Middletown, NY Homes for Sale

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  /33

  $620,000

  $20K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 2,354 Sq Ft

  282 Derby Rd, Middletown, NY 10940

  Tucked at the end of a long, paved drive on a quiet country road, this secluded 4-bedroom, 2.5 bath retreat feels worlds away — while still being minutes from everything you need. Five minutes away from major highways and less than ten minutes away from shopping and restaurants. Located in the desirable Pine Bush School District.Step inside to a light-filled first floor featuring maple

  Thomas Grazier I Realty LLC

  282 Derby Rd, Middletown, NY 10940
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• 

  

  

  /22

  $510,000

  • 4 Beds
  • 3 Baths
  • 2,308 Sq Ft

  326 North St, Middletown, NY 10940

  Welcome to a move-in ready, three-story home designed for easy & comfortable living. The open floor plan feels bright and spacious, with freshly primed walls, updated lighting, and durable flooring that stands up to daily life. You will appreciate practical features like a dedicated laundry room and plenty of closet space for organization. The kitchen comes fully equipped with new cabinets and

  Ahida Mercado Real Broker NY LLC

  326 North St, Middletown, NY 10940
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  /18

  $469,000

  • 4 Beds
  • 2.5 Baths
  • 1,796 Sq Ft

  1413 Goshen Turnpike, Middletown, NY 10941

  Welcome to 1413 Goshen Turnpike, a spacious home offering comfortable living in a convenient Middletown location. With approximately 1,796 square feet of living space, this home provides plenty of room for everyday living, entertaining, and working from home. The desirable layout includes four bedrooms, two full baths, and a convenient half bath.Enjoy the best of both convenience and

  Giulianna Rojas Curasi Realty, Inc.

  1413 Goshen Turnpike, Middletown, NY 10941
• 

  

  

  /18

  $178,500

  New Construction $11K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  412 4th Ave, Middletown, NY 10940

  This beautiful high end home is located in the desirable Valley View Community. The home is brand new and offers a modern contemporary feel and it is ready to be yours! Ideal commuter friendly location just minutes to the train to NYC. Bright and airy 2 bedroom, 2 bath home with close to 1,000 square feet of space! Gorgeous gourmet kitchen with upgraded cabinets featuring an abundance of

  Sandra Spector Howard Hanna Rand Realty

  412 4th Ave, Middletown, NY 10940
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  /8

  $1,450,000

  • Land
  • 20.1 Acres
  • $72,139 per Acre

  686 Route 17m, Middletown, NY 10940

  20+ Prime Commercial Acres with 7,000 SF Barn on Route 17M. This 20.10-acre parcel offers endless possibilities for developers, end-users, and investors, sitting along high-traffic Route 17M in the Town of Wallkill. While the original farmhouse is gone, the land is prepped for its next chapter, anchored by a massive 7,000 sq ft outbuilding/barn—ideal for immediate storage, staging, or operational

  Joseph Baratta Joseph Baratta Company Realty

  686 Route 17m, Middletown, NY 10940
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  /4

  $1,650,000

  • Land
  • 7.5 Acres
  • $220,000 per Acre

  32 Gibbs Ct, Middletown, NY 10940

  32 Gibbs Court | Wallkill, NYPrime 3.20 Acre Commercial Development PAD on 7.5-acre lot Opportunity in the Heart of WallkillUnlock the full potential of this premier 3.20 PAD on a 7.5-acre commercial parcel, ideally located in the thriving Town of Wallkill. Situated within the highly desirable Town Center District, 32 Gibbs Court offers a rare development opportunity with broad zoning

  Peter Janis Berkshire Hathaway HS NE Prop.

  32 Gibbs Ct, Middletown, NY 10940
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  /35

  $424,999

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  11 Sunnyside Ave, Middletown, NY 10940

  Calling all investors and future house hackers! This versatile duplex is the perfect opportunity to grow your rental portfolio or offset your mortgage by living in one unit while renting the other.Each apartment offers 2 bedrooms and 1 full bathroom, featuring spacious living areas, an open-concept layout, and generously sized bedrooms. One of the units also includes a dedicated office

  Valerie Jewis Keller Williams Realty

  11 Sunnyside Ave, Middletown, NY 10940
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  /18

  $489,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,932 Sq Ft

  12 Walnut Ln, Middletown, NY 10940

  Beautifully maintained home in a desirable Middletown neighborhood featuring a bright, functional layout and a spacious backyard. One of the most valuable features of this property is its flexible bedroom layout. Four total bedrooms, including two conveniently located on the first floor, offering rare flexibility for multi-generational living, guests, a home office, or easy single-level living.

