Middletown, NY Homes

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  /16

  $449,999

  • 6 Beds
  • 2 Baths
  • 1,878 Sq Ft

  19 Wawayanda Ave, Middletown, NY 10940

  A Must see... Fully available opportunity knocks to own this colonial home, located in the heart of the Hudson Valley. Entering this home with a long foyer that leads into a living room, spacious dining room with plenty of natural light, eat in kitchen, Kitchen is updated with lots of cabinet space front deck, back porch, new flooring for the entire house. New roof, stainless steel appliances,

  Samar Tarazi Keller Williams Realty

  19 Wawayanda Ave, Middletown, NY 10940
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  /15

  $1,700 per month

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

  382 County Route 22 Unit 6, Middletown, NY 10940

  Slate Hill now offers a ground level 2 bedroom with Minisink Schools!! A 2 bedroom/1 bath apartment with plenty of window light. Enter into a living room, followed by a eat-in kitchen. 2 spacious bedrooms and a full bath. Common laundry available on site. Private parking for your convenience. Lawn maintenance, snpw removal, garbage pickup and water included. Heat and electric paid by tenant.

  Sandra Arnez Keller Williams Hudson Valley

  382 County Route 22 Unit 6, Middletown, NY 10940
• 

  $556,900 Sold May 20, 2025

  • 2,153 Sq Ft
  • $259/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  15 Sage Ct, Middletown, NY 10940

  Something Special!! Carefree living awaits you in this open and spacious 2163 sq. ft. 2 BR, 2 Bath beauty in Wildflowers at Wallkill, a vibrant 55+ community! Large windows let in lots of natural light! Wonderful upgrades throughout! Oversized deck with awning overlooks the private, wooded backyard! Solid wood floors! Lovely crown molding! Gourmet kitchen with expanded kitchen island opens to

  Linda Clark Hudson Valley Griffith

  15 Sage Ct, Middletown, NY 10940
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft

  4 Fortune Rd W Unit A, Middletown, NY 10941

  4 Fortune Rd W Unit A, Middletown, NY 10941
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  /8

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft

  2 Rivervale Rd, Middletown, NY 10940

  Charming Corner Townhouse in Middletown – No HOA Fees!Welcome to 2 Riverdale Road, a delightful 3-bedroom, 1.5-bathroom townhouse nestled in the heart of Middletown, NY. This spacious 1,484 sq ft home offers a perfect blend of comfort and convenience, making it an ideal choice for families and first-time homebuyers.Key Features:Spacious Living: Enjoy the warmth of hardwood floors throughout and

  Kilimanjaro Toussaint YourHomeSold Guaranteed Realty

  2 Rivervale Rd, Middletown, NY 10940
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  /25

  $1,780 - $4,090 per month

  Imperial Gardens Apartment Homes

  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

  225 Berkman Dr, Middletown, NY 10941
• 

  $640,000 Sold May 20, 2025

  • 2,376 Sq Ft
  • $269/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  223 Mt Orange Rd, Middletown, NY 10940

  MINISINK VALLEY SCHOOL DISTRICT! COLONIAL ON 2 ACRES! HEATED SALT WATER IN-GROUND POOL!! Welcome to this stunning colonial, perfectly located in the highly sought-after Minisink Valley School District! Offering an unbeatable combination of convenience and tranquility, this property is nestled in a peaceful setting while remaining incredibly central to everything you need. Step inside to find a

  Frank Muccari Cronin & Company Real Estate

  223 Mt Orange Rd, Middletown, NY 10940
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  Est $511,262 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,746 Sq Ft

  75 Pine Grove Rd, Middletown, NY 10940

  75 Pine Grove Rd, Middletown, NY 10940
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  /34

  $259,000

  • 2 Beds
  • 2 Baths
  • 1,146 Sq Ft

  67 Deer Court Dr, Middletown, NY 10940

  Bright, Beautiful & Move-In Ready – Second Floor 2BR/2BA Condo in Sought-After Deer Run!Welcome to the only one-level unit currently available in the highly desirable Deer Run community in Middletown! This spacious 2-bedroom, 2-bath condo is located on the second floor, offering privacy and peaceful living in a well-maintained complex. With large front-facing windows, the home is flooded with

  Gail Rachlin Keller Williams Hudson Valley

  67 Deer Court Dr, Middletown, NY 10940
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  /10

  $2,000 per month

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

  27 Prince St, Middletown, NY 10940

  Bright & Spacious 2-Bedroom Apartment For Rent!This beautifully renovated 2-bedroom, 1-bath apartment is located on the 2nd floor and offers an abundance of natural light throughout. Featuring hardwood floors, a separate dining room, and a private back deck, this charming space is both clean and spacious—perfect for comfortable living. Enjoy the convenience of off-street parking and a

