Middletown, NY Homes

• 

  

  

  /47

  $570,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,072 Sq Ft

  572 Greenville Turnpike, Middletown, NY 10940

  Set back from the road, where life feels just a little more private and peaceful, there is a home that invites you to slow down... and stay awhile. Follow the charming brick path as it leads you to the front porch and into a space that immediately feels warm, welcoming, and filled with light. This move-in ready, Colonial home, offers a layout that simply makes sense for the way you want to live

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 210-1675

  572 Greenville Turnpike, Middletown, NY 10940
• Explore Middletown

• 

  

  

  /28

  $2,300 Per Month

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

  3 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) 210-5679

  3 Giada Ln Unit 2, 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 $565,667

  Last Listing Agent Chris Ogden Realty Promotions Inc

  264 Lybolt Rd, Middletown, NY 10941
• 

  Est $639,322 Not Listed For Sale

  17 Academy Ave, Middletown, NY 10940

  • 6 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1900

  17 Academy Ave, Middletown, NY 10940

  Last Sold Summary

  • 3% Above List Price
  • $258/SF
  • 34 Days On Market

  • Last Sold Price $620,000
  • Apr 29, 2025

  Last Listing Agent Sandra Arnez Keller Williams Hudson Valley
• 

  

  

  /32

  $1,700,000

  • 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
• 

  

  /25

  Starting at $1,630 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 commuters 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
• 

  $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 $771,524 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

  • 1% Above List Price
  • $258/SF
  • 24 Days On Market

  • Last Sold Price $763,846
  • Aug 22, 2024

  Last Listing Agent Juan Bautista Serhant LLC
• 

  

  /50

  $568,000

  • 7 Beds
  • 4.5 Baths
  • 3,592 Sq Ft

  104-108 Highland Ave, Middletown, NY 10940

  Historic Elegance Meets Modern-Day Convenience in this circa 1860 home in the heart of Middletown, NY. Pristinely positioned back from the road, set on just shy of an acre, this historic gem offers 3500+ square feet of timeless character and space. From the moment you enter, soaring ceilings, rich hardwood floors, built-ins and detailed crown molding set the tone. The expansive dining room,

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  (329) 210-1132

  104-108 Highland Ave, Middletown, NY 10940
• 

  

  /25

  $2,650 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,418 Sq Ft
  • Condo for Rent

  100 Hillside Dr Unit G8, Middletown, NY 10941

  FULLY RENOVATED DPLX CONDO FULL 3BR/2.5BTH AT THE PRESTIGE SECURITY GATED HILLSIDE VILLAGE CONDOMINIUMS IN GOSHEN SCHOOLS. YOU WILL HAVE TWO PARKING SPOTS INCLUDING IN RENT AND THERE'S WASHER AND DRYER IN THE UNIT. GREAT LOCATION, NEAR EVERYTHING LESS THAN 5 MINUTES TO MIDDLETOWN TRAIN TO PENN STATION AT NYCITY, GALIARIA MALL PLUS ALL MEGA STORES OF WALLMART, HOME DEPOT, SAM'S CLUB, LOWIS AND

  

  Mohamed Elgoarany

  All American Realty Management

  (329) 219-0392

  100 Hillside Dr Unit G8, Middletown, NY 10941
• 

  $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 $478,512

  Last Listing Agent Andrea Rose Keller Williams Hudson Valley

  39 Brookline Ave, Middletown, NY 10940
• 

  Est $729,411 Not Listed For Sale

  175 Elise Dr, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,626 Sq Ft
  • Built 2021

  175 Elise Dr, Middletown, NY 10941

  Last Sold Summary

  • 18% Above List Price
  • $236/SF
  • 152 Days On Market

  • Last Sold Price $620,000
  • May 04, 2023

  Last Listing Agent Bonnie Natt Realty Promotions Inc
• 

  

  /32

  $499,000 Pending

  • 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) 209-8770

  22 Sharon Dr, Middletown, NY 10941
• 

  

  /18

  Starting at $2,175 Per Month

  • 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,

  Southgate Middletown

  (845) 479-6353

  

  20 Uhlig Rd, 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 $399,032

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  112 Monhagen Ave, Middletown, NY 10940
• 

  Est $562,079 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

  • 7% Above List Price
  • $197/SF
  • 23 Days On Market

  • Last Sold Price $525,000
  • Jun 30, 2023

  Last Listing Agent Sharon Reynolds Keller Williams Hudson Valley
• 

  

  /40

  $509,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,052 Sq Ft

  127 Sproat St, Middletown, NY 10940

  There is a reason a raised ranch continues to stand the test of time... it just lives right. From the moment you step inside this move-in ready 4 bedroom, 3 bathroom home in Middletown, you feel the ease of a layout designed for real life. Head upstairs and you are immediately welcomed into a bright, open living space where natural light pours in and hardwood floors carry warmth throughout. The

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 210-2066

  127 Sproat St, Middletown, NY 10940
• 

  

