255 Upper Rd, Middletown, NY 10940
OFF MARKET

255 Upper Rd
Middletown, NY 10940

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

$496,600

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $3,303/mo*
Refinance Your Home

$496,600

Trulia Estimate
as of May 19, 2026
Est. Refi. Payment $3,303/mo*
Refinance Your Home
3 Beds
2 Baths
1,806 sqft
(on 6.85 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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***
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 255 Upper Rd

DatePriceEventSource
08/05/2016$204,000Sold
OneKey® MLS as distributed by MLS GRID #H4607430
07/06/2016$199,900Listed For SaleAgent Provided
04/22/2016$500Sold
N/A
02/26/2016$199,900Listed For SaleAgent Provided
01/12/2016$0ListingRemovedAgent Provided
01/07/2016$117,620PriceChange
Agent Provided
12/15/2015$0Listed For SaleAgent Provided
04/11/2002$46,500Sold
N/A
08/20/1998$27,616Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$480,600
Home facts updated by county records

Comparable Sales for 255 Upper Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
214 Spruce Road, Middletown, NY
0.26
Single-Family Home
$360,000
07/10/25
2
2.5
1,580
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
44 Karen Joy Drive, Middletown, NY
0.37
Single-Family Home
$425,000
08/11/25
4
1.5
2,706
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
14 Cornfield Road, Middletown, NY
0.56
Single-Family Home
$360,000
06/04/25
3
1.5
1,152
22 Witte Drive, Middletown, NY
0.47
Single-Family Home
$430,000
08/04/25
3
1
1,316
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

Assigned Schools

These are the assigned schools for 255 Upper Rd.
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 Middletown

At least 783 Trulia users voted on each feature.

