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 Courthouse Hwy estimated to be worth?

Trulia's estimated value for Courthouse Hwy in Windsor, VA is $204,500 .

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 Courthouse Hwy?

The closest schools to Courthouse Hwy 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).

How big is the lot at Courthouse Hwy?

The lot at Courthouse Hwy in Windsor, VA is about 2.7 acres .

OFF MARKET

$204,500

Trulia Estimate

Studio

Courthouse Hwy, Windsor, VA 23487

Est. Refi. Payment $1,221/mo*

Refinance Your Home

Home Value

Trulia Estimate

$205K

Since last month

$6K (-2.9%)

Since last year

$24K (+12.9%)

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 decreased by -13% in the last 10 years

Month	Estimated value
2026
August 2026	$208K
June 2026	$214K
May 2026	$204K
April 2026	$204K
March 2026	$215K
February 2026	$193K
January 2026	$187K
2025
December 2025	$187K
November 2025	$177K
October 2025	$173K
September 2025	$182K
August 2025	$184K
June 2025	$182K
May 2025	$193K
2024
March 2024	$187K
February 2024	$172K
January 2024	$184K
2023
August 2023	$160K
July 2023	$162K
April 2023	$103K
March 2023	$101K
February 2023	$94K
2022
December 2022	$94K
November 2022	$94K
October 2022	$93K
2021
July 2021	$150K
June 2021	$177K
May 2021	$213K
April 2021	$202K
March 2021	$182K
January 2021	$206K
2020
December 2020	$208K
November 2020	$198K
October 2020	$189K
September 2020	$186K
August 2020	$177K
June 2020	$177K
May 2020	$174K
April 2020	$168K
March 2020	$285K
February 2020	$284K
January 2020	$282K
2019
December 2019	$263K
November 2019	$298K
October 2019	$290K
September 2019	$290K
August 2019	$292K
July 2019	$293K
June 2019	$286K
May 2019	$288K
April 2019	$272K
March 2019	$259K
February 2019	$256K
January 2019	$238K
2018
December 2018	$263K
November 2018	$247K
October 2018	$247K
September 2018	$230K
August 2018	$234K
July 2018	$237K
June 2018	$246K
May 2018	$239K
April 2018	$260K
March 2018	$258K
February 2018	$255K
January 2018	$249K
2017
December 2017	$254K
November 2017	$268K
October 2017	$258K
September 2017	$254K
August 2017	$253K
July 2017	$247K
June 2017	$253K
May 2017	$255K
April 2017	$252K
March 2017	$260K
February 2017	$262K
January 2017	$261K
2016
December 2016	$259K
November 2016	$241K
October 2016	$234K
September 2016	$255K
August 2016	$239K

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
17314 Jolly Cir, Windsor, VA	0.10	Single-Family Home	$490,000	07/16/26	4	3	1,749
17359 Courthouse Hwy, Windsor, VA	0.08	Single-Family Home	$435,000	10/27/25	3	2	1,782
16290 Trump Town Rd, Windsor, VA	1.02	Single-Family Home	$490,000	05/01/26	3	2	2,022
13067 Poor House Rd, Windsor, VA	0.78	Single-Family Home	$329,900	03/02/26	3	2	1,515
14014 Bowling Green Rd, Windsor, VA	1.58	Single-Family Home	$90,000	05/18/26	3	2	1,352
17009 Florida Ave, Windsor, VA	1.68	Single-Family Home	$310,000	08/03/26	3	1.5	1,438
10121 Magnolia Manor Ln, Windsor, VA	2.20	Single-Family Home	$65,601	04/23/26	3	2	2,222
14375 Uzzell Church Rd, Smithfield, VA	2.32	Single-Family Home	$186,000	03/09/26	3	1	1,576
16584 Bob White Rd, Smithfield, VA	2.14	Single-Family Home	$225,000	03/02/26	3	1	1,274
14494 Bowling Green Rd, Windsor, VA	2.35	Single-Family Home	$415,000	01/23/26	3	2	2,010

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
17359 Courthouse Hwy, Windsor, VA 23487	0.08	$444,200	3	2	1,782	Off Market
17314 Jolly Cir, Windsor, VA 23487	0.10	$490,000	4	3	1,749	Recently Sold
17479 Courthouse Hwy, Windsor, VA 23487	0.37	$624,990	4	2.5	2,775	For Sale
13067 Poor House Rd, Windsor, VA 23487	0.78	$329,900	3	2	1,515	Recently Sold
16621 Courthouse Hwy, Smithfield, VA 23430	0.78	$353,100	4	2.5	1,770	Off Market
16290 Trump Town Rd, Windsor, VA 23487	1.02	$490,000	3	2	2,022	Recently Sold
13540 Bowling Green Rd, Windsor, VA 23487	1.41	$249,100	3	1	960	Off Market
17044 N Carolina Ave, Windsor, VA 23487	1.49	$409,400	3	2	1,848	Off Market
17009 Mount Olive Ave, Windsor, VA 23487	1.50	$250,000	3	2	1,134	Recently Sold

Local Information

Map ViewExplore the area around Courthouse Hwy.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

2.66 acres

About this House

This single-family home is located at Courthouse Hwy, Windsor, VA. Courthouse Hwy is in Windsor, VA and in ZIP code 23487. This property has a lot size of 2.66 acres.

Courthouse Hwy, Windsor, VA 23487 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $204,500, with a rent estimate of $2,132/month.

Home Details for Courthouse Hwy

Property Information
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 2.66 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$568	$73,300

Home facts updated by county records

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 Courthouse Hwy

What is Courthouse Hwy estimated to be worth?
Trulia's estimated value for Courthouse Hwy in Windsor, VA is $204,500.
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 Courthouse Hwy?
The closest schools to Courthouse Hwy 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).
How big is the lot at Courthouse Hwy?
The lot at Courthouse Hwy in Windsor, VA is about 2.7 acres.