  Patricia Lucey Picture It Sold, LLC

  27 Prince St, Middletown, NY 10940
• 

  $615,000 Sold May 20, 2025

  • 2,380 Sq Ft
  • $258/SF
  • 51 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  525 Silver Lake Scotchtown Rd, Middletown, NY 10941

  Welcome to 525 Silver Lake Scotchtown Road, a charming colonial home nestled on a sprawling 2.1-acre lot in Scotchtown. This spacious 2,380 sq. ft. residence offers 4 bedrooms, 3.5 bathrooms, and a layout designed for both comfort and functionality.Step inside to discover a bright and inviting interior, including a cozy living room with a fireplace, perfect for relaxing evenings. The full

  Matthew Gibbs Keller Williams Hudson Valley

  525 Silver Lake Scotchtown Rd, Middletown, NY 10941
• 

  Est $249,105 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft

  119 Ruth Ct, Middletown, NY 10940

  119 Ruth Ct, Middletown, NY 10940
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  /23

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  11 Dogwood Dr, Middletown, NY 10940

  Well maintained 3 bedroom, 2 bath Bilevel in an established residential neighborhood. This attractive home features Stainless Steel appliances, a Master Bedroom suite and a 1 car garage. Sq. Footage does not include an additional 774 sq. Ft. unfinished lower level, which could be a Family Room, Bedroom, .5 bath, or use your imagination. All window treatments will stay. Conveniently located

  Gloria Allan John J Lease REALTORS Inc

  11 Dogwood Dr, Middletown, NY 10940
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  /18

  $2,734 - $4,396 per month

  Sterling Parc at Middletown

  1-2 Beds

  23 James P Kelly Way, Middletown, NY 10940

  Sterling Parc at Middletown is located at 23 James P Kelly Way Middletown, NY and is managed by Solomon Management LLC, a reputable property management company with verified listings on RENTCafe. Sterling Parc at Middletown offers one and two bedroom apartments ranging in size from 816 to 1,231 sq.ft. Amenities include Carpeting, Dishwasher, Fireplace, Clubhouse, Concierge, and more. This rental

  23 James P Kelly Way, Middletown, NY 10940
• 

  $310,000 Sold May 19, 2025

  • 1,248 Sq Ft
  • $248/SF
  • 22 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  6 Thomas Jefferson Place, Middletown, NY 10940

  Step into a new chapter of homeownership with this charming ranch in the heart of Middletown! From the moment you arrive, you’ll feel the warm embrace of single-level living—an ideal setup whether you’re a first-time buyer, downsizing, or looking for your next investment. Imagine lazy Sunday mornings spent sipping coffee on your cozy back patio, or hosting summer barbecues in a yard that’s just

  Brian Caplicki Keller Williams Hudson Valley

  6 Thomas Jefferson Place, Middletown, NY 10940
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  Est $488,932 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft

  105 Jasmine Dr, Middletown, NY 10940

  105 Jasmine Dr, Middletown, NY 10940
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  /40

  $430,000

  • 3 Beds
  • 1.5 Baths
  • 1,794 Sq Ft

  118 White Bridge Rd, Middletown, NY 10940

  This pristine Cape in Mount Hope NY is almost 1800 square feet featuring heated two-car attached garage, full size basement sit on 1.6 acres parcel with nice view. 3 bedrooms, large eat in kitchen, Formal Dr, 1st floor Master Bedroom suite, and addition one office on the 1st floor. 2nd. floor has 2 large bedrooms, Exterior has 2 decks, 1 patio, storage shed, great views and beautiful sunsets. New

  Feng Chang Acer Realty Inc

  118 White Bridge Rd, Middletown, NY 10940
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  /28

  $2,450 per month

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Townhouse for Rent

  105 Sheffield Dr, Middletown, NY 10940

  Now Renting in Middletown, NY!Spacious 3 bed / 1.5 bath townhome with a large yard and a balcony off the primary bedroom — perfect for your morning coffee or evening unwind.Centrally located near it all: Galleria Mall • Shopping Centers • Schools • Garnet Health Medical Center • Grocery Stores • Restaurants — plus close to highways for easy commuteComfort, convenience, and space — all in one

  Cindy-Lee Dorcely Keller Williams Hudson Valley

  105 Sheffield Dr, Middletown, NY 10940
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  $445,000 Sold May 19, 2025

  • 2,427 Sq Ft
  • $183/SF
  • 264 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2008

  9 Arden Ct, Middletown, NY 10940

  WOODSIDE KNOLLS! Open Floor Plan! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Large Living Room with Marble Flooring! Dining Area! Master Bedroom Suite with Walk In Closet & Soaking Tub! Natural Decor! Recessive Lighting! Full Finished Basement for Endless Possibilities! Country Club Living! Clubhouse and Pool! Perfect Commuter Location! Close to Major Highways, Trains, Buses &

