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Middletown Real Estate Search

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Middletown NY Real Estate

  • Living in Middletown NY
  • Middletown Commute
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You can search for all Middletown and Orange County NY homes, condos, co-ops, and foreclosures for sale. Sign up to get new property listings daily that meet your search criteria. 

Middletown Properties For Sale

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Living in Middletown NY

Population (2010 census): 28,086 over 5.14 square miles 
Median Age: 32.3
Median Income: $53,446
% of Population with Bachelor's Degree or Higher: 19.1%
% Households with Children Under 18: 38.8%

Middletown is one of three cities (the other two being Port Jervis and Newburgh) in Orange County, New York. 

Middletown had an important place in the railway history of the region. Most residents were employed at the many factories in the town.

By the 1960s, like the rest of the country, many of the factories started to close. At the same time, shopping centers were being built right outside the downtown area in Wallkill. Residents started to live in the suburbs that are more spread out, leading to empty store fronts on Main Street. Some of the Middletown businesses actually had to move to the Orange Plaza.

The first Lloyd's Supercenter was built in Wallkill, and then came the Galleria at Crystal Run and Orange Plaza. The section of Route 211 where all these shopping centers were built was dubbed the "Miracle Mile". It was a prime example of the birth of shopping centers. Actually even more shopping centers and big box stores have opened in Middletown over the years, making it even more convenient.

Nowadays, the downtown area of Middletown is still lined with beautiful Victorian homes. Visitors to Middletown can enjoy seeing a film at the Paramount Movie Theater, or visit a children's museum called the Interactive Museum. You will find many ethnic businesses, especially compared to the surrounding suburbs, in the city. 

Middletown commute

Middletown is approximately 65 miles North of New York City. Driving to both Albany and New York City takes around 90 minutes.

There is a Middletown Metro North station on the Port Jervis Line, which connects Secacus Station, and a transfer to Penn Station in New York City. The ride from Middletown to Secacus is approximately 90 minutes.

Middletown Schools

The Middletown Central School District has 4 elementary schools, 2 middle schools and 1 high school for its students. SUNY Orange, the community college for the county, is located in Middletown. 

Visit our Orange County School Districts page to find out more information about each school district in the county.

Middletown Real Estate

42.2% of the properties in Middletown are detached single family homes. You will also find a good selection of multifamily homes and apartment buildings. Many of the homes are older, some still retaining its historic charms. 51.8% of the homes were built before 1940. 

About half the homes in Middletown are owner occupied, with the other half being tenant occupied.

In 2014, there were 126 single family homes sold in Middletown. The median sales price was $133,750. There were also 30 condos sold with a median sales price for $121,250.   

Some of the popular condo and townhouse developments in Middletown include:

  • Deer Run condo and townhouse development, built in 2002
  • Canterbury Knolls townhouses was built in several phases. The development has a clubhouse complete with a fitness room, tennis courts and playground.
  • Oak Hill Manor, a newer development built in 2006.
  • Mountside Hills townhouses
  • Highrose Ridge, a new construction townhouse development of 133 homes. 
  • Woodside Knolls, a beautiful development built after 2008. The development has a clubhouse, swimming pool, tennis courts, basketball court and playground
  • Maple Fields, a townhouse development built after 2016. The amenities include a swimming pool, basketball court, playground, gym, and common area maintenance.

Other popular developments in Middletown include:

  • The Fairways, a lovely development of townhouses and single family homes at a golf course. 
  • Wildflower at Wallkill, a large development of 283 single family homes for active adults 55+. There are plenty of amenities and activities for residents
  • Scotchtown Estates, a new construction homes development
  • Robinn Meadows, a newer construction homes development

Middletown Links

Middletown website: www.middletown-ny.com

Looking for more communities like this?

  • See all Middletown School District Homes for Sale
  • See all Orange County Condos and Townhouses for Sale
  • See all Orange County 55+ Active Adult Communities
  • See all New Construction Homes for Sale in Orange County
  • See all Foreclosure Homes for Sale in Orange County

 Orange County Towns | Orange County School Districts

63 Phillips Street, Middletown image
63 Phillips Street, Middletown $399,900

This lovely bilevel is just waiting for you to call home and create new memories. The 3 bedroom 2.5 bath home located in the City of Middletown, has plenty of space for y...

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  • 3 Beds
  • 3 Baths
  • H6269869 MLS
  • ACTIVE Status
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26 Maple Drive, Middletown image
26 Maple Drive, Middletown $429,900

Nestled within the heart of Middletown, this exquisite, raised ranch home offers the perfect blend of comfort and convenience. You'll enjoy easy access to schools, parks...

