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 14044 Poor House Rd estimated to be worth?

Trulia's estimated value for 14044 Poor House Rd in Windsor, VA is $595,000 .

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 14044 Poor House Rd?

The closest schools to 14044 Poor House Rd in Windsor, VA are Smithfield High School (rated 5/10), Smithfield Middle School (rated 7/10), Windsor Elementary School (Pre-K, rated 7/10).

Does 14044 Poor House Rd have air conditioning?

Yes, 14044 Poor House Rd in Windsor, VA has air conditioning.

How big is the lot at 14044 Poor House Rd?

The lot at 14044 Poor House Rd in Windsor, VA is about 1.4 acres .

OFF MARKET

$595,000

Trulia Estimate

4 Beds
3.5 Baths
3,100 sqft (on 1.40 acres)

14044 Poor House Rd, Windsor, VA 23487

Est. Refi. Payment $3,605/mo*

Refinance Your Home

Home Value

Trulia Estimate

$595K

Since last month

$12K (+2.1%)

Since last year

$18K (+3.2%)

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 +77% in the last 10 years

Month	Estimated value
2026
August 2026	$599K
August 2026	$596K
July 2026	$587K
June 2026	$593K
May 2026	$590K
April 2026	$587K
March 2026	$579K
February 2026	$579K
January 2026	$566K
2025
December 2025	$567K
November 2025	$565K
October 2025	$568K
September 2025	$572K
August 2025	$580K
July 2025	$580K
June 2025	$577K
May 2025	$577K
April 2025	$565K
March 2025	$555K
February 2025	$550K
January 2025	$542K
2024
December 2024	$542K
November 2024	$552K
October 2024	$570K
September 2024	$565K
August 2024	$568K
July 2024	$567K
June 2024	$559K
May 2024	$537K
April 2024	$531K
March 2024	$530K
February 2024	$525K
January 2024	$508K
2023
December 2023	$503K
November 2023	$508K
October 2023	$503K
September 2023	$505K
August 2023	$508K
July 2023	$506K
June 2023	$497K
May 2023	$505K
April 2023	$497K
March 2023	$485K
February 2023	$473K
January 2023	$472K
2022
December 2022	$471K
November 2022	$470K
October 2022	$476K
September 2022	$473K
August 2022	$471K
July 2022	$478K
June 2022	$481K
May 2022	$479K
April 2022	$475K
March 2022	$467K
February 2022	$460K
January 2022	$458K
2021
December 2021	$453K
November 2021	$454K
October 2021	$446K
September 2021	$448K
August 2021	$445K
July 2021	$444K
June 2021	$439K
May 2021	$428K
April 2021	$403K
March 2021	$395K
February 2021	$393K
January 2021	$387K
2020
December 2020	$384K
November 2020	$381K
October 2020	$370K
September 2020	$363K
August 2020	$375K
July 2020	$374K
June 2020	$375K
May 2020	$371K
April 2020	$364K
March 2020	$361K
February 2020	$359K
January 2020	$361K
2019
December 2019	$355K
November 2019	$384K
October 2019	$377K
September 2019	$369K
August 2019	$366K
July 2019	$367K
June 2019	$370K
May 2019	$372K
April 2019	$364K
March 2019	$358K
February 2019	$354K
January 2019	$353K
2018
December 2018	$358K
November 2018	$347K
October 2018	$352K
September 2018	$352K
August 2018	$369K
July 2018	$366K
June 2018	$345K
May 2018	$342K
April 2018	$343K
March 2018	$341K
February 2018	$339K
January 2018	$340K
2017
December 2017	$343K
November 2017	$343K
October 2017	$345K
September 2017	$356K
August 2017	$353K
July 2017	$356K
June 2017	$355K
May 2017	$352K
April 2017	$339K
March 2017	$344K
February 2017	$342K
January 2017	$340K
2016
December 2016	$341K
November 2016	$341K
October 2016	$336K
September 2016	$338K