  Amanda Dnistrian ARC Realty 1 in Sales

  9 Arden Ct, Middletown, NY 10940
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  Est $474,679 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft

  107 Jasmine Dr, Middletown, NY 10940

  107 Jasmine Dr, Middletown, NY 10940
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  /36

  $469,999

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  338 Route 211 W, Middletown, NY 10940

  Welcome to your dream home! This meticulously renovated ranch-style residence in the heart of Middletown, NY, combines timeless charm with modern elegance. Carefully reimagined from top to bottom, this home features a bright, open-concept layout designed for both comfort and entertaining. At the heart of the home is a stunning, fully updated kitchen, showcasing rich dark cabinetry, sleek quartz

  Jeffrie Peña Locqube New York, Inc.

  338 Route 211 W, Middletown, NY 10940
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  /26

  $1,625 - $2,200 per month

  Rockwood Gardens Apartments

  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

  51 Rockwood Cir, Middletown, NY 10941
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  $269,900 Sold May 16, 2025

  • 1,020 Sq Ft
  • $265/SF
  • 190 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1945

  247 Shaw Rd, Middletown, NY 10941

  A/O as of 2/23 This adorable 2 bedroom ranch has many new features such as New Roof in 2022, new floors, closet doors, new ceiling fans, wood blinds, new kitchen back splash, molding, new flood lights, new Stainless Steele Fridge, and newer Stove, Dishwasher and new plywood and shingles on the shed. The open floor plan makes the rooms feel spacious. There is a lovely sunroom that has a CofO

  Christina Gordon I Realty LLC

  247 Shaw Rd, Middletown, NY 10941
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  Est $633,279 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,538 Sq Ft

  172 Stony Ford Rd, Middletown, NY 10941

  172 Stony Ford Rd, Middletown, NY 10941
• 

  

  /30

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 1,987 Sq Ft

  7 Roosevelt Ave, Middletown, NY 10940

  Welcome to this charming ranch-style home located on a desirable corner lot in the city of Middletown. Spanning just under 2,000 square feet, this inviting residence features spacious rooms throughout. As you enter, you'll be greeted by custom woodwork and elegant wainscoting that add a touch of sophistication throughout this home. The layout is accentuated by tile flooring that flows seamlessly

  Patricia Sassi RE/MAX Benchmark Realty Group

  7 Roosevelt Ave, Middletown, NY 10940
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  /32

  $3,200 per month

  • 2 Beds
  • 2.5 Baths
  • 1,785 Sq Ft
  • Condo for Rent

  6 Putters Way, Middletown, NY 10940

  Enjoy Country Club style living at its best in this charming and well kept townhouse located in the Fairways, Orange County's premier gated community. This well maintained and spacious townhouse includes a vaulted primary bedroom and bathroom and a second bedroom that features a walk in closet, and additional room that can be used as an office or another bedroom. Enjoy entertaining in an open

  Thomas Folino BHG Real Estate Green Team

  6 Putters Way, Middletown, NY 10940
• 

  $439,889 Sold May 16, 2025

  • 2,482 Sq Ft
  • $177/SF
  • 245 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  674 Dosen Rd, Middletown, NY 10940

  Beautiful Sprawling Ranch Home situated on almost an acre of Privacy. LOW LOW TAXES !! This Wonderful Home Features a split Floor Plan, New Recessed Lighting, All New Smoke/ Carbon Detectors. Brand New House Roof And Garage Roof !! Large Sundrenched Living Room, Formal Dining Rm, Very Spacious Eat in Kitchen offering a nice Breakfast Bar, Stunning Cabinetry, Lots of Countertop Space, Hardwood

  John Biasi Howard Hanna Rand Realty

  674 Dosen Rd, Middletown, NY 10940
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  Est $397,824 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,818 Sq Ft

  14 W Jackson Ave, Middletown, NY 10940

  14 W Jackson Ave, Middletown, NY 10940
• 

  

  /15

  $425,000

  • 6 Beds
  • 2 Baths
  • 2,748 Sq Ft

  225 Highland Ave, Middletown, NY 10940

  Great Opportunity For Future Owner Occupant Or An Investor Who Is Looking To Collect $4,450 Of Current Rental Income With Tenants In Place.Fully Renovated In 2020. The Property Was Originally A 2 Family And Has Two Levels, Basement And A Full Attic. 2 Forced Hot Air Systems With Separate Gas And Electric Services. Both Sides Are Set With First Floor Kitchen With Door To Deck On Rear. Living Room

