20 Windsor Dr, Wareham, MA 02571
OFF MARKET

$499,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,500 sqft (on 0.48 acres)

20 Windsor Dr, Wareham, MA 02571

Weweantic
Est. Refi. Payment $3,310/mo*
Refinance Your Home

Home Value

Trulia Estimate
$500K
Since last month
Decreased$8K (-1.5%)
Since last year
Increased$28K (+6%)
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 +84% in the last 10 years
MonthEstimated value
2026
September 2026$500K
September 2026$500K
August 2026$507K
July 2026$510K
June 2026$516K
May 2026$512K
April 2026$500K
March 2026$495K
February 2026$475K
January 2026$468K
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
9 Woodville Way, Wareham, MA
0.10
Single-Family Home
$600,000
04/06/26
3
1.5
924
3 Windsor Dr, Wareham, MA
0.23
Single-Family Home
$530,000
10/24/25
3
2
1,456
119 Hathaway St, Wareham, MA
0.17
Single-Family Home
$695,000
09/28/26
3
2.5
2,269
88 Hathaway St, Wareham, MA
0.16
Single-Family Home
$495,000
07/31/26
3
1.5
1,170
26 Cromesett Rd, Wareham, MA
0.32
Single-Family Home
$450,000
09/15/26
3
1
1,316
136 Marion Rd, Wareham, MA
0.67
Single-Family Home
$545,000
10/31/25
3
2
1,408
51 Swifts Beach Rd, Wareham, MA
0.55
Single-Family Home
$525,000
05/18/26
3
2
1,661
7 Highland Bay Dr, Wareham, MA
0.55
Single-Family Home
$433,000
07/09/26
3
2
840
90 Hathaway St, Wareham, MA
0.15
Single-Family Home
$484,900
06/26/26
3
1
1,092
4 Wilson St, Wareham, MA
0.81
Single-Family Home
$580,000
07/31/26
3
2
1,633

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
18 Windsor Dr, Wareham, MA 02571
0.03
$602,100
2
2
1,879
Off Market
22 Windsor Dr, Wareham, MA 02571
0.03
$576,400
4
2
1,591
Off Market
21 Windsor Dr, Wareham, MA 02571
0.04
$525,000
4
3
2,186
Recently Sold
23 Windsor Dr, Wareham, MA 02571
0.04
$472,800
3
1
1,030
Off Market
19 Windsor Dr, Wareham, MA 02571
0.05
$621,300
3
2.5
1,654
Off Market
16 Windsor Dr, Wareham, MA 02571
0.05
$485,000
3
1
1,248
Off Market
25 Windsor Dr, Wareham, MA 02571
0.05
$467,700
3
1
1,028
Off Market
24 Windsor Dr, Wareham, MA 02571
0.06
$538,100
3
2
1,796
Off Market
13 Woodville Way, Wareham, MA 02571
0.06
$521,100
3
2
1,080
Off Market
17 Windsor Dr, Wareham, MA 02571
0.07
$630,100
3
4
1,668
Off Market
11 Woodville Way, Wareham, MA 02571
0.08
$547,900
5
2
2,200
Off Market
14 Windsor Dr, Wareham, MA 02571
0.08
$453,800
3
1
1,028
Off Market
17 Woodville Way, Wareham, MA 02571
0.08
$479,400
2
2
1,224
Off Market
15 Windsor Dr, Wareham, MA 02571
0.09
$728,700
4
3
2,508
Off Market
18 Woodville Way, Wareham, MA 02571
0.10
$590,400
4
2
1,986
Off Market
16 Woodville Way, Wareham, MA 02571
0.10
$531,600
3
1.5
1,356
Off Market
9 Woodville Way, Wareham, MA 02571
0.10
$600,000
3
1.5
924
Recently Sold
20 Woodville Way, Wareham, MA 02571
0.10
$548,100
4
2
1,752
Off Market
14 Woodville Way, Wareham, MA 02571
0.11
$735,600
3
3
2,023
Off Market
293 Marion Rd, Wareham, MA 02571
0.11
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 20 Windsor Dr.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1978
0.48 acre lot
1,500 sqft
$333/sqft

About this House

This single-family home is located at 20 Windsor Dr, Wareham, MA. 20 Windsor Dr is in the Weweantic neighborhood in Wareham, MA and in ZIP code 02571. This property has 3 bedrooms, 2 bathrooms and approximately 1,500 sqft of floor space. This property has a lot size of 0.48 acres and was built in 1978.
20 Windsor Dr, Wareham, MA 02571 is a 3 bedroom, 2 bathroom, 1,500 sqft single-family home in Weweantic, built in 1978. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $499,600, with a rent estimate of $3,275/month.

Home Details for 20 Windsor Dr

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 6
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.48 acres

Price and Tax history

YearProperty taxTax assessment
2025
$4,441
$426,200
Home facts updated by county records

Market trends in Wareham

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
99
10MoM

Around this home

Neighborhood Overview

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

What Locals Say about Weweantic

At least 4 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 100 % Say it's dog friendly

  • 100 % Say kids play outside

  • 100 % Say car is needed

  • 83 % Say yards are well-kept

  • 80 % Say parking is easy

  • 75 % Say it's quiet

  • 75 % Say there's holiday spirit

  • 74 % Say neighbors are friendly

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

  • 50 % Say people would walk alone at night

  • 50 % Say there are sidewalks

  • 43 % Say it's walkable to grocery stores

  • 33 % Say it's walkable to restaurants

  • 13 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Product 3.
    "It’s right off 195. Also cranberry highway and route 6 that goes to RI. It’s not bad. Mostly town roads aside from the 195"
    8
    Flag
  • worstwow
    "Almost one year since purchasing a home on Marks Cove in Wareham. Not too much real estate turnover in this section of Wareham. Not very easy to get to by walking. Closest grocery store is 2 miles. Cannot hear any traffic at night. No commuter rail in Wareham."
    3
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Windsor Dr

  • What is 20 Windsor Dr estimated to be worth?
    Trulia's estimated value for 20 Windsor Dr in Wareham, MA is $499,600.
  • Is Wareham a buyer's or seller's market?
    Wareham is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 20 Windsor Dr?
    The closest schools to 20 Windsor Dr in Wareham, MA are Wareham Elementary School (Pre-K, rated 5/10), Wareham Middle School (Elementary, rated 6/10), Wareham Senior High School (Middle, rated 3/10).
  • How big is the lot at 20 Windsor Dr?
    The lot at 20 Windsor Dr in Wareham, MA is about 0.48 acres (20,908 sq ft).

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

25 rentals with a washer/dryer in Wareham, MA

Apartments for Rent

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Off Market Homes Near 20 Windsor Dr

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