Middletown, NY Homes

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  /30

  $410,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  25 Fairways Dr Unit 1, Middletown, NY 10940

  Step into this fully updated, move-in ready luxury condo located in one of the area’s most sought-after gated communities. This stunning first-floor residence has been meticulously upgraded from top to bottom—featuring designer finishes, fresh modern paint tones, and premium luxury flooring throughout. The custom kitchen is outfitted with elegant cabinetry, granite countertops, and stylish

  

  Randolph Rogers

  eXp Realty

  (845) 299-8068

  25 Fairways Dr Unit 1, Middletown, NY 10940
• 

  Explore Middletown

• 

  

  

  /24

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 917 Sq Ft
  • Condo for Rent

  100 Hillside Dr Unit D6, Middletown, NY 10941

  Don’t miss this beautifully updated first-floor condo in the desirable, Hillside Village Community in the Town of Wallkill. This gated community is located within the sought-after Goshen School District.This well-maintained 2-bedroom, 1-bath unit features a modern galley kitchen with stainless steel appliances, a spacious dining area and a large living room with wall A/C unit. The sliding

  

  Kathy White

  Exit Realty Connections

  (845) 609-1382

  100 Hillside Dr Unit D6, Middletown, NY 10941
• 

  $605,000 Sold Sep 19, 2025

  • 2,410 Sq Ft
  • $251/SF
  • 71 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  344 Ingrassia Rd, Middletown, NY 10940

  Welcome to 344 Ingrassia Rd in Middletown, NY. This stunning Italian custom built Mediterranean home sits on 3.1 acres of land, offering 2,410 sqft of elegant living space. The property features 4 spacious bedrooms and 2.5 bathrooms.Upon entering, you'll notice the beautiful marble tile flooring that flows into the open kitchen. This Grommet kitchen boasts a large island, energy efficient

  Travis Thompson Keller Williams Hudson Valley

  344 Ingrassia Rd, Middletown, NY 10940
• 

  Est $747,624 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,960 Sq Ft

  147 Elise Dr, Middletown, NY 10941

  147 Elise Dr, Middletown, NY 10941
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  /41

  $539,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,130 Sq Ft

  63 Brimstone Hill Rd, Middletown, NY 10941

  Welcome to this outstanding, beautifully maintained Cape Cod-style home nestled on a serene 1.7-acre lot. This unique property combines timeless charm with thoughtful modern touches, offering both privacy and nature. Step onto the oversized front porch and take in the picturesque view of the front yard and classic natural fieldstone wall. As you enter through the soaring foyer, you'll be struck

  

  Jennifer Loprieno

  Howard Hanna Rand Realty

  (329) 219-0768

  63 Brimstone Hill Rd, Middletown, NY 10941
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  /10

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  13 Center St Unit 2, Middletown, NY 10940

  This second-floor apartment features two bedrooms and one bathroom, thoughtfully updated with modern finishes throughout. The kitchen is equipped with brand-new appliances, white cabinetry, and stylish countertops. A spacious living area provides enough room for both a dining table and comfortable living room furniture. Large windows in both bedrooms allow natural light to fill the space, while

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 201-5854

  13 Center St Unit 2, Middletown, NY 10940
• 

  $496,000 Sold Sep 18, 2025

  • 2,000 Sq Ft
  • $248/SF
  • 24 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1971

  7 Ross Ln, Middletown, NY 10941

  THIS IS THE ONE!! Wonderful family home in the heart of Scotchtown. FIRST time on the market in over half a century!! Well maintained, must see to believe! Located on over 1/3 of an acre, this home is one of a kind! Hardwood floors throughout the home have been recently treated. The eat in kitchen provides convenience AND easy access to the HUGE, two-tiered back deck. The home offers a Formal

  David Furlin BHHS Hudson Valley Properties

  7 Ross Ln, Middletown, NY 10941
• 

  Est $716,907 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,626 Sq Ft

  175 Elise Dr, Middletown, NY 10941

  175 Elise Dr, Middletown, NY 10941
• 

  

  /25

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  71 Commonwealth Ave, Middletown, NY 10940

  Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 436-3953

  71 Commonwealth Ave, Middletown, NY 10940
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  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  8 Giada Ln Unit 6, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 216-1278

  8 Giada Ln Unit 6, Middletown, NY 10940
• 

  $155,000 Sold Sep 18, 2025

  • 735 Sq Ft
  • $211/SF
  • 63 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1989

  268 Concord Ln, Middletown, NY 10940

  Welcome to your new home! This bright and inviting 1-bedroom, 1-bathroom condo offers the perfect blend of comfort, style, and convenience. Located in a well-maintained community, this unit features a sun-drenched private balcony—ideal for morning coffee, container gardening, or enjoying a cocktail after a long day.Some Key Features: A generously sized bedroom with ample closet space, New

  Chris Cardinal Keller Williams Realty

  268 Concord Ln, Middletown, NY 10940
• 

  Est $576,565 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  37 Orange Terrace, Middletown, NY 10940

