3 Dennett Rd, Winchester, MA 01890
Property image
Property image
OFF MARKET

3 Dennett Rd
Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,128 sqft (on 0.39 acres)

$1,737,500

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $10,396/mo*
Refinance Your Home

$1,737,500

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $10,396/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,128 sqft
(on 0.39 acres)

Home Value

Trulia Estimate
$1.74M
Since last month
Decreased$32K (-1.8%)
Since last year
Increased$43K (+2.5%)
Since last sale
Increased$794K (+83.5%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$1.74M
July 2026$1.78M
June 2026$1.78M
May 2026$1.79M
April 2026$1.78M
March 2026$1.74M
February 2026$1.65M
January 2026$1.64M
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
17 Dennett Rd, Winchester, MA
0.11
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283
58 Jefferson Rd, Winchester, MA
0.14
Single-Family Home
$1,850,000
04/23/26
4
2.5
2,910
17 Cranston Rd, Winchester, MA
0.16
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
22 Hollywood Rd, Winchester, MA
0.06
Single-Family Home
$2,150,000
07/13/26
5
3
3,136
4 Sargent Rd, Winchester, MA
0.28
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865
446 Highland Ave, Winchester, MA
0.30
Single-Family Home
$940,000
12/23/25
2
1.5
2,033
6 Marchant Rd, Winchester, MA
0.32
Single-Family Home
$1,325,000
04/22/26
3
2.5
2,153
6 Alden Ln, Winchester, MA
0.23
Single-Family Home
$1,275,000
06/25/26
3
2
1,511
35 Hollywood Rd, Winchester, MA
0.17
Single-Family Home
$1,755,000
05/01/26
4
4.5
3,906
89 Main St, Winchester, MA
0.35
Single-Family Home
$1,150,000
11/14/25
3
2.5
2,648

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
10 Clearwater Rd, Winchester, MA 01890
0.05
$1,999,800
4
2.5
2,688
Off Market
5 Clearwater Rd, Winchester, MA 01890
0.06
$2,923,700
6
7.5
5,658
Off Market
22 Hollywood Rd, Winchester, MA 01890
0.06
$2,150,000
5
3
3,136
Recently Sold
22 Willowdale Rd, Winchester, MA 01890
0.08
$2,105,800
4
2.5
2,973
Off Market
21 Willowdale Rd, Winchester, MA 01890
0.09
$2,170,000
5
3.5
4,591
Recently Sold
94 Lawson Rd, Winchester, MA 01890
0.10
$2,334,300
5
4
5,484
Off Market
57 Jefferson Rd, Winchester, MA 01890
0.10
$2,391,200
4
3.5
3,274
Off Market
17 Dennett Rd, Winchester, MA 01890
0.11
$1,535,700
3
2.5
2,283
Off Market
17 Cranston Rd, Winchester, MA 01890
0.16
$1,560,000
4
2.5
2,578
Recently Sold
58 Jefferson Rd, Winchester, MA 01890
0.14
$1,850,000
4
2.5
2,910
Recently Sold
382 S Border Rd, Winchester, MA 01890
0.14
$2,450,000
6
5.5
4,563
Recently Sold
39 Town Way, Winchester, MA 01890
0.17
$3,200,000
6
6
5,709
Recently Sold

Local Information

  • Map ViewExplore the area around 3 Dennett Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1964
Lot Size
0.39 acres
Living Area
2,128 sqft
Price/Sqft
$816
Parking
Garage

About this House

Frustrated by the search? Need a quiet street? 4 Bedrooms? Fireplaced family room of the eat-in kitchen? Screened porch? 3 car garage? Classic floorpan, hardwood floors? first floor washer dryer hookups? Full basement? 2 1/2 baths? Gracious and private lot? What are you waiting for?
3 Dennett Rd, Winchester, MA 01890 is a 4 bedroom, 3 bathroom, 2,128 sqft single-family home built in 1964. It last sold for $951,000 on May 4, 2018. It is currently off market. The Trulia Estimate is $1,737,500, with a rent estimate of $5,799/month.

Home Details for 3 Dennett Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1964
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
May 4, 2018
Source: N/A
Sold
$951,000
Feb 27, 2018
Source: Agent Provided
Listed For Sale
$935,000

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

Frequently asked questions about 3 Dennett Rd

  • What is 3 Dennett Rd estimated to be worth?
    Trulia's estimated value for 3 Dennett Rd in Winchester, MA is $1,737,500.
  • What is the price history for 3 Dennett Rd?
    3 Dennett Rd in Winchester, MA last sold for $951,000 in May 2018.
  • 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.
  • How big is the lot at 3 Dennett Rd?
    The lot at 3 Dennett Rd in Winchester, MA is about 0.39 acres (16,988 sq ft).
  • Does 3 Dennett Rd have a garage?
    Yes, 3 Dennett Rd in Winchester, MA has a garage.

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