Is parking easy in Windsor, MO?

As of early 2026, 100% of users say parking is easy

Are yards well-kept in Windsor, MO?

As of early 2026, 100% of users say yards are well-kept

Is Windsor, MO dog-friendly?

As of early 2026, 93% of users say it's dog friendly

Do kids play outside in Windsor, MO?

As of early 2026, 90% of users say kids play outside

Does Windsor, MO show holiday spirit?

As of early 2026, 83% of users say there's holiday spirit

Is a car needed in Windsor, MO?

As of early 2026, 82% of users say car is needed

Would people walk alone at night in Windsor, MO?

As of early 2026, 80% of users say people would walk alone at night

Is Windsor, MO walkable to grocery stores?

As of early 2026, 79% of users say it's walkable to grocery stores

Is there wildlife in Windsor, MO?

As of early 2026, 77% of users say there's wildlife

Is Windsor, MO walkable to restaurants?

As of early 2026, 75% of users say it's walkable to restaurants

Is Windsor, MO quiet?

As of early 2026, 64% of users say it's quiet

Does Windsor, MO have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are neighbors friendly in Windsor, MO?

As of early 2026, 57% of users say neighbors are friendly

Do residents of Windsor, MO plan to stay at least 5 years?

As of early 2026, 36% of users say they plan to stay for at least 5 years

Are the streets well-lit in Windsor, MO?

As of early 2026, 33% of users say streets are well-lit

Are there community events in Windsor, MO?

As of early 2026, 15% of users say there are community events

What is 415 Hillcrest Dr estimated to be worth?

Trulia's estimated value for 415 Hillcrest Dr in Windsor, MO is $485,500 .

Is Windsor a buyer's or seller's market?

Windsor is currently a buyer's market, based on recent for-sale activity.

What do residents say about Windsor?

Residents describe Windsor, MO as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, MO .

What are the closest schools to 415 Hillcrest Dr?

The closest schools to 415 Hillcrest Dr in Windsor, MO are Windsor Elementary School (rated 5/10), Windsor High School (Middle, rated 2/10).

OFF MARKET

$485,500

Trulia Estimate

Studio

415 Hillcrest Dr, Windsor, MO 65360

Est. Refi. Payment $3,023/mo*

Refinance Your Home

Home Value

Trulia Estimate

$486K

Since last month

$2K (+0.5%)

Since last year

$95K (+24.4%)

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 +24% in the last 10 years

Month	Estimated value
2026
September 2026	$486K
August 2026	$483K
July 2026	$479K
June 2026	$504K
May 2026	$391K
April 2026	$389K
March 2026	$389K
February 2026	$390K
January 2026	$388K
2025
December 2025	$388K
November 2025	$391K
October 2025	$390K

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
403 S Olive St, Windsor, MO	0.24	Single-Family Home	-	10/01/25	2	1	1,144
209 E Kentucky St, Windsor, MO	0.41	Single-Family Home	-	04/10/26	2	1	1,064
605 Poplar Dr, Windsor, MO	0.41	Single-Family Home	-	07/14/26	3	1	1,056
102 S Feaster St, Windsor, MO	0.42	Single-Family Home	-	01/12/26	3	2	1,969
307 Phelps St, Windsor, MO	0.44	Single-Family Home	-	07/28/26	3	1	1,551
406 Phelps St, Windsor, MO	0.45	Single-Family Home	-	11/21/25	3	2	2,488
103 Lindy Ln, Windsor, MO	0.50	Single-Family Home	-	05/12/26	3	2	2,860
406 E Washington St, Windsor, MO	0.51	Single-Family Home	-	06/15/26	3	1	1,400
606 S Windsor St, Windsor, MO	0.52	Single-Family Home	-	09/30/25	2	1	1,204
218 Century St, Windsor, MO	0.52	Single-Family Home	-	07/16/26	4	2	1,792

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
424 Hillcrest Dr, Windsor, MO 65360	0.07	-	4	2	2,341	Recently Sold
428 E Hillcrest Dr, Windsor, MO 65360	0.11	$160,700	3	2	1,080	Off Market
421 Olive St, Windsor, MO 65360	0.16	$252,400	4	3	2,460	Off Market
415 S Olive St, Windsor, MO 65360	0.19	$212,100	3	2	1,512	Off Market
410 E Indiana St, Windsor, MO 65360	0.23	$201,300	3	1.5	1,846	Off Market
403 S Olive St, Windsor, MO 65360	0.24	$152,500	2	1	1,144	Off Market
303 S Olive St, Windsor, MO 65360	0.34	$234,300	4	2	1,920	Off Market
503 E Poplar Dr, Windsor, MO 65360	0.38	$115,100	2	1	720	Off Market
303 E Indiana St, Windsor, MO 65360	0.36	$180,900	3	2	1,565	Off Market
302 E Kentucky St, Windsor, MO 65360	0.37	$49,900	3	1	1,004	Off Market
605 Poplar Dr, Windsor, MO 65360	0.41	-	3	1	1,056	Recently Sold
506 Poplar Dr, Windsor, MO 65360	0.42	$151,600	2	1	1,056	Off Market

Local Information

Map ViewExplore the area around 415 Hillcrest Dr.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

What's unique:Granite countertopsPremium materialsIn-unit laundryLuxury flooringHigh-quality constructionCustom cabinetry

415 Hillcrest Dr is in Windsor, MO and in ZIP code 65360.

415 Hillcrest Dr, Windsor, MO 65360 is a studio property. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $485,500, with a rent estimate of $1,377/month.

Price and Tax history

Date	Event	Price
Dec 4, 2025 Source: Central Missouri BOR #25-338	ListingRemoved	$395,000
Oct 3, 2025 Source: Central Missouri BOR #25-338	Listed For Sale	$395,000

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Windsor Elementary School
K-6
Public
356 Students
Henry County R-I School District
5/10
GreatSchools Rating
Parent Rating Average
No reviews available for this school.

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.

100 % Say parking is easy
100 % Say yards are well-kept
93 % Say it's dog friendly
90 % Say kids play outside
83 % Say there's holiday spirit
82 % Say car is needed
80 % Say people would walk alone at night
79 % Say it's walkable to grocery stores
77 % Say there's wildlife
75 % Say it's walkable to restaurants
64 % Say it's quiet
62 % Say there are sidewalks
57 % Say neighbors are friendly
36 % Say they plan to stay for at least 5 years
33 % Say streets are well-lit
15 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Usafmerrell
Resident
6y ago
"My neighborhood is nice a quiet off of Willa ln. just down from the park and feels like living I. The country "
1
Flag
Patrick L.
Resident
7y ago
"the school district is lacking in the special education programs and will not test for autism at the parents' request. also they have a policy that gives them the ability to not have IEP and 504 meetings with parents recorded."
2
Flag

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Frequently asked questions about 415 Hillcrest Dr

What is 415 Hillcrest Dr estimated to be worth?
Trulia's estimated value for 415 Hillcrest Dr in Windsor, MO is $485,500.
Is Windsor a buyer's or seller's market?
Windsor is currently a buyer's market, based on recent for-sale activity.
What do residents say about Windsor?
Residents describe Windsor, MO as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Windsor, MO.
What are the closest schools to 415 Hillcrest Dr?
The closest schools to 415 Hillcrest Dr in Windsor, MO are Windsor Elementary School (rated 5/10), Windsor High School (Middle, rated 2/10).