453 Prosperous Valley Rd, Middletown, NY 10940

Off market sep 2016 for $165K

$416,947

Est. refi paymentEst. refi $1,235/mo

•

2,031

sq ft

453 Prosperous Valley Rd, Middletown, NY 10940

About this home

Originally an old school house, this home has lots of history. With the Cape Cod addition, it has lots of space too! This combination home would make a great extended family home. Nice size Eat-in-kitchen, Living Room/Dining Room, 2 bedrooms and bath in the main house with a large Family Room connecting to the school house. School house first floor has Kitchenette area and wood stove in sitting area with a full bath and loft style bedroom. Exposed beams really show the character of the original structure. The second floor of the Cape is currently unfinished, with potential for 2 more bedrooms with a chase already in the wall. There is a crawl space below the schoolhouse and a full, unfinished basement below the Cape with Bilco doors. It is clean and dry and great for storage. There is also a shed for storage, all on a square acre of property in Pine Bush School District. Tons of potential in this spacious home! Additional Information: HeatingFuel:Oil Below Ground,

Single-familyProperty Type

1995Year Built

1 acresLot Size

$205Est. Price/Sq.Ft.

Listing by Elizabeth Vasapolli • Howard Hanna Rand Realty

Bought with Corinne Bocsusis • Howard Hanna Rand Realty

Redfin checked: a minute ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4529878

Redfin Estimate

$416,947

$252K since sold in September 2016$11K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.2% lower than the average sale price ($480K) of 5 comparable homes.

SOLD OCT 1, 2026
$530,000
A
3 beds2 baths2,065 sq ft
225 Upper Rd, Middletown, NY 10940
Listing by KW Hudson Valley United
SOLD JUL 17, 2026
$395,000
B
3 beds2 baths1,314 sq ft
21 Philcox Rd, Middletown, NY 10940
Listing by KW Hudson Valley United
SOLD OCT 20, 2026
$545,000
C
3 beds2.5 baths2,225 sq ft
18 Hickory Pl, Middletown, NY 10941
Listing by HomeSmart Homes & Estates
SOLD OCT 9, 2026
$477,000
D
3 beds2.5 baths2,184 sq ft
33 Seaman Rd, Circleville, NY 10919
Listing by Howard Hanna Rand Realty
SOLD APR 27, 2026
$455,000
E
3 beds1.5 baths1,786 sq ft
587 Winterton Rd, Bloomingburg, NY 12721
Listing by Cronin & Company Real Estate

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$287,930

Est. take-home

List your home with Redfin and save $4,169

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,773/mo

Redfin rental estimate

List your home for rent

Market trends in 10940, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.8%

0.1% MoM

Median sale price

$425K

$10K MoM

Avg. days on market

30d

1 days MoM

Recently sold homes

117

5 MoM

New listings for sale

$330,000
2 beds2.5 baths1,836 sq ft
92 Deer Court Dr, Middletown, NY 10940
Listing by Century 21 Alliance Realty Grp
$199,900
2 beds1 bath994 sq ft
47 Ruth Ct, Middletown, NY 10940
Listing by KW Hudson Valley United
$439,900
3 beds1.5 baths1,664 sq ft
15 Eisenhower Dr, Middletown, NY 10940
Listing by RE/MAX Benchmark Realty Group
$365,000
3 beds2 baths1,088 sq ft
926 Route 17m, Middletown, NY 10940
Listing by KW Hudson Valley United
OPEN SUN, 1PM TO 3PM
$365,000
3 beds1 bath1,008 sq ft
7 Ontario Ave, Middletown, NY 10940
Listing by eXp Realty
$225,000
3 beds2 baths1,516 sq ft
149 Wisner Ave, Middletown, NY 10940
Listing by eRealty Advisors, Inc
$399,999
3 beds2.5 baths1,623 sq ft
7 Hanover Mews, Middletown, NY 10940
Listing by Locqube New York, Inc.
$475,000
3 beds2.5 baths2,026 sq ft
6 Walnut Ln, Middletown, NY 10940
Listing by Coldwell Banker Realty
$619,000
4 beds3 baths2,696 sq ft
421 Mt Orange Rd, Middletown, NY 10940
Listing by Curasi Realty, Inc.
$400,000
4 beds2 baths1,842 sq ft
25 Guymard Tpke, Middletown, NY 10940
Listing by KW Hudson Valley United
See all