  37 Orange Terrace, Middletown, NY 10940
• 

  

  /42

  $475,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,542 Sq Ft

  138 Reinhardt Rd, Middletown, NY 10940

  Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 208-2838

  138 Reinhardt Rd, Middletown, NY 10940
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  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  8 Giada Ln Unit 4, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-2072

  8 Giada Ln Unit 4, Middletown, NY 10940
• 

  $620,000 Sold Sep 18, 2025

  • 4,491 Sq Ft
  • $138/SF
  • 26 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1900

  122 W Main St, Middletown, NY 10940

  GREAT CASHFLOW INVESTMENT PROPERTY available in Middletown !!! Priced to Sell! This 4 unit multi family property offers 4 units with 3 1 BEDROOMS AND 1 BATH and 1 3 bedrooms. The property offers PRIVATE PARKING IN THE REAR and a second driveway on the other side of the property. The property has a newer roof, boiler and newer water heaters. All units the tenant occupied and each pays for their

  Joao Rodrigues Preferred Properties Real Esta

  122 W Main St, Middletown, NY 10940
• 

  Est $559,750 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  16 4th St, Middletown, NY 10940

  16 4th St, Middletown, NY 10940
• 

  

  /9

  $213,999 Pending

  • 2 Beds
  • 2 Baths
  • 955 Sq Ft

  350 Concord Ln, Middletown, NY 10940

  Welcome to this beautiful 2-bedroom, 2-bathroom condo located in the heart of Middletown, NY! Situated on the first floor, this unit offers convenience and comfort with a spacious dining room, a fully equipped kitchen, and an in-unit washer and dryer. The condo association covers pool access, snow removal, and landscaping, ensuring a stress-free living experience. Enjoy the prime location, just

  Yaakov Rosenberg

  eXp Realty

  (845) 244-5278

  350 Concord Ln, Middletown, NY 10940
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  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  8 Giada Ln Unit 2, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 210-3098

  8 Giada Ln Unit 2, Middletown, NY 10940
• 

  $575,000 Sold Sep 18, 2025

  • 2,230 Sq Ft
  • $258/SF
  • 141 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1900

  19 Academy Ave, Middletown, NY 10940

  STUNNING MIDDLETOWN MULTI-FAMILY is now available for your purchase!! This Colonial is in C-3 zoning where a Commercial business is allowed on the 1st floor! This 2-family is in turn-key condition and offers all the space that you need with nothing left to do but unpack. Ideal for an extended family, or run your business in the 1st level and live on the 2nd, or lastly allow the rental income of

  Sandra Arnez Keller Williams Hudson Valley

  19 Academy Ave, Middletown, NY 10940
• 

  Est $531,901 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,996 Sq Ft

  44 Highrose Ridge Way, Middletown, NY 10940

  44 Highrose Ridge Way, Middletown, NY 10940
• 

  /2

  $250,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  13 Smith St, Middletown, NY 10940

  Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 299-0839

  13 Smith St, Middletown, NY 10940
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  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  8 Giada Ln Unit 1, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 210-5918

  8 Giada Ln Unit 1, Middletown, NY 10940
• 

  $314,900 Sold Sep 17, 2025

  • 1,216 Sq Ft
  • $259/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2007

  936 Tower Ridge Cir, Middletown, NY 10941

  Looking for resort lifestyle living, Welcome to Tower Ridge Grande. Lovely Evergreen model with 2 Bedroom/2 Bath end unit with amazing views has so much to offer. Airy and open floor plan as you walk into the eat in kitchen area with granite countertops, custom backsplash, stainless steel appliances and ample sized 2 Tier Island.Access to private balcony, gleaming hardwood floors, spacious living

  Angelo Acierno Keller Williams Realty

  936 Tower Ridge Cir, Middletown, NY 10941
• 

  Est $705,434 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,422 Sq Ft

  239 Sands Rd, Middletown, NY 10941

  239 Sands Rd, Middletown, NY 10941
• 

  

  /9

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  34 Poplar Ln, Middletown, NY 10941

  This well-maintained home offers comfort, space, and convenience in a desirable location close to shopping, dining, and public transportation. Step inside to find generously sized bedrooms with vaulted ceilings that create an open and airy feel. The rear bedroom features a private balcony—perfect for morning coffee or unwinding at the end of the day. A full basement provides ample storage space,

  

  John Olivero

  Keller Williams Realty

  (329) 210-4787

  34 Poplar Ln, Middletown, NY 10941
• 

  

  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  8 Giada Ln Unit 3, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 201-4184

  8 Giada Ln Unit 3, Middletown, NY 10940
• 

  $240,000 Sold Sep 17, 2025

  • 974 Sq Ft
  • $246/SF
  • 51 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1988

  38 Brittany Dr, Middletown, NY 10940

  Welcome to 38 Brittany Drive, located in a desirable ground-level condo nestled in a quiet, well-maintained community! This two-bedroom, one-bath unit features a functional galley kitchen with generous cabinetry, a spacious living area, and an in-unit washer/dryer for added convenience. Additionally, a 6x8 storage unit is located in the lower level (common area) of the basement. The monthly HOA

