Middletown, NY Homes

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  /33

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  189 School House Rd, Middletown, NY 10940

  Home sweet home! This beautiful custom built three bedroom, two and a half bathroom 2086sqft ranch is located on a gorgeous landscaped 5 acres in the Minisink Valley School District. You'll feel right at home from the moment you enter this park-like property. You have many choices of places to enjoy this home, both inside and outside. The 1900sqft main floor is open and spacious. The central

  

  Joseph Paoli

  Howard Hanna Rand Realty

  189 School House Rd, Middletown, NY 10940
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  /26

  Starting at $1,750 Per Month

  • 1 - 2 Beds

  51 Rockwood Cir, Middletown, NY 10941

  Rockwood sits high atop a hill with beautiful vistas, on park like grounds. Each apartment is meticulously maintained. We provide our residents with spacious rooms, fully equipped kitchens and tremendous closet space. Laundry facilities and additional private storage spaces are available in each building. An assigned parking space comes with each apartment complemented by ample extra parking for

  Rockwood Gardens Apartments

  51 Rockwood Cir, Middletown, NY 10941
• 

  $385,000

  Sold Nov 24, 2025

  5 Perrins Mews Unit 6, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft
  • Built 2000

  Last Sold Summary

  • $245/SF
  • 16 Days On Market

  Current Estimated Value $389,746

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  5 Perrins Mews Unit 6, Middletown, NY 10940
• 

  Est $596,491

  Not Listed For Sale

  15 Sage Ct, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 2,153 Sq Ft
  • Built 2016

  15 Sage Ct, Middletown, NY 10940

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Linda Clark Hudson Valley Griffith
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  /13

  $239,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  16 Woodland Rd, Middletown, NY 10940

  Welcome home to this very nice three bedroom seasonal ranch located in the Minisink Valley School District in a quiet neighborhood! This private property is surrounded by nature with a large open yard to play and have fun in the sun. The large deck overlooks the private back yard and surrounding woods. The roof has been recently replaced. Sale includes an additional lot of 0.11 acres to bring the

  

  Joseph Paoli

  Howard Hanna Rand Realty

  16 Woodland Rd, Middletown, NY 10940
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  /28

  $3,250

  Total Monthly Price

  • 2 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • House for Rent

  94 Woodlake Dr, Middletown, NY 10940

  Spacious 2-Bedroom Townhouse Near the Pond – Available Now!Enjoy comfortable, low-maintenance living in this stunning waterfront-adjacent townhouse.Key Features:Bedrooms: 2 large bedrooms, each featuring a spacious walk-in closet.Bathrooms: 2 full and 2 half baths for ultimate convenience.Living Space: Main living area features a cozy gas fireplace, perfect

  94 Woodlake Dr, Middletown, NY 10940
• 

  $453,000

  Sold Oct 05, 2025

  8-10 Mercer St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 2,006 Sq Ft
  • Built 1951

  Last Sold Summary

  • 4% Above List Price
  • $226/SF
  • 44 Days On Market

  Current Estimated Value $432,213

  Last Listing Agent Sandra Arnez KW Hudson Valley United

  8-10 Mercer St, Middletown, NY 10940
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  /16

  Est $374,523

  Not Listed For Sale

  31-33 Linden Ave, Middletown, NY 10940

  • 7 Beds
  • 2.5 Baths
  • 2,026 Sq Ft
  • Built 1880

  31-33 Linden Ave, Middletown, NY 10940

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Karen Smith Anderson 1st Kander Realty Inc
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  /48

  $425,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,074 Sq Ft

  57 Boorman Rd, Middletown, NY 10940

  Seller is willing to contribute towards closing costs. Welcome home to this fully renovated Dutch Colonial set on 5+ private acres in the desirable Minisink Valley Central School District, located just minutes from Middletown! Step inside to a beautifully updated kitchen featuring sleek quartz countertops, ceramic tile flooring, a subway tile backsplash, new cabinetry, and stainless steel

  

  Lynelle Alessi

  KW Hudson Valley United

  57 Boorman Rd, Middletown, NY 10940
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  /10

  Starting at $2,195 Per Month

  • 1 - 2 Beds

  48-54 North St, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Residents can indulge in a

  The North Court Apartments.

