16 Upper Rd, Middletown, NY 10940
OFF MARKET

16 Upper Rd
Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,950 sqft (on 13.90 acres)

$775,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $5,260/mo*
Refinance Your Home

$775,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $5,260/mo*
Refinance Your Home
3 Beds
2 Baths
1,950 sqft
(on 13.90 acres)

Home Value

Trulia Estimate
$776K
Since last month
Increased$12K (+1.5%)
Since last year
Increased$91K (+13.2%)
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 +135% in the last 10 years
MonthEstimated value
2026
August 2026$776K
July 2026$764K
June 2026$780K
May 2026$763K
April 2026$757K
March 2026$754K
February 2026$754K
January 2026$710K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
676 Winterton Road, Bloomingburg, NY
0.11
Single-Family Home
$539,900
11/07/25
3
2.5
1,721
853 Winterton Road, Bloomingburg, NY
0.70
Single-Family Home
$450,000
10/07/25
3
2
2,108
587 Winterton Road, Bloomingburg, NY
0.52
Single-Family Home
$455,000
04/27/26
3
1.5
1,786
815 Winterton Road, Bloomingburg, NY
0.51
Single-Family Home
$520,000
08/27/25
5
3
3,126
29 Cornfield Road, Middletown, NY
0.91
Single-Family Home
$425,000
12/09/25
3
1.5
1,780
204 Brola Road, Middletown, NY
1.24
Single-Family Home
$839,000
06/26/26
4
4
3,200
50 Brola Road, Middletown, NY
0.98
Single-Family Home
$325,000
08/05/26
3
1
1,196
574 Old Mountain Road, Otisville, NY
1.61
Single-Family Home
$450,000
01/08/26
4
2
1,832
18 Maureen Lane, Middletown, NY
1.36
Single-Family Home
$550,000
08/11/26
4
2
1,704
273 Pine Grove Road, Middletown, NY
1.48
Single-Family Home
$790,000
01/09/26
4
2.5
3,129

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
676 Winterton Road, Bloomingburg, NY 12721
0.11
$539,900
3
2.5
1,721
Recently Sold
77 Upper rd Road, Middletown, NY 10940
0.27
$560,000
4
3
2,162
For Sale
768 Winterton Road, Middletown, NY 10940
0.35
$446,700
3
2
1,260
Off Market
Lot 2 Winters Lane, Middletown, NY 10940
0.38
$799,000
4
3.5
2,696
For Sale
47 Wildwood Circle, Bloomingburg, NY 12721
0.43
$477,300
3
3
2,076
Off Market
704 Mountain Road, Bloomingburg, NY 12721
0.41
$1,750,000
3
3.5
3,108
For Sale
1 Silver Mine Road, Middletown, NY 10940
0.41
$465,200
3
2.5
1,930
Off Market
614 Winterton Road, Bloomingburg, NY 12721
0.46
$435,400
5
2.5
2,352
Off Market
752 Mountain Road, Bloomingburg, NY 12721
0.44
$538,700
4
2
2,427
Off Market
12 Wildwood Circle, Bloomingburg, NY 12721
0.50
$412,900
3
2
2,380
Off Market
587 Winterton Road, Bloomingburg, NY 12721
0.52
$455,000
3
1.5
1,786
Recently Sold
669 Mountain Road, Bloomingburg, NY 12721
0.51
$579,000
6
3.5
2,948
For Sale

Local Information

  • Map ViewExplore the area around 16 Upper Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1996
Lot Size
13.9 acres
Living Area
1,950 sqft
Price/Sqft
$398
Parking
Garage

About this House

This single-family home is located at 16 Upper Rd, Middletown, NY. 16 Upper Rd is in Middletown, NY and in ZIP code 10940. This property has 3 bedrooms, 2 bathrooms and approximately 1,950 sqft of floor space. This property has a lot size of 13.90 acres and was built in 1996.
16 Upper Rd, Middletown, NY 10940 is a 3 bedroom, 2 bathroom, 1,950 sqft single-family home built in 1996. It is currently off market. The Trulia Estimate is $775,800, with a rent estimate of $2,577/month.

Home Details for 16 Upper Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1.5

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 13.90 acres

Price and Tax history

YearProperty taxTax assessment
2025Unavailable
$1,121,500
Home facts updated by county records

Market trends in Bloomingburg

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
42
4MoM

Around this home

What Locals Say about Bloomingburg

At least 16 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 89 % Say parking is easy

  • 86 % Say yards are well-kept

  • 82 % Say it's quiet

  • 71 % Say there's holiday spirit

  • 67 % Say there's wildlife

  • 55 % Say kids play outside

  • 55 % Say it's dog friendly

  • 54 % Say they plan to stay for at least 5 years

  • 52 % Say neighbors are friendly

  • 37 % Say people would walk alone at night

  • 26 % Say streets are well-lit

  • 21 % Say there are sidewalks

  • 17 % Say it's walkable to grocery stores

  • 11 % Say there are community events

  • 10 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Bernice Rivera
    "Peaceful and friendly …safe as well. Neighbors are courteous and respectful. Quiet and calmness. Not as noisy as living in the city."
    0
    Flag
  • Qmxm9yc948
    "Wonderful wilderness beautiful mountains. friendly neighbors, beautiful landscape, private, and peaceful"
    0
    Flag
  • Chasity M
    "You can get a fenced in yard so your dog can run freely. A lot of the dogs in the neighborhood are walked in leashes when outside "
    0
    Flag
  • Sarah E.
    "It’s a nice place to raise a family, there are nice parks, good schools, and good food. It’s fairly affordable "
    0
    Flag
  • Jmich93
    "this a clean, quiet, friendly, and family oriented neighborhood. my daughter loves her school and it's a really safe place to live."
    0
    Flag
  • Ninad F.
    "I know My neighborhood has people just like me. Working single or couple, maybe dog, want to make most of the limited time they have. "
    0
    Flag
  • Michael D. S.
    "its quite here they would love it but no stores are nearby that's the bad about my neighborhood "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 16 Upper Rd

  • What is 16 Upper Rd estimated to be worth?
    Trulia's estimated value for 16 Upper Rd in Middletown, NY is $775,800.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Middletown?
    Residents describe Middletown, NY as easy to park in, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Middletown, NY.
  • What are the closest schools to 16 Upper Rd?
    The closest schools to 16 Upper Rd in Middletown, NY are Circleville Elementary School (Pre-K, rated 3/10), Circleville Middle School (rated 7/10), Pine Bush Senior High School (rated 6/10).
  • How big is the lot at 16 Upper Rd?
    The lot at 16 Upper Rd in Middletown, NY is about 13.9 acres.
  • Does 16 Upper Rd have a garage?
    Yes, 16 Upper Rd in Middletown, NY has a garage.

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Apartments for Rent

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Off Market Homes Near 16 Upper Rd

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Homes for sale near 16 Upper Rd

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