  Xiaohui Cui KW Hudson Valley United

  12 Walnut Ln, Middletown, NY 10940
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  /14

  $314,000

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  35 Lexington Way, Middletown, NY 10940

  Prime Location & NeighborhoodCommuter Convenience: Minutes from Route 17 (Future I-86), Interstate 84, and the Middletown Metro-North train station, providing a straightforward commute toward NYC and Westchester.Proximity to Key Amenities: Close to Garnet Health Medical Center, SUNY Orange, and the Route 211 commercial corridor (major shopping centers, dining, and grocery

  Zhiheng Tang KW Hudson Valley United

  35 Lexington Way, Middletown, NY 10940
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  /35

  $469,000

  $16K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,084 Sq Ft

  1 High Ridge Ln, Middletown, NY 10940

  Welcome to refined, low maintenance living in one of Middletown’s most sought after gated communities. This beautifully maintained end unit townhouse offers the perfect balance of space, comfort, and convenience, with over 2,000 square feet of living space designed for today’slifestyle. Step inside to find a bright and inviting layout featuring spacious bedrooms each with generous closet

  Jason Madison eXp Realty

  1 High Ridge Ln, Middletown, NY 10940
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  /32

  $380,000

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  13 Old Anvil Ln, Middletown, NY 10940

  Welcome to 13 Old Anvil Lane, a conveniently located Middletown home offering comfort, flexibility, and easy access to everything the area has to offer. With several updates already completed, the home feels fresh and move-in ready while still leaving room to add your own personal touch.Inside, you’ll find a comfortable and functional layout designed for everyday living. Plenty of

  Hilary Ryan Goldman Howard Hanna Rand Realty

  13 Old Anvil Ln, Middletown, NY 10940
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  /36

  $300,000

  • Land
  • 27.9 Acres
  • $10,753 per Acre

  00 Exp Hwy 17, Middletown, NY 10941

  Located in the Town of Wallkill, Orange County, NY, and within the Goshen School District, this approximately 27.9-acre parcel offers strong potential for a variety of uses. The property is accessed via a right-of-way (ROW) from Mt. Joy Road and is situated in an area surrounded by established homes and horse farms. The property features rolling terrain with a blend of open, fallow fields and

  Clint Carlson WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00 Exp Hwy 17, Middletown, NY 10941
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  /36

  $579,000

  $21K PRICE DROP

  • 6 Beds
  • 3.5 Baths
  • 2,948 Sq Ft

  669 Mountain Rd, Middletown, NY 10940

  COUNTRY RETREAT WITH 6 BEDROOMS, AN INGROUND POOL AND 3.38 ACRES! Located at 669 Mountain Road in the Middletown area, this spacious Hudson Valley home offers approximately 2,948 square feet, 6 bedrooms, 3 full bathrooms, 1 half bathroom, a first-floor bedroom and full bathroom, full walk-out basement, full walk-up attic and a detached 2-car garage.Built in 1820, the home blends timeless

  Michelle Gruberger Real Estate Circuit Inc

  669 Mountain Rd, Middletown, NY 10940
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  /48

  $899,900

  • 4 Beds
  • 4 Baths
  • 3,699 Sq Ft

  19-21 Lincoln Terrace Unit 19, Middletown, NY 10940

  Set on a private, wooded one-acre property in Middletown, this remarkable mid-century modern residence offers a rare opportunity to own a home designed and personally occupied by renowned local architect Dennis Jurow. With more than 4,000 square feet of living space, the home reflects Jurow’s distinctive architectural vision through its dramatic design, abundant natural light, and seamless

  Patricia Sassi RE/MAX Benchmark Realty Group

  19-21 Lincoln Terrace Unit 19, Middletown, NY 10940
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  /23

  $579,000

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  30 Daly Rd, Middletown, NY 10940

