Middletown, NY Homes

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  /25

  $360,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  71 Commonwealth Ave, Middletown, NY 10940

  Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 212-0993

  71 Commonwealth Ave, Middletown, NY 10940
• Explore Middletown

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  /9

  $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
• 

  $319,000 Sold Nov 26, 2025

  • 1,124 Sq Ft
  • $284/SF
  • 26 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1929

  82 Houston Ave, Middletown, NY 10940

  Tucked on a dead-end street, this updated 3-bedroom, 1-bath home offers a welcoming blend of character and modern comfort. The cozy living room sets the tone - perfect for everyday living and casual entertaining. A traditional layout flows into a dedicated dining area and an updated kitchen with direct access to a private outdoor space this is ideal for year-round grilling and low-maintenance

  Wendy Beck Krumpfer Realty Group, LLC

  82 Houston Ave, Middletown, NY 10940
• 

  Est $744,120 Not Listed For Sale

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

  147 Elise Dr, Middletown, NY 10941

  147 Elise Dr, Middletown, NY 10941
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  /34

  $277,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  193 Deer Ct Dr, Middletown, NY 10940

  Motivated seller. This corner penthouse suite is move-in ready and located in Middletown School District. The kitchen has newer appliances, a new microwave, a pantry and plenty of storage cabinets. With an open concept Livingroom and Dining Room with a wall mounted TV, this suite provides ample room for family gatherings, relaxing and entertainment. The main bedroom boasts a large walk-in closet

  

  Kathy White

  Exit Realty Connections

  (329) 207-0952

  193 Deer Ct Dr, Middletown, NY 10940
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  /24

  $2,450 per month

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft
  • Condo for Rent

  51 Deer Ct Dr, Middletown, NY 10940

  A new rental available in Deer Run offers two levels of living in this beautifully maintained two bed, two and one-half bath condo. The updated kitchen features maple cabinets, stainless steel appliances, and a stunning Tiffany light fixture that is located in the eat-in kitchen. An open-concept layout connects the living and dining areas, with sliding doors that lead to a peaceful, private

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 207-0940

  51 Deer Ct Dr, Middletown, NY 10940
• 

  $338,500 Sold Nov 26, 2025

  • 1,408 Sq Ft
  • $240/SF
  • 33 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1979

  12 Columbine Ct, Middletown, NY 10940

  Don’t miss this beautifully updated end-unit 4-bedroom, 1.5-bath townhouse in the heart of Middletown, NY! This spacious home features a long list of recent upgrades including brand-new siding, boiler, driveway, concrete patio, flooring, carpeting upstairs in the bedrooms, Kitchen cabinets, counter tops and appliances. As an end unit, it offers extra privacy and natural light, along with a fully

  Christina Gilligan HomeSmart Homes & Estates

  12 Columbine Ct, Middletown, NY 10940
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  Est $723,111 Not Listed For Sale

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

  175 Elise Dr, Middletown, NY 10941

  175 Elise Dr, Middletown, NY 10941
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  /45

  $385,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  12 State St, Middletown, NY 10940

  Charming ranch-style home is on the market for the first time! A rocking chair front porch welcomes you home, setting the tone for the warmth and comfort you'll find inside this well-maintained 2-bedroom, 1.5-bath that offers true one-level living with laundry on the main floor. Spacious living and dining area filled with an abundance of natural light, and cozy wall-to-wall carpet. This classic

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  (329) 999-6974

  12 State St, Middletown, NY 10940
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  /42

  $3,500 per month

  • 5 Beds
  • 2 Baths
  • 2,526 Sq Ft
  • House for Rent

  8 Badami Dr, Middletown, NY 10941

  **** Scotchtown Raised Ranch Rental Home Ready for Immediate Occupancy! *** From the moment you step inside, you’re greeted by an inviting open-concept layout that effortlessly connects the foyer to the sunlit living room, dining area, and kitchen—offering a natural flow that makes everyday living and entertaining feel effortless. The living room is a bright and welcoming space, bathed in

