29 Windsor Rd, Needham, MA 02492
OFF MARKET

29 Windsor Rd
Needham, MA 02492

  • 5 Beds
  • 4 Baths
  • 4,191 sqft (on 1.02 acres)

$2,471,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $14,748/mo*
Refinance Your Home

$2,471,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $14,748/mo*
Refinance Your Home
5 Beds
4 Baths
4,191 sqft
(on 1.02 acres)

Local Information

  • Map ViewExplore the area around 29 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
1960
Lot Size
1.02 acres
Living Area
4,191 sqft
Price/Sqft
$590
Parking
Garage

About this House

One of Needham's premier estate neighborhoods with all acre lots and many large new construction homes. This 1960 5 bedroom colonial was renovated and expanded in 2002 providing an open concept kitchen / family room and a suite for au pair or office apart from the four family bedrooms. 3 full/2 half baths. The granite and stainless kitchen has a large island and a spacious eating area adjacent to the inviting family room. The living room is front to back and has a wonderful screen porch overlooking the yard and woods beyond. The large dining room gets great afternoon sun and looks out over the yard. First floor office and half bath. Side entry with wall of pantry cabinets and half bath. Mudroom with a cubbies, hooks and bench. Beautiful wood floors. Walk out basement playroom with fireplace and big windows. Wine cellar, excellent storage.
29 Windsor Rd, Needham, MA 02492 is a 5 bedroom, 5 bathroom, 4,191 sqft single-family home built in 1960. It last sold for $1,575,000 on Nov 20, 2020. It is currently off market. The Trulia Estimate is $2,471,100, with a rent estimate of $7,931/month.

Home Details for 29 Windsor Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Gas, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Number of Rooms: 10Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle Not Wood
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.02 acres

Price History for 29 Windsor Rd

DatePriceEventSource
11/20/2020$1,575,000Sold
N/A
09/01/2020$1,599,000PendingAgent Provided
08/26/2020$1,599,000Listed For SaleAgent Provided
08/15/2005$1,493,500Sold
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
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Property Tax and Assessment

Year2025
Tax$20,303
Assessment$1,915,400
Home facts updated by county records

Comparable Sales for 29 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
24 Moseley Ave, Needham, MA
0.20
Single-Family Home
$1,735,000
03/27/26
5
3.5
3,669
362 Country Way, Needham, MA
0.15
Single-Family Home
$1,700,000
02/25/26
4
3.5
2,293
1125 South St, Needham, MA
0.43
Single-Family Home
$1,300,000
11/06/25
5
3
2,428
37 Carleton Dr, Needham, MA
0.50
Single-Family Home
$3,980,000
04/16/26
4
4
4,420
34 Stratford Rd, Needham, MA
0.08
Single-Family Home
$4,925,000
05/05/26
7
7.5
10,047
1574 Central Ave, Needham, MA
0.61
Single-Family Home
$1,400,000
10/10/25
3
2.5
2,603
20 Burr Dr, Needham, MA
0.70
Single-Family Home
$2,650,000
06/25/26
4
3.5
7,023
189 Bridle Trail Rd, Needham, MA
0.65
Single-Family Home
$2,850,000
04/13/26
4
5
5,689
130 Bridle Trail Rd, Needham, MA
0.52
Single-Family Home
$3,100,000
08/22/25
4
6
8,118
52 Willow St, Dover, MA
0.55
Single-Family Home
$2,640,000
03/25/26
4
3
4,137

Nearby homes

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Assigned Schools

These are the assigned schools for 29 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
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  • 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
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  • Andrew M.
    "Family friendly safe neighborhood. Convenient to the town center, restaurants, stores, medical and dental service providers, etc."
    0
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  • 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
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  • 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
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  • 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

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18 rentals with a washer/dryer in Needham, MA

Homes for sale near 29 Windsor Rd

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Off Market Homes Near 29 Windsor Rd

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Frequently asked questions about 29 Windsor Rd

  • What is 29 Windsor Rd estimated to be worth?
    Trulia's estimated value for 29 Windsor Rd in Needham, MA is $2,471,100.
  • What is the price history for 29 Windsor Rd?
    29 Windsor Rd in Needham, MA last sold for $1,575,000 in November 2020.
  • 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 29 Windsor Rd have air conditioning?
    Yes, 29 Windsor Rd in Needham, MA has air conditioning.
  • How big is the lot at 29 Windsor Rd?
    The lot at 29 Windsor Rd in Needham, MA is about 1 acre.