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 19165 Longview Dr estimated to be worth?

Trulia's estimated value for 19165 Longview Dr in Windsor, VA is $649,100 .

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 19165 Longview Dr?

The closest schools to 19165 Longview Dr in Windsor, VA are Smithfield High School (rated 5/10), Smithfield Middle School (rated 7/10), Windsor Elementary School (Pre-K, rated 7/10).

How big is the lot at 19165 Longview Dr?

The lot at 19165 Longview Dr in Windsor, VA is about 51 acres .

OFF MARKET

$649,100

Trulia Estimate

4 Beds
3 Baths
2,574 sqft (on 51 acres)

19165 Longview Dr, Windsor, VA 23487

Est. Refi. Payment $3,733/mo*

Refinance Your Home

Home Value

Trulia Estimate

$649K

Since last month

$4K (-0.6%)

Since last year

$72K (+12.5%)

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 +136% in the last 10 years

Month	Estimated value
2026
August 2026	$647K
July 2026	$651K
June 2026	$654K
May 2026	$659K
April 2026	$630K
March 2026	$657K
February 2026	$618K
January 2026	$607K
2025
December 2025	$612K
November 2025	$592K
October 2025	$601K
September 2025	$567K
August 2025	$575K
July 2025	$580K
June 2025	$570K
May 2025	$573K
April 2025	$578K
March 2025	$601K
February 2025	$598K
January 2025	$593K
2024
December 2024	$604K
November 2024	$607K
October 2024	$593K
September 2024	$601K
August 2024	$600K
July 2024	$609K
June 2024	$603K
May 2024	$600K
April 2024	$591K
March 2024	$577K
February 2024	$565K
January 2024	$550K
2023
December 2023	$533K
November 2023	$565K
October 2023	$544K
September 2023	$553K
August 2023	$549K
July 2023	$571K
June 2023	$527K
May 2023	$478K
April 2023	$469K
March 2023	$464K
February 2023	$455K
January 2023	$460K
2022
December 2022	$477K
November 2022	$487K
October 2022	$500K
September 2022	$502K
August 2022	$499K
July 2022	$519K
June 2022	$530K
May 2022	$541K
April 2022	$518K
March 2022	$471K
February 2022	$420K
January 2022	$429K
2021
December 2021	$415K
November 2021	$421K
October 2021	$410K
September 2021	$405K
August 2021	$408K
July 2021	$410K
June 2021	$410K
May 2021	$408K
April 2021	$333K
March 2021	$323K
February 2021	$318K
January 2021	$315K
2020
December 2020	$311K
November 2020	$311K
October 2020	$312K
September 2020	$306K
August 2020	$305K
July 2020	$304K
June 2020	$302K
May 2020	$299K
April 2020	$289K
March 2020	$288K
February 2020	$289K
January 2020	$293K
2019
December 2019	$291K
November 2019	$276K
October 2019	$285K
September 2019	$290K
August 2019	$277K
July 2019	$274K
June 2019	$276K
May 2019	$272K
April 2019	$273K
March 2019	$272K
February 2019	$260K
January 2019	$259K
2018
December 2018	$266K
November 2018	$260K
October 2018	$263K
September 2018	$260K
August 2018	$256K
July 2018	$260K
June 2018	$265K
May 2018	$277K
April 2018	$272K
March 2018	$279K
February 2018	$277K
January 2018	$288K
2017
December 2017	$285K
November 2017	$279K
October 2017	$271K
September 2017	$265K
August 2017	$257K
July 2017	$257K
June 2017	$248K
May 2017	$246K
April 2017	$257K
March 2017	$254K
February 2017	$245K
January 2017	$244K
2016
December 2016	$246K
November 2016	$240K
October 2016	$243K
September 2016	$251K
August 2016	$274K