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  • 4 Beds
  • 2 Baths
  • H6269599 MLS
  • ACTIVE Status
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35 Woodlake Drive, Middletown image
35 Woodlake Drive, Middletown — Spring Hollow Community $235,000

This End-Unit waterfront townhome has 3 bedrooms and 1 and a half bathrooms, located in the Spring Hollow community complex in Middletown, which has LOW taxes and LOW HOA...

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  • 3 Beds
  • 2 Baths
  • H6269408 MLS
  • Spring Hollow Community Bldg.
  • ACTIVE Status
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3 Wickham Avenue, Middletown image
3 Wickham Avenue, Middletown $375,000

Discover the allure of the spacious historical home waiting for your personal touch. 3 Wickham Avenue boasts an array of original features that will transport you back to...

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  • 6 Beds
  • 3 Baths
  • H6269449 MLS
  • ACTIVE Status
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14 Smith Street, Middletown image
14 Smith Street, Middletown $155,000

Three bedroom, two bathroom two-story home on a quiet side street in the City of Middletown! Renovations needed. Exterior inspections only at this time. Close to s...

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  • 3 Beds
  • 2 Baths
  • H6269199 MLS
  • ACTIVE Status
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82 Prospect Avenue, Middletown image
82 Prospect Avenue, Middletown $350,000

Huge 5 Bedroom Home in Middletown. You can enter from the main Front Door into the Huge living room, on the main floor is the Kitchen, Huge Dining Room, 2 Large Living ro...

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  • 5 Beds
  • 2 Baths
  • H6267802 MLS
  • ACTIVE Status
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177 High Barney Road, Middletown image
177 High Barney Road, Middletown $469,000

This Beautiful home is a spacious house on a 2.3 acre lot in Cul-De-Sac. Property has a vaulted living room with fireplace and arched picture window. lovely open kitchen ...

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  • 4 Beds
  • 3 Baths
  • H6268603 MLS
  • ACTIVE Status
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104 Monhagen Avenue, Middletown image
104 Monhagen Avenue, Middletown $539,000

Fully renovated, 4 bedroom / 2.5 bathroom Victorian with hardwood floors throughout. This home has been lovingly restored with period appropriate finishes and ample atten...

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  • 4 Beds
  • 3 Baths
  • H6267209 MLS
  • ACTIVE Status
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1 Highrose Ridge Way, Middletown image
1 Highrose Ridge Way, Middletown $520,000

Discover a 4-bedroom townhouse blending modern elegance with classic charm, just 70 miles from NYC. Nestled at 1 Highrose Ridge Way, Middletown, NY, this home offers an e...

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  • 4 Beds
  • 3 Baths
  • 3503856 MLS
  • ACTIVE Status
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57 Lexington Way, Middletown image
57 Lexington Way, Middletown — Mountainside Hills Condo $324,000

Welcome to the ONLY unit available in Mountainside Hills Condominium Community! This end unit will not disappoint you! When you enter you will notice the open floor conce...

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  • 3 Beds
  • 3 Baths
  • H6268273 MLS
  • Mountainside Hills Condo Bldg.
  • ACTIVE Status
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14 Academy Avenue, Middletown image
14 Academy Avenue, Middletown $499,000

Huge opportunity to own a piece of prime commercial real estate on a busy road in Middletown, NY. This high traffic corner lot is home to a successful repair shop and car...

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  • H6268112 MLS
  • ACTIVE Status
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33-49 Mulberry Street, Middletown image
33-49 Mulberry Street, Middletown $4,450,000

potential development opportunities commercial & residential

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  • H6268137 MLS
  • ACTIVE Status
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165 Highland Avenue, Middletown image
165 Highland Avenue, Middletown $429,000

Come see this pristine center hall Colonial on Highland Ave. Many of the orginal features are still there. Beautiful cooks kitchen with a natural gas range , plenty of ca...

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  • 3 Beds
  • 2 Baths
  • H6268086 MLS
  • ACTIVE Status
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78 Watkins Avenue, Middletown image
78 Watkins Avenue, Middletown $399,000 ▲

Must-See 4 Bedroom Home in Middletown's Tranquil Neighborhood! Discover your dream home in this stunning 4 bedroom residence, boasting move-in condition and located in a...

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  • 4 Beds
  • 2 Baths
  • 3503271 MLS
  • ACTIVE Status
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32 Birch Drive, Middletown image
32 Birch Drive, Middletown $325,000

Lovely three bedroom, one and a half bathroom home located on a quiet street in Middletown. The peaceful and serene private back yard is perfect for relaxing and to enjoy...

