269 E Main St, Middletown, NY 10940
OFF MARKET

269 E Main St
Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 2,610 sqft

$392,700

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $2,636/mo*
Refinance Your Home

$392,700

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $2,636/mo*
Refinance Your Home
4 Beds
1.5 Baths
2,610 sqft

Local Information

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

Description

Pride of home ownership shows in this beautiful Craftsman Style home. So much potential here that you have to see. You have room to grow with a full walk up attic that could be converted in to living space or expansive master bedroom or choose to create living space in the walk out basement. All the woodwork, including pocket doors leading from living room to dining room, have been preserved adding to the charm of this home. Beautiful wood floors throughout. Close to schools, shopping, highways, bus and train. This home is a must see.
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
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 269 E Main St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard

Property Information

Year Built
Year Built: 1915Year Updated: 1936
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 4791 sqft

Price History for 269 E Main St

DatePriceEventSource
12/11/2020$247,000Sold
OneKey® MLS as distributed by MLS GRID #H6069623
09/14/2020$249,000Listed For SaleAgent Provided
10/01/2011$189,000ListingRemovedAgent Provided
03/24/2011$189,000Listed For SaleAgent Provided
07/07/2010$220,000ListingRemovedAgent Provided
02/26/2010$220,000Listed For SaleAgent Provided
10/24/2009$220,000ListingRemovedAgent Provided
08/01/2009$220,000Listed For SaleAgent Provided
05/06/2004$135,000Sold
N/A
03/13/2000$90,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$283,300
Home facts updated by county records

Comparable Sales for 269 E Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 Ridge Street, Middletown, NY
0.12
Single-Family Home
$315,000
03/31/26
4
2
1,998
143 Prospect Ave, Middletown, NY
0.16
Single-Family Home
$268,745
02/17/26
3
2
1,523
57 Prince Street, Middletown, NY
0.16
Single-Family Home
$315,000
08/08/25
3
2
1,650
4 New St, Middletown, NY
0.16
Single-Family Home
$250,000
01/23/26
4
2
1,488
10 Myrtle Avenue, Middletown, NY
0.25
Single-Family Home
$315,000
01/29/26
3
2
1,608
8 New St, Middletown, NY
0.17
Single-Family Home
$270,000
11/28/25
3
1.5
1,310
55 Prince Street, Middletown, NY
0.17
Single-Family Home
$360,000
11/07/25
3
2
1,537
15 Rowan Street #13, Middletown, NY
0.29
Single-Family Home
$405,000
09/26/25
5
2
1,920
77 Prince Street, Middletown, NY
0.07
Single-Family Home
$395,000
01/29/26
3
2.5
1,245
47 Prince Street, Middletown, NY
0.22
Single-Family Home
$405,000
12/17/25
4
2.5
1,620

Nearby homes

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Assigned Schools

These are the assigned schools for 269 E Main St.
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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269 E Main St, Middletown, NY 10940 is a 4 bedroom, 2 bathroom, 2,610 sqft single-family home built in 1915. This property is not currently available for sale. 269 E Main St was last sold on Dec 11, 2020 for $247,000. The current Trulia Estimate for 269 E Main St is $392,700.