Provided by Redfin

Sale history for 453 Prosperous Valley Rd

Date

Event

Price

Public Records

Nov 16, 2016

Sold

$165,000

$81/sq ft

HGMLS #4529878

Sep 19, 2016

Price Changed

$165,000

$81/sq ft

Sep 19, 2016

Sold

$165,000

$81/sq ft

Jul 5, 2016

Contingent

—

Jul 5, 2016

Price Changed

$179,999

$89/sq ft

Dec 3, 2015

Price Changed

$179,999

$89/sq ft

Oct 5, 2015

Listed

$190,000

$94/sq ft

OneKey® MLS as Distributed by MLS Grid #H4529878

Sep 19, 2016

Sold

$165,000

$81/sq ft

Oct 5, 2015

Listed

$179,999

$89/sq ft

Public Records

May 8, 1989

Sold

$54,000

$27/sq ft

Public Records

Jul 18, 1980

Sold

$15,150

$7/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$6,587

$7,500 + $34,100

$41,600

2025

$6,587 (+4.7%)

$7,500 + $34,100

$41,600

2024

$6,291 (+1.4%)

$7,500 + $34,100

$41,600

2023

$6,201 (−5.2%)

$7,500 + $34,100

$41,600

2022

$6,542 (−4.4%)

$7,500 + $34,100

$41,600

2021

$6,840 (−3.1%)

$7,500 + $34,100

$41,600

2020

$7,061 (+4.2%)

$7,500 + $34,100

$41,600

2019

$6,777 (+18.1%)

$7,500 + $34,100

$41,600

2018

$5,737 (+0.3%)

$7,500 + $34,100

$41,600

2017

$5,721 (+2.8%)

$7,500 + $28,700

$36,200

2016

$5,564 (−0.7%)

$7,500 + $28,700

$36,200

2015

$5,606 (+0.7%)

$7,500 + $28,700

$36,200

2014

$5,568

$7,500 + $28,700

$36,200

Tax history for 453 Prosperous Valley Rd

Year

Property tax

Land + Additions

Assessment*

2026

$6,587

$7,500 + $34,100

$41,600

2025

$6,587 (+4.7%)

$7,500 + $34,100

$41,600

2024

$6,291 (+1.4%)

$7,500 + $34,100

$41,600

2023

$6,201 (−5.2%)

$7,500 + $34,100

$41,600

2022

$6,542 (−4.4%)

$7,500 + $34,100

$41,600

2021

$6,840 (−3.1%)

$7,500 + $34,100

$41,600

2020

$7,061 (+4.2%)

$7,500 + $34,100

$41,600

2019

$6,777 (+18.1%)

$7,500 + $34,100

$41,600

2018

$5,737 (+0.3%)

$7,500 + $34,100

$41,600

2017

$5,721 (+2.8%)

$7,500 + $28,700

$36,200

2016

$5,564 (−0.7%)

$7,500 + $28,700

$36,200

2015

$5,606 (+0.7%)

$7,500 + $28,700

$36,200

2014

$5,568

$7,500 + $28,700

$36,200

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

1.5

Lot width

—

Lot depth

—

Lot size

1 Acre

Year renovated

1931

Sq. Ft.

2,444

Year built

1850

Style

Single Family Residential

County

Orange County

APN

335200A00600000010310000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Property details

Parking

Parking Information
Parking Features: Off Street

Interior

Fireplace Information
Fireplace Features: Wood Burning Stove

Heating & Cooling
Cooling: None
Heating: Baseboard, Oil

Interior Features
Interior Features: Cathedral Ceiling(s),Formal Dining,First Floor Bedroom
Appliances: Oil Water Heater
Flooring: Carpet
Levels: Two
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: Full,See Remarks
Rooms Total: 7
Basement: Full, Unfinished

Bathroom Information
Bathrooms Full: 2

Exterior

Exterior Features
Construction Materials: Other, Vinyl Siding
Other Structures: Shed(s)
Foundation Details: Other
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Level

Property Information
Stories: 2
Living Area Source: Other
Property Sub Type: Single Family Residence
Property Condition: Estimated