  Nicholas Cuomo Keller Williams Realty

  38 Brittany Dr, Middletown, NY 10940
• 

  Est $714,800 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft

  249 Sands Rd, Middletown, NY 10941

  249 Sands Rd, Middletown, NY 10941
• 

  

  /20

  $399,990

  • 3 Beds
  • 2 Baths
  • 1,614 Sq Ft

  2 Saint Eve Ct, Middletown, NY 10940

  Welcome to 2 Saint Eve Ct, a versatile home offering comfort and space in a convenient Middletown location. This well-maintained property features 3 bedrooms and 2 full baths, along with a spacious eat-in kitchen perfect for everyday living and entertaining. Above the garage, a large rec room provides endless possibilities—use it as a fourth bedroom, family room, or bonus space to suit your

  

  Haakim Byrd

  HomeSmart Homes & Estates

  (329) 210-5621

  2 Saint Eve Ct, Middletown, NY 10940
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  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  7 Giada Ln Unit 6, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 201-5406

  7 Giada Ln Unit 6, Middletown, NY 10940
• 

  $459,000 Sold Sep 16, 2025

  • 2,567 Sq Ft
  • $179/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2009

  49 Cornwall Ln, Middletown, NY 10940

  3-Bedroom End Unit Townhome in Woodside Knolls – Middletown, NY. Welcome to 49 Cornwall, a lovely end-unit townhome nestled in the highly sought-after Woodside Knolls community of Middletown, NY. Perched on a quiet hilltop cul-de-sac, this spacious 2,567 sq. ft. home offers the perfect blend of comfort, convenience, and community amenities. This residence features 3 generous bedrooms, 2.5

  Susan Giordano John J Lease REALTORS Inc

  49 Cornwall Ln, Middletown, NY 10940
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  /9

  Not Listed For Sale

  Lot 11 Meadowbrook Dr, Middletown, NY 12455

  

  Lot 11 Meadowbrook Dr, Middletown, NY 12455
• 

  

  /18

  $249,999

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  215 Ruth Ct, Middletown, NY 10940

  One-Level Living at It's Finest – First Floor Condo in Middletown, NYWelcome to effortless living in this beautifully maintained first-floor condo, located in the heart of Middletown, NY. This spacious unit features brand new hardwood floors throughout, offering a warm and modern feel from the moment you step inside. The primary bedroom features a generous walk-in closet and a private

  

  Chativa Bowen

  Keller Williams Realty

  (329) 223-6211

  215 Ruth Ct, Middletown, NY 10940
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  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  7 Giada Ln Unit 4, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 201-5418

  7 Giada Ln Unit 4, Middletown, NY 10940
• 

  $347,500 Sold Sep 16, 2025

  • 1,486 Sq Ft
  • $234/SF
  • 27 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1920

  184 Highland Ave, Middletown, NY 10940

  Here you have a beautiful Victorian style home, centrally located in Middletown NY. This home features a beautiful wrap around porch that presents a charming appeal to all visitors of the property. The property has been upgraded by the current owner, they have put in $55k of upgrades which include an updated kitchen, new central air system, new doors, and new windows! The home encompasses 4

  Jorge Lugo Real Broker NY LLC

  184 Highland Ave, Middletown, NY 10940
• 

  Est $382,319 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft

  237 Route 211 W, Middletown, NY 10940

  237 Route 211 W, Middletown, NY 10940
• 

  

  /11

  $350,000

  • 4 Beds
  • 2.5 Baths
  • 2,088 Sq Ft

  19 Randall Terrace, Middletown, NY 10940

  Looking for all investors who want to buy now and get the process started in order to work on the exterior before the cold weather begins. All reasonable offers will be considered. Home features an eat in kitchen with breakfast nook, diningroom, and large step down livingroom on first floor with fireplace. Upstairs find a primary bedroom suite with separate bath. Down the hall is three more

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 216-0798

  19 Randall Terrace, Middletown, NY 10940
• 

  

  /29

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  7 Giada Ln Unit 3, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 210-4234

  7 Giada Ln Unit 3, Middletown, NY 10940
• 

  $180,000 Sold Sep 15, 2025

  • 2,269 Sq Ft
  • $79/SF
  • 35 Days On Market

  • Built 1900

  97 E Main St, Middletown, NY 10940

  Don’t miss your chance to own a versatile property in one of Orange County’s fastest-growing areas. Located in the heart of Middletown, this mixed-use building offers a unique opportunity for both residential living and commercial investment in a high-demand market. Just 70 miles from New York City, Middletown offers the perfect blend of suburban comfort and urban accessibility, with direct

  Savannah Miceli Century 21 Alliance Rlty Group

  97 E Main St, Middletown, NY 10940
• 

  Est $444,082 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,330 Sq Ft

  366 North St, Middletown, NY 10940

  366 North St, Middletown, NY 10940

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