Is parking easy in Windsor, VA?

As of early 2026, 93% of users say parking is easy

Is a car needed in Windsor, VA?

As of early 2026, 92% of users say car is needed

Are yards well-kept in Windsor, VA?

As of early 2026, 92% of users say yards are well-kept

Is Windsor, VA dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Does Windsor, VA show holiday spirit?

As of early 2026, 86% of users say there's holiday spirit

Do kids play outside in Windsor, VA?

As of early 2026, 82% of users say kids play outside

Would people walk alone at night in Windsor, VA?

As of early 2026, 79% of users say people would walk alone at night

Is there wildlife in Windsor, VA?

As of early 2026, 71% of users say there's wildlife

Are neighbors friendly in Windsor, VA?

As of early 2026, 62% of users say neighbors are friendly

Does Windsor, VA have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Is Windsor, VA quiet?

As of early 2026, 55% of users say it's quiet

Are the streets well-lit in Windsor, VA?

As of early 2026, 50% of users say streets are well-lit

Are there community events in Windsor, VA?

As of early 2026, 45% of users say there are community events

Do residents of Windsor, VA plan to stay at least 5 years?

As of early 2026, 33% of users say they plan to stay for at least 5 years

Is Windsor, VA walkable to grocery stores?

As of early 2026, 23% of users say it's walkable to grocery stores

Is Windsor, VA walkable to restaurants?

As of early 2026, 17% of users say it's walkable to restaurants

What is 8 Mathews Dr estimated to be worth?

Trulia's estimated value for 8 Mathews Dr in Windsor, VA is $316,000 .

Is Windsor a buyer's or seller's market?

Windsor is currently a balanced market, based on recent for-sale activity.

What do residents say about Windsor?

Residents describe Windsor, VA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, VA .

What are the closest schools to 8 Mathews Dr?

The closest schools to 8 Mathews Dr in Windsor, VA are Georgie D. Tyler Middle (rated 7/10), Windsor Elementary School (Pre-K, rated 7/10), Windsor High School (rated 5/10).

OFF MARKET

8 Mathews Dr
Windsor, VA 23487

2 Beds

$316,000

Trulia Estimate

as of Aug 21, 2026

Est. Refi. Payment $1,875/mo*

Refinance Your Home

$316,000

Trulia Estimate

as of Aug 21, 2026

Est. Refi. Payment $1,875/mo*

Refinance Your Home

2 Beds

Home Value

Trulia Estimate

$316K

Since last month

$45K (+16.8%)

Since last year

$35K (+12.3%)

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 +85% in the last 10 years

Month	Estimated value
2026
August 2026	$316K
July 2026	$271K
June 2026	$294K
May 2026	$267K
April 2026	$305K
March 2026	$292K
February 2026	$323K
January 2026	$277K
2025
December 2025	$292K
November 2025	$281K
October 2025	$237K
September 2025	$255K
August 2025	$281K
July 2025	$242K
June 2025	$222K
May 2025	$245K
April 2025	$329K
March 2025	$285K
February 2025	$284K
January 2025	$285K
2024
December 2024	$277K
November 2024	$285K
October 2024	$249K
September 2024	$345K
August 2024	$308K
July 2024	$329K
June 2024	$271K
May 2024	$242K
April 2024	$234K
March 2024	$294K
February 2024	$296K
January 2024	$288K
2023
December 2023	$352K
November 2023	$303K
October 2023	$319K
September 2023	$346K
August 2023	$313K
July 2023	$353K
June 2023	$357K
May 2023	$291K
April 2023	$296K
March 2023	$282K
February 2023	$272K
January 2023	$273K
2022
December 2022	$269K
November 2022	$279K
October 2022	$280K
September 2022	$271K
August 2022	$277K
July 2022	$280K
June 2022	$289K
May 2022	$288K
April 2022	$296K
March 2022	$279K
February 2022	$255K
January 2022	$249K
2021
December 2021	$277K
November 2021	$273K
October 2021	$258K
September 2021	$256K
August 2021	$247K
July 2021	$247K
June 2021	$260K
May 2021	$204K
2020
August 2020	$158K
July 2020	$156K
June 2020	$159K
May 2020	$158K
April 2020	$202K
March 2020	$168K
February 2020	$162K
January 2020	$164K
2019
December 2019	$154K
November 2019	$145K
October 2019	$160K
September 2019	$163K
August 2019	$152K
July 2019	$138K
June 2019	$146K
May 2019	$156K
April 2019	$157K
March 2019	$155K
February 2019	$155K
January 2019	$154K
2018
December 2018	$166K
November 2018	$161K
October 2018	$158K
September 2018	$157K
August 2018	$177K
July 2018	$174K
June 2018	$176K
May 2018	$174K
April 2018	$179K
March 2018	$180K
February 2018	$169K
January 2018	$179K
2017
December 2017	$187K
November 2017	$186K
October 2017	$186K
September 2017	$184K
August 2017	$182K
July 2017	$182K
June 2017	$181K
May 2017	$180K
April 2017	$178K
March 2017	$173K
February 2017	$174K
January 2017	$164K
2016
December 2016	$149K
November 2016	$167K
October 2016	$173K
September 2016	$166K
August 2016	$171K