  

  Christina Rowan

  Howard Hanna Rand Realty

  (329) 207-1014

  8 Badami Dr, Middletown, NY 10941
• 

  $665,000 Sold Nov 26, 2025

  • 2,078 Sq Ft
  • $320/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  18 Beyers Rd, Middletown, NY 10941

  New construction colonial on 3+ acres featuring 4 bedrooms, 2.5 baths, laundry room, Central A/C, cozy fireplace, gleaming hard wood floors through out first floor and plush new carpet in all bedrooms. Beautiful kitchen complete with custom cabinetry, kitchen island, decorative tiled back splash. Retreat to the primary bedroom with spacious walk in closet and private bathroom with double vanity,

  Chris Ogden Realty Promotions Inc

  18 Beyers Rd, Middletown, NY 10941
• 

  Est $575,503 Not Listed For Sale

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

  37 Orange Terrace, Middletown, NY 10940

  37 Orange Terrace, Middletown, NY 10940
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  /33

  $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
• 

  

  /20

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Apartment for Rent

  49 Lake Ave Unit 2, Middletown, NY 10940

  Beautifully renovated upstairs apartment featuring two bedrooms and one bathroom. An additional room offers the perfect space for a home office. This rental includes a cozy kitchen, a comfortable living room, and an oversized laundry room. Upstairs, you’ll find a storage area (not permitted for sleeping purposes). Two parking spaces are designated for tenant use, and a back patio provides a nice

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 666-0569

  49 Lake Ave Unit 2, Middletown, NY 10940
• 

  $335,000 Sold Nov 26, 2025

  • 1,340 Sq Ft
  • $250/SF
  • 20 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1977

  26 Sycamore Dr, Middletown, NY 10940

  Welcome Home to Clemson Park!Discover this beautifully updated townhouse in the desirable Clemson Park community. Featuring 2 bedrooms and 1.5 bathrooms, this home offers a spacious open floor plan perfect for both everyday living and entertaining. The bright living/dining area includes gleaming hardwood floors, a cozy brick wood-burning fireplace, and sliding glass doors that open to a

  Dulce M Ferrera Keller Williams Hudson Valley

  26 Sycamore Dr, Middletown, NY 10940
• 

  Est $550,974 Not Listed For Sale

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

  16 4th St, Middletown, NY 10940

  16 4th St, Middletown, NY 10940
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  /33

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  270 Crystal Run Rd, Middletown, NY 10941

  Middletown opportunity that pulls double duty. Walk through the front door and feel how easy life becomes when comfort and possibility meet in one place. This move in ready three bedroom two bathroom home welcomes you with vaulted ceilings, warm wood detail, and a bright living room that opens through glass doors to your deck. The kitchen surrounds you with wood cabinetry and generous workspace

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 209-8831

  270 Crystal Run Rd, Middletown, NY 10941
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  /29

  $2,300 per month

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

  6 Giada Ln Unit 3, 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) 216-1674

  6 Giada Ln Unit 3, Middletown, NY 10940
• 

  $460,000 Sold Nov 25, 2025

  • 2,856 Sq Ft
  • $161/SF
  • 27 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1870

  7 Orchard St, Middletown, NY 10940

  Welcome to this charming five-bedroom colonial nestled in the heart of Middletown! Step inside and you’ll be greeted by a spacious living room adorned with beautiful woodwork, flowing seamlessly into a generous dining area perfect for hosting holiday gatherings. The elegant family room connects to a well-appointed kitchen that opens to a private backyard, complete with a detached two-car garage

  Patrick Taylor BHG Real Estate Green Team

  7 Orchard St, Middletown, NY 10940
• 

  Est $516,539 Not Listed For Sale

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

  44 Highrose Ridge Way, Middletown, NY 10940

  44 Highrose Ridge Way, Middletown, NY 10940
• 

  

