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 14 Randolph Dr estimated to be worth?

Trulia's estimated value for 14 Randolph Dr in Windsor, VA is $375,500 .

What is the price history for 14 Randolph Dr?

14 Randolph Dr in Windsor, VA last sold for $243,000 in June 2010.

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 .

Does 14 Randolph Dr have air conditioning?

Yes, 14 Randolph Dr in Windsor, VA has air conditioning.

How big is the lot at 14 Randolph Dr?

The lot at 14 Randolph Dr in Windsor, VA is about 0.36 acres (15,681 sq ft).

OFF MARKET

$375,500

Trulia Estimate

3 Beds
2 Baths
1,510 sqft (on 0.36 acres)

14 Randolph Dr, Windsor, VA 23487

Est. Refi. Payment $2,179/mo*

Refinance Your Home

Currently Off Market - Sold Jun 28, 2010 for $243,000

Home Value

Trulia Estimate

$376K

Since last month

$700 (+0.2%)

Since last year

$11K (+3%)

Since last sale

$132K (+54.4%)

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 +69% in the last 10 years

Month	Estimated value
2026
August 2026	$375K
July 2026	$374K
June 2026	$375K
May 2026	$373K
April 2026	$368K
March 2026	$365K
February 2026	$362K
January 2026	$357K
2025
December 2025	$355K
November 2025	$360K
October 2025	$359K
September 2025	$364K
August 2025	$364K
July 2025	$367K
June 2025	$360K
May 2025	$355K
April 2025	$357K
March 2025	$351K
February 2025	$347K
January 2025	$343K
2024
December 2024	$343K
November 2024	$346K
October 2024	$348K
September 2024	$345K
August 2024	$344K
July 2024	$348K
June 2024	$349K
May 2024	$346K
April 2024	$344K
March 2024	$345K
February 2024	$341K
January 2024	$335K
2023
December 2023	$331K
November 2023	$330K
October 2023	$332K
September 2023	$332K
August 2023	$331K
July 2023	$329K
June 2023	$321K
May 2023	$332K
April 2023	$328K
March 2023	$327K
February 2023	$323K
January 2023	$324K
2022
December 2022	$324K
November 2022	$325K
October 2022	$329K
September 2022	$326K
August 2022	$324K
July 2022	$328K
June 2022	$327K
May 2022	$327K
April 2022	$323K
March 2022	$319K
February 2022	$317K
January 2022	$314K
2021
December 2021	$309K
November 2021	$311K
October 2021	$306K
September 2021	$307K
August 2021	$307K
July 2021	$306K
June 2021	$304K
May 2021	$299K
April 2021	$300K
March 2021	$284K
February 2021	$283K
January 2021	$280K
2020
December 2020	$284K
November 2020	$284K
October 2020	$280K
September 2020	$288K
August 2020	$275K
July 2020	$275K
June 2020	$271K
May 2020	$275K
April 2020	$265K
March 2020	$266K
February 2020	$265K
January 2020	$264K
2019
December 2019	$262K
November 2019	$255K
October 2019	$248K
September 2019	$250K
August 2019	$248K
July 2019	$248K
June 2019	$245K
May 2019	$245K
April 2019	$245K
March 2019	$244K
February 2019	$247K
January 2019	$247K
2018
December 2018	$248K
November 2018	$247K
October 2018	$245K
September 2018	$245K
August 2018	$246K
July 2018	$246K
June 2018	$245K
May 2018	$249K
April 2018	$247K
March 2018	$244K
February 2018	$243K
January 2018	$241K
2017
December 2017	$235K
November 2017	$235K
October 2017	$234K
September 2017	$233K
August 2017	$233K
July 2017	$235K
June 2017	$234K
May 2017	$234K
April 2017	$233K
March 2017	$232K
February 2017	$232K
January 2017	$232K
2016
December 2016	$232K
November 2016	$231K
October 2016	$228K
September 2016	$224K
August 2016	$221K