  New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft

  Jonathon Lee KW Hudson Valley United

  30 Daly Rd, Middletown, NY 10940
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  /30

  $834,000

  $15K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,764 Sq Ft

  238 S Centerville Rd, Middletown, NY 10940

  Spacious Country Retreat on 22.6 Acres in Minisink Valley School DistrictThis exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character

  Linda VanDeWeert BHG Real Estate Green Team

  238 S Centerville Rd, Middletown, NY 10940
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  /23

  $134,999

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  79 Stern Scenic Dr, Middletown, NY 10940

  Welcome to this updated 3-bedroom, 2-bath double-wide mobile home offering comfort, space, and convenience in Middletown. Recent updates enhance both style and functionality, while the open and spacious layout provides plenty of room to relax or entertain. The primary bedroom features a private bath, and the additional bedrooms are generously sized. Conveniently located near local shopping,

  Ivan Carvalho Exit Realty Connections

  79 Stern Scenic Dr, Middletown, NY 10940
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  /30

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,593 Sq Ft

  568 County Route 49 Unit 2C, Middletown, NY 10940

  Privately set in a quiet and intimate four-unit HOA community, this bright and welcoming home offers comfort, space, and convenience throughout. An open foyer leads into the updated kitchen featuring Quartz/Quartzite countertops, crisp white cabinetry, and ample storage. Natural light pours into the spacious dining and living areas, highlighted by beautiful flooring and a large closet ideal for

  Hazel Cello KW Hudson Valley United

  568 County Route 49 Unit 2C, Middletown, NY 10940
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  /6

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 2,696 Sq Ft

  Lot 2 Winters Ln, Middletown, NY 10940

  Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 2 of the coveted Lane Meadow Farm subdivision, located in the Town of Mamakating, Sullivan County, NY. Enjoy the serenity and natural beauty of one of Sullivan County's newest and most sought-after neighborhoods, where peaceful country living meets exceptional craftsmanship. Featuring

  Jacob Silberstein Parcel Realty LLC

  Lot 2 Winters Ln, Middletown, NY 10940
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  /36

  $349,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  26 1/2 Ridge St, Middletown, NY 10940

  Beautifully renovated single-family home offering a clean, comfortable layout with thoughtful updates throughout. This residence features 4 spacious bedrooms filled with natural light and a brand-new kitchen equipped with appliances and ample cabinetry. Fresh finishes throughout the home create a bright, move-in-ready feel. Enjoy additional storage space in both the attic and basement, providing

  Cheskel Werzberger Mount Realty

  26 1/2 Ridge St, Middletown, NY 10940
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  /2

  $55,000

  $10K PRICE DROP

  • Land
  • 10,454 Sq Ft
  • $229,167 per Acre

  1 S Shore Dr, Middletown, NY 10940

  Quarter acre waterfront parcel located on Pocatello Lake. Scenic water views, and a peaceful setting with convenient access to local amenities in the City of Middletown and Town of Wallkill. Rare opportunity for lakefront land ownership in a desirable location.

  Soleil Jackman Howard Hanna Rand Realty

  1 S Shore Dr, Middletown, NY 10940
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  /38

  $899,900

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas

  Jonathon Lee KW Hudson Valley United

  255 Howells Rd, Middletown, NY 10940
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  /50

  $549,999

  • 4 Beds
  • 3.5 Baths
  • 2,298 Sq Ft

  19 Davidge Rd, Middletown, NY 10940

  Welcome to 19 Davidge Road, where luxury, comfort, and functionality come together in one exceptional home. Nestled in the highly sought-after Presidential Heights neighborhood, this impressive 4-bedroom, 4-bathroom residence offers the perfect blend of elegant living spaces and incredible amenities designed for today's lifestyle.From the moment you enter, you'll be captivated by the soaring

  Kevin Grier KW Hudson Valley United

  19 Davidge Rd, Middletown, NY 10940
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  /21

  $324,999

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  63 Greenway Terrace, Middletown, NY 10941

  On the market for the first time in nearly 20 years! Welcome to 63 Greenway Terrace, a well-loved and maintained three-level townhome offering comfort, convenience, and plenty of living space. The open floor plan creates an inviting flow throughout the main level, complemented by three generously sized bedrooms and 1.5 bathrooms. Enjoy the convenience of newer appliances and a private, fenced