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  • 3 Beds
  • 2 Baths
  • H6267840 MLS
  • ACTIVE Status
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21 North Street, Middletown image
21 North Street, Middletown $849,900

PRIME COMMERCIAL PROPERTY in the Heart of Middletown's Thriving Business District!! So Many Possibilities. Situated in a Dynamic Mixed-Use Zoning in the Premier dow...

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  • H6263036 MLS
  • ACTIVE Status
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38 Eisenhower Drive, Middletown image
38 Eisenhower Drive, Middletown $349,000

Welcome to this charming 3-bedroom, 1-bathroom ranch-style house nestled in the heart of Middletown, New York. We're delighted to introduce you to this beautiful home, wh...

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  • 3 Beds
  • 1 Baths
  • H6267094 MLS
  • ACTIVE Status
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30 Madelaine Terrace, Middletown image
30 Madelaine Terrace, Middletown $325,900 ▼

Are you looking for a cozy and inviting home that perfectly blends comfort and style? Look no further! This ranch-style home just may be exactly what you're looking for! ...

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  • 2 Beds
  • 1 Baths
  • H6267246 MLS
  • ACTIVE Status
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71-96 Bennett Street, Middletown image
71-96 Bennett Street, Middletown $289,000

Centrally Located in the City of Middletown this is a rare find! Municipal Water and Sewer available. C-2 Zoning. These multiple lots together bring you just over 3 acre...

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  • H6266238 MLS
  • ACTIVE Status
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25 Jackson Street, Middletown image
25 Jackson Street, Middletown $349,000

This property in the Hudson Valley has it all! Private and quiet location. First floor primary master bedroom, Open plan living, hardwood floors as seen, second and third...

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  • 3 Beds
  • 2 Baths
  • H6266330 MLS
  • ACTIVE Status
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15 Grandview Avenue, Middletown image
15 Grandview Avenue, Middletown $240,000

location location across from Orange county community college. perfect for student rental, close to shops and downtown eateries.

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  • 2 Beds
  • 1 Baths
  • H6266198 MLS
  • ACTIVE Status
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49 Ruth Court, Middletown image
49 Ruth Court, Middletown — Eastview Condominium $189,000

Location at it's best! This 2 bedroom is centrally located in the City of Middletown, Close to all shopping,schools,hwy's and public transportation. This well maintained ...

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  • 2 Beds
  • 1 Baths
  • H6265845 MLS
  • Eastview Condominium Bldg.
  • ACTIVE Status
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53 Horton Avenue, Middletown image
53 Horton Avenue, Middletown $350,000

Ideal 2 family home. Live in one unit and rent out the other to help pay the mortgage. The main level features large sitting room with living room to the left side. Th...

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  • 3 Beds
  • 2 Baths
  • H6263596 MLS
  • ACTIVE Status
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202 Concord Lane, Middletown image
202 Concord Lane, Middletown — Buttonwood $289,900

Newly Renovated Townhouse located in the Heart of Middletown. This 1300 Sq. Ft. home offers 3 Bedrooms & 2 1/2 Bathrooms. Brand new central air unit. Brand New Luxury Vin...

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  • 3 Beds
  • 3 Baths
  • H6264414 MLS
  • Buttonwood Bldg.
  • ACTIVE Status
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60 Peach Place, Middletown image
60 Peach Place, Middletown — Swan Village Estates $150,000

3 Bedroom, 3 1/2 Bath Townhouse.This property is part of an online bidding event and bids can only be placed on the event website during the Auction period 9/25/23 to 9/2...

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  • 3 Beds
  • 4 Baths
  • H6263800 MLS
  • Swan Village Estates Bldg.
  • ACTIVE Status
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272 E Main Street, Middletown image
272 E Main Street, Middletown $349,900

Beautiful two family in the city of Middletown. Both units currently rented. Just renovated this year to include new roof, attic insulation, kitchens, flooring, freshly p...

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  • 3 Beds
  • 2 Baths
  • H6263586 MLS
  • ACTIVE Status
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30 Chestnut Street, Middletown image
30 Chestnut Street, Middletown $319,900 ▼

Charming family home with vintage character. This exquisite home showcases the beauty of a bygone era with its original beveled glass front door, a testament to its rich ...

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  • 3 Beds
  • 1 Baths
  • H6242887 MLS
  • ACTIVE Status
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293 E Main Street, Middletown image
293 E Main Street, Middletown $325,000

Cozy Multi-Family Duplex in Prime Middletown Location! Discover this charming and well-maintained multi-family 2-unit property in the heart of Middletown. Ideal for inves...