Financial

Tax Information
Tax Year: 2015
Tax Source: Municipality
Tax Annual Amount: $5,605

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

School Information
Elementary School: Circleville Elementary School
Middle Or Junior School: Circleville Middle School
High School: Pine Bush Senior High School
High School District: Pine Bush

Location Information
Hamlet: Wallkill
Directions: Route 17M to Prosperous Valley Rd. Make left & right to follow Prosperous Valley around. Just past the Orchid Farm on the right.
County Or Parish: Orange County

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 2,444
Stories: 1.5
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 1850
Year Renovated: 1931
County: Orange County
APN: 335200A00600000010310000000

Home facts updated by county records on Oct 8, 2026

Around this home

Schools

K - 12
Preschool & daycare

Circleville Elementary School

Public PreK-5 • Assigned • 3.3mi

3/10

Circleville Middle School

Public 6-8 • Assigned • 3.6mi

7/10

Pine Bush Senior High School

Public 9-12 • Assigned • 9.0mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

3/10 Wind Factor

7% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Middletown, NY • 10940

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 3.7 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

3.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$397,000 – $480,000

Reach more buyers when you sell with Redfin. Save up to $4,169 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$749,000

3 beds3 baths2,826 sq ft

99 Whitlock Rd, Otisville, NY 10963

Sweeping views • Expansive deck • Private pool

Listing by eRealty Advisors, Inc

$849,000

5 beds4.5 baths4,200 sq ft

255 Howells Rd, Middletown, NY 10940

Two-story barn • Horse stalls • Natural pond

Listing by KW Hudson Valley United

NEW CONSTRUCTION

$799,000

4 beds3.5 baths2,696 sq ft

76 Winters Ln, Middletown, NY 10940

Custom kitchen • Covered front porch • Rear deck

Listing by Parcel Realty LLC

$209,999

2 beds1 bath1,131 sq ft

32 Tarbell Rd, Bloomingburg, NY 12721

Private setting • Mature trees • Eat-in kitchen

Listing by KW Hudson Valley United

FOR SALE BY OWNER

$797,000

4 beds3 baths1,768 sq ft

11 Altamont Rd, Bloomingburg, NY 12721

Fully renovated • Log siding • Exposed beams

$449,000

3 beds2 baths1,370 sq ft

28 Sunrise Ter, Bloomingburg, NY 12721

Metal roof • Wood siding • Outdoor spaces

Listing by Real Estate Circuit Inc

New listings for sale in 10940

$330,000

2 beds2.5 baths1,836 sq ft

92 Deer Court Dr, Middletown, NY 10940

Galley-style kitchen • Tennis courts • Pickleball

Listing by Century 21 Alliance Realty Grp

$199,900

2 beds1 bath994 sq ft

47 Ruth Ct, Middletown, NY 10940

First floor • Natural gas heat • Wall a c

Listing by KW Hudson Valley United

$439,900

3 beds1.5 baths1,664 sq ft

15 Eisenhower Dr, Middletown, NY 10940

Hardwood floors • Built-in shelving • Abundant cabinetry

Listing by RE/MAX Benchmark Realty Group

$365,000

3 beds2 baths1,088 sq ft

926 Route 17m, Middletown, NY 10940

Open floor layout • Brand new kitchen • Trendy backsplash

Listing by KW Hudson Valley United

OPEN SUN, 1PM TO 3PM

$365,000

3 beds1 bath1,008 sq ft

7 Ontario Ave, Middletown, NY 10940

Single-level living • Hardwood floors • Dining area

Listing by eXp Realty

$225,000

3 beds2 baths1,516 sq ft

149 Wisner Ave, Middletown, NY 10940

Covered front porch • 5,510 sq ft lot • Built 1910

Listing by eRealty Advisors, Inc

$399,999

3 beds2.5 baths1,623 sq ft

7 Hanover Mews, Middletown, NY 10940

New garage door • New front entry door • Upgraded windows

Listing by Locqube New York, Inc.