  

  48-54 North St, Middletown, NY 10940
• 

  $515,000

  Sold Jul 16, 2026

  17 Woodrose Ct, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,763 Sq Ft
  • Built 2020

  Last Sold Summary

  • $186/SF
  • 71 Days On Market

  Current Estimated Value $504,384

  Last Listing Agent Ermelinda Mclaughlin eXp Realty

  17 Woodrose Ct, Middletown, NY 10940
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  Not Listed For Sale

  206 #200 E Main St, Middletown, NY 10940

  206 #200 E Main St, Middletown, NY 10940

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Angela Ingham BHHS Hudson Valley Properties
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  /18

  $235,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  100 Hillside Dr Unit C6, Middletown, NY 10941

  Prime Location in located in Goshen School District!Welcome to this first-floor, 2-bedroom end unit condo offering 2-full baths in the desirable gated community of Hillside Village. This home offers the convenience of one-level living featuring a galley kitchen with an abundance of cabinetry. The spacious living room has sliding glass doors leading to a private patio—perfect for relaxing or

  

  Kathy White

  Exit Realty Connections

  100 Hillside Dr Unit C6, Middletown, NY 10941
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  /18

  Starting at $1,750 Per Month

  • 1 - 2 Beds

  92 Fitzgerald Dr, Middletown, NY 10940

  Welcome to Crestwood!Discover tranquility and affordability at Crestwood Apartments in Middletown, NYNestled amidst the rolling hills of Middletown, NY, Crestwood Apartments offers a welcoming haven for those seeking comfortable living at an exceptional value. Whether you're a young professional, a family starting out, or a seasoned resident looking for a peaceful retreat, Crestwood

  Crestwood Apartments

  

  92 Fitzgerald Dr, Middletown, NY 10940
• 

  $290,000

  Sold Aug 20, 2025

  20 Columbia Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1920

  Last Sold Summary

  • 5% Above List Price
  • $235/SF
  • 3 Days On Market

  Current Estimated Value $300,285

  Last Listing Agent Brian Caplicki KW Hudson Valley United

  20 Columbia Ave, Middletown, NY 10940
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  Not Listed For Sale

  3 Fortune Rd W Unit H, Middletown, NY 10941

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft
  • Built 1972

  3 Fortune Rd W Unit H, Middletown, NY 10941

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent James LaTempa Compass Greater NY, LLC
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  /9

  $499,000

  • Land
  • 39.9 Acres
  • $12,506 per Acre

  700 van Burenville Rd, Middletown, NY 10940

  Discover your own 40-acre sanctuary in the Hudson Valley, a landscape of rolling meadows, a peaceful pond that set the stage for a truly picturesque retreat. Perfectly suited for equestrian pursuits, cattle, or recreational hunting.

  

  Joao Rodrigues

  Preferred Properties Real Esta

  700 van Burenville Rd, Middletown, NY 10940
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  /9

  Starting at $2,000 Per Month

  • 2 Beds

  22-26 Stoneridge Rd, Middletown, NY 10941

  Stoneridge Manor Apartments - This is an elegant new construction 1,100 square foot two bedroom, two bathroom condo style apartment located in the Goshen Central School District. It is nestled quietly off Route 211 West yet conveniently situated next to the Galleria Mall as well as a Hannaford Supermarket and Shoprite. It is also close to the train station into NYC. It is a beautiful open floor

  Stoneridge Manor Apartments

  22-26 Stoneridge Rd, Middletown, NY 10941
• 

  $335,000

  Sold May 20, 2026

  36 Bert Crawford Rd, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 836 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Above List Price
  • $401/SF
  • 5 Days On Market

