Middletown, NY Homes

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  $489,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,763 Sq Ft

  38 Highrose Ridge Way, Middletown, NY 10940

  Welcome to a beautifully maintained 6-year-young home offering comfort, style, and an unbeatable location. This spacious residence features 3 generously sized bedrooms and multiple living spaces, including a warm and inviting living room and a bright, open family room perfect for gatherings or quiet evenings in.The heart of the home is the well-appointed kitchen, offering plenty of counter

  

  Donna Reese

  Keller Williams Hudson Valley

  (329) 201-4609

  38 Highrose Ridge Way, Middletown, NY 10940
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  $2,200 per month

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

  100 Hillside Dr Unit D6, Middletown, NY 10941

  This beautifully updated first-floor condo is located in the desirable, Hillside Village Community in the Town of Wallkill. This gated community is located within the highly 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

  

  Kathy White

  Exit Realty Connections

  (845) 609-1382

  100 Hillside Dr Unit D6, Middletown, NY 10941
• 

  $493,000 Sold Nov 21, 2025

  • 1,858 Sq Ft
  • $265/SF
  • 27 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2010

  38 Cobblestone Ln, Middletown, NY 10940

  Must see !!! 3 bedroom 2.5 bathroom townhome with crown molding throughout 3 levels of living space Hardwood floors (Acacia)in most rooms with the exception of 1 bedroom and basement which is carpeted.Home features living room with gas fireplace custom mantle and granite surround ,sliding doors to patio and private backyard.2 story open foyer with chandelier. Study / office with French doors for

  Sandra Johnson Keller Williams Realty

  38 Cobblestone Ln, Middletown, NY 10940
• 

  Est $524,939 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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  $359,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  33 Red Barn Ln, Middletown, NY 10940

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhouse perfectly situated near schools, shopping, and major highways for an easy commute. Pride of ownership is evident throughout with spacious living areas, a functional layout, and thoughtful updates. The finished lower level offers additional living space, while the 1-car garage provides convenience and storage. Set at the end of

  

  Donna Reese

  Keller Williams Hudson Valley

  (329) 216-8293

  33 Red Barn Ln, Middletown, NY 10940
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  $2,300 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
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  $220,000 Sold Nov 21, 2025

  • Land
  • 15.23 Acres
  • $14,445 per Acre

  • 46 Days On Market

  778 Bragg Hollow Rd, Middletown, NY 12438

  Set on beautiful Bragg Hollow Road in Halcottsville—arguably the prettiest little village in the area—this gently sloping 15-acre parcel is a rare find. A mix of open meadows, stone walls, wildflowers and mature trees creates a delightful landscape that is ready for your dream home.A graded meandering driveway leads to the approved build site, complete with a successful perc test and septic

  Sarah Broach Listing by Keller Williams Upstate NY Properties

  

  778 Bragg Hollow Rd, Middletown, NY 12438
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  Est $577,667 Not Listed For Sale

  • Studio

  328 Stony Ford Rd, Middletown, NY 10941

  328 Stony Ford Rd, Middletown, NY 10941
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  $410,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  31 Beattie Ave, Middletown, NY 10940

  Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-3980

  31 Beattie Ave, Middletown, NY 10940
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  $2,375 - $3,000 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
• 

  $445,000 Sold Nov 19, 2025

  • 2,447 Sq Ft
  • $182/SF
  • 42 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1973

  2 Mountain Ave, Middletown, NY 10940

  Step into this spacious and versatile raised-ranch style two-family home OWNER OCCUPIED, perfectly located in the quiet neighborhood of Middletown!This well-maintained property offers a total of 5 bedrooms, 2 full bathrooms, and a bonus room ideal for a home office, playroom, gym, or guest space tailored to fit your lifestyle.The upper-level unit features a bright and open layout with a

  Jeaneth Pino-Bartchak RE/MAX Benchmark Realty Group

  2 Mountain Ave, Middletown, NY 10940
• 

  Est $686,570 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  20 Nicaj Ct, Middletown, NY 10941