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
40 W Windsor Blvd, Windsor, VA	0.26	Single-Family Home	$198,000	06/22/26	2	1	962
24 N Court St, Windsor, VA	0.41	Single-Family Home	$370,000	04/07/26	3	1.5	1,785
16 W Windsor Blvd, Windsor, VA	0.43	Single-Family Home	$225,000	12/30/25	3	2	1,076
9545 W Windsor Blvd, Windsor, VA	0.57	Single-Family Home	$250,000	08/11/26	2	1	1,086
10176 Bank St, Windsor, VA	0.44	Single-Family Home	$384,999	07/28/26	3	2	1,725
10174 Bank St, Windsor, VA	0.46	Single-Family Home	$384,999	07/27/26	3	2	1,725
10 Church St, Windsor, VA	0.60	Single-Family Home	$349,900	12/04/25	3	2.5	2,000
105 S Court St, Windsor, VA	0.66	Single-Family Home	$354,999	06/08/26	3	2.5	1,480
112 S Court St, Windsor, VA	0.66	Single-Family Home	$345,000	11/18/25	3	2.5	1,400
Bear Trap Cir, Windsor, VA	0.79	Single-Family Home	$335,000	07/20/26	2	1	816

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
24 N Court St, Windsor, VA 23487	0.41	$370,000	3	1.5	1,785	Recently Sold
14 B Ave, Windsor, VA 23487	0.43	$265,000	2	1	1,232	For Sale
16 W Windsor Blvd, Windsor, VA 23487	0.43	$225,000	3	2	1,076	Recently Sold
Prcl 1 Bank St, Windsor, VA 23487	0.44	$50,000	-	-	-	Recently Sold
10176 Bank St, Windsor, VA 23487	0.44	$384,999	3	2	1,725	Recently Sold
18 B Ave, Windsor, VA 23487	0.45	$230,000	6	2	3,600	Recently Sold
10174 Bank St, Windsor, VA 23487	0.46	$384,999	3	2	1,725	Recently Sold
20 Clydes Ln #20, Windsor, VA 23487	0.49	$91,900	2	2	930	For Sale
68 Clydes Ln #68, Windsor, VA 23487	0.49	$82,900	3	2	1,140	For Sale
Lot 2 Walters Hwy #2, Windsor, VA 23487	0.51	-	-	-	-	Off Market
9545 W Windsor Blvd, Windsor, VA 23487	0.57	$250,000	2	1	1,086	Recently Sold
4 S Court St, Windsor, VA 23487	0.57	$45,000	-	-	-	Recently Sold

Local Information

Map ViewExplore the area around 8 Mathews Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1972

Parking

None

About this House

This single-family home is located at 8 Mathews Dr, Windsor, VA. 8 Mathews Dr is in Windsor, VA and in ZIP code 23487. This property has 2 bedrooms. This property was built in 1972.

8 Mathews Dr, Windsor, VA 23487 is a 2 bedroom single-family home built in 1972. More recently, it was listed as a rental in November 2019 with an asking price of $250 per month. That rental listing was removed on January 18, 2021. It is currently off market. The Trulia Estimate is $316,000, with a rent estimate of $2,072/month.

Home Details for 8 Mathews Dr

Exterior Features
Exterior Home Features Roof: Other
Parking & Garage Parking: None

Property Information
Year Built Year Built: 1972
Property Type / Style Property Type: Single Family Home

Interior Features
Levels, Entrance, & Accessibility Floors: Other

Price and Tax history

Date	Event	Price
Jan 18, 2021 Source: REIN Inc.	ListingRemoved
Nov 22, 2019 Source: Agent Provided	Listed For Rent	$250
Feb 15, 2019 Source: Agent Provided	ListingRemoved	$250
Jan 29, 2019 Source: Agent Provided	Listed For Rent	$250

Additional Cost

Market trends in Windsor

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

6MoM

Around this home

Windsor Elementary School
PK-5
Public
624 Students
Isle Of Wight County Public Schools
7/10
GreatSchools Rating
Parent Rating Average
We love Windsor and so far the Elementary and Middle School are wonderful for our kids. It was the best move we made.
Parent Review
2y ago
3 Reviews

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 Windsor

At least 9 Trulia users voted on each feature.

93 % Say parking is easy
92 % Say car is needed
92 % Say yards are well-kept
91 % Say it's dog friendly
86 % Say there's holiday spirit
82 % Say kids play outside
79 % Say people would walk alone at night
71 % Say there's wildlife
62 % Say neighbors are friendly
58 % Say there are sidewalks
55 % Say it's quiet
50 % Say streets are well-lit
45 % Say there are community events
33 % Say they plan to stay for at least 5 years
23 % Say it's walkable to grocery stores
17 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

Ashley H.
Resident
6y ago
"I've lived here all my life and wouldn't move anywhere else. I love the close knit community as well as the Holiday festivities."
0
Flag
Braden38351
Resident
8y ago
"I’ve lived here for four years and love it! We are about to have our second child and wouldn’t want to live anywhere else"
3
Flag
Jennifer B.
12y ago
"I lived in this area with my children for 7 years. I like the schools and the community is very friendly. Windsor woods is a very nice area to live in. "
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 8 Mathews Dr

What is 8 Mathews Dr estimated to be worth?
Trulia's estimated value for 8 Mathews Dr in Windsor, VA is $316,000.
Is Windsor a buyer's or seller's market?
Windsor is currently a balanced market, based on recent for-sale activity.
What do residents say about Windsor?
Residents describe Windsor, VA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, VA.
What are the closest schools to 8 Mathews Dr?
The closest schools to 8 Mathews Dr in Windsor, VA are Georgie D. Tyler Middle (rated 7/10), Windsor Elementary School (Pre-K, rated 7/10), Windsor High School (rated 5/10).