  /50

  $620,000

  • 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

  Keller Williams Hudson Valley

  (329) 207-0914

  179 Reservoir Rd, Middletown, NY 10940
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  /29

  $2,300 per month

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

  6 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) 212-1265

  6 Giada Ln Unit 5, Middletown, NY 10940
• 

  $385,000 Sold Nov 24, 2025

  • 1,570 Sq Ft
  • $245/SF
  • 16 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2000

  5 Perrins Mews Unit 6, Middletown, NY 10940

  THE MOST VERSATILE FLOOR PLAN IN THE COMMUNITY! OFFERING THE POTENTIAL FOR ONE-LEVEL LIVING!!! Turn-key and move-in ready, this special home welcomes you with a first-floor primary suite complete with a connected full bath—a rare and highly desirable feature as this home could provide ease of living for those looking to avoid stairs. Extra wide doorways to assist with maneuverability! The special

  Frank Muccari Cronin & Company Real Estate

  5 Perrins Mews Unit 6, Middletown, NY 10940
• 

  Est $667,079 Not Listed For Sale

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

  239 Sands Rd, Middletown, NY 10941

  239 Sands Rd, Middletown, NY 10941
• 

  

  /32

  $1,799,000

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

  3 Bristol Dr, Middletown, NY 10941

  LG PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING OF THIS Amazing Mini Mansion Luxury Hse on this one ! For those that look for the very best and finest that the Hudson Valley has to offer you are sure to be amazed as you enter this 11200 plus sq ft luxurious brick colonial mansion including 3200 sq ft Indoor Pool room ! Yes you read that correctly, this home is one of the very few that

  

  Mohamed Elgoarany

  All American Realty Management

  (329) 215-0309

  3 Bristol Dr, Middletown, NY 10941
• 

  

  /29

  $2,300 per month

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

  6 Giada Ln Unit 6, 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) 216-1096

  6 Giada Ln Unit 6, Middletown, NY 10940
• 

  $285,000 Sold Nov 24, 2025

  • 2,088 Sq Ft
  • $136/SF
  • 55 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1953

  19 Randall Terrace, Middletown, NY 10940

  Looking for all investors who want to buy now and get the process started in order to work on the exterior before the cold weather begins. All reasonable offers will be considered. Home features an eat in kitchen with breakfast nook, diningroom, and large step down livingroom on first floor with fireplace. Upstairs find a primary bedroom suite with separate bath. Down the hall is three more

  Lynelle Alessi Keller Williams Hudson Valley

  19 Randall Terrace, Middletown, NY 10940
• 

  Est $676,592 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft

  249 Sands Rd, Middletown, NY 10941

  249 Sands Rd, Middletown, NY 10941
• 

  

  /50

  $849,000

  • 4 Beds
  • 2.5 Baths
  • 3,437 Sq Ft

  3 Kings Dr, Middletown, NY 10941

  Luxury Living in Hamptonburgh. Nestled in the prestigious Windsor Estates enclave, within the sought-after Goshen School District, this exceptional Contemporary residence offers a rare blend of elegance, comfort, and convenience. With nearly 3,500 sqft of thoughtfully designed living space, this striking home features 4 spacious bedrooms, 3 bathrooms, and a 3-car garage. Step into a grand

  

  Christina Rowan

  Howard Hanna Rand Realty

  (845) 393-3879

  3 Kings Dr, Middletown, NY 10941
• 

  

  /29

  $2,300 per month

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

  6 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) 207-0978

  6 Giada Ln Unit 2, Middletown, NY 10940
• 

  $279,900 Sold Nov 24, 2025

  • 1,188 Sq Ft
  • $236/SF
  • 122 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1978

  4 Red Barn Ln, Middletown, NY 10940

  ROLLING MEADOWS! Low HOA! 3 Bedrooms! 1 1/2 Bathrooms! Eat In Kitchen! Large Living Room! Master Bedroom with Walk In Closet! Sliders to Fenced in Yard! Perfect Commuter Location! Close to Major Highways, Trains, Buses and Shopping! Walk to Clubhouse, Community Pool, Playground, Tennis and Basket Ball!

