27 Winstead Ave, Dedham, MA 02026
OFF MARKET

$903,000

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 2,564 sqft (on 0.25 acres)

27 Winstead Ave, Dedham, MA 02026

Greenlodge
Est. Refi. Payment $5,438/mo*
Refinance Your Home

Home Value

Trulia Estimate
$903K
Since last month
Decreased$31K (-3.4%)
Since last year
Decreased$13K (-1.4%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$904K
July 2026$936K
June 2026$949K
May 2026$964K
April 2026$929K
March 2026$916K
February 2026$889K
January 2026$878K
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
29 Southgate St, Dedham, MA
0.11
Single-Family Home
$1,455,000
01/28/26
5
3
3,200
30 Granite St, Dedham, MA
0.13
Single-Family Home
$970,000
10/16/25
4
3
2,233
11 Granite St, Dedham, MA
0.12
Single-Family Home
$1,100,000
01/22/26
3
2.5
2,796
23 Granite St, Dedham, MA
0.13
Single-Family Home
$865,000
09/12/25
3
2.5
1,771
34 Preston St, Dedham, MA
0.30
Single-Family Home
$995,000
07/30/26
5
3.5
3,255
25 Cynthia Rd, Dedham, MA
0.31
Single-Family Home
$1,150,000
07/17/26
4
2.5
2,001
88 Fox Meadow Ln, Dedham, MA
0.28
Single-Family Home
$775,000
11/26/25
4
1.5
2,344
1044 East St, Dedham, MA
0.18
Single-Family Home
$850,000
08/20/26
3
2.5
2,243
1139 East St, Dedham, MA
0.23
Single-Family Home
$720,000
07/21/26
5
2
1,936
13 Willard St, Dedham, MA
0.25
Single-Family Home
$815,000
08/01/26
4
2
1,846

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
60 Ridgeway St #60, Dedham, MA 02026
0.06
-
3
2
1,212
Off Market
67 S Gate St, Dedham, MA 02026
0.03
$1,267,200
5
2.5
2,728
Off Market
113 Ledgewood Rd, Dedham, MA 02026
0.04
$715,000
3
1.5
1,512
Recently Sold
137 Ledgewood Rd, Dedham, MA 02026
0.09
$878,100
4
1.5
1,566
Off Market
11 Granite St, Dedham, MA 02026
0.12
$1,100,000
3
2.5
2,796
Recently Sold
30 Granite St, Dedham, MA 02026
0.13
$1,006,700
4
3
2,233
Off Market
23 Granite St, Dedham, MA 02026
0.13
$895,000
3
2.5
1,771
Off Market
15 Intervale Rd, Dedham, MA 02026
0.09
$800,200
4
1
1,440
Off Market
29 S Gate St, Dedham, MA 02026
0.11
$1,502,000
3
1.5
1,530
Off Market
29 Southgate St, Dedham, MA 02026
0.11
$1,455,000
5
3
3,200
Recently Sold
25 Coronation Dr, Dedham, MA 02026
0.14
$876,700
3
1.5
1,372
Off Market
1 Intervale Rd, Dedham, MA 02026
0.10
$1,213,900
4
2.5
3,059
Off Market

Local Information

  • Map ViewExplore the area around 27 Winstead Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1963
Lot Size
0.25 acres
Living Area
2,564 sqft
Price/Sqft
$352
Parking
Garage

About this House

This single-family home is located at 27 Winstead Ave, Dedham, MA. 27 Winstead Ave is in the Greenlodge neighborhood in Dedham, MA and in ZIP code 02026. This property has 5 bedrooms, 3 bathrooms and approximately 2,564 sqft of floor space. This property has a lot size of 10890 sqft and was built in 1963.
27 Winstead Ave, Dedham, MA 02026 is a 5 bedroom, 3 bathroom, 2,564 sqft single-family home in Greenlodge, built in 1963. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $903,000, with a rent estimate of $5,414/month.

Home Details for 27 Winstead Ave

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

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

Property Information

Year Built
Year Built: 1963
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 10890 sqft

Price and Tax history

YearProperty taxTax assessment
2025
$10,391
$823,400
Home facts updated by county records

Market trends in Dedham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$770K
Sale-to-List Price
102.6%
Price per sq ft
$475
Available listings
80
1MoM

Around this home

Neighborhood Overview

Greenlodge
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greenlodge

At least 16 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 96 % Say there's holiday spirit

  • 96 % Say yards are well-kept

  • 94 % Say it's quiet

  • 94 % Say streets are well-lit

  • 91 % Say there are sidewalks

  • 91 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say car is needed

  • 83 % Say there's wildlife

  • 79 % Say they plan to stay for at least 5 years

  • 78 % Say kids play outside

  • 74 % Say there are community events

  • 71 % Say neighbors are friendly

  • 43 % Say it's walkable to restaurants

  • 14 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Meghan
    "Horrible ride on I-95 to Burlington every morning and evening at least an hour, sometimes 1 1/2 hours."
    0
    Flag
  • Ke j.
    "Walk to train and Dedham square. Highway access and legacy place. Community feel with neighbors who talk to each other. "
    9
    Flag
  • Lauren
    "Near Boston and major highways. Suburban but close to urban areas. Quick and easy to get everywhere "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Winstead Ave

  • What is 27 Winstead Ave estimated to be worth?
    Trulia's estimated value for 27 Winstead Ave in Dedham, MA is $903,000.
  • Is Dedham a buyer's or seller's market?
    Dedham is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Dedham?
    The median sale price in Dedham is $770K.
  • What do residents say about the Greenlodge neighborhood?
    Residents describe the Greenlodge neighborhood in Dedham, MA as dog-friendly, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Greenlodge, Dedham.
  • How big is the lot at 27 Winstead Ave?
    The lot at 27 Winstead Ave in Dedham, MA is about 0.25 acres (10,890 sq ft).
  • Does 27 Winstead Ave have a garage?
    Yes, 27 Winstead Ave in Dedham, MA has a garage.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Apartments for Rent

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Off Market Homes Near 27 Winstead Ave

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