  Mark Karten Karten Real Estate Svcs LLC

  225 Highland Ave, Middletown, NY 10940
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  /35

  $1,750 - $2,150 per month

  Sherwood Forest Garden Apartments

  1-2 Beds

  507 Sherwood Dr N, Middletown, NY 10941

  Sherwood Forest Garden Apartments, located in Middletown, NY, consists of six garden apartment-style buildings spread over 18 lushly landscaped acres. Your rent includes Heat/AC, Hot Water, Cooking Gas, and Trash. In addition, there is an outdoor pool, with an adjacent fitness center, BBQ Grills and Unassigned Parking. ALL are available, without charge, to residents of the property. Ground level

  507 Sherwood Dr N, Middletown, NY 10941
• 

  $350,000 Sold May 15, 2025

  • 2,016 Sq Ft
  • $174/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1920

  20 California Ave, Middletown, NY 10940

  Wonderful opportunity to invest in this great 2-family house. Live in one while you renovate and rent the other. Being sold as-is. Looking for quick close. Both units have 2 beds, 1bath.

  Derek Greene Greene Realty Group

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

  • 12 Beds
  • 3 Baths
  • 4,924 Sq Ft

  540 County Route 49, Middletown, NY 10940

  540 County Route 49, Middletown, NY 10940
• 

  

  /25

  $425,000

  • 4 Beds
  • 1.5 Baths
  • 2,706 Sq Ft

  44 Karen Joy Dr, Middletown, NY 10940

  BRAND NEW ROOF JUST INSTALLED!!! INCREDIBLE VALUE AND POTENTIAL TO MAKE THIS YOUR DREAM HOME!!! OVER 2700 Sq. Ft.!!! Discover a truly unique opportunity in the highly sought-after Minisink Valley School District! This expansive split-level home boasts an impressive floor plan with endless possibilities. Bring your ideas and your vision—this gem won’t take much to restore its former glory! Step

  Frank Muccari Cronin & Company Real Estate

  44 Karen Joy Dr, Middletown, NY 10940
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  /7

  $1,750 per month

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

  74 Jogee Rd Unit 1, Middletown, NY 10940

  Come home to this recently renovated 2 bedroom country gem! All new appliances, updated kitchens and bath. Brand new vinyl floors for easy cleaning! About a mile from the Minisink Valley School complex and right off of County Route 6 makes it easy to commute anywhere in Orange County. Oh and did we forget to say that this property is pet friendly for an additional monthly fee? Apartment is

  Julianna Green BHG Real Estate Green Team

  74 Jogee Rd Unit 1, Middletown, NY 10940
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  $239,000 Sold May 14, 2025

  • 830 Sq Ft
  • $288/SF
  • 44 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1977

  99 Sycamore Dr, Middletown, NY 10940

  Cozy and well maintained complex in Clemson Park available now! Welcome to this oversized one bedroom one bathroom unit, wide opened living room, directly walk out to the balcony. Newly renovated quartz countertops and new appliances are ready to enjoy. Community provides clubhouse and in-ground pool in summer times. Assigned parking is included! HOA covers landscaping, snow removal, roofing,

  Xiaohui Cui Keller Williams Hudson Valley

  99 Sycamore Dr, Middletown, NY 10940
• 

  Est $462,377 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft

  338 van Duzer Rd, Middletown, NY 10940

  338 van Duzer Rd, Middletown, NY 10940
• 

  

  /41

  $480,000

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location!Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an ideal

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
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  /16

  $2,300 - $2,500 per month

  The Regency Club

  1-2 Beds

  1200 Regency Ct, Middletown, NY 10940

  The Regency Club offers spacious living and dining areas, and modern kitchens in one bedroom with den and two bedroom floor plans. Apartments boast 9 ft. ceilings, ceramic tiles in the bathrooms and kitchens and a full appliance package. Residents enjoy the clubhouse, outdoor pool, state-of-the-art fitness center, and expansive club room as well as the outdoor tennis court and playground. The

  1200 Regency Ct, Middletown, NY 10940
• 

  $699,999 Sold May 14, 2025

  • 3,000 Sq Ft
  • $233/SF
  • 96 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  201 White Bridge Rd, Middletown, NY 10940

  FULLY AVAILABLE - BRAND NEW HOME in Minisink Schools (Completion - Feb 2025) - 3000 sq ft Affordable LUXURY Modern COLONIAL on a Premium 4 ACRE Wooded Lot. NYC COMMUTER LOCATION (10 Mins to Middletown) MAIN LEVEL offers Spacious OPEN CONCEPT floor plan with access to Large Deck, 9' High ceilings, hardwood floors, Living & Family Rm, Fireplace, formal dinning rm, breakfast rm & powder rm. Large

  Philip Barnao eXp Realty

  201 White Bridge Rd, Middletown, NY 10940
• 

  Not Listed For Sale

  • 9 Beds
  • 3 Baths
  • 3,090 Sq Ft

  704 Route 211 W Unit 706, Middletown, NY 10940

  704 Route 211 W Unit 706, Middletown, NY 10940

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