  20 Nicaj Ct, Middletown, NY 10941
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  $269,900 Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  89 Sycamore Dr, Middletown, NY 10940

  This 2 bedrooms, 1 batrhroom condo in the desirable Clemson Park complex won't last. Ideal for someone looking for a ground floor unit. Unit has been freshly painted and the gleaming hardwood floors have just been brought back to life. This unit is simply waiting on your personal touches. Sliding glass doors lead to an oversize deck where you can enjoy your morning coffee or just sit back and

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 214-0413

  89 Sycamore Dr, Middletown, NY 10940
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  /20

  $2,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • House for Rent

  41 Woodlake Dr Unit 41, Middletown, NY 10940

  Great 2 Bedroom Townhome with new appliances & fresh paint. Spacious layout, nice kitchen, slider to patio, 1/2 bath on the1st floor and and a large living room & dining area. Large primary bedroom with 2 large closets. 2nd bedroom offers great space & large closet. A full bathroom w/jetted tub and laundry room complete the upper level. A final cleaning of the carpet & unit being done next week.

  Regina Clark Real Estate Circuit Inc

  41 Woodlake Dr Unit 41, Middletown, NY 10940
• 

  $541,000 Sold Nov 19, 2025

  • 2,130 Sq Ft
  • $254/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  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 in the Pine Bush School District. 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

  Jennifer Loprieno Howard Hanna Rand Realty

  63 Brimstone Hill Rd, Middletown, NY 10941
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  Est $552,040 Not Listed For Sale

  • 4 Beds

  775 van Burenville Rd, Middletown, NY 10940

  775 van Burenville Rd, Middletown, NY 10940
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  $750,000 Pending

  • 8 Beds
  • 5 Baths
  • 4,000 Sq Ft

  256 E Main St, Middletown, NY 10940

  Nestled in the heart of Middletown, NY, this distinguished property offers an exceptional investment opportunity with a blend of residential charm and commercial viability. Situated at 256 E Main St, this detached multi-family gem boasts an impressive investment, perfectly accommodating a wide spectrum of living arrangements and lifestyles.Beyond its generous living quarters, this

  Hershel Reisz

  eRealty Advisors, Inc

  (845) 217-3892

  256 E Main St, Middletown, NY 10940
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  $1,800 - $2,100 per month

  Slatewood Apartments

  1 - 3 Beds

  579 E Main St, Middletown, NY 10940

  Slatewood Apartments offers a great mix of convenience and serenity, with its wooded setting providing a peaceful environment while still being close to essential amenities. The proximity to the new state-of-the-art Medical Center is a particularly nice touch for residents who might need easy access to healthcare services. With options for one-, two-, and three-bedroom apartments, it caters to a

  579 E Main St, Middletown, NY 10940
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  $625,000 Sold Nov 19, 2025

  • 1,992 Sq Ft
  • $314/SF
  • 11 Days On Market

  • 9 Beds
  • 3 Baths
  • Built 1890

  11 East Ave, Middletown, NY 10940

  Attention Investors & Savvy Buyers! Don’t miss this incredible opportunity to own a fully renovated three-family home in the heart of Middletown. Perfectly located within walking distance to public transportation, schools, parks, and shopping, this property offers convenience and strong rental potential. Each of the three spacious units features 3 bedrooms and 1 full bathroom, all newly renovated

  Susan Giordano John J Lease REALTORS Inc

  11 East Ave, Middletown, NY 10940
• 

  Est $420,180 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  47 Pinto Rd E, Middletown, NY 10941

  47 Pinto Rd E, Middletown, NY 10941
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  $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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  $1,800 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  217 King Rd, Middletown, NY 10941

  Lovely 2-bedroom, 1-bath farmhouse available for rent. Enjoy an inviting living area, functional kitchen and in-unit washer and dryer. Property offers plenty of outdoor space and a quaint country setting while still being just minutes from town. All freshly painted and move-in ready. No pets. 3 months rent due at lease signing (first months, security deposit and realtor fee). Utilities are