$475,000

3 beds2.5 baths2,026 sq ft

6 Walnut Ln, Middletown, NY 10940

0.25 acre lot • Garage • Built 1999

Listing by Coldwell Banker Realty

$619,000

4 beds3 baths2,696 sq ft

421 Mt Orange Rd, Middletown, NY 10940

Private 2 acre lot • Natural light • Recent upgrades

Listing by Curasi Realty, Inc.

Home values near 453 Prosperous Valley Rd

Data from public records.

Address	Redfin Estimate
364 Prosperous Valley Rd, Middletown, NY 4 Beds \| 4 Baths \| 4300 Sq. Ft.	$1,092,498
437 Prosperous Valley Rd, Middletown, NY 4 Beds \| 3 Baths \| 2120 Sq. Ft.	$561,208
417 Prosperous Valley Rd Apt A, Bloomingburg, NY 5 Beds \| 5 Baths \| 1968 Sq. Ft.	$593,878
371 Prosperous Valley Rd, Middletown, NY 3 Beds \| 1 Baths \| 1104 Sq. Ft.	$315,628
511 Prosperous Valley Rd, Middletown, NY 3 Beds \| 2.5 Baths \| 3490 Sq. Ft.	$693,191
423 Prosperous Valley Rd, Middletown, NY 6 Beds \| 3.5 Baths \| 2659 Sq. Ft.	$319,545
417 Prosperous Valley Rd Apt A, Middletown, NY 6 Beds \| 5 Baths \| 1968 Sq. Ft.	$636,831

Address	Redfin Estimate
348 Prosperous Valley Rd, Bloomingburg, NY 3 Beds \| 2.5 Baths \| 2336 Sq. Ft.	$334,394
401 Prosperous Valley Rd, Middletown, NY 3 Beds \| 1 Baths \| 1044 Sq. Ft.	$401,851
529 Prosperous Valley Rd, Middletown, NY 5 Beds \| 2 Baths \| 2320 Sq. Ft.	$386,567
471 Prosperous Valley Rd, Middletown, NY 4 Beds \| 2.5 Baths \| 1890 Sq. Ft.	$471,223
428 Prosperous Valley Rd, Middletown, NY 3 Beds \| 2.5 Baths \| 2678 Sq. Ft.	$736,378
510 Prosperous Valley Rd, Middletown, NY 4 Beds \| 2.5 Baths \| 3308 Sq. Ft.	$1,152,788
22 Hubbard Rd, Bloomingburg, NY 1 Beds \| 1 Baths \| 1760 Sq. Ft.	$330,179

Address	Redfin Estimate
370 Prosperous Valley Rd, Middletown, NY 5 Beds \| 3 Baths \| 3395 Sq. Ft.	$714,667
411 Prosperous Valley Rd, Middletown, NY 2 Beds \| 1 Baths \| 1288 Sq. Ft.	$341,192
381 Prosperous Valley Rd, Middletown, NY 4 Beds \| 2 Baths \| 2200 Sq. Ft.	$426,644
461 Prosperous Valley Rd, Middletown, NY 3 Beds \| 2 Baths \| 1794 Sq. Ft.	$492,525
445 Prosperous Valley Rd, Middletown, NY 4 Beds \| 2.5 Baths \| 2627 Sq. Ft.	$570,786
525 Prosperous Valley Rd, Middletown, NY 4 Beds \| 1.5 Baths \| 1680 Sq. Ft.	$378,907

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2015. This data may not match . Learn more.

More real estate resources

Neighborhoods
Zip Codes
Minor Civil Divisions
Cities
Popular Searches

Downtown homes for sale
Presidential Heights homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

10924 homes for sale
10916 homes for sale
10940 homes for sale
12549 homes for sale
10941 homes for sale

Vernon Township homes for sale
Hardyston Township homes for sale
Mahwah Township homes for sale
Wantage Township homes for sale
West Milford Township homes for sale

Houses for rent in Wallkill	Agents near me	White Plains, NY homes for sale	Wallkill Housing Market
Houses for sale near me	New York, NY homes for sale	Yonkers, NY homes for sale
Land for sale near me	Manhattan, NY homes for sale	Scarsdale, NY homes for sale
Open Houses near me	Rochester, NY homes for sale	Wallkill Property Records
Condos for sale near me	Buffalo, NY homes for sale	NY New Listings

Newburgh homes for sale
Warwick homes for sale
Middletown homes for sale