  • 86 % Say car is needed

  • 82 % Say it's dog friendly

  • 81 % Say parking is easy

  • 75 % Say yards are well-kept

  • 74 % Say there's holiday spirit

  • 63 % Say kids play outside

  • 63 % Say there's wildlife

  • 60 % Say it's quiet

  • 57 % Say there are sidewalks

  • 56 % Say they plan to stay for at least 5 years

  • 54 % Say people would walk alone at night

  • 48 % Say neighbors are friendly

  • 45 % Say streets are well-lit

  • 44 % Say it's walkable to restaurants

  • 42 % Say it's walkable to grocery stores

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Rjeancharles430
    "Quietly respect each other’s and safety for every one ,I love my area and my family love it too even when my friends come to visit they’re always love my neighborhood.they want to stay."
    0
    Flag
  • Chrisfatkinson
    "The area is rapidly improving with significant investment and renovation to many properties and infrastructure. There are so many amazing restaurants and shops, and great parks and services for children, like craft stations at the parks and free lunches! "
    0
    Flag
  • Nikolaus Wong
    "Manageable sometimes riddled with traffic but not terrible. Once in a while strategic and time consuming."
    0
    Flag
  • Vincent colaneri
    "Farmers market, festivals. Lively Halloween output. Parades in town and lots of outreach. Announcements by the city are made online. North street is on the way up. Really enjoy living here and the sense of community we have "
    0
    Flag
  • Trulia User
    "They're isn't many sidewalks to walk your dogs or other dogs animals outside. How many yards is that and how many yards are you walking to "
    0
    Flag
  • Specks1998
    "People walk their dogs freely some off the leash a lot of open land spaces for walking a dog, but they’re also designated dog walk areas to. "
    0
    Flag
  • Gerard Lewis
    "I lived in this neighborhood for over twenty four years and it has grown, but still a lovely place to live. "
    0
    Flag
  • Anny Guzman
    "The town is save for the kid and family, this is a beautiful place, quiet, save and the people care for others "
    0
    Flag
  • Brixza Hernandez
    "It’s a very nice community, everything is nearby. "
    6
    Flag
  • Kaylak1214
    "Dogs are welcome in the neighborhood, but not in the parks. There are bags provided as well near all the parks. "
    1
    Flag
  • Msjclark
    "I live by parks and lakes it’s wonderful here. Plenty of things to do. Your within mins of other states."
    15
    Flag
  • Ashdally1068
    "Quiet neighborhood where you have space for yourself and can enjoy nature with your family and pets. Stores not too far away with wineries and breweries within this county."
    0
    Flag
  • Danielle L.
    "Lived here all my life and it's a great place to raise a family with great schools as well. I absolutely love living here. It's very safe and everything you need is within a 10 mile radius."
    1
    Flag
  • Jlacenere
    "it's open and plenty of space for people who own animals from dogs to goats. Definitely a good location "
    0
    Flag
  • Jlacenere
    "easy access to transit for commuting, every major retailer is close by, quaint County feel but close to every convenience you can want. "
    0
    Flag
  • Mayra C.
    "every one knows each other and every one is polite to each other, horses stables, cows, corn fields. this is a very county and rural place, with beautiful nature. the Galeria Mall and every shopping center restaurants and other entertainment venues are a couple of minutes away. exits to different highways are a few minutes away. you get both of best worlds. "
    0
    Flag
  • Tessa C. .
    "great area...no crime...quiet...clean area. close to to main road that leads to bigger roads to get you to the big stores!!!"
    8
    Flag
  • Cynthiacastillo3021
    "There are many activities in the neighborhood for the summer for family oriented and very safe to participate "
    10
    Flag
  • Martin Y. B.
    "The town of Wallkill surrounds the Town Of Middletown. There are vast amounts of out door activities to enjoy. Go to the trail, skate park, ice cream and mini golf. It is a quaint town with a big city vibe. There is a huge diverse group of families. Due to city families seeking a change of scenery."
    0
    Flag
  • Bcollins2336
    "People need to slow down. My dog was killed from a car speeding and they never stopped Drivers drive too fast"
    10
    Flag
  • Bennett10940
    "The Middletown police are horrible and regardless of race, you will be treated as a criminal. They have been rude, unprofessional, and corrupt "
    35
    Flag
  • Kristina J.
    "There are no designated sidewalks but it is VERY rare for you to see a car driving by anyway. You do feel very safe on the roads because of its desolate nature. "
    0
    Flag
  • Maime J.
    "lots of outside space to run. but also lots of outside space to disappear into lol dog run at Shannon Park. "
    0
    Flag
  • Sydney S.
    "I've lived here my whole life. Scotchtown has only improved over the years. It's clean and safe, that's why I continue to look for a place to live out here. "
    0
    Flag
  • Cknights1989
    "Scotchtown is an amazing neighborhood and community to be apart of. Friendly ppl, awesome school district! "
    0
    Flag
  • Eric T.
    "Try to get your children into Circleville elementary for their education. It's the better of the local schools. "
    0
    Flag
  • Jennifer D.
    "lived here my whole life. Diversity is a big one. You have so many different races, food cultures the people and so on. "
    7
    Flag
  • Allie R.
    "I don’t commute but I drive around town, etc. and have never really had much of an issue. As for public transportation, last I checked it was cleanly and not too horrible. "
    0
    Flag
  • Lattaallan
    "The people are nice stay to themselves no issues whatsoever. I love how everyone care about the environment "
    0
    Flag
  • Neenasantos
    "They have busses and cars, but that could be costly, and take too long. It’s best to own a car. If you’re traveling into NYC, the metro north would be best. "
    18
    Flag
  • Cynthiapwagner
    "I’ve lived here 5 years. Great schools and neighbors! Otisville schools are amazing! Highly recommend!"
    0
    Flag
  • Kamelia M.
    "Nice and quiet living area. Private parking, open spaces, HOA, access to swimming pool, tennis and basketball court. Neighbors are friendly and there is a neighborhood watch."
    0
    Flag
  • Cql617
    "It is a quiet area. It is centrally located. close to shopping and banking, hospital and urgent care facilities. there are lots of barbers, hair salons, and eateries. "
    2
    Flag
  • Antonio R.
    "Neighborhood is great and some areas are bad but it’s not that bad depending where you live at taxes are pretty high neighborhood cat crime drugs but the cops respond right away"
    28
    Flag
  • Hector D. Q.
    "Music fairs concerts and Christmas tree lighting. breweries. Restaurants. Middletown theatre. "
    6
    Flag
  • Wendy P.
    "We have friendly neighbors. cookout is our favorite time to talk, laugh and eat into our children's is playing, running around. Cookout is memorable. "
    0
    Flag
  • Wendy P.
    "Is really quiet place. Good neighbors. Access to many stores, schools, gas stations, churches supermarkets. etc."
    0
    Flag
  • Leobregon
    "Growing , needs more work , needs to be cleaned up More parks an things to do for kids . Needs more cameras in the area "
    2
    Flag
  • Robert C.
    "While Middletown is currently on an upswing it still has a bit to go with some areas still being not the best or safest"
    7
    Flag
  • Poelzl1955
    "It's a beautiful area. Still pretty rural but it is close to alot of shopping so it is convenient. Good schools good people too ."
    0
    Flag

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255 Upper Rd, Middletown, NY 10940 is a 3 bedroom, 2 bathroom, 1,806 sqft single-family home built in 2003. This property is not currently available for sale. 255 Upper Rd was last sold on Aug 5, 2016 for $204,000. The current Trulia Estimate for 255 Upper Rd is $496,600.