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 12 Randolph Dr estimated to be worth?

Trulia's estimated value for 12 Randolph Dr in Windsor, VA is $586,200 .

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 12 Randolph Dr?

The closest schools to 12 Randolph Dr 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).

Does 12 Randolph Dr have air conditioning?

Yes, 12 Randolph Dr in Windsor, VA has air conditioning.

How big is the lot at 12 Randolph Dr?

The lot at 12 Randolph Dr in Windsor, VA is about 0.78 acres (33,976 sq ft).

OFF MARKET

$586,200

Trulia Estimate

5 Beds
4 Baths
3,162 sqft (on 0.78 acres)

12 Randolph Dr, Windsor, VA 23487

Est. Refi. Payment $3,379/mo*

Refinance Your Home

Home Value

Trulia Estimate

$586K

Since last month

$7K (+1.2%)

Since last year

$18K (+3.1%)

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 +63% in the last 10 years

Month	Estimated value
2026
August 2026	$585K
July 2026	$578K
June 2026	$589K
May 2026	$575K
April 2026	$560K
March 2026	$552K
February 2026	$540K
January 2026	$540K
2025
December 2025	$540K
November 2025	$545K
October 2025	$546K
September 2025	$558K
August 2025	$567K
July 2025	$583K
June 2025	$568K
May 2025	$560K
April 2025	$555K
March 2025	$552K
February 2025	$545K
January 2025	$534K
2024
December 2024	$535K
November 2024	$550K
October 2024	$550K
September 2024	$547K
August 2024	$545K
July 2024	$550K
June 2024	$551K
May 2024	$518K
April 2024	$511K
March 2024	$514K
February 2024	$509K
January 2024	$496K
2023
December 2023	$493K
November 2023	$494K
October 2023	$497K
September 2023	$496K
August 2023	$496K
July 2023	$491K
June 2023	$483K
May 2023	$495K
April 2023	$487K
March 2023	$484K
February 2023	$469K
January 2023	$467K
2022
December 2022	$467K
November 2022	$469K
October 2022	$477K
September 2022	$475K
August 2022	$475K
July 2022	$484K
June 2022	$485K
May 2022	$483K
April 2022	$478K
March 2022	$463K
February 2022	$449K
January 2022	$448K
2021
December 2021	$437K
November 2021	$441K
October 2021	$435K
September 2021	$441K
August 2021	$442K
July 2021	$445K
June 2021	$443K
May 2021	$433K
April 2021	$472K
March 2021	$457K
February 2021	$451K
January 2021	$448K
2020
December 2020	$447K
November 2020	$444K
October 2020	$445K
September 2020	$448K
August 2020	$438K
July 2020	$436K
June 2020	$435K
May 2020	$439K
April 2020	$439K
March 2020	$437K
February 2020	$437K
January 2020	$436K
2019
December 2019	$431K
November 2019	$380K
October 2019	$373K
September 2019	$370K
August 2019	$364K
July 2019	$361K
June 2019	$359K
May 2019	$359K
April 2019	$355K
March 2019	$349K
February 2019	$351K
January 2019	$346K
2018
December 2018	$351K
November 2018	$340K
October 2018	$335K
September 2018	$340K
August 2018	$346K
July 2018	$353K
June 2018	$353K
May 2018	$344K
April 2018	$347K
March 2018	$346K
February 2018	$345K
January 2018	$342K
2017
December 2017	$356K
November 2017	$357K
October 2017	$346K
September 2017	$351K
August 2017	$347K
July 2017	$357K
June 2017	$348K
May 2017	$350K
April 2017	$342K
March 2017	$342K
February 2017	$347K
January 2017	$345K
2016
December 2016	$347K
November 2016	$349K
October 2016	$352K
September 2016	$353K
August 2016	$359K