  Valerie Jewis Keller Williams Realty

  63 Greenway Terrace, Middletown, NY 10941
• 

  

  /20

  $420,000

  Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  4 Westminster Dr, Middletown, NY 10940

  Welcome home to this beautifully updated 3-bedroom, 1.5-bathroom house located in a quiet neighborhood! This home features new flooring and fresh paint throughout, an updated kitchen, and a large deck with an expansive yard—perfect for relaxing or entertaining.The property includes private driveway parking and a full basement providing ample storage. With the added convenience of an

  Elena James Keller Williams Realty

  4 Westminster Dr, Middletown, NY 10940
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  /26

  $199,000

  $51K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 360 Sq Ft

  51 S Shore Dr, Middletown, NY 10940

  Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp,

  Arya Rabinovits eRealty Advisors, Inc

  51 S Shore Dr, Middletown, NY 10940
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  /46

  $789,900

  Open House 10/03 $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,958 Sq Ft

  158 Reiss Rd, Middletown, NY 10940

  This spacious farmhouse colonial pairs timeless style with thoughtful design, custom details and an exceptional setting in the Minisink Valley School District. Built in 2019, this home is like new construction but with smart upgrades and additions. Inside, rustic elegance takes center stage with beautiful wood accents, barn doors and warm finishes throughout. Designed with entertaining in mind,

  Danielle Bartula Howard Hanna Rand Realty

  158 Reiss Rd, Middletown, NY 10940
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  /33

  $589,000

  Open Sun 1PM - 3PM $86K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,481 Sq Ft

  5 Decker Dr, Middletown, NY 10940

  Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs

  Dominick Tufano RE/MAX Benchmark Realty Group

  5 Decker Dr, Middletown, NY 10940
• 

  

  /22

  $285,000

  • 2 Beds
  • 1.5 Baths
  • 1,133 Sq Ft

  65 Jimal Dr, Middletown, NY 10940

  Welcome to 65 Jimal Drive, where comfortable living meets the convenience of a low-maintenance lifestyle. This well-kept two-bedroom, one-and-a-half-bath condo offers a bright and inviting layout with updated vinyl flooring flowing through the main living spaces. The spacious living room provides plenty of room to relax or entertain and opens naturally into the dining area and kitchen, creating

  Rebecca Kane KW Hudson Valley United

  65 Jimal Dr, Middletown, NY 10940
• 

  

  /13

  $989,900

  • 8 Beds
  • 4 Baths
  • 3,698 Sq Ft

  393 North St, Middletown, NY 10940

  An excellent investment opportunity in the City of Middletown: three properties with several sources of rental income in one portfolio: The offering includes a four-family home, a two-family home, and a separate parcel with income-producing billboards and a five-bay garage. All six apartments are occupied and consists of two-bedroom units. The tenants pay for their own electric and gas. Each unit

  Patricia Sassi RE/MAX Benchmark Realty Group

  393 North St, Middletown, NY 10940
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  /26

  $295,000

  $25K PRICE DROP

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

  18 Deer Ct Dr, Middletown, NY 10940

  Welcome to 18 Deer Court Dr, located in the desirable Deer Run community. This well-appointed second floor end unit offers approximately 1,291sqft, with 2 bedrooms, and 2 full bathrooms. This spacious condo combines comfort, style, and convenience in a wonderful Hudson Valley setting.Step inside to an open and inviting living and dining area featuring beautiful hardwood floors, creating a

  David Wilson Hudson Premium Realty

  18 Deer Ct Dr, Middletown, NY 10940
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  /31

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 3,217 Sq Ft

  112 Elise Dr, Middletown, NY 10941

  Welcome to Scotchtown Estates, where this stunning, three -year-young Center Hall Colonial combines the pristine feel of new construction with thoughtful upgrades, beautiful landscaping, and premium amenities already in place. Originally showcased as one of the neighborhood’s model homes, this exceptional residence offers approximately 3,200 square feet of beautifully designed living space, with