  Current Estimated Value $325,432

  Last Listing Agent Jin Pang Panorama Realty

  36 Bert Crawford Rd, Middletown, NY 10940
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  Not Listed For Sale

  100 Hillside Dr Unit F10, Middletown, NY 10941

  • 2 Beds
  • 2.5 Baths
  • 1,216 Sq Ft
  • Built 1986

  100 Hillside Dr Unit F10, Middletown, NY 10941

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
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  /41

  $375,000

  $20K PRICE INCREASE Pending

  • 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. Updates include a brand new roof. Some rooms and garage have been freshly painted. Step inside to find gleaming hardwood floors throughout, complemented by porcelain tiles in the entryway and kitchen. The Homeowner's Association makes life easier by handling all exterior

  

  Dulce M Ferrera

  KW Hudson Valley United

  4 Eaton Ct, Middletown, NY 10940
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  /20

  Starting at $2,400 Per Month

  • 1 - 2 Beds

  430 E Main St, Middletown, NY 10940

  Welcome to The Park at Main.The Park at Main, located in the Town of Wallkill, NY, is the area’s latest apartment community, offering residents an exclusive amenity-driven lifestyle. This community features 116 newly constructed 1- and 2-bedroom apartments across seven buildings. Private amenities include a seasonal pool and lounge deck, a luxury clubhouse with a billiard room, a fitness

  The Park At Main

  

  430 E Main St, Middletown, NY 10940
• 

  $450,000

  Sold Mar 27, 2026

  9 Michele Ct, Middletown, NY 10941

  • 4 Beds
  • 1.5 Baths
  • 2,132 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Above List Price
  • $211/SF
  • 34 Days On Market

  Current Estimated Value $461,509

  Last Listing Agent Brian Caplicki KW Hudson Valley United

  9 Michele Ct, Middletown, NY 10941
• 

  Est $507,665

  Not Listed For Sale

  20 Magnolia Park Rd, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 2,000 Sq Ft
  • Built 2019

  20 Magnolia Park Rd, Middletown, NY 10940

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Eileen Ploschke BHHS Hudson Valley Properties
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  /25

  $359,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  252 Toad Pasture Rd, Middletown, NY 10940

  Welcome home to this beautifully maintained ranch nestled on 2.2 private acres in the highly sought-after Minisink School District. Offering the perfect blend of comfort and country living, this home features 3 spacious bedrooms, 1 full bathroom, hardwood floors freshly restored. This home has a walk-out basement with endless possibilities for additional living space, a workshop, or storage.

  

  Joao Rodrigues

  Preferred Properties Real Esta

  252 Toad Pasture Rd, Middletown, NY 10940
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  /2

  Call for Price

  • 1 Bed

  28-38 Stoneridge Rd, Middletown, NY 10941

  Cambridge Manor

  28-38 Stoneridge Rd, Middletown, NY 10941
• 

  $150,000

  Sold Mar 22, 2026

  551 5th, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1997

  Last Sold Summary

  • $112/SF
  • 253 Days On Market

  Last Listing Agent Dulce M Ferrera KW Hudson Valley United

  551 5th, Middletown, NY 10941
• 

  Est $359,253

  Not Listed For Sale

  161 Deer Court Dr Unit 10, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 1991

  161 Deer Court Dr Unit 10, Middletown, NY 10940

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Aylin Ippolito Cronin & Company Real Estate
• 

  

  /21

  $119,000

  • Land
  • 4.27 Acres
  • $27,869 per Acre

  0 Hog Mountain Cir, Middletown, NY 12430

  This is the property with a view you have been looking for. 4.27 acres of cleared, ready to build land in the Catskill Mountains just two hours from the George Washington Bridge. Whether it is a weekend retreat you have in mind or a forever home, the view is unmatched and will bring you the peace and serenity the Catskills have to offer. This property is only 10 minutes from Belleayre Ski

  

