Middletown, NY Homes

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  /34

  $277,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  193 Deer Ct Dr, Middletown, NY 10940

  Motivated seller. This corner penthouse suite is move-in ready and located in Middletown School District. The kitchen has newer appliances, a new microwave, a pantry and plenty of storage cabinets. With an open concept Livingroom and Dining Room with a wall mounted TV, this suite provides ample room for family gatherings, relaxing and entertainment. The main bedroom boasts a large walk-in closet

  

  Kathy White

  Exit Realty Connections

  (329) 207-0952

  193 Deer Ct Dr, Middletown, NY 10940
• Explore Middletown

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  /29

  $2,300 per month

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

  6 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) 216-1096

  6 Giada Ln Unit 6, Middletown, NY 10940
• 

  $541,000 Sold Nov 19, 2025

  63 Brimstone Hill Rd, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1991

  Last Sold Summary

  • $254/SF
  • 49 Days On Market

  Last Listing Agent Jennifer Loprieno Howard Hanna Rand Realty

  63 Brimstone Hill Rd, Middletown, NY 10941
• 

  Est $736,665 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
• 

  

  

  /25

  $360,000

  • 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

  (329) 212-0993

  71 Commonwealth Ave, Middletown, NY 10940
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  /20

  $2,250 per month

  • 2 Beds
  • 1.5 Baths
  • 1,115 Sq Ft
  • Condo for Rent

  10 Kensington Way, Middletown, NY 10940

  Experience this beautifully renovated two-bedroom, one-and-a-half-bath townhouse in Water Edge, Middletown. Step inside to find brand-new kitchen appliances, stunning new hardwood floors, and fresh paint throughout. The updated bathrooms feature modern vanities that add a stylish, elegant touch. Enjoy the added convenience of an in-unit washer and dryer.Ideally located just across from serene

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 209-8776

  10 Kensington Way, Middletown, NY 10940
• 

  $383,000 Sold Dec 29, 2025

  12 State St, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 1,222 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 21 Days On Market

  Last Listing Agent JoAnn Maxwell Howard Hanna Rand Realty

  12 State St, Middletown, NY 10940
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  Est $675,307 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
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  /25

  $150,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  551 5th, Middletown, NY 10941

  Well maintained 3 bedrooms, 2 bathrooms mobile home in the Valley View mobile home community.Simple one level living, short distance from major highways and shops. Located in the Valley Central School District. Very easy to see. Call today for your own private tour.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 217-4085

  551 5th, Middletown, NY 10941
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  /3

  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,486 Sq Ft
  • House for Rent

  184 Highland Ave, Middletown, NY 10940

  Welcome to this beautiful Victorian-style rental, centrally located in the heart of Middletown, NY. From the moment you arrive, the charming wrap-around porch sets a warm and inviting tone, perfectly complementing the home’s classic character. Inside, you’ll find an updated interior featuring a modern kitchen, a brand-new central air system, new windows, and new doors, providing both comfort and

  

  Chativa Bowen

  Keller Williams Realty

  (329) 219-0850

  184 Highland Ave, Middletown, NY 10940
• 

  $170,000 Sold Jun 27, 2025

  156 School House Rd, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1970

  Last Sold Summary

  • $184/SF
  • 62 Days On Market

  Last Listing Agent Tracy McNamara Keller Williams Realty

  156 School House Rd, Middletown, NY 10940
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  Est $579,493 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
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  /32

  $1,799,000

  • 5 Beds
  • 9 Baths
  • 7,794 Sq Ft

  3 Bristol Dr, Middletown, NY 10941

  LG PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING OF THIS Amazing Mini Mansion Luxury Hse on this one ! For those that look for the very best and finest that the Hudson Valley has to offer you are sure to be amazed as you enter this 11200 plus sq ft luxurious brick colonial mansion including 3200 sq ft Indoor Pool room ! Yes you read that correctly, this home is one of the very few that

  