  Tammy Scotto Keller Williams Realty

  112 Elise Dr, Middletown, NY 10941
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  /32

  $714,000

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,733 Sq Ft

  210 Howells Turnpike, Middletown, NY 10940

  Nestled on 2.5 peaceful acres, this colonial-style home has been lovingly cared for by the same owner since it was built in 2006. The dramatic cathedral ceiling foyer welcomes you with a sense of grandeur, opening to a spacious interior filled with natural light. Hardwood floors flow throughout, enhanced by a refreshed staircase with updated balusters and designer lighting.The custom kitchen

  Cecilia Lewis Century 21 Elite Realty

  210 Howells Turnpike, Middletown, NY 10940
• 

  

  /17

  $609,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  744 Mt Hope Rd, Middletown, NY 10940

  Welcome to this stunning new Colonial home, currently under construction and set on approximately 3 beautiful acres in the desirable Town of Wallkill. Offering approximately 2,600 square feet of finished living space, including a finished basement, this spacious home features 4 bedrooms, 3 full bathrooms, and a one-car garage. The inviting open-concept design showcases gleaming hardwood floors

  Anita S. Cristiano HomeSmart Homes & Estates

  744 Mt Hope Rd, Middletown, NY 10940
• 

  

  /49

  $489,999

  Open Sat 12PM - 2PM $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  58 Cobblestone Ln, Middletown, NY 10940

  Welcome to this beautifully maintained 2,500 sq. ft. townhouse in the desirable Woodside Knolls community. This spacious home offers 3 bedrooms, each featuring a walk-in closet, and 2.5 bathrooms. The open-concept floor plan seamlessly connects the living area and modern kitchen, creating an inviting space for everyday living and entertaining.Additional features include a two-car attached

  Doreen Crowther Howard Hanna Rand Realty

  58 Cobblestone Ln, Middletown, NY 10940
• 

  

  /35

  $375,000

  Open Fri 11AM - 1PM $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  80 Beattie Ave, Middletown, NY 10940

  Welcome Home to Comfort, Style & Convenience in the Heart of Middletown!This beautifully renovated two-story Colonial blends timeless charm with modern updates, offering the perfect place to call home. Featuring 3 bedrooms, 1 full bathroom, and thoughtfully designed living spaces throughout, this move-in-ready property has been updated to maximize both functionality and style.From

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
• 

  

  /5

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  41 Clinton St, Middletown, NY 10940

  3 Bedroom 1 bath ranch in Middletown! Close to Commuter Highways, Trains & ShoppingSOLD AS-IS SIGHT UNSEEN! CASH ONLY! DO NOT DISTURB OCCUPANTS!!

  Ernie Acampora River Realty Services, Inc.

  41 Clinton St, Middletown, NY 10940
• 

  

  /50

  $419,900

  $10K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  21 Harrison St, Middletown, NY 10940

  Welcome to this well-maintained 4-bedroom, 1.5-bath Victorian home offering a functional layout with numerous updates throughout. A covered front porch welcomes you inside, where the main level features a spacious living room, formal dining room, comfortable family room, updated kitchen, and a convenient half bath. Upstairs, you'll find four bedrooms and a full bathroom, providing a practical

  Jie Liu KW Hudson Valley United

  21 Harrison St, Middletown, NY 10940
• 

  

  /22

  $399,000

  $26K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,337 Sq Ft

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to a move-ready condo in the desirable Walkill community. This splendid duplex has been upgraded with modern paint tones and the latest finishes. Bright and sunny rooms with updated lighting throughout. The kitchen boasts sleek, brand-new appliances and classic wood cabinetry. The bathrooms have been meticulously maintained. Cathedral ceilings in both bedrooms lend a dramatic vibe for a

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  

  /7

  $849,999

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  241 Midland Lake Rd, Middletown, NY 10941

  NEW CONSTRUCTION! Set against a peaceful backdrop, this Colonial pairs timeless curb appeal with a practical, beautifully planned interior. This home offers a modern living space with four bedrooms, two and a half baths, a dedicated den, a generous kitchen with island, formal dining and living rooms, second-floor laundry, and a spacious bonus room that doubles as the fourth bedroom.A

  Hilary Ryan Goldman Howard Hanna Rand Realty

  241 Midland Lake Rd, Middletown, NY 10941

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