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
18390 Oliver Dr, Smithfield, VA	0.74	Single-Family Home	$490,000	06/29/26	4	3	3,024
18517 Shady Pine Ln, Windsor, VA	0.95	Single-Family Home	$651,000	07/24/26	4	3	3,666
18513 Shady Pine Ln, Windsor, VA	0.81	Single-Family Home	$651,000	07/23/26	5	5	3,868
100 Longview Cir, Smithfield, VA	0.89	Single-Family Home	$470,000	12/22/25	4	2	2,100
304 Longview Cir, Smithfield, VA	1.02	Single-Family Home	$455,000	02/04/26	4	3	1,985
19263 Oliver Dr, Smithfield, VA	0.95	Single-Family Home	$392,000	01/15/26	3	2	1,744
6341 Godwin Blvd, Suffolk, VA	1.21	Single-Family Home	$750,000	01/28/26	5	3.5	2,592
1414 Wharf Hill Dr, Smithfield, VA	1.19	Single-Family Home	$668,235	12/23/25	5	3	3,047
1326 Wharf Hill Dr, Smithfield, VA	1.19	Single-Family Home	$634,504	04/07/26	5	4	3,691
20277 Cherry Grove Rd N, Smithfield, VA	1.65	Single-Family Home	$340,000	03/24/26	3	2.5	1,664

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
124 Holloway Dr, Smithfield, VA 23430	0.64	$675,000	4	2.5	2,620	For Sale
18390 Oliver Dr, Smithfield, VA 23430	0.74	$490,000	4	3	3,024	Recently Sold
19034 Oliver Drive, Smithfield, VA 23430	0.79	$562,900	4	2.5	2,750	Off Market
18513 Shady Pine Ln, Windsor, VA 23487	0.81	$651,000	5	5	3,868	Recently Sold
100 Longview Cir, Smithfield, VA 23430	0.89	$470,000	4	2	2,100	Recently Sold
19263 Oliver Dr, Smithfield, VA 23430	0.95	$392,000	3	2	1,744	Recently Sold
Shady Pine Ln, Suffolk, VA 23434	0.97	$785,000	-	-	-	Recently Sold
304 Longview Cir, Smithfield, VA 23430	1.02	$455,000	4	3	1,985	Recently Sold
1326 Wharf Hill Dr, Smithfield, VA 23430	1.19	$634,504	5	4	3,691	Recently Sold
1414 Wharf Hill Dr, Smithfield, VA 23430	1.19	$668,235	5	3	3,047	Recently Sold
Mm Highland At Mallory Pointe, Smithfield, VA 23430	1.19	$582,900	4	2.5	2,687	For Sale
Mm Rembert At Mallory Pointe, Smithfield, VA 23430	1.19	$619,900	4	2.5	3,175	For Sale

Local Information

Map ViewExplore the area around 19165 Longview 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

1976

Lot Size

51 acres

Living Area

2,574 sqft

Price/Sqft

$252

About this House

This single-family home is located at 19165 Longview Dr, Windsor, VA. 19165 Longview Dr is in Windsor, VA and in ZIP code 23487. This property has 4 bedrooms, 3 bathrooms and approximately 2,574 sqft of floor space. This property has a lot size of 51.00 acres and was built in 1976.

19165 Longview Dr, Windsor, VA 23487 is a 4 bedroom, 3 bathroom, 2,574 sqft single-family home built in 1976. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $649,100, with a rent estimate of $2,960/month.

Home Details for 19165 Longview Dr

Interior Features
Heating & Cooling Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 8

Exterior Features
Exterior Home Features Roof: AsphaltExterior: BrickFoundation Type: Crawl Raised

Property Information
Year Built Year Built: 1976
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 51.00 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$2,301	$412,900

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
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Frequently asked questions about 19165 Longview Dr

What is 19165 Longview Dr estimated to be worth?
Trulia's estimated value for 19165 Longview Dr in Windsor, VA is $649,100.
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 19165 Longview Dr?
The closest schools to 19165 Longview Dr in Windsor, VA are Smithfield High School (rated 5/10), Smithfield Middle School (rated 7/10), Windsor Elementary School (Pre-K, rated 7/10).
How big is the lot at 19165 Longview Dr?
The lot at 19165 Longview Dr in Windsor, VA is about 51 acres.