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
26 N Court St, Windsor, VA	0.23	Single-Family Home	$355,000	08/26/26	4	2	1,739
17 Randolph Dr, Windsor, VA	0.04	Single-Family Home	$400,000	08/05/26	4	2	1,300
10 Church St, Windsor, VA	0.28	Single-Family Home	$349,900	12/04/25	3	2.5	2,000
112 S Court St, Windsor, VA	0.52	Single-Family Home	$345,000	11/18/25	3	2.5	1,400
16 Holland Dr, Windsor, VA	0.34	Single-Family Home	$419,900	04/20/26	3	2	2,033
11 Holland Ln, Windsor, VA	0.46	Single-Family Home	$440,000	06/26/26	3	2	1,635
25 E Griffin St, Windsor, VA	0.52	Single-Family Home	$340,000	05/11/26	4	1	2,133
11072 Wythe Dr, Windsor, VA	0.99	Single-Family Home	$507,000	06/05/26	5	3	2,997
23068 Andrew Ct, Windsor, VA	0.95	Single-Family Home	$456,500	02/25/26	5	3	2,797
53 Pine Ln, Windsor, VA	0.58	Single-Family Home	$384,900	05/05/26	3	2	1,554

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
17 Randolph Dr, Windsor, VA 23487	0.04	$400,000	4	2	1,300	Recently Sold
26 N Court St, Windsor, VA 23487	0.23	$355,000	4	2	1,739	Recently Sold
24 N Court St, Windsor, VA 23487	0.24	$370,000	3	1.5	1,785	Recently Sold
10 Church St, Windsor, VA 23487	0.28	$349,900	3	2.5	2,000	Recently Sold
Par A Holland Dr, Windsor, VA 23487	0.33	$59,500	-	-	-	Recently Sold
4 S Court St, Windsor, VA 23487	0.34	$45,000	-	-	-	Recently Sold
16 W Windsor Blvd, Windsor, VA 23487	0.33	$225,000	3	2	1,076	Recently Sold
16 Holland Dr, Windsor, VA 23487	0.34	$419,900	3	2	2,033	Recently Sold
47AC Holland Dr, Windsor, VA 23487	0.37	$588,900	4	2.5	2,342	For Sale
105 S Court St, Windsor, VA 23487	0.46	$354,999	3	2.5	1,480	Recently Sold
66 Church St, Windsor, VA 23487	0.45	$150,000	-	-	-	Recently Sold
40 Holland Ln, Windsor, VA 23487	0.48	$200,000	-	-	-	For Sale

Local Information

Map ViewExplore the area around 12 Randolph 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

1982

Lot Size

0.78 acres

Living Area

3,162 sqft

Price/Sqft

$185

Parking

Garage

About this House

This single-family home is located at 12 Randolph Dr, Windsor, VA. 12 Randolph Dr is in Windsor, VA and in ZIP code 23487. This property has 5 bedrooms, 4 bathrooms and approximately 3,162 sqft of floor space. This property has a lot size of 0.78 acres and was built in 1982.

12 Randolph Dr, Windsor, VA 23487 is a 5 bedroom, 4 bathroom, 3,162 sqft single-family home built in 1982. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $586,200, with a rent estimate of $2,978/month.

Home Details for 12 Randolph Dr

Interior Features
Heating & Cooling Heating: OilAir ConditioningCooling System: CentralHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 9
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: AsphaltExterior: BrickFoundation Type: Crawl Raised
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1982
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.78 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$4,475	$577,400

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

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Frequently asked questions about 12 Randolph Dr

What is 12 Randolph Dr estimated to be worth?
Trulia's estimated value for 12 Randolph Dr in Windsor, VA is $586,200.
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 12 Randolph Dr?
The closest schools to 12 Randolph Dr 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).
Does 12 Randolph Dr have air conditioning?
Yes, 12 Randolph Dr in Windsor, VA has air conditioning.
How big is the lot at 12 Randolph Dr?
The lot at 12 Randolph Dr in Windsor, VA is about 0.78 acres (33,976 sq ft).