  Mohamed Elgoarany

  All American Realty Management

  (329) 215-0309

  3 Bristol Dr, Middletown, NY 10941
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  /22

  $3,300 per month

  • 4 Beds
  • 3 Baths
  • 1,859 Sq Ft
  • House for Rent

  79 Monhagen Ave, Middletown, NY 10940

  Welcome to this spacious and wonderfully unique home for rent in the City of Middletown. As you step onto the welcoming front porch and make your way inside, you’ll be greeted by an open floor plan that seamlessly connects the dining and living areas to a generously sized kitchen. This kitchen is truly one of a kind, featuring a gas cooktop, a separate gas stove/oven, two refrigerators, two

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 208-2557

  79 Monhagen Ave, Middletown, NY 10940
• 

  $482,500 Sold Oct 06, 2025

  39 Brookline Ave, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 26 Days On Market

  Current Estimated Value $483,560

  Last Listing Agent Andrea Rose Keller Williams Hudson Valley

  39 Brookline Ave, Middletown, NY 10940
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  Est $540,161 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
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  /34

  $599,999 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,188 Sq Ft

  26 Kyleigh Way, Middletown, NY 10940

  Welcome to this stunning, 5-year-young home located in the desirable Sunrise Hills development.This beautifully maintained residence offers 4 spacious bedrooms, 3 full bathrooms, and 1 half bathroom. The grand cathedral entryway features an elegant chandelier that can be admired from both inside and out, highlighting the top landing of the staircase. The large fourth bedroom is currently set

  

  Delroy Smith

  List 4 Less Realty

  (329) 216-1650

  26 Kyleigh Way, Middletown, NY 10940
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  /28

  $2,300 per month

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

  3 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) 219-0738

  3 Giada Ln Unit 1, Middletown, NY 10940
• 

  $360,000 Sold May 01, 2025

  142 South St, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 2,151 Sq Ft
  • Built 1928

  Last Sold Summary

  • 31% Above List Price
  • $167/SF
  • 140 Days On Market

  Current Estimated Value $364,816

  Last Listing Agent Sharon Sheil Coldwell Banker Realty

  142 South St, Middletown, NY 10940
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  Est $528,095 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
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  /50

  $620,000

  • 3 Beds
  • 2 Baths
  • 3,080 Sq Ft

  179 Reservoir Rd, Middletown, NY 10940

  Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 207-0914

  179 Reservoir Rd, Middletown, NY 10940
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  /27

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 930 Sq Ft
  • House for Rent

  65 Monhagen Ave, Middletown, NY 10940

  This rental offers the convenience of a primary bedroom on the main floor, along with a spacious living room and a large dining room. The kitchen includes updated countertops and a matching backsplash, along with a brand-new refrigerator and new flooring. Hardwood floors run throughout the main level. Upstairs are two additional bedrooms and a second full bathroom. The property includes a

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 213-1077

  65 Monhagen Ave, Middletown, NY 10940
• 

  $390,000 Sold Sep 25, 2025

  112 Monhagen Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft
  • Built 1870

  Last Sold Summary

  • 5% Above List Price
  • $232/SF
  • 27 Days On Market

  Current Estimated Value $388,494

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  112 Monhagen Ave, Middletown, NY 10940
• 

  Est $650,320 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
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  /32

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  22 Sharon Dr, Middletown, NY 10941

  Welcome to 22 Sharon Drive in Middletown, a well-maintained raised ranch offering space, comfort, and a highly convenient location. The main level features hardwood floors throughout, a large living room with high ceilings, and an expansive dining area ideal for everyday living and entertaining. The kitchen is finished with granite countertops and offers great functionality. The upper level

  

  Ammar Iqbal

  eXp Realty

  (329) 223-6823

  22 Sharon Dr, Middletown, NY 10941
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  /9

  $2,100 per month

  • 3 Beds
  • 1 Bath
  • 948 Sq Ft
  • Apartment for Rent

  56 Watkins Ave, Middletown, NY 10940

  Spacious 3BR/1BA Second-Floor Unit. Bright and nicely updated second-floor unit featuring 3 bedrooms and 1 bathroom. Enjoy a sunny eat-in kitchen, fresh paint throughout, and newer hardwood flooring. Additional attic space included, attic space is ONLY for storage use. Located in a quiet neighborhood just a short distance from parks, the YMCA, shops, commuter trains, and bus lines. Tenant pays