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
14014 Bowling Green Rd, Windsor, VA	0.72	Single-Family Home	$90,000	05/18/26	3	2	1,352
14494 Bowling Green Rd, Windsor, VA	0.94	Single-Family Home	$415,000	01/23/26	3	2	2,010
16584 Bob White Rd, Smithfield, VA	0.65	Single-Family Home	$225,000	03/02/26	3	1	1,274
13067 Poor House Rd, Windsor, VA	0.93	Single-Family Home	$329,900	03/02/26	3	2	1,515
14375 Uzzell Church Rd, Smithfield, VA	1.09	Single-Family Home	$186,000	03/09/26	3	1	1,576
17314 Jolly Cir, Windsor, VA	1.56	Single-Family Home	$490,000	07/16/26	4	3	1,749
17359 Courthouse Hwy, Windsor, VA	1.51	Single-Family Home	$435,000	10/27/25	3	2	1,782
18688 Orbit Rd, Windsor, VA	1.62	Single-Family Home	$70,000	08/12/26	3	1	1,152
5009 Melanie Ct, Suffolk, VA	1.92	Single-Family Home	$511,240	08/27/26	4	2.5	2,804
15492 Carroll Bridge Rd, Smithfield, VA	2.10	Single-Family Home	$690,000	03/26/26	3	2.5	3,042

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
14068 Bowling Green Rd, Windsor, VA 23487	0.68	$383,100	3	2	1,664	Off Market
14014 Bowling Green Rd, Windsor, VA 23487	0.72	$90,000	3	2	1,352	Recently Sold
93AC Courthouse Hwy, Windsor, VA 23487	0.85	$75,000	-	-	-	For Sale
13540 Bowling Green Rd, Windsor, VA 23487	0.88	$249,100	3	1	960	Off Market
14494 Bowling Green Rd, Windsor, VA 23487	0.94	$415,000	3	2	2,010	Recently Sold
13067 Poor House Rd, Windsor, VA 23487	0.93	$329,900	3	2	1,515	Recently Sold
16621 Courthouse Hwy, Smithfield, VA 23430	0.99	$349,600	4	2.5	1,770	Off Market
16010 Courthouse Hwy, Smithfield, VA 23430	1.20	$100,000	-	-	-	Recently Sold
17359 Courthouse Hwy, Windsor, VA 23487	1.51	$444,200	3	2	1,782	Off Market

Local Information

Map ViewExplore the area around 14044 Poor House Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2010

1.4 acre lot

3,100 sqft

$192/sqft

Garage

About this House

This single-family home is located at 14044 Poor House Rd, Windsor, VA. 14044 Poor House Rd is in Windsor, VA and in ZIP code 23487. This property has 4 bedrooms, 4 bathrooms and approximately 3,100 sqft of floor space. This property has a lot size of 1.40 acres and was built in 2010.

14044 Poor House Rd, Windsor, VA 23487 is a 4 bedroom, 4 bathroom, 3,100 sqft single-family home built in 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $595,000, with a rent estimate of $3,318/month.

Home Details for 14044 Poor House Rd

Interior Features
Heating & Cooling Heating: OilAir ConditioningCooling System: CentralHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 1.5
Interior Details Number of Rooms: 8
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: AsphaltFoundation Type: Crawl Raised
Parking & Garage GarageParking: Garage Attached, Garage Detached

Property Information
Year Built Year Built: 2010
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 1.40 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$4,169	$537,900

Home facts updated by county records

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

4MoM

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
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LGBTQ Local Legal Protections

Frequently asked questions about 14044 Poor House Rd

What is 14044 Poor House Rd estimated to be worth?
Trulia's estimated value for 14044 Poor House Rd in Windsor, VA is $595,000.
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 14044 Poor House Rd?
The closest schools to 14044 Poor House Rd in Windsor, VA are Smithfield High School (rated 5/10), Smithfield Middle School (rated 7/10), Windsor Elementary School (Pre-K, rated 7/10).
Does 14044 Poor House Rd have air conditioning?
Yes, 14044 Poor House Rd in Windsor, VA has air conditioning.
How big is the lot at 14044 Poor House Rd?
The lot at 14044 Poor House Rd in Windsor, VA is about 1.4 acres.