29 Kenwin Rd, Winchester, MA 01890
Property image
Property image
OFF MARKET

$1,600,300

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,132 sqft (on 0.36 acres)

29 Kenwin Rd, Winchester, MA 01890

Est. Refi. Payment $9,539/mo*
Refinance Your Home
Currently Off Market - Sold May 31, 2024 for $1,450,000

Home Value

Trulia Estimate
$1.6M
Since last month
Decreased$34K (-2.1%)
Since last year
Increased$98K (+6.5%)
Since last sale
Increased$150K (+10.4%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$1.6M
August 2026$1.6M
July 2026$1.63M
June 2026$1.64M
May 2026$1.66M
April 2026$1.65M
March 2026$1.64M
February 2026$1.6M
January 2026$1.53M
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
41 Englewood Rd, Winchester, MA
0.13
Single-Family Home
$1,038,500
12/01/25
3
1.5
1,683
40 Englewood Rd, Winchester, MA
0.10
Single-Family Home
$1,218,000
05/20/26
4
2
1,841
102 Hillcrest Pkwy, Winchester, MA
0.34
Single-Family Home
$1,425,000
12/01/25
4
2
1,755
1 Orient St, Winchester, MA
0.19
Single-Family Home
$1,330,000
05/28/26
3
1.5
2,222
10 Bonad Rd, Winchester, MA
0.11
Single-Family Home
$1,620,000
07/06/26
4
2.5
2,233
162 Forest St, Winchester, MA
0.37
Single-Family Home
$1,280,000
10/03/25
4
1.5
1,900
147 Highland Ave, Winchester, MA
0.35
Single-Family Home
$1,200,000
09/25/25
3
2
1,884
15 Englewood Rd, Winchester, MA
0.16
Single-Family Home
$1,425,000
05/07/26
4
3
1,903
7 Appalachian Rd, Winchester, MA
0.11
Single-Family Home
$2,150,000
02/02/26
4
4.5
3,263
18 Grayson Rd, Winchester, MA
0.08
Single-Family Home
$1,738,000
07/28/26
3
2.5
2,992

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
32 Grayson Rd, Winchester, MA 01890
0.04
$1,570,400
3
1.5
1,996
Off Market
20 Grayson Rd, Winchester, MA 01890
0.07
$1,995,600
5
4.5
3,825
Off Market
18 Grayson Rd, Winchester, MA 01890
0.08
$1,738,000
3
2.5
2,992
Recently Sold
19 Kenwin Rd, Winchester, MA 01890
0.06
$1,448,400
3
2
1,875
Off Market
14 Bonad Rd, Winchester, MA 01890
0.10
$1,731,800
3
2.5
2,516
Off Market
40 Englewood Rd, Winchester, MA 01890
0.10
$1,218,000
4
2
1,841
Recently Sold
10 Bonad Rd, Winchester, MA 01890
0.11
$1,620,000
4
2.5
2,233
Recently Sold
41 Englewood Rd, Winchester, MA 01890
0.13
$1,038,500
3
1.5
1,683
Recently Sold
18 Englewood Rd, Winchester, MA 01890
0.13
$1,774,500
5
2.5
2,597
Off Market
7 Appalachian Rd, Winchester, MA 01890
0.11
$2,150,000
4
4.5
3,263
Recently Sold
25 Englewood Rd, Winchester, MA 01890
0.15
$1,785,600
4
4
3,061
Off Market

Local Information

  • Map ViewExplore the area around 29 Kenwin Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1930
0.36 acre lot
2,132 sqft
$751/sqft
Garage

About this House

Charming 1930's Cape with arched doorways, built-ins, period details and several recent updates. Located in the desirable "Highlands" section of Winchester and within walking distance of the Muraco Elementary School, Leonard Field, the Fells Reservation and Winchester Hospital . Enjoy spacious rooms with several improvements including a striking remodeled eat in kitchen with white cabinets, granite countertops, and stainless steel appliances. Featuring gleaming hardwood floors and a three season porch on the first floor as well as a formal dining room, renovated bath, and 2 bedrooms. Flexible 2nd floor offers 2 large bedrooms and a remodeled bath. Enjoy outdoor fun in the private backyard with a newer patio, privacy fence, and room for future expansion. All of this and more in a convenient commuter location. It's time to make this welcoming home your own!
29 Kenwin Rd, Winchester, MA 01890 is a 4 bedroom, 2 bathroom, 2,132 sqft single-family home built in 1930. It last sold for $1,450,000 on May 31, 2024 (26% above the $1,150,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,600,300, with a rent estimate of $5,380/month.
Last check for updates: about 4 hours ago
Listed by Judith Moore, (781) 264-2661
Barrett Sotheby's International Realty, (781) 862-1700
Bought with: Brad Hartz, (617) 991-6052, Compass, (781) 365-9954
Source: MLS PIN, MLS#73228043

Home Details for 29 Kenwin Rd

Interior Features

Interior Details
Basement: Interior Entry,Bulkhead,Sump Pump,Concrete,UnfinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bathroom 1, Bathroom 2, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2132 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer HookupAppliances: Electric Water Heater, Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, DryerDishwasherDisposalDryerLaundry: In Basement,Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Storm Window(s), ScreensDoor: Insulated Doors, Storm Door(s), French DoorsFlooring: Tile, Carpet, Hardwood
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Screened, PatioExterior: Porch - Screened, Patio, Rain Gutters, Sprinkler System, ScreensFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 3No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Detached,Garage Door Opener,Paved Drive
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:002 B:0061 L:0, 894609

Price & Status

Price
List Price: $1,150,000
Status Change & Dates
Off Market Date: Tue Apr 30 2024

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WinchesterCommunity: Highlands
School Information
Elementary School: MuracoJr High / Middle School: MccallHigh School: Whs

Building

Building Area
Building Area: 2132 Square Feet

Community

Community Features: Public Transportation, Park, Walk/Jog Trails, Medical Facility, Highway Access, House of Worship, Public SchoolNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.36 acres

Miscellaneous

BasementMls Number: 73228043

Additional Information

Public TransportationParkWalk/Jog TrailsMedical FacilityHighway AccessHouse of WorshipPublic School

Price and Tax history

DateEventPrice
May 31, 2024
Source: MLS PIN #73228043
Sold
$1,450,000
Apr 24, 2024
Source: MLS PIN #73228043
Listed For Sale
$1,150,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$62.83KMoM
Sale-to-List Price
101.9%
0.2%MoM
Price per sq ft
$574
$3MoM
Available listings
64
13MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

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.

Frequently asked questions about 29 Kenwin Rd

  • What is 29 Kenwin Rd estimated to be worth?
    Trulia's estimated value for 29 Kenwin Rd in Winchester, MA is $1,600,300.
  • What is the price history for 29 Kenwin Rd?
    29 Kenwin Rd in Winchester, MA last sold for $1,450,000 in May 2024.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.47M. That is up $62.83K from the prior month.
  • Does 29 Kenwin Rd have laundry facilities?
    Yes, 29 Kenwin Rd in Winchester, MA has in-unit laundry.
  • How big is the lot at 29 Kenwin Rd?
    The lot at 29 Kenwin Rd in Winchester, MA is about 0.36 acres (15,621 sq ft).

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