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

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 Whispering Pines Trl?

The closest schools to Whispering Pines Trl 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 Whispering Pines Trl?

The lot at Whispering Pines Trl in Windsor, VA is about 2.5 acres .

OFF MARKET

$2,500

Tax assessed value

Studio

Whispering Pines Trl, Windsor, VA 23487

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
9161 Whispering Pines Trl, Windsor, VA	0.10	Single-Family Home	$550,000	11/25/25	3	2.5	1,742
8193 Peanut Dr, Windsor, VA	1.55	Single-Family Home	$330,000	05/26/26	3	2	1,733
17009 Florida Ave, Windsor, VA	1.45	Single-Family Home	$310,000	08/03/26	3	1.5	1,438
10121 Magnolia Manor Ln, Windsor, VA	1.74	Single-Family Home	$65,601	04/23/26	3	2	2,222
15211 Strawberry Plains Rd, Ivor, VA	1.64	Single-Family Home	$425,000	06/18/26	3	2	1,950
15535 Strawberry Plains Rd, Ivor, VA	1.59	Single-Family Home	$500,300	07/23/26	3	2	1,664
17050 Florida Ave, Windsor, VA	1.38	Single-Family Home	$301,000	06/30/26	3	2	1,200
Strawberry Plains Rd, Ivor, VA	1.60	Single-Family Home	$182,500	06/02/26		-	-
16290 Trump Town Rd, Windsor, VA	2.48	Single-Family Home	$490,000	05/01/26	3	2	2,022
13531 Raynor Rd, Ivor, VA	2.68	Single-Family Home	$190,000	04/24/26	2	1	960

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
9161 Whispering Pines Trl, Windsor, VA 23487	0.10	$550,000	3	2.5	1,742	Recently Sold
8368 Whispering Pines Trl, Windsor, VA 23487	0.62	$400,000	3	2	2,208	For Sale
17050 Florida Ave, Windsor, VA 23487	1.38	$301,000	3	2	1,200	Recently Sold
17009 Florida Ave, Windsor, VA 23487	1.45	$310,000	3	1.5	1,438	Recently Sold

Local Information

Map ViewExplore the area around Whispering Pines Trl.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

2.5 acre lot

About this House

This single-family home is located at Whispering Pines Trl, Windsor, VA. Whispering Pines Trl is in Windsor, VA and in ZIP code 23487. This property has a lot size of 2.50 acres.

Whispering Pines Trl, 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 rent is $2,434/month.

Home Details for Whispering Pines Trl

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

Community
Units in Building: 1

Lot Information
Lot Area: 2.50 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$19	$2,500

Home facts updated by county records

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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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
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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 Whispering Pines Trl

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 Whispering Pines Trl?
The closest schools to Whispering Pines Trl 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 Whispering Pines Trl?
The lot at Whispering Pines Trl in Windsor, VA is about 2.5 acres.