  

  Jennifer Loprieno

  Howard Hanna Rand Realty

  (329) 224-0247

  56 Watkins Ave, Middletown, NY 10940
• 

  $300,000 Sold Jul 15, 2025

  103 Deer Court Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $231/SF
  • 15 Days On Market

  Current Estimated Value $309,656

  Last Listing Agent Tanya Von Montague BHHS Hudson Valley Properties

  103 Deer Court Dr, 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
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  /9

  $250,000 Pending

  • 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) 212-1039

  34 Poplar Ln, Middletown, NY 10941
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  /24

  $2,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft
  • Condo for Rent

  51 Deer Ct Dr, Middletown, NY 10940

  A new rental available in Deer Run offers two levels of living in this beautifully maintained two bed, two and one-half bath condo. The updated kitchen features maple cabinets, stainless steel appliances, and a stunning Tiffany light fixture that is located in the eat-in kitchen. An open-concept layout connects the living and dining areas, with sliding doors that lead to a peaceful, private

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 209-9143

  51 Deer Ct Dr, Middletown, NY 10940
• 

  $480,000 Sold Mar 06, 2025

  31 Lindentree Ln, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 1,723 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $279/SF
  • 88 Days On Market

  Current Estimated Value $497,009

  Last Listing Agent Larry Curasi Curasi Realty, Inc.

  31 Lindentree Ln, Middletown, NY 10940
• 

  Est $389,721 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
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  /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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  /20

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Apartment for Rent

  49 Lake Ave Unit 2, Middletown, NY 10940

  Beautifully renovated upstairs apartment featuring two bedrooms and one bathroom. An additional room offers the perfect space for a home office. This rental includes a cozy kitchen, a comfortable living room, and an oversized laundry room. Upstairs, you’ll find a storage area (not permitted for sleeping purposes). Two parking spaces are designated for tenant use, and a back patio provides a nice

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 666-0569

  49 Lake Ave Unit 2, Middletown, NY 10940
• 

  $265,000 Sold Oct 28, 2025

  242 1/2 W Main St, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 20 Days On Market

  Last Listing Agent Sharon Reynolds Keller Williams Hudson Valley

  242 1/2 W Main St, Middletown, NY 10940
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  Est $468,453 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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  /32

  $310,000

  • 4 Beds
  • 2 Baths
  • 1,998 Sq Ft

  21 Ridge St, Middletown, NY 10940

  Don’t miss this 4-bedroom, 2-bath Colonial located in the City of Middletown near Touro College and downtown amenities. including eateries, shopping and local amenities. Featuring generous living space and a traditional Colonial layout, this property offers strong potential for owner-occupants or investors alike. Plenty of parking. Close to dining, shopping, transportation, and schools, this is a

  

  Donna Reese

  Keller Williams Hudson Valley

  (329) 210-4027

  21 Ridge St, Middletown, NY 10940
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  /30

  $2,150 - $2,900 per month

  Southgate Middletown

  1 - 2 Beds

  20 Uhlig Rd, Middletown, NY 10940

  The brand new residences at Southgate Middletown offer a community feel in the center of rapidly growing Middletown, N.Y. Here, an amenity-rich lifestyle awaits, with beautiful homes that feature only the finest in custom appointments and design. See for yourself how easy it would be to call Southgate home. The style of Southgate living features soaring 9-foot ceilings, exquisite luxury flooring,

  20 Uhlig Rd, Middletown, NY 10940
• 

  $603,000 Sold Jun 03, 2025

  33 Highland View Place, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,411 Sq Ft
  • Built 1985

  Last Sold Summary

  • 11% Below List Price
  • $250/SF
  • 65 Days On Market

  Current Estimated Value $613,632

  Last Listing Agent Warren Shelley Reliable Realty Group

  33 Highland View Place, Middletown, NY 10940
• 

  Est $539,115 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,993 Sq Ft

  9 Neptune Ln, Middletown, NY 10940

  9 Neptune Ln, Middletown, NY 10940

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