  /11

  $2,300 Per Month

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft
  • Apartment for Rent

  132 Prospect Ave, Middletown, NY 10940

  Spacious 3-bedroom, 1-bathroom second-floor apartment located in a well-maintained two-family home. Conveniently situated within walking distance to a variety of shops, restaurants, and everyday essentials. The apartment is clean, freshly painted, and move-in ready, offering a comfortable and inviting living space. Landlord requirements include a completed application with references, a minimum

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 210-5677

  132 Prospect 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 $309,440

  Last Listing Agent Tanya Von Montague Corcoran Country Living

  103 Deer Court Dr, Middletown, NY 10940
• 

  Est $554,262 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

  • 11% Above List Price
  • $221/SF
  • 13 Days On Market

  • Last Sold Price $500,000
  • Feb 14, 2024

  Last Listing Agent Michael Guattery Keller Williams Realty
• 

  

  /33

  $278,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,142 Sq Ft

  108 Sproat St, Middletown, NY 10940

  Charming 1930 Vintage Home with Retro Flair – Close to Train & Local Attractions! Step back in time with this delightful circa-1930 two-bedroom, 1 bath Old Style home brimming with character and nostalgic charm. From the moment you enter, you’ll appreciate the authentic retro vibe featuring warm wood paneling, original hardwood floors, and unique vintage details. The kitchen brings you back in

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  (329) 209-9956

  108 Sproat St, Middletown, NY 10940
• 

  

  /55

  Starting at $2,200

  Total Monthly Price

  • 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
• 

  $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 $279,257

  Last Listing Agent Sharon Reynolds Keller Williams Hudson Valley

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

  Est $510,129 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

  • 1% Above List Price
  • $169/SF
  • 17 Days On Market

  • Last Sold Price $505,000
  • May 02, 2024

  Last Listing Agent Ermelinda Mclaughlin eXp Realty
• 

  

  /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
• 

  

  /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

  Keller Williams Hudson Valley

  (329) 212-1472

  1 Giada Ln Unit 5, 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 $612,136

  Last Listing Agent Warren Shelley Reliable Realty Group

  33 Highland View Place, 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

  • $96/SF
  • 79 Days On Market

  • Last Sold Price $125,500
  • Feb 14, 2025

  Last Listing Agent Carol Cruz Keller Williams Hudson Valley
• 

  

  /50

  $849,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,407 Sq Ft

  29 Hubbard Rd, Middletown, NY 10940

  New construction colonial on a beautiful 9+ acre lot with views of the Shawangunk Mountain Ridge, a spring fed pond and open fields and woods located on a private dead end road in the Pine Bush S/D. and close to major highways. The Sienna model features include 4 bedrooms, 3.5 baths, gorgeous red oak hardwood floors and spacious rooms. Relax in the cozy living room by the warm inviting fireplace

  

  Chris Ogden

  Realty Promotions Inc

  (845) 209-0146

  29 Hubbard Rd, Middletown, NY 10940
• 

  

  /55

  Starting at $2,629 Per Month

  • 1 - 3 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
• 

  $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 $468,414

  Last Listing Agent Virginia Corbett eXp Realty

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940
• 

  Est $668,593 Not Listed For Sale

  239 Sands Rd, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,422 Sq Ft
  • Built 2022

  239 Sands Rd, Middletown, NY 10941

  Last Sold Summary

  • 9% Above List Price
  • $254/SF
  • 59 Days On Market

  • Last Sold Price $615,000
  • May 03, 2023

  Last Listing Agent Marion Bruhns Howard Hanna Rand Realty
• 

  

  /33

  $429,000

  • 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

  Keller Williams Hudson Valley

  (329) 213-1496

  79 Vincent Dr, Middletown, NY 10940
• 

  

  /3

  $3,500 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
• 

  $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 $485,092

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

  93 Rolling Meadows Rd, Middletown, NY 10940
• 

  Est $383,316 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

  • 20% Above List Price
  • $195/SF
  • 33 Days On Market

  • Last Sold Price $320,000
  • Aug 03, 2023

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group
• 

  

  /30

  $339,999 Pending

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

  5 Mills Ave, Middletown, NY 10940

  LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

  

  Richard Baxter

  Keller Williams Realty

  (845) 599-1094

  5 Mills Ave, Middletown, NY 10940
• 

  

  /46

  Starting at $1,720 Per Month

  • 1 - 2 Beds

  2 Underhill Rd, Middletown, NY 10940

  Living at Sutton Hill located in Middletown, NY, provides you with the peaceful, pastoral setting of the Catskill's and the Pocono's, and only an hour away from New York City.Convenient to the Metro North RR, near Orange Regional Medical center - schools, shopping and entertainment, all at your fingertips.Relax and enjoy our great amenities: Fitness Center, Pool, Playground,

  Sutton Hill Apartments

  (845) 415-7703

  

  2 Underhill Rd, 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 $382,901

  Last Listing Agent John Olivero Keller Williams Realty

  29 Euclid Ave, Middletown, NY 10940
• 

  Est $469,770 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

  • 29% Above List Price
  • $109/SF
  • 52 Days On Market

  • Last Sold Price $363,000
  • Sep 21, 2023

  Last Listing Agent Anthony Gnagnarelli Keller Williams Valley Realty

Showing Results 1 - 40, Page 1 of 18