  Terence Lynch

  Century 21 New West Properties

  0 Hog Mountain Cir, Middletown, NY 12430
• 

  

  /20

  $2,800 Per Month

  • 4 Beds
  • 2 Baths
  • House for Rent

  22 Grant St, Middletown, NY 10940

  Property Id: 1170010 Welcome to your new cozy 4 bedroom, 2 bathroom single family home in the heart of Middletown, NY! This charming property features hardwood floors, a spacious lawn, and is conveniently located near parks. With amenities such as a freezer, refrigerator, and oven included. Don't miss out on this great opportunity to make 22 Grant St your new home! Apply now before it's too

  22 Grant St, Middletown, NY 10940
• 

  $354,000

  Sold Oct 31, 2025

  6 Perrins Mews, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 2000

  Last Sold Summary

  • 1% Above List Price
  • $220/SF
  • 12 Days On Market

  Current Estimated Value $373,824

  Last Listing Agent Maureen Cronin Cronin & Company Real Estate

  6 Perrins Mews, Middletown, NY 10940
• 

  Not Listed For Sale

  208 2nd Ave, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2024

  208 2nd Ave, Middletown, NY 10941

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty
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  /28

  $299,900

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  32 W Conkling Ave, Middletown, NY 10940

  Some houses greet you at the door. This one wraps around you the moment you walk in. Step through the light-filled sunroom, all glass and morning sun, and into a main floor paneled in warm honey pine that has been cared for across a hundred years and wears every one of them beautifully. You notice the beamed ceilings, the way the afternoon light pools on the wood, the rooms that flow one into the

  

  Brian Caplicki

  KW Hudson Valley United

  32 W Conkling Ave, Middletown, NY 10940
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  /8

  $2,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • Condo for Rent

  390 Crystal Run Rd, Middletown, NY 10941

  Property Id: 1833609 Vibrant location in the midst of very desirable tenants as Neighbors. Only one unit left. Must see for location. Services like 24-hour fire surveillance, sprinkler system in place, well manicured and maintained premises, lots of parking.

  390 Crystal Run Rd, Middletown, NY 10941
• 

  

  /27

  $340,000

  Sold Jun 01, 2026

  164 Brookline Ave, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Below List Price
  • $324/SF
  • 14 Days On Market

  Current Estimated Value $332,772

  Last Listing Agent Scott Alvarez Coldwell Banker Prime Properties

  164 Brookline Ave, Middletown, NY 10940
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  Not Listed For Sale

  268 Howells Turnpike, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,209 Sq Ft
  • Built 2025

  268 Howells Turnpike, Middletown, NY 10940

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Chris Ogden Realty Promotions Inc
• 

  

  /50

  $550,000

  Open Sun 12:30PM - 2:30PM $70K PRICE DROP

  • 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

  KW Hudson Valley United

  179 Reservoir Rd, Middletown, NY 10940
• 

  

  /5

  $2,000 Per Month

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  280 Wisner Ave Unit 2, Middletown, NY 10940

  Property Id: 2228735 Private entrance- top floor -1 bed 1 bath- just updated! $2000/month includes ALL UTILITIES including cantral air conditioning. Private secure gated off street parking, snow removal and landscaping included. Close to schools, entertainment and shopping. Please contact David to schedule a showing of this unit at

  280 Wisner Ave Unit 2, Middletown, NY 10940
• 

  $327,000

  Sold May 26, 2026

  5 Mills Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • Built 1883

  Last Sold Summary

  • 18% Below List Price
  • $282/SF
  • 243 Days On Market

  Current Estimated Value $322,188

  Last Listing Agent Richard Baxter Keller Williams Realty

  5 Mills Ave, Middletown, NY 10940
• 

  Not Listed For Sale

  250 Howells Turnpike, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft
  • Built 2025

  250 Howells Turnpike, Middletown, NY 10940

  Last Sold Summary

  • 184 Days On Market

  Last Listing Agent Chris Ogden Realty Promotions Inc

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