Tax$18,878
Assessment$1,780,900
Home facts updated by county records

Comparable Sales for 20 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
362 Country Way, Needham, MA
0.11
Single-Family Home
$1,700,000
02/25/26
4
3.5
2,293
24 Moseley Ave, Needham, MA
0.18
Single-Family Home
$1,735,000
03/27/26
5
3.5
3,669
37 Carleton Dr, Needham, MA
0.45
Single-Family Home
$3,980,000
04/16/26
4
4
4,420
189 Bridle Trail Rd, Needham, MA
0.61
Single-Family Home
$2,850,000
04/13/26
4
5
5,689
34 Stratford Rd, Needham, MA
0.04
Single-Family Home
$4,925,000
05/05/26
7
7.5
10,047
20 Burr Dr, Needham, MA
0.73
Single-Family Home
$2,650,000
06/25/26
4
3.5
7,023
130 Bridle Trail Rd, Needham, MA
0.48
Single-Family Home
$3,100,000
08/22/25
4
6
8,118
52 Willow St, Dover, MA
0.58
Single-Family Home
$2,640,000
03/25/26
4
3
4,137
1125 South St, Needham, MA
0.45
Single-Family Home
$1,300,000
11/06/25
5
3
2,428
1574 Central Ave, Needham, MA
0.56
Single-Family Home
$1,400,000
10/10/25
3
2.5
2,603

Nearby homes

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Assigned Schools

These are the assigned schools for 20 Windsor 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
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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
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  • 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
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  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

22 pet-friendly rentals in Needham, MA

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Explore by feature - Air Conditioning

20 rentals with air conditioning in Needham, MA

Explore by feature - Washer/dryer

18 rentals with a washer/dryer in Needham, MA

Homes for sale near 20 Windsor Rd

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Off Market Homes Near 20 Windsor Rd

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Frequently asked questions about 20 Windsor Rd

  • What is 20 Windsor Rd estimated to be worth?
    Trulia's estimated value for 20 Windsor Rd in Needham, MA is $2,367,500.
  • What is the price history for 20 Windsor Rd?
    20 Windsor Rd in Needham, MA last sold for $2,289,000 in May 2025.
  • 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 20 Windsor Rd have air conditioning?
    Yes, 20 Windsor Rd in Needham, MA has air conditioning.
  • Does 20 Windsor Rd have a pool?
    Yes, 20 Windsor Rd in Needham, MA has a pool.
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.