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 23366 Caseys Cir estimated to be worth?

Trulia's estimated value for 23366 Caseys Cir in Windsor, VA is $291,700 .

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 23366 Caseys Cir?

The closest schools to 23366 Caseys Cir 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 23366 Caseys Cir have air conditioning?

Yes, 23366 Caseys Cir in Windsor, VA has air conditioning.

OFF MARKET

23366 Caseys Cir
Windsor, VA 23487

3 Beds
2 Baths

$291,700

Trulia Estimate

as of Aug 23, 2026

Est. Refi. Payment $1,737/mo*

Refinance Your Home

$291,700

Trulia Estimate

as of Aug 23, 2026

Est. Refi. Payment $1,737/mo*

Refinance Your Home

3 Beds

2 Baths

Home Value

Trulia Estimate

$292K

Since last month

$7K (+2.5%)

Since last year

$34K (+13.1%)

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 +110% in the last 10 years

Month	Estimated value
2026
August 2026	$292K
July 2026	$285K
June 2026	$312K
May 2026	$312K
April 2026	$295K
March 2026	$341K
February 2026	$290K
January 2026	$279K
2025
December 2025	$296K
November 2025	$294K
October 2025	$259K
September 2025	$271K
August 2025	$258K
July 2025	$251K
June 2025	$270K
May 2025	$270K
April 2025	$277K
March 2025	$278K
February 2025	$270K
January 2025	$276K
2024
December 2024	$237K
November 2024	$248K
October 2024	$260K
September 2024	$273K
August 2024	$306K
July 2024	$300K
2023
September 2023	$294K
August 2023	$289K
July 2023	$297K
June 2023	$291K
May 2023	$321K
April 2023	$327K
March 2023	$321K
February 2023	$310K
January 2023	$312K
2022
December 2022	$317K
November 2022	$320K
October 2022	$327K
September 2022	$322K
August 2022	$320K
July 2022	$327K
June 2022	$331K
May 2022	$351K
April 2022	$331K
March 2022	$329K
February 2022	$291K
January 2022	$285K
2021
December 2021	$295K
November 2021	$291K
October 2021	$282K
September 2021	$277K
August 2021	$266K
July 2021	$257K
June 2021	$243K
April 2021	$205K
March 2021	$187K
February 2021	$191K
January 2021	$199K
2020
December 2020	$202K
November 2020	$200K
October 2020	$192K
September 2020	$178K
August 2020	$150K
June 2020	$154K
May 2020	$152K
April 2020	$144K
2019
December 2019	$139K

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
9545 W Windsor Blvd, Windsor, VA	0.11	Single-Family Home	$250,000	08/11/26	2	1	1,086
23227 Stave Mill Rd, Windsor, VA	0.24	Single-Family Home	$150,000	03/25/26	2	1	750
10176 Bank St, Windsor, VA	0.97	Single-Family Home	$384,999	07/28/26	3	2	1,725
10174 Bank St, Windsor, VA	0.97	Single-Family Home	$384,999	07/27/26	3	2	1,725
24 N Court St, Windsor, VA	1.08	Single-Family Home	$370,000	04/07/26	3	1.5	1,785
16 W Windsor Blvd, Windsor, VA	1.09	Single-Family Home	$225,000	12/30/25	3	2	1,076
10419 Sylvia Cir, Windsor, VA	1.16	Single-Family Home	$410,000	01/23/26	3	2	2,141
24456 Walters Hwy, Windsor, VA	1.04	Single-Family Home	$335,000	07/17/26	3	2.5	1,600
24465 Curve Dr, Windsor, VA	1.19	Single-Family Home	$178,000	12/15/25	3	1.5	926
40 W Windsor Blvd, Windsor, VA	0.92	Single-Family Home	$198,000	06/22/26	2	1	962

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
9545 W Windsor Blvd, Windsor, VA 23487	0.11	$250,000	2	1	1,086	Recently Sold
23227 Stave Mill Rd, Windsor, VA 23487	0.24	$150,000	2	1	750	Recently Sold
20 Clydes Ln #20, Windsor, VA 23487	0.82	$91,900	2	2	930	For Sale
68 Clydes Ln #68, Windsor, VA 23487	0.82	$82,900	3	2	1,140	For Sale
Lot 2 Walters Hwy #2, Windsor, VA 23487	0.95	-	-	-	-	Off Market
15 Courthouse Hwy, Windsor, VA 23487	0.92	$200,000	-	-	-	For Sale
10174 Bank St, Windsor, VA 23487	0.97	$384,999	3	2	1,725	Recently Sold
10176 Bank St, Windsor, VA 23487	0.97	$384,999	3	2	1,725	Recently Sold
Prcl 1 Bank St, Windsor, VA 23487	1.02	-	-	-	-	Off Market
24456 Walters Hwy, Windsor, VA 23487	1.04	$335,000	3	2.5	1,600	Recently Sold
18 B Ave, Windsor, VA 23487	1.03	$230,000	6	2	3,600	Recently Sold
14 B Ave, Windsor, VA 23487	1.03	$265,000	2	1	1,232	For Sale

Local Information

Map ViewExplore the area around 23366 Caseys Cir.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1985

About this House

This single-family home is located at 23366 Caseys Cir, Windsor, VA. 23366 Caseys Cir is in Windsor, VA and in ZIP code 23487. This property has 3 bedrooms and 2 bathrooms. This property was built in 1985.

23366 Caseys Cir, Windsor, VA 23487 is a 3 bedroom, 2 bathroom single-family home built in 1985. More recently, it was listed as a rental in December 2019 with an asking price of $900 per month. That rental listing was removed on January 4, 2020. It is currently off market. The Trulia Estimate is $291,700, with a rent estimate of $1,963/month.

Home Details for 23366 Caseys Cir

Interior Features
Heating & Cooling Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Interior Details Types of Rooms: Walk In Closet, Pantry
Appliances & Utilities DishwasherRefrigerator
Levels, Entrance, & Accessibility Floors: Hardwood, Linoleum Vinyl

Exterior Features
Exterior Home Features Roof: AsphaltDeck

Property Information
Year Built Year Built: 1985
Property Type / Style Property Type: Single Family Home

Price and Tax history

Date	Event	Price
Jan 4, 2020 Source: Agent Provided	ListingRemoved	$900
Dec 4, 2019 Source: Agent Provided	Listed For Rent	$900

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

LGBTQ Local Legal Protections

Frequently asked questions about 23366 Caseys Cir

What is 23366 Caseys Cir estimated to be worth?
Trulia's estimated value for 23366 Caseys Cir in Windsor, VA is $291,700.
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 23366 Caseys Cir?
The closest schools to 23366 Caseys Cir 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 23366 Caseys Cir have air conditioning?
Yes, 23366 Caseys Cir in Windsor, VA has air conditioning.