7 Dennett Rd, Winchester, MA 01890
OFF MARKET

7 Dennett Rd
Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,500 sqft (on 0.35 acres)

$2,225,500

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $13,272/mo*
Refinance Your Home

$2,225,500

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $13,272/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,500 sqft
(on 0.35 acres)

Local Information

  • Map ViewExplore the area around 7 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
0.35 acres
Living Area
3,500 sqft
Price/Sqft
$636
Parking
Garage

About this House

This beautiful Colonial, located in a quiet neighborhood, is in “move in” condition. This four bedroom, three and a half bath home boasts many unique features, such as heated tile floors, towel warmers, and a technology package that includes Cat5 and cable TV wiring throughout, “whole house” indoor/outdoor audio speaker system, projection screen and surround sound.
The brightly lit eat-in kitchen has a vaulted ceiling, granite counter tops, custom cherry cabinets, gas stove with griddle, Bosch wall oven, 48 bottle wine chiller, recessed lighting, ceiling fan, dishwasher, and heated tile floor. It leads out to a large deck, perfect for entertaining. The adjacent dining room has a lovely lighted corner cabinet, hardwood floor, chair rail and chandelier. The spacious living room, with hardwood floor and gas fireplace, runs the length of the house. A sunny playroom with three tel-data hookups provides lots of space for children’s entertainment. A first floor office is perfect for working at home if desired. A mud room/ laundry with heated tile floor, towel warmer, and lots of storage, leads to the rear deck. A half bath completes the first floor.
The second floor master suite is the perfect place to relax, boasting a vaulted ceiling, large walk in closet with custom shelving, and a built-in linen closet with laundry hampers. The adjoining bath has an oversized shower, Jacuzzi, heated tile floor, his and her towel warmers, and custom stained glass overlays on the windows. It is also wired for cable TV. Three additional bedrooms on this level have spacious closets and hardwood floors. Two full baths complete the second floor.
The lower level is designed for family entertainment, boasting a media room with 84” projection system, and gas fireplace. Also on this level is a large walk-out basement with storage/workroom, equipped with B- Dry Basement System and access to the heated garage.

7 Dennett Rd, Winchester, MA 01890 is a 4 bedroom, 4 bathroom, 3,500 sqft single-family home built in 1964. It last sold for $1,499,000 on Apr 8, 2019. It is currently off market. The Trulia Estimate is $2,225,500, with a rent estimate of $7,567/month.

Home Details for 7 Dennett Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Laundry Room, Master Bath, Mud Room, Office, Recreation Room, WorkshopCeiling Fan
Heating & Cooling
Heating: Baseboard, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
DishwasherDisposal
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodLawnSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: 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: 0.35 acres

Price History for 7 Dennett Rd

DatePriceEventSource
04/08/2019$1,499,000Sold
N/A
04/02/2009$959,000ListingRemovedAgent Provided
01/31/2009$959,000Listed For SaleAgent Provided
01/15/2009$941,000Sold
N/A
09/23/2008$959,000Listed For SaleAgent Provided
07/22/1997$450,000Sold
N/A
07/14/1994$350,000Sold
N/A

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.41M
Sale-to-List Price
101.7%
Price per sq ft
$571
Available listings
77
2MoM
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Property Tax and Assessment

Year2025
Tax$21,332
Assessment$1,923,500
Home facts updated by county records

Comparable Sales for 7 Dennett Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Hollywood Rd, Winchester, MA
0.08
Single-Family Home
$2,150,000
07/13/26
5
3
3,136
17 Dennett Rd, Winchester, MA
0.08
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283
35 Hollywood Rd, Winchester, MA
0.14
Single-Family Home
$1,755,000
05/01/26
4
4.5
3,906
58 Jefferson Rd, Winchester, MA
0.16
Single-Family Home
$1,850,000
04/23/26
4
2.5
2,910
21 Willowdale Rd, Winchester, MA
0.09
Single-Family Home
$2,170,000
07/31/26
5
3.5
4,591
17 Cranston Rd, Winchester, MA
0.17
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
4 Sargent Rd, Winchester, MA
0.29
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865
8 Felsdale Close, Winchester, MA
0.35
Single-Family Home
$1,930,000
01/09/26
4
2.5
3,658
382 S Border Rd, Winchester, MA
0.16
Single-Family Home
$2,450,000
11/17/25
6
5.5
4,563
71 Sargent Rd, Winchester, MA
0.38
Single-Family Home
$1,399,000
06/30/26
3
3.5
2,936

Nearby homes

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Assigned Schools

These are the assigned schools for 7 Dennett 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 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

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Homes for sale near 7 Dennett Rd

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Off Market Homes Near 7 Dennett Rd

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Frequently asked questions about 7 Dennett Rd

  • What is 7 Dennett Rd estimated to be worth?
    Trulia's estimated value for 7 Dennett Rd in Winchester, MA is $2,225,500.
  • What is the price history for 7 Dennett Rd?
    7 Dennett Rd in Winchester, MA last sold for $1,499,000 in April 2019.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.41M.
  • Does 7 Dennett Rd have air conditioning?
    Yes, 7 Dennett Rd in Winchester, MA has air conditioning.
  • Does 7 Dennett Rd have laundry facilities?
    Yes, 7 Dennett Rd in Winchester, MA has laundry facilities.