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 18257 Quaker Rd estimated to be worth?

Trulia's estimated value for 18257 Quaker Rd in Windsor, VA is $373,500 .

What is the price history for 18257 Quaker Rd?

18257 Quaker Rd in Windsor, VA last sold for $94,500 in April 2015.

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 .

How big is the lot at 18257 Quaker Rd?

The lot at 18257 Quaker Rd in Windsor, VA is about 2 acres .

OFF MARKET

$373,500

Trulia Estimate

4 Beds
2 Baths
2,240 sqft (on 2 acres)

18257 Quaker Rd, Windsor, VA 23487

Est. Refi. Payment $2,303/mo*

Refinance Your Home

Currently Off Market - Sold Apr 21, 2015 for $94,500

Home Value

Trulia Estimate

$374K

Since last month

$2K (-0.6%)

Since last year

$12K (+3.4%)

Since last sale

$278K (+294.2%)

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 +278% in the last 10 years

Month	Estimated value
2026
September 2026	$373K
August 2026	$375K
July 2026	$368K
June 2026	$375K
May 2026	$372K
April 2026	$363K
March 2026	$360K
February 2026	$354K
January 2026	$345K
2025
December 2025	$350K
November 2025	$352K
October 2025	$350K
September 2025	$360K
August 2025	$364K
July 2025	$365K
June 2025	$352K
May 2025	$349K
April 2025	$349K
March 2025	$350K
February 2025	$347K
January 2025	$344K
2024
December 2024	$348K
November 2024	$352K
October 2024	$364K
September 2024	$363K
August 2024	$367K
July 2024	$376K
June 2024	$375K
May 2024	$370K
April 2024	$363K
March 2024	$358K
February 2024	$350K
January 2024	$336K
2023
December 2023	$333K
November 2023	$339K
October 2023	$336K
September 2023	$345K
August 2023	$341K
July 2023	$341K
June 2023	$333K
May 2023	$333K
April 2023	$329K
March 2023	$329K
February 2023	$329K
January 2023	$337K
2022
December 2022	$339K
November 2022	$340K
October 2022	$346K
September 2022	$344K
August 2022	$343K
July 2022	$348K
June 2022	$351K
May 2022	$351K
April 2022	$346K
March 2022	$340K
February 2022	$336K
January 2022	$334K
2021
December 2021	$328K
November 2021	$332K
October 2021	$326K
September 2021	$330K
August 2021	$330K
July 2021	$329K
June 2021	$315K
May 2021	$284K
April 2021	$279K
March 2021	$274K
February 2021	$271K
January 2021	$268K
2020
December 2020	$267K
November 2020	$264K
October 2020	$262K
September 2020	$260K
August 2020	$260K
July 2020	$260K
June 2020	$260K
May 2020	$258K
April 2020	$257K
March 2020	$259K
February 2020	$258K
January 2020	$259K
2019
December 2019	$257K
November 2019	$277K
October 2019	$274K
September 2019	$273K
August 2019	$275K
July 2019	$273K
June 2019	$266K
May 2019	$269K
April 2019	$262K
March 2019	$259K
February 2019	$265K
January 2019	$260K
2018
December 2018	$260K
November 2018	$260K
October 2018	$255K
September 2018	$254K
August 2018	$256K
July 2018	$247K
June 2018	$227K
May 2018	$173K
April 2018	$121K
March 2018	$105K
February 2018	$104K
January 2018	$104K
2017
December 2017	$103K
November 2017	$103K
October 2017	$103K
September 2017	$102K
August 2017	$102K
July 2017	$102K
June 2017	$101K
May 2017	$101K
April 2017	$101K
March 2017	$100K
February 2017	$100K
January 2017	$100K
2016
December 2016	$99K
November 2016	$99K
October 2016	$99K
September 2016	$98K

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
17381 Carroll Bridge Rd, Smithfield, VA	1.03	Single-Family Home	$549,000	08/11/26	4	4	2,529
14494 Bowling Green Rd, Windsor, VA	1.71	Single-Family Home	$415,000	01/23/26	3	2	2,010
17403 Carroll Bridge Rd, Windsor, VA	0.92	Single-Family Home	$549,000	08/10/26	4	3.5	3,918
14014 Bowling Green Rd, Windsor, VA	2.44	Single-Family Home	$90,000	05/18/26	3	2	1,352
18390 Oliver Dr, Smithfield, VA	2.10	Single-Family Home	$490,000	06/29/26	4	3	3,024
202 Appaloosa Way, Smithfield, VA	2.07	Single-Family Home	$599,000	09/14/26	3	2.5	2,304
15410 Burnt Mill Ln, Windsor, VA	2.38	Single-Family Home	$260,000	07/15/26	3	2	1,927
17134 Longview Dr, Smithfield, VA	2.22	Single-Family Home	$665,000	10/27/25	3	2	2,500
100 Longview Cir, Smithfield, VA	2.53	Single-Family Home	$470,000	12/22/25	4	2	2,100
15522 Carroll Bridge Rd, Smithfield, VA	2.46	Single-Family Home	$548,000	10/10/25	4	2	2,074

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
16311 Porters Ln, Windsor, VA 23487	0.08	$239,500	Studio	-	-	Off Market

Local Information

Map ViewExplore the area around 18257 Quaker Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2002

2 acre lot

2,240 sqft

$167/sqft

About this House

LARGE 4 BEDROOM, 2 BATH RANCH HOME ON 2 ACRES IN WINDSOR. BUILT IN 2006 AND HAS 2240 SQUARE FEET, BACK DECK AND PAVED DRIVEWAY.

18257 Quaker Rd, Windsor, VA 23487 is a 4 bedroom, 2 bathroom, 2,240 sqft single-family home built in 2002. It last sold for $94,500 on Apr 21, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $373,500, with a rent estimate of $2,550/month.

Home Details for 18257 Quaker Rd

Interior Features
Heating & Cooling Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 1Floors: Carpet, Linoleum Vinyl
Interior Details Number of Rooms: 7
Appliances & Utilities DishwasherWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: VinylFoundation Type: Crawl Raised

Property Information
Year Built Year Built: 2002
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community
Units in Building: 1

Lot Information
Lot Area: 2.00 acres

Price and Tax history

Date	Event	Price
Apr 21, 2015 Source: N/A	Sold	$94,500
Mar 13, 2015 Source: Agent Provided	PriceChange	$94,500 Price decreased by 9%
Feb 28, 2015 Source: Agent Provided	PriceChange	$103,900 Price decreased by 9%
Jan 23, 2015 Source: Agent Provided	PriceChange	$113,900 Price decreased by 8%
Dec 24, 2014 Source: Agent Provided	PriceChange	$123,500 Price decreased by 8%
Dec 2, 2014 Source: Agent Provided	PriceChange	$134,900 Price decreased by 9%
Nov 1, 2014 Source: Agent Provided	PriceChange	$148,500 Price decreased by 10%
Oct 5, 2014 Source: Agent Provided	Listed For Sale	$165,000

Year	Property tax	Tax assessment
2025	$2,287	$295,100

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 18257 Quaker Rd

What is 18257 Quaker Rd estimated to be worth?
Trulia's estimated value for 18257 Quaker Rd in Windsor, VA is $373,500.
What is the price history for 18257 Quaker Rd?
18257 Quaker Rd in Windsor, VA last sold for $94,500 in April 2015.
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.
How big is the lot at 18257 Quaker Rd?
The lot at 18257 Quaker Rd in Windsor, VA is about 2 acres.