  Amanda Dnistrian ARC Realty 1 in Sales

  4 Red Barn Ln, Middletown, NY 10940
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  /9

  Not Listed For Sale

  Lot 11 Meadowbrook Dr, Middletown, NY 12455

  

  Lot 11 Meadowbrook Dr, Middletown, NY 12455
• 

  

  /33

  $349,900 Pending

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

  29 Euclid Ave, Middletown, NY 10940

  Step inside 29 Euclid Avenue and you will immediately notice the space and warmth this home offers. There are three comfortable bedrooms and two full baths, along with beautiful hardwood floors that carry throughout the main living areas. The home is larger than it appears from the front, with a layout that flows easily from room to room and provides plenty of space for everyday living. Out back,

  

  John Olivero

  Keller Williams Realty

  (329) 214-1698

  29 Euclid Ave, Middletown, NY 10940
• 

  

  /29

  $2,300 per month

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

  5 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) 217-4615

  5 Giada Ln Unit 5, Middletown, NY 10940
• 

  $440,000 Sold Nov 21, 2025

  • 1,560 Sq Ft
  • $282/SF
  • 20 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1957

  6 Randall Terrace, Middletown, NY 10940

  Value lies in quality, location, and long-term potential — and this property delivers on all three. Thoughtfully renovated from top to bottom, this home is turn key and provides long-term peace of mind.Step inside to find brand-new hardwood floors throughout, a completely remodeled kitchen featuring quartz countertops, new appliances, and a complementing tile backsplash — a space built for

  Rachel Hunt Realty Promotions Inc

  6 Randall Terrace, Middletown, NY 10940
• 

  Est $375,167 Not Listed For Sale

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

  237 Route 211 W, Middletown, NY 10940

  237 Route 211 W, Middletown, NY 10940
• 

  

  /33

  $420,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  18 Rondack Rd, Middletown, NY 10941

  Tucked into a charming neighborhood street, this well-kept raised ranch offers the kind of comfort and flexibility that just makes life easier. Lovingly maintained from top to bottom, it’s move-in ready and waiting for its next chapter — a space that’s clean, solid, and full of potential for your own personal touches. Upstairs, the layout flows effortlessly from room to room, with natural light

  

  Michael Kahns

  Compass Greater NY, LLC

  (329) 217-4556

  18 Rondack Rd, Middletown, NY 10941
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  /17

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • House for Rent

  492 Midland Lake Rd Unit 1, Middletown, NY 10941

  Set back off the road, this beautiful rental offers both privacy and convenience. Unit 1 is one of two attached single-family homes and provides a spacious, flexible layout. The first floor features a primary bedroom that can easily be converted into two separate rooms, each with its own closet. A full bathroom, open-concept kitchen and dining area, and a large living room complete this level,

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 208-2269

  492 Midland Lake Rd Unit 1, Middletown, NY 10941
• 

  $366,000 Sold Nov 21, 2025

  • 1,800 Sq Ft
  • $203/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  1 Lexington Way, Middletown, NY 10940

  The Place You've Been Looking For! The Perfection Home in the Perfect Location! This end-unit condo is within 5 miles of all your needs. This updated 3 bedroom, 2.5 bathroom comes with a great open kitchen, new vinyl flooring, granite bathroom countertops, stainless steel appliances, and the space you want! Outside you can enjoy the basketball court, professionally maintained yards and snow

  Jordan Spordone HomeSmart Homes & Estates

  1 Lexington Way, Middletown, NY 10940
• 

  Est $434,070 Not Listed For Sale

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

  366 North St, Middletown, NY 10940

  366 North St, Middletown, NY 10940

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