  Britanni Gaucher Keller Williams Realty

  217 King Rd, Middletown, NY 10941
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  $99,000 Sold Nov 19, 2025

  • Land
  • 0.11 Acre
  • $880,000 per Acre

  • 8 Days On Market

  40 Adams Ave, Middletown, NY 10940

  Ready-to-build lot with foundation already in place and approvals secured, this exceptional property at 40 Adams Ave in Middletown presents an incredible opportunity to bring your dream home to life. The architectural plan is thoughtfully designed for a charming three-bedroom residence, complemented by an additional unfinished level that provides endless possibilities—it can be transformed into a

  Chaim Katz Metrex Realty INC

  40 Adams Ave, Middletown, NY 10940
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft

  2 Fortune Rd W Unit K, Middletown, NY 10941

  2 Fortune Rd W Unit K, Middletown, NY 10941
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  $369,900 Pending

  • 5 Beds
  • 2 Baths
  • 2,440 Sq Ft

  44 Houston Ave, Middletown, NY 10940

  Excellent opportunity to own a 2 family house whether you are an investor or want to live in one of the units and rent the second one. Spacious apartments. First floor apartment has 3 bedrooms and 1 bathroom, second floor apartment has 2 bedrooms and 1 bath. Conveniently located, walking distance to Touro College where students are always looking for close by rentals. Minutes to I86 and I84,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 497-6793

  44 Houston Ave, Middletown, NY 10940
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  $1,850 - $2,200 per month

  Country Manor Apartments

  1 - 2 Beds

  700 Stratford Ln, Middletown, NY 10940

  Welcome to Country Manor Apartments in Middletown, NY! Tucked into a peaceful suburban neighborhood, our pet-friendly community offers spacious and thoughtfully designed one- and two-bedroom homes perfect for every lifestyle.Your rent includes heat, hot water, gas, and trash removal— making your living experience simple and stress-free. We offer onsite laundry, high-speed internet access,

  700 Stratford Ln, Middletown, NY 10940
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  $220,000 Sold Nov 18, 2025

  • 830 Sq Ft
  • $265/SF
  • 9 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1976

  65 Sycamore Dr, Middletown, NY 10940

  Come see this awesome completely udated unit , new kitchen with great looking cabinets and new flooring. Great view from the patio and a awning to keep out the sun. washer and dryer in the unit.No showings before 12 Noon

  Corinne Bocsusis Howard Hanna Rand Realty

  65 Sycamore Dr, Middletown, NY 10940
• 

  Not Listed For Sale

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

  206 2nd Ave, Middletown, NY 10941

  206 2nd Ave, Middletown, NY 10941
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  $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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  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,207 Sq Ft
  • Property for Rent

  496 Bloomingburg Rd, Middletown, NY 10940

  Cape Style- Single Family home in the Middletown School District offering 3 Bedrooms, 1-1/2 Bath is available to lease immediately. Freshly painted, Hardwood flooring throughout. Washer/dryer hook-up. Enjoy the enclosed sun porch - a great addition for 3 seasons. Extra storage on the 2nd floor. Ample off street parking.Tenant responsible for all utilities. Call to view today.

  Dawn Gregg Curasi Realty, Inc.

  496 Bloomingburg Rd, Middletown, NY 10940
• 

  $274,000 Sold Nov 17, 2025

  • 1,012 Sq Ft
  • $271/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  100 Hillside Dr Unit C15, Middletown, NY 10941

  Charming 2-Bedroom, 2-Bathroom Home in a Gated Community – Excellent Goshen Schools! Spacious 2nd Floor Apartment – Great Amenities! This bright and inviting second-floor unit features 2 full bathrooms, wall-to-wall carpeting, and abundant closet space throughout. Enjoy relaxing on your private balcony, and take advantage of the convenience of an in-unit washer and dryer. The modern kitchen is

  Regina Wittosch Howard Hanna Rand Realty

  100 Hillside Dr Unit C15, Middletown, NY 10941
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  /17

  Est $400,558 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,876 Sq Ft

  363 Highland Ave, Wallkill Town, NY 10940

  363 Highland Ave, Wallkill Town, NY 10940
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  $449,000 Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft

  6 Tice Ln, Middletown, NY 10941

  Set on 3 peaceful acres in a private country setting, this well-maintained raised ranch offers the perfect balance of seclusion and convenience. Located in the Pine Bush School District and just moments from the charming Village of Circleville, this 3-bedroom, 2-bath home is ideal for those looking for space, comfort, and accessibility.The thoughtful floor plan centers around a bright

  

  John Olivero

  Keller Williams Realty

  (329) 218-0933

  6 Tice Ln, Middletown, NY 10941
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  $1,900 - $2,150 per month

  Stevens Manor Apartments

  1 - 2 Beds

  644 Silver Lake Scotchtown Rd, Middletown, NY 10941

  Get a FREE month off any of our units—limited time Black Friday offer!Welcome to Stevens Manor Apartments in Middletown, NY! Tucked into a peaceful suburban neighborhood, our pet-friendly community offers spacious and thoughtfully designed studios, one-, and two-bedroom homes perfect for every lifestyle. Your rent includes heat, hot water, gas, and trash removal— making your

  644 Silver Lake Scotchtown Rd, Middletown, NY 10941
• 

  $385,000 Sold Nov 17, 2025

  • 1,144 Sq Ft
  • $337/SF
  • 70 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  5 Peace Dr, Middletown, NY 10941

  Commuter's Dream in the Town Of Wallkill ! This 3 Bedroom Raised Ranch offers hardwood flooring throughout main living area, bow window which allows tons of natural light to illuminate living & dining area. Enjoy Cooking? Large kitchen with granite counter tops & tons of cabinet space. Plenty of room on lower level for a family room or home office. Walk out to your rear deck with your morning

  Ernie Acampora River Realty Services, Inc.

  5 Peace Dr, Middletown, NY 10941
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  Est $399,704 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 1,760 Sq Ft

  28 Roosevelt Ave, Middletown, NY 10940

  28 Roosevelt Ave, Middletown, NY 10940
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  $355,000

  • 3 Beds
  • 1.5 Baths
  • 1,470 Sq Ft

  4 Eaton Ct, Middletown, NY 10940

  Welcome to Canterbury Knolls! This beautifully maintained 3-bedroom, 1.5-bathroom home is move-in ready and filled with charm. Step inside to find gleaming hardwood floors throughout, complemented by porcelain tiles in the entryway and kitchen. Enjoy peace of mind with a newer heating system and hot water heater already in place. The Homeowner's Association makes life easier by handling all

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 213-1652

  4 Eaton Ct, Middletown, NY 10940
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  $2,150 per month

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • Condo for Rent

  266 Ruth Ct, Middletown, NY 10940

  Great CONDO with 2 BD + 2 full BA - - Brand New LVT FlooringNO PETS-- NO SMOKING. Tenant to pay 1 month Broker Fee. Owner Requires a MINIMUM CREDIT SCORE 690+ & MINIMUM VERIFIABLE INCOME OF $77,000, subject to full credit report & background check. Great CONDO with 2 Bedrooms + 2 full Baths. Brand new wood-like vinyl floors just installed, just painted, cleaned throughout, and ready to move

  Allan Leeds ON SITE Sales & Marketing, LLC

  266 Ruth Ct, Middletown, NY 10940
• 

  $480,000 Sold Nov 14, 2025

  • 2,055 Sq Ft
  • $234/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1979

  93 Rolling Meadows Rd, Middletown, NY 10940

  Looking for more space, peace and comfort while still being close to New York City? Welcome to this beautiful four bedroom PLUS home nestled in one of the most desirable counties. With easy access to major highways, NYC commuter route and just minutes from the famous Woodbury Common Premium Outlets, this home offers the best of both convenience and tranquility. Step inside and discover updated

  Suzanne Bongiorno Century 21 E & M Williams Rlty

  93 Rolling Meadows Rd, Middletown, NY 10940
• 

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,225 Sq Ft

  20 State St, Middletown, NY 10940

  20 State St, Middletown, NY 10940

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