Middletown, NY Homes

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  /46

  $574,900

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,432 Sq Ft

  180 Mt Orange Rd, Middletown, NY 10940

  The primary suite alone tells you what kind of home this is. A vaulted cathedral ceiling overhead, a spa-style bath built around a deep soaking tub, and proportions that hold a quiet hour at the end of a long day the way a private retreat is supposed to. It is the kind of room that quietly redefines what you expect a ranch to feel like. By the time the water is running, the day has already

  

  Brian Caplicki

  KW Hudson Valley Untied

  (329) 210-5539

  180 Mt Orange Rd, Middletown, NY 10940
• Explore Middletown

• 

  

  

  /22

  $2,200 Per Month

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

  1 Ruth Ct, Middletown, NY 10940

  Welcome to this beautifully updated and spacious first floor corner condo in Middletown, NY. This well-maintained home offers comfortable one level living with a large living room, two generously sized bedrooms, and one full bath. The modern walk-through kitchen features new stainless steel appliances and an adjacent dining area. Wall A/C units in the living room and both bedrooms provide

  

  Kathy White

  Exit Realty Connections

  (329) 209-8678

  1 Ruth Ct, Middletown, NY 10940
• 

  $753,000

  Sold Mar 11, 2026

  264 Lybolt Rd, Middletown, NY 10941

  • 4 Beds
  • 3.5 Baths
  • 2,823 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 198 Days On Market

  Current Estimated Value $703,039

  Last Listing Agent Chris Ogden Realty Promotions Inc

  264 Lybolt Rd, Middletown, NY 10941
• 

  Est $768,752

  Not Listed For Sale

  147 Elise Dr, Middletown, NY 10941

  • 5 Beds
  • 3.5 Baths
  • 2,960 Sq Ft
  • Built 2024

  147 Elise Dr, Middletown, NY 10941

  Last Sold Summary

  • 24 Days On Market
• 

  

  

  /32

  $1,700,000

  $188K PRICE DROP

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

  3 Bristol Dr, Middletown, NY 10941

  PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING.....HURRY UP....WILL NOT LAST.............................Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 8.55-bathroom residence features

  

  Mohamed Elgoarany

  All American Realty Management

  (329) 215-0309

  3 Bristol Dr, Middletown, NY 10941
• 

  

  /18

  Starting at $2,900 Per Month

  • 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,

  Southgate Middletown

  (845) 479-6353

  

  20 Uhlig Rd, 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
• 

  Est $574,636

  Not Listed For Sale

  37 Orange Terrace, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft
  • Built 2019

  37 Orange Terrace, Middletown, NY 10940

  Last Sold Summary

  • 23 Days On Market
• 

  

  /25

  $165,000

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  226 Concord Ln, Middletown, NY 10940

  Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located close to Rte 17 and 84 for those of you commuting a distance to work. Just turn the key and move in, no work is needed. Kitchen has newer cabinets with crown molding and stainless LG appliances with a convection/air fry oven that can be controlled by your phone along with granite counters. Kitchen counter has

  

  Lynelle Alessi

  KW Hudson Valley Untied

  (329) 225-8141

  226 Concord Ln, Middletown, NY 10940
• 

  

  /3

  $2,750 Per Month

  • 3 Beds
  • 1 Bath
  • 1,466 Sq Ft
  • Apartment for Rent

  153 Wisner Ave Unit 157, Middletown, NY 10940

  Beautifully updated 3-bedroom apartment located on the first floor of a well-maintained duplex. This bright and inviting home features hardwood floors throughout, an updated kitchen with modern appliances, and an abundance of windows that fill the space with natural light. The landlord pays for heat, while the tenant is responsible for electricity. Ample parking is available in the rear of the

  

  Dulce M Ferrera

  KW Hudson Valley Untied

  (329) 201-2511

  153 Wisner Ave Unit 157, 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 $479,099

  Last Listing Agent Andrea Rose KW Hudson Valley Untied

  39 Brookline Ave, Middletown, NY 10940
• 

  Est $551,195

  Not Listed For Sale

  16 4th St, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 2023

  16 4th St, Middletown, NY 10940

  Last Sold Summary

  • 13 Days On Market
• 

  

  /25

  $490,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,211 Sq Ft

  28 Magnolia Park Rd, Middletown, NY 10940

  Lifestyle and Location without all the work- this home has all the perks of homeownership with the ease and amenities of a townhome in the sought-after Magnolia Park community. Spacious and light filled living across 3 levels, the first floor boasts an open floor plan and well appointed kitchen with granite countertops, dining area, living area, and half bath for guests. Upstairs, the 3 bedrooms

  

  Lisbeth Furke

  World Homes Realty

  (329) 214-1660

  28 Magnolia Park Rd, Middletown, NY 10940
• 

  