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  • 4 Beds
  • 2 Baths
  • H6260489 MLS
  • ACTIVE Status
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32 Houston Ave Ext, Middletown image
32 Houston Ave Ext, Middletown $179,000 ▼

Calling all investors. Add this to your rental portfolio. Up for sale is this charming 605 sq feet 1 bed 1 bath home located in Middletown NY. Quiet street and house sits...

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  • 1 Beds
  • 1 Baths
  • H6261876 MLS
  • ACTIVE Status
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77 Commonwealth Avenue, Middletown image
77 Commonwealth Avenue, Middletown $561,000 ▼

Price reduction! Motivated seller. This stunning 4-bedroom, 3-bathroom home is located in the heart of town, just minutes from everything you need. The floor plan is perf...

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  • 4 Beds
  • 3 Baths
  • H6261120 MLS
  • ACTIVE Status
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86 Linden Avenue, Middletown image
86 Linden Avenue, Middletown $299,000

The possibilities are ENDLESS with this one. Come check out the biggest bang for your buck in Middletown. This is a 4 bedroom 1 bathroom house with TREMENDOUS potential.A...

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  • 4 Beds
  • 1 Baths
  • H6260630 MLS
  • ACTIVE Status
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330 North Street, Middletown image
330 North Street, Middletown $385,000

Step into luxury when you enter this elegant, fully-renovated 4 Bedroom 3 full bathroom home. It has beautiful vinyl plank flooring throughout first and second levels. K...

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  • 4 Beds
  • 3 Baths
  • H6260844 MLS
  • ACTIVE Status
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18 Chestnut Street, Middletown image
18 Chestnut Street, Middletown $399,000

Each unit boasts two spacious bedrooms and a well-appointed bathroom. Both units are currently fully rented, ensuring immediate rental income for the new owner. The prope...

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  • 4 Beds
  • 2 Baths
  • H6260155 MLS
  • ACTIVE Status
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221 E Main Street E, Middletown image
221 E Main Street E, Middletown $465,000

AMAZING OPPORTUNITY. COME VIEW IN PERSON AND LET IT SPEAK FOR ITSELF. INVESTORS WELCOME!

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  • 6 Beds
  • 4 Baths
  • H6259624 MLS
  • ACTIVE Status
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103 Concord Lane, Middletown image
103 Concord Lane, Middletown — Buttonwood Condominiums $109,900

This studio apartment is a great investment!! Move in condition updated kitchen and bathroom. Features include a large walk in closet, assigned parking and many common s...

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  • 1 Baths
  • H6259339 MLS
  • Buttonwood Condominiums Bldg.
  • ACTIVE Status
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2 Dubois Street, Middletown image
2 Dubois Street, Middletown $299,000

Accepted offer, But can still show for backup. Great hidden potential - In Fantastic area in Middletown. Living Room, Kitchen, 2 Full Baths, 4 Bedroom, Owner did some wo...

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  • 4 Beds
  • 2 Baths
  • H6258913 MLS
  • ACTIVE Status
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103 Linden Avenue, Middletown image
103 Linden Avenue, Middletown $405,000

GREAT INVESTMENT PROPERTY 4 FAMILY EACH UNIT HAS 1 BEDROOM AND 1 BATH. NICE YARD SPACE. THE OWNER MUST OCCUPY AT LEAST ONE UNIT.

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  • 4 Beds
  • 4 Baths
  • H6258656 MLS
  • ACTIVE Status
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116 Wawayanda Avenue, Middletown image
116 Wawayanda Avenue, Middletown $439,000 ▼

A great deal in Summer 2023! Please check this beautiful colonial home with 4 bedrooms 2.5 full bathroom and an unfinished basement. It is under construction and it will ...

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  • 4 Beds
  • 3 Baths
  • H6258414 MLS
  • ACTIVE Status
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105 Lake Avenue, Middletown image
105 Lake Avenue, Middletown $344,000

Fully renovated dream home in Middletown, NY! This charming Cape Cod style house is the perfect haven for those seeking comfort, style, and easy living. Step inside and y...

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  • 3 Beds
  • 2 Baths
  • H6184437 MLS
  • ACTIVE Status
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8 Canterbury Drive, Middletown image
8 Canterbury Drive, Middletown $375,000 ▼

Available for the first time in 53 years, this lovely colonial is just waiting for you to come and create new memories. This 4 bedroom/2.5 bath home located in the City o...

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  • 4 Beds
  • 3 Baths
  • H6252066 MLS
  • ACTIVE Status
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Information Copyright 2023, OneKey® MLS. All Rights Reserved. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

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