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
17 Randolph Dr, Windsor, VA	0.04	Single-Family Home	$400,000	08/05/26	4	2	1,300
16 Holland Dr, Windsor, VA	0.33	Single-Family Home	$419,900	04/20/26	3	2	2,033
24129 Johnson Ave, Windsor, VA	0.49	Single-Family Home	$315,000	08/21/26	3	2	1,225
10 Church St, Windsor, VA	0.29	Single-Family Home	$349,900	12/04/25	3	2.5	2,000
54 Pine Ln, Windsor, VA	0.54	Single-Family Home	$315,000	04/30/26	3	2	1,557
11 Holland Ln, Windsor, VA	0.44	Single-Family Home	$440,000	06/26/26	3	2	1,635
53 Pine Ln, Windsor, VA	0.57	Single-Family Home	$384,900	05/05/26	3	2	1,554
10174 Bank St, Windsor, VA	0.70	Single-Family Home	$384,999	07/27/26	3	2	1,725
112 S Court St, Windsor, VA	0.53	Single-Family Home	$345,000	11/18/25	3	2.5	1,400
203 Hidden Acres Cir, Windsor, VA	0.77	Single-Family Home	$357,900	09/15/25	3	2	1,715

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
10 Church St, Windsor, VA 23487	0.29	$349,900	3	2.5	2,000	Recently Sold
24 N Court St, Windsor, VA 23487	0.26	$370,000	3	1.5	1,785	Recently Sold
Par A Holland Dr, Windsor, VA 23487	0.32	$59,500	-	-	-	Recently Sold
16 Holland Dr, Windsor, VA 23487	0.33	$419,900	3	2	2,033	Recently Sold
47AC Holland Dr, Windsor, VA 23487	0.36	$588,900	4	2.5	2,342	For Sale
4 S Court St, Windsor, VA 23487	0.36	$45,000	-	-	-	Recently Sold
16 W Windsor Blvd, Windsor, VA 23487	0.36	$225,000	3	2	1,076	Recently Sold
66 Church St, Windsor, VA 23487	0.43	$150,000	-	-	-	Recently Sold
40 Holland Ln, Windsor, VA 23487	0.45	$200,000	-	-	-	For Sale
105 S Court St, Windsor, VA 23487	0.47	$354,999	3	2.5	1,480	Recently Sold
24129 Johnson Ave, Windsor, VA 23487	0.49	$315,000	3	2	1,225	Recently Sold

Local Information

Map ViewExplore the area around 14 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

2003

Lot Size

0.36 acres

Living Area

1,510 sqft

Price/Sqft

$249

Parking

Garage

About this House

Brick Ranch for the starting up or paring down. Master Bedroom with Tray Ceiling, walk-in closet and private Bath. Cul-de-Sac Lot with privacy courtyard Style patio. New HVAC. Bedrooms have New Carpet.

14 Randolph Dr, Windsor, VA 23487 is a 3 bedroom, 2 bathroom, 1,510 sqft single-family home built in 2003. It last sold for $243,000 on Jun 28, 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $375,500, with a rent estimate of $2,177/month.

Home Details for 14 Randolph Dr

Interior Features
Heating & Cooling Heating: OilAir ConditioningCooling System: CentralHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 6
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: 2003
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.36 acres

Price and Tax history

Date	Event	Price
Aug 6, 2020 Source: Agent Provided	ListingRemoved	$274,900
May 22, 2020 Source: Agent Provided	PriceChange	$274,900 Price decreased by 1%
May 15, 2020 Source: Agent Provided	Listed For Sale	$279,000
Jun 28, 2010 Source: N/A	Sold	$243,000
Jan 9, 2010 Source: Agent Provided	Listed For Sale	$249,975
Sep 2, 2003 Source: N/A	Sold	$150,000

Year	Property tax	Tax assessment
2025	$2,322	$299,600

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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LGBTQ Local Legal Protections

Frequently asked questions about 14 Randolph Dr

What is 14 Randolph Dr estimated to be worth?
Trulia's estimated value for 14 Randolph Dr in Windsor, VA is $375,500.
What is the price history for 14 Randolph Dr?
14 Randolph Dr in Windsor, VA last sold for $243,000 in June 2010.
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.
Does 14 Randolph Dr have air conditioning?
Yes, 14 Randolph Dr in Windsor, VA has air conditioning.
How big is the lot at 14 Randolph Dr?
The lot at 14 Randolph Dr in Windsor, VA is about 0.36 acres (15,681 sq ft).