20 Bennett St, Middletown, NY 10940
Property image
Property image
OFF MARKET

$275,900

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,365 sqft

20 Bennett St, Middletown, NY 10940

Est. Refi. Payment $1,954/mo*
Refinance Your Home

Home Value

Trulia Estimate
$276K
Since last month
Decreased$300 (-0.1%)
Since last year
Increased$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 +128% in the last 10 years
MonthEstimated value
2026
August 2026$276K
August 2026$275K
July 2026$276K
June 2026$278K
May 2026$280K
April 2026$273K
March 2026$270K
February 2026$266K
January 2026$266K
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
11 1/2 Dolson Avenue, Middletown, NY
0.11
Single-Family Home
$330,000
09/26/25
3
1
1,263
9 Grandview Avenue, Middletown, NY
0.18
Single-Family Home
$363,740
10/10/25
2
1
1,324
58 Wawayanda Avenue, Middletown, NY
0.31
Single-Family Home
$220,000
04/08/26
2
1
820
5 Mills Avenue, Middletown, NY
0.19
Single-Family Home
$327,000
05/26/26
3
1.5
1,160
18-20 Bedford Avenue, Middletown, NY
0.21
Single-Family Home
$275,000
07/30/26
2
1
864
41 Clinton Street, Middletown, NY
0.40
Single-Family Home
$301,475
07/31/26
3
1
1,224
6 Randall Terrace, Middletown, NY
0.18
Single-Family Home
$440,000
11/21/25
3
1.5
1,560
23 W Conkling Ave, Middletown, NY
0.44
Single-Family Home
$91,300
01/07/26
3
1
1,600
121 Sprague Avenue, Middletown, NY
0.32
Single-Family Home
$285,000
04/21/26
2
1.5
1,200
9 Genung Street, Middletown, NY
0.25
Single-Family Home
$265,000
05/20/26
3
2
1,240

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
145 Academy Avenue, Middletown, NY 10940
0.04
$455,000
4
2
2,545
Recently Sold
11 1/2 Dolson Avenue, Middletown, NY 10940
0.12
$340,600
3
1
1,263
Off Market
49 Bedford Avenue, Middletown, NY 10940
0.13
$454,300
3
2
1,636
Off Market
11 Dolson, Middletown, NY 10940
0.12
$440,000
3
2.5
1,795
Recently Sold
26 Mills Avenue, Middletown, NY 10940
0.10
$377,800
5
3
2,200
Off Market
21 Dolson Avenue, Middletown, NY 10940
0.13
$289,000
2
1
1,181
For Sale
10 Hoffman Street, Middletown, NY 10940
0.13
$157,200
3
2
1,200
Recently Sold
50 Bedford Avenue, Middletown, NY 10940
0.16
$398,100
3
2
1,460
Off Market
2 Dubois Street, Middletown, NY 10940
0.17
$372,300
4
2
1,896
Off Market
142 South Street, Middletown, NY 10940
0.17
$455,500
4
1.5
2,151
Off Market
6 Randall Terrace, Middletown, NY 10940
0.18
$440,000
3
1.5
1,560
Recently Sold
21 Bedford Avenue, Middletown, NY 10940
0.19
$403,500
3
2
1,524
Off Market

Local Information

  • Map ViewExplore the area around 20 Bennett St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1920
1,365 sqft
$202/sqft
Garage

About this House

NOW AVAILABLE TO SCHEDULE AN APPOINTMENT. Enjoy living in the historic heart of Middletown! Close to shops, restaurants, parks, and right around the corner from SUNY Orange -where the learning possibilities are limitless! This home offers an oversized front porch as the gateway to your sun-drenched sanctuary! Featuring a wonderful open floor plan, original handcrafted wood crown molding, and a plethora of windows that allow the sunlight complete access to brighten your every day. A welcoming foyer, a living room, a dining room with a built-in china cabinet, a kitchen with a cozy breakfast nook, and a 12by14-foot family room are all located on the first floor. Upstairs has two bedrooms, a full bathroom, and a great multi-use space that can serve as a home office, a workout area, or your own getaway zen zone! Another great feature is the full-size unfinished basement already plumbed for a bathroom, with an additional separate outside entrance that can be converted into additional living space for yourself or your loved ones. The possibilities are endless! Don't let this gem slip away!
20 Bennett St, Middletown, NY 10940 is a 2 bedroom, 1 bathroom, 1,365 sqft single-family home built in 1920. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $275,900, with a rent estimate of $2,090/month.

Home Details for 20 Bennett St

Interior Features

Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Interior Details
Number of Rooms: 6

Property Information

Year Built
Year Built: 1920Year Updated: 1931
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 3920 sqft

Price and Tax history

DateEventPrice
Dec 1, 2020
Source: Agent Provided
ListingRemoved
$179,000
May 25, 2020
Source: Agent Provided
Listed For Sale
$179,000

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.
  • Liam Bolger
    "Plenty of places to take your dog for walks"
    0
    Flag
  • 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
    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
  • 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 20 Bennett St

  • What is 20 Bennett St estimated to be worth?
    Trulia's estimated value for 20 Bennett St in Middletown, NY is $275,900.
  • 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 20 Bennett St?
    The lot at 20 Bennett St in Middletown, NY is about 0.09 acres (3,920 sq ft).
  • Does 20 Bennett St have a garage?
    Yes, 20 Bennett St in Middletown, NY has a garage.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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