255 Upper Rd, Middletown, NY 10940
Property image
Property image
OFF MARKET

255 Upper Rd
Middletown, NY 10940

New Vernon
  • 3 Beds
  • 2 Baths
  • 1,806 sqft (on 6.85 acres)

$486,500

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $3,307/mo*
Refinance Your Home

$486,500

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $3,307/mo*
Refinance Your Home
3 Beds
2 Baths
1,806 sqft
(on 6.85 acres)

Home Value

Trulia Estimate
$487K
Since last month
Decreased$12K (-2.3%)
Since last year
Increased$4K (+0.8%)
Since last sale
Increased$289K (+141.4%)
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 +150% in the last 10 years
MonthEstimated value
2026
August 2026$493K
July 2026$494K
June 2026$504K
May 2026$490K
April 2026$483K
March 2026$476K
February 2026$475K
January 2026$465K
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
853 Winterton Road, Bloomingburg, NY
0.52
Single-Family Home
$450,000
10/07/25
3
2
2,108
574 Old Mountain Road, Otisville, NY
0.78
Single-Family Home
$450,000
01/08/26
4
2
1,832
18 Maureen Lane, Middletown, NY
0.63
Single-Family Home
$550,000
08/11/26
4
2
1,704
29 Cornfield Road, Middletown, NY
0.64
Single-Family Home
$425,000
12/09/25
3
1.5
1,780
22 Mark Drive, Middletown, NY
0.54
Single-Family Home
$460,000
01/09/26
3
2.5
2,832
815 Winterton Road, Bloomingburg, NY
0.53
Single-Family Home
$520,000
08/27/25
5
3
3,126
676 Winterton Road, Bloomingburg, NY
0.92
Single-Family Home
$539,900
11/07/25
3
2.5
1,721
23 Forest Hills Lane, Otisville, NY
1.14
Single-Family Home
$740,000
02/02/26
4
2.5
3,000
8 Dot Calm Drive, Otisville, NY
0.95
Single-Family Home
$615,000
06/23/26
4
3
2,256
4 Bijou Lane, Otisville, NY
1.36
Single-Family Home
$436,000
12/11/25
3
1.5
2,275

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
276 Spruce Road, Middletown, NY 10940
0.06
$499,000
4
2.5
2,688
For Sale
295 Spruce Road, Middletown, NY 10940
0.22
$477,300
3
2
1,881
Off Market
22 Nicole Place, Middletown, NY 10940
0.23
$445,100
3
2
1,332
Off Market
214 Spruce Road, Middletown, NY 10940
0.26
$354,800
2
2.5
1,580
Off Market
8 Jean Ridge Road, Middletown, NY 10940
0.28
$444,300
3
2
1,924
Off Market
25 Karen Joy Drive, Middletown, NY 10940
0.28
$436,300
3
2
2,080
Off Market
50 Nicole Place, Middletown, NY 10940
0.33
$444,000
4
2
2,088
Off Market
296 Upper Road, Otisville, NY 10963
0.36
$272,700
3
2
1,300
Off Market
44 Karen Joy Drive, Middletown, NY 10940
0.37
$419,800
4
1.5
2,706
Off Market
31 Witte Drive, Wurtsboro, NY 10940
0.43
$506,800
3
1.5
1,907
Off Market
818 Winterton Road, Bloomingburg, NY 12721
0.46
$540,300
3
2
2,154
Off Market
22 Witte Drive, Middletown, NY 10940
0.47
$424,500
3
1
1,316
Off Market

Local Information

  • Map ViewExplore the area around 255 Upper Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2003
Lot Size
6.85 acres
Living Area
1,806 sqft
Price/Sqft
$269

About this House

Awesome Opportunity!! 2003 Cape Cod with contemporary flair on 6.85 private acres. Open floor plan, living room with vaulted ceilings and fireplace, 2nd floor master suite with loft overlooking living room, walk-out basement with 10 foot ceilings and full size windows and much more. Home needs work and would be perfect candidate for 203K financing. $500 HOW Incentive. Offers w/financing must be accompanied by pre-qual letter & down payment proof of funds; cash offers w/proof of funds. Sold as-is. ***AGENTS - see confidential remarks for additional instructions***
255 Upper Rd, Middletown, NY 10940 is a 3 bedroom, 2 bathroom, 1,806 sqft single-family home in New Vernon, built in 2003. It last sold for $204,000 on Aug 5, 2016. It is currently off market. The Trulia Estimate is $486,500, with a rent estimate of $2,543/month.

Home Details for 255 Upper Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Dining Room, Family Room, Master Bath, OfficeCeiling Fan
Heating & Cooling
Heating: Baseboard, Other, Propane Butane, Wood PelletAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylGardenLawnPorch
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 6.85 acres

Price and Tax history

DateEventPrice
Aug 5, 2016
Source: OneKey® MLS as distributed by MLS GRID #H4607430
Sold
$204,000
Jul 6, 2016
Source: Agent Provided
Listed For Sale
$199,900
Apr 22, 2016
Source: N/A
Sold
$500
Feb 26, 2016
Source: Agent Provided
Listed For Sale
$199,900
Jan 12, 2016
Source: Agent Provided
ListingRemoved
$0

Market trends in Middletown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$402K
$1.67KMoM
Sale-to-List Price
99.8%
Price per sq ft
$249
$11MoM
Available listings
195
2MoM
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Around this home

Neighborhood Overview

New Vernon
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

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Homes for sale near 255 Upper Rd

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Off Market Homes Near 255 Upper Rd

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Frequently asked questions about 255 Upper Rd

  • What is 255 Upper Rd estimated to be worth?
    Trulia's estimated value for 255 Upper Rd in Middletown, NY is $486,500.
  • What is the price history for 255 Upper Rd?
    255 Upper Rd in Middletown, NY last sold for $204,000 in August 2016.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Middletown?
    The median sale price in Middletown is $402K. That is down $1.67K from the prior month.
  • Does 255 Upper Rd have air conditioning?
    Yes, 255 Upper Rd in Middletown, NY has air conditioning.
  • Does 255 Upper Rd have laundry facilities?
    Yes, 255 Upper Rd in Middletown, NY has in-unit laundry.