  /25

  Starting at $1,905 Per Month

  • Studio - 2 Beds

  225 Berkman Dr, Middletown, NY 10941

  Welcome Home to Imperial Gardens Apartments in Middletown, NY! Located in a country setting, our fabulous location is about an hour from New York City. Just minutes from the Metro North, and major highways: RT 17, I-84, and I-87 (NYS Thruway), we are a commuter's dream! We are located just minutes from RT 211 where there is an abundance of shopping, dining, and entertainment such as Galleria at

  Imperial Gardens Apartment Homes

  (845) 479-6102

  

  225 Berkman Dr, Middletown, NY 10941
• 

  $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 $390,110

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  112 Monhagen Ave, Middletown, NY 10940
• 

  Est $530,008

  Not Listed For Sale

  44 Highrose Ridge Way, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,996 Sq Ft
  • Built 2014

  44 Highrose Ridge Way, Middletown, NY 10940

  Last Sold Summary

  • 17 Days On Market
• 

  

  /47

  $528,000

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  18 Maureen Ln, Middletown, NY 10940

  Custom built and lovingly maintained by its original owners, this beautiful 4-bedroom ranch is being offered for the very first time. Nestled at the end of a quiet cul-de-sac in the highly sought-after Minisink Valley School District, with Otisville Elementary, this special home reflects years of pride in ownership and thoughtful care. A welcoming covered front porch invites you inside to a

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  (329) 215-0405

  18 Maureen Ln, Middletown, NY 10940
• 

  

  /11

  $1,790 Per Month

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

  102 North St Unit 8, Middletown, NY 10940

  Welcome to a RENOVATED two-bedroom apartment located in the heart of the vibrant City of Middletown! This beautifully upgraded apartment is situated on the second floor and offers a stylish and comfortable living space. The prime location of this apartment is close to a plethora of stores and restaurants, with many just a short walk away. A laundromat is also located across the street, making

  

  Hazel Cello

  KW Hudson Valley Untied

  (329) 666-0375

  102 North St Unit 8, 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 $305,043

  Last Listing Agent Tanya Von Montague Corcoran Country Living

  103 Deer Court Dr, Middletown, NY 10940
• 

  Not Listed For Sale

  2607 State Route 17k, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 2009

  2607 State Route 17k, Middletown, NY 10941

  Last Sold Summary

  • 79 Days On Market
• 

  

  /25

  $310,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,061 Sq Ft

  205 Linden Ave, Middletown, NY 10940

  Nestled in the heart of Middletown, this charming home at 205 Linden Avenue offers a delightful blend of historic character and modern comfort. Built around 1900, the home spans approximately 1,061 square feet and sits on a generous 5,000-square-foot lot. Step inside to discover three cozy bedrooms and two bathrooms, perfect for those seeking extra space. The home features a detached garage,

  

  Omar Harper

  Epique Realty

  (329) 210-1914

  205 Linden Ave, Middletown, NY 10940
• 

  

  /55

  Starting at $2,672 Per Month

  • 1 - 2 Beds

  122 Golf Links Rd, Middletown, NY 10940

  158 Unit Luxury Housing Community with 1,2 and 3 Bedroom Units. Situated on a Lush Championship 18 Hole Golf Course that offers a Private Country Club Experience 24 hours a day. Apartments feature Spacious Open Layouts, Beautiful Kitchens with Quartz Countertops and Stainless Steel Appliances, Front Loading Washers and Dryers, Balconies, Walk-In Closets, Beautiful Engineered Wide Plank

  Residences at West Hills Country Club

  (845) 412-8078

  

  122 Golf Links Rd, 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

  Current Estimated Value $278,341

  Last Listing Agent Sharon Reynolds KW Hudson Valley Untied

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

  Est $362,328

  Not Listed For Sale

  237 Route 211 W, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft
  • Built 1900

  237 Route 211 W, Middletown, NY 10940

  Last Sold Summary

  • 33 Days On Market
• 

  

  /41

  $375,000

  $20K PRICE INCREASE

  • 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 Untied

  (329) 224-0137

  4 Eaton Ct, Middletown, NY 10940
• 

  

  /7

  $1,650 Per Month

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft
  • Apartment for Rent

  102 North St Unit 1, Middletown, NY 10940

  Welcome to a RENOVATED one-bedroom apartment located in the heart of the vibrant City of Middletown! This beautifully upgraded apartment is situated on the second floor and offers a stylish and comfortable living space. The prime location of this apartment is close to a variety of stores and restaurants, with many just a short walk away. A laundromat is also located across the street, making

  

  Hazel Cello

  KW Hudson Valley Untied

  (329) 212-0267

  102 North St Unit 1, Middletown, NY 10940
• 

  $420,000

  Sold Feb 19, 2026

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft
  • Built 2011

  Last Sold Summary

  • 7% Below List Price
  • $226/SF
  • 55 Days On Market

  Current Estimated Value $448,095

  Last Listing Agent Virginia Corbett eXp Realty

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940
• 

  Est $436,728

  Not Listed For Sale

  366 North St, Middletown, NY 10940

  • 6 Beds
  • 3 Baths
  • 3,330 Sq Ft
  • Built 1880

  366 North St, Middletown, NY 10940

  Last Sold Summary

  • 52 Days On Market
• 

  

