55 Hill Rd, Middletown, NY 10941
OFF MARKET

55 Hill Rd
Middletown, NY 10941

  • 2 Beds
  • 1.5 Baths
  • 970 sqft (on 1.21 acres)

$298,700

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $2,070/mo*
Refinance Your Home

$298,700

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $2,070/mo*
Refinance Your Home
2 Beds
1.5 Baths
970 sqft
(on 1.21 acres)

Home Value

Trulia Estimate
$299K
Since last month
Increased$9K (+3.1%)
Since last year
Decreased$1K (-0.4%)
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 +2% in the last 10 years
MonthEstimated value
2026
August 2026$299K
July 2026$290K
June 2026$288K
May 2026$277K
April 2026$266K
March 2026$264K
February 2026$255K
January 2026$276K
2025
2024

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
14 Briarwood Drive, Middletown, NY
0.08
Single-Family Home
$440,000
10/21/25
3
2
2,558
599 Guymard Turnpike, Middletown, NY
0.62
Single-Family Home
$480,000
05/21/26
3
2
1,852
9 Finchville Turnpike, Middletown, NY
0.76
Single-Family Home
$660,000
09/08/25
3
2
2,037
180 Ridge Drive, Middletown, NY
0.93
Single-Family Home
$635,000
07/13/26
3
2.5
2,008
153 Ridge Drive, Middletown, NY
1.06
Single-Family Home
$585,000
07/31/26
3
3
2,133
2059 Guymard Turnpike, Godeffroy, NY
1.73
Single-Family Home
$290,000
12/03/25
2
1.5
1,352
3 Kohler, Middletown, NY
1.18
Single-Family Home
$425,000
09/26/25
3
1.5
1,920
174 Guymard Tpke Turnpike, Middletown, NY
1.42
Single-Family Home
$554,900
09/11/25
3
2.5
2,865
7 Charles Rd, Godeffroy, NY
1.86
Single-Family Home
$260,000
07/27/26
2
1
1,152
749 Eatontown Road, Pt Jervis, NY
1.55
Single-Family Home
$535,000
08/12/26
3
2
1,508

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
14 Briarwood Drive, Middletown, NY 10940
0.08
$455,700
3
2
2,558
Off Market
12 Briarwood Drive, Middletown, NY 10940
0.15
-
3
2.5
2,184
Off Market
3 Hill Road, Middletown, NY 10940
0.26
$497,900
3
2
1,700
Off Market
14 Heather Lane, Middletown, NY 10940
0.30
$500,100
4
2.5
2,404
Off Market
141 Hill Road, Middletown, NY 10940
0.34
$657,700
4
3.5
3,312
Off Market
495 Guymard Turnpike, Middletown, NY 10940
0.29
$469,000
5
3
2,448
For Sale
16 Elm Road, Middletown, NY 10940
0.33
$512,600
4
2.5
2,220
Off Market
25 Heather Ln, Middletown, NY 10940
0.34
$532,300
3
3
2,136
Off Market
6 Thistle Lane, Middletown, NY 10940
0.34
$507,700
3
2
2,128
Off Market
34 Heather Lane, Middletown, NY 10940
0.38
$530,000
4
2.5
1,930
Off Market
25 Wedgewood Lane, Middletown, NY 10940
0.51
$487,100
4
3
2,344
Off Market
108 Homestead Lane, Otisville, NY 10963
0.54
$210,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 55 Hill Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1880
Lot Size
1.21 acres
Living Area
970 sqft
Price/Sqft
$308

About this House
55 Hill Rd, Middletown, NY 10941 is a 2 bedroom, 2 bathroom, 970 sqft single-family home built in 1880. It is currently off market. The Trulia Estimate is $298,700, with a rent estimate of $2,537/month.

Home Details for 55 Hill Rd

Exterior Features

Exterior Home Features
Roof: AsphaltDeck

Property Information

Year Built
Year Built: 1880
Property Type / Style
Property Type: Single Family Home

Interior Features

Appliances & Utilities
Cable Ready

Lot Information

Lot Area: 1.21 acres

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

Around this home

What Locals Say about Middletown

At least 784 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.
  • Primorider
    "If home shopping just know… The City of Middletown and Middletown, NY are not the same thing… Middletown, NY is comprised of City of Middletown, Town of WallKill, Town of Mount Hope, Scotchtown and a few others I’m forgetting. City of Middletown feels like living in an older but better part of NYC."
    0
    Flag
  • Hector D Quinones
    "There’s a local dog park And a local man made lake with walking trails for dog "
    0
    Flag
  • 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
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  • 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
  • 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
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 55 Hill Rd

  • What is 55 Hill Rd estimated to be worth?
    Trulia's estimated value for 55 Hill Rd in Middletown, NY is $298,700.
  • 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.
  • What do residents say about Middletown?
    Residents describe Middletown, NY as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Middletown, NY.
  • How big is the lot at 55 Hill Rd?
    The lot at 55 Hill Rd in Middletown, NY is about 1.2 acres.

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Off Market Homes Near 55 Hill Rd

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