  /33

  $429,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,043 Sq Ft

  79 Vincent Dr, Middletown, NY 10940

  Don’t miss this turn-key 3-bedroom, 1-bath ranch on a quiet, tree-lined street in Middletown. Set on a level, fully fenced 0.27-acre lot, this move-in ready home offers comfort, style, and convenience.Inside, you’ll find hardwood floors and a cozy brick wood-burning fireplace with a new door and mantel. The eat-in kitchen features stainless steel appliances and updated lighting, while the

  

  Donna Reese

  KW Hudson Valley Untied

  (329) 213-1496

  79 Vincent Dr, Middletown, NY 10940
• 

  

  /40

  Starting at $2,300

  Total Monthly Price

  • 2 Beds

  700 Stratford Ln, Middletown, NY 10940

  Welcome to Country Manor Apartments in Middletown, NY! Our pet-friendly community is set among rustic, large, grassy areas, creating a peaceful and open environment. We offer one- and two-bedroom apartments featuring updated kitchens, premium bathrooms, and private decks. Your rent includes heat, hot water, sewer, and trash removal. We also offer 24/7 maintenance services.

  Country Manor Apartments

  (845) 412-9632

  

  700 Stratford Ln, Middletown, NY 10940
• 

  $480,000

  Sold Nov 14, 2025

  93 Rolling Meadows Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,055 Sq Ft
  • Built 1979

  Last Sold Summary

  • $234/SF
  • 23 Days On Market

  Current Estimated Value $475,741

  Last Listing Agent Suzanne Bongiorno Century 21 E & M Williams Rlty

  93 Rolling Meadows Rd, Middletown, NY 10940
• 

  Est $521,341

  Not Listed For Sale

  9 Neptune Ln, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 1,993 Sq Ft
  • Built 2024

  9 Neptune Ln, Middletown, NY 10940

  Last Sold Summary

  • 20 Days On Market
• 

  

  /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

  (845) 415-6387

  0 Hog Mountain Cir, Middletown, NY 12430
• 

  

  /30

  $2,300 Per Month

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

  1 Giada Ln Unit 5, 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

  KW Hudson Valley Untied

  (329) 212-1472

  1 Giada Ln Unit 5, Middletown, NY 10940
• 

  $372,000

  Sold Dec 19, 2025

  29 Euclid Ave, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Above List Price
  • $246/SF
  • 33 Days On Market

  Current Estimated Value $376,832

  Last Listing Agent John Olivero Keller Williams Realty

  29 Euclid Ave, Middletown, NY 10940
• 

  Est $491,472

  Not Listed For Sale

  38 Anthony St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2024

  38 Anthony St, Middletown, NY 10940

  Last Sold Summary

  • 238 Days On Market
• 

  

  /48

  $483,900

  Pending

  • 3 Beds
  • 3.5 Baths
  • 2,521 Sq Ft

  53 Cornwall Ln, Middletown, NY 10940

  Beautifully renovated 3-bedroom, 3.5-bathroom townhouse with a 2-car garage, located in the highly desirable Woodside Knolls community. This spacious home offers modern updates throughout, providing comfort, style, and functionality for today’s living. Conveniently situated just minutes from the Garnet Health Medical Center, Galleria Mall, Metro-North, shops, supermarkets, and major highways,

  

  Dulce M Ferrera

  KW Hudson Valley Untied

  (329) 217-0628

  53 Cornwall Ln, Middletown, NY 10940
• 

  

  /55

  Starting at $1,900

  Total Monthly Price

  • 1 - 2 Beds

  644 Silver Lake Scotchtown Rd, Middletown, NY 10941

  Welcome to Stevens Manor Apartments in Middletown, NY! Our pet-friendly community is set among expansive grassy areas, creating a peaceful and open environment.Choose from studios, one-, or two-bedroom apartments, each thoughtfully designed with updated kitchens, premium bathrooms, dishwashers, and air-conditioning.Your rent includes heat, hot water, gas, and trash removal. We

  Stevens Manor Apartments

  (845) 524-9637

  

  644 Silver Lake Scotchtown Rd, Middletown, NY 10941
• 

  $440,000

  Sold Nov 21, 2025

  6 Randall Terrace, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Above List Price
  • $282/SF
  • 20 Days On Market

  Current Estimated Value $426,070

  Last Listing Agent Rachel Hunt Realty Promotions Inc

  6 Randall Terrace, Middletown, NY 10940
• 

  /2

  Est $609,329

  Not Listed For Sale

  328 Stony Ford Rd, Middletown, NY 10941

  • 4 Beds
  • 3 Baths
  • 1,664 Sq Ft
  • Built 2024

  328 Stony Ford Rd, Middletown, NY 10941

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