Middletown, NY Homes for Sale

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  /37

  $289,900

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

  141 Ruth Ct, Middletown, NY 10940

  Welcome to 141 Ruth Court! This move-in-ready two-bedroom, two-full-bath home has been freshly painted and features new carpeting throughout, offering a clean and inviting space that’s ready for you to make your own. With a comfortable layout, two bedrooms, and two full baths, this home is a wonderful opportunity for easy, turnkey living. Cathedral ceilings, 2 floors, open floor plan offering

  Dawn Gregg Curasi Realty, Inc.

  141 Ruth Ct, Middletown, NY 10940
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  /31

  $339,000

  Open Sat 1PM - 3PM

  • 2 Beds
  • 1 Bath
  • 992 Sq Ft

  26 Gardner Ave, Middletown, NY 10940

  A cozy and beautifully maintained home in a convenient location, this charming 2-bedroom, 1-bath property offers comfort, character, and thoughtful updates throughout. The updated kitchen and bathroom complement the warm hardwood floors on the main level, while raised dormers upstairs create a more spacious feel.The home features numerous important updates, including the roof, heating and

  Julie Kim Howard Hanna Rand Realty

  26 Gardner Ave, Middletown, NY 10940
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  /50

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,781 Sq Ft

  37 Meadow View Dr, Middletown, NY 10940

  Welcome to this beautifully updated end-unit townhouse with numerous upgrades completed in 2023! The bright and open main level features hardwood flooring, a spacious kitchen with granite countertops, a complementary tile backsplash, stainless steel appliances, abundant cabinetry, a large center island, pendant lighting, and recessed lighting. The kitchen flows seamlessly into the dining area and

  Jie Liu KW Hudson Valley United

  37 Meadow View Dr, Middletown, NY 10940
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  /6

  $599,000

  $31K PRICE DROP

  • 10 Beds
  • 4 Baths

  309-317 E Main St Unit 309, Middletown, NY 10940

  Welcome to this beautiful two-family home located on E Main Street! Perfect for owner-occupants, investors, or extended family living, this spacious property offers incredible flexibility and charm. One unit features 6 bedrooms, while the second unit offers 4 bedrooms, providing plenty of spac. Both units have separate front and side entrances for added privacy and convenience. The property sits

  Betzaida Vericain Q Home Sales

  309-317 E Main St Unit 309, Middletown, NY 10940
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  /16

  $369,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,416 Sq Ft

  4 Harding St, Middletown, NY 10940

  Middletown Central Gem with Lots of Space and Super Low Taxes!Located just minutes from Downtown Middletown, this solid house has a very practical layout with 4 spacious bedrooms and 2 full bathrooms, making it perfect for a growing family or an investor. On top of the great living space, you get a huge attic and a full basement that give you tons of extra room for storage or a workshop. The

  Hai Li KW Hudson Valley United

  4 Harding St, Middletown, NY 10940
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  /16

  $499,000

  $196K PRICE DROP

  • Land
  • 5.07 Acres
  • $98,422 per Acre

  0 Route 28 Unit 20261954, Middletown, NY 12455

  Rare opportunity: PRIME waterfront commercial lot in the heart of Margaretville on State Highway 28 -- unmatched visibility on the busy corridor. Zoned commercial with municipal sewer and water available. The East Branch of the Delaware River parallels the full length of the parcel, providing exceptional waterfront exposure and strong development potential. Seller has detailed plans available

  Katherine Keys The Catskill Dream Team

  0 Route 28 Unit 20261954, Middletown, NY 12455
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  /50

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  8 Green Ct, Middletown, NY 10940

  Welcome to this well-maintained 3-level townhome in The Fairways, a gated community conveniently located next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, restaurants, and everyday conveniences. This home offers a 2-car garage, a finished lower level with direct garage access, and a functional floor plan designed for comfortable everyday living.

  Jie Liu KW Hudson Valley United

  8 Green Ct, Middletown, NY 10940
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  /9

  $1,590,000

  New Construction

  • 4 Beds
  • 4 Baths
  • 5,600 Sq Ft

  375 Blumel Rd, Middletown, NY 10941

  Located at 375 Blumel Road in Scotchtown, New York, this exceptional historic multi-family investment property offers a rare opportunity to own a fully restored income-producing asset in the heart of Orange County in New York's Hudson Valley. Originally constructed in 1787 and completely renovated in 2024, the property combines historic architecture with modern upgrades and strong income

  Keegan Rehill ZORA REI

  375 Blumel Rd, Middletown, NY 10941
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  /9

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft

  18 Black Stallion Ct, Middletown, NY 10940

  This inviting 3-bedroom, 1.5-bath townhome offers comfort, space and a welcoming layout. Owned by the same family for over 50 years, this home is now ready for its next chapter. Inside, you’ll find a large, comfortable living room that’s perfect for gathering and relaxing. The eat-in kitchen has been updated with new flooring and appliances, making it both functional and stylish. New carpeting

  Jennifer Kubler eRealty Advisors, Inc

  18 Black Stallion Ct, Middletown, NY 10940
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  /5

  $215,000

  • Land
  • 1.1 Acres
  • $195,455 per Acre

  429 van Burenville Rd, Middletown, NY 10940

  Engineered lot pending approvals. Over 1 acre of land in the Town of Wallkill with Pine Bush Schools. This lot is "shovel ready", building docs have been submitted to the town and it's pending approvals. The lot is lovely, already cleared with the driveway conveniently cut in. There used to be a structure and it has been properly removed with permits, creating a perfect site to start building

  Valeria Rios KW Hudson Valley United

  429 van Burenville Rd, Middletown, NY 10940
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  /43

  $469,000

  • 5 Beds
  • 3 Baths
  • 2,448 Sq Ft

  495 Guymard Turnpike, Middletown, NY 10940

  Welcome home to this breathtaking Farmhouse-style retreat, perfectly set back from the main road amidst mature hydrangeas and Rose of Sharon. Step onto the sprawling, large rocking chair front porch—part of an expansive covered porch that wraps around three sides of the home—and experience true rustic charm before you even step inside. Upon entry, you’ll be in awe of the soaring vaulted ceilings,

  Maureen Cronin Cronin & Company Real Estate

  495 Guymard Turnpike, Middletown, NY 10940
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  /21

  $455,000

  • 4 Beds
  • 2 Baths
  • 1,466 Sq Ft

  225 Monhagen Ave, Middletown, NY 10940

  Great Location with C-2 Mixed-Use Zoning Potential! Located at 225 Monhagen Avenue in Middletown, this nicely maintained property offers a comfortable and practical layout along with exceptional flexibility for homeowners, investors, and business-minded buyers. The home features 4 bedrooms and 2 full bathrooms, providing generous space for comfortable family living. A finished basement adds

  Jin Pang Panorama Realty

  225 Monhagen Ave, Middletown, NY 10940
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  /41

  $699,000

  $130K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,340 Sq Ft

  571 Route 17m, Middletown, NY 10940

  Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level.The first floor offers a warm and

  Angela Murphy BHG Real Estate Green Team

  571 Route 17m, Middletown, NY 10940
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  /49

  $725,000

  • 5 Beds
  • 5 Baths
  • 4,188 Sq Ft

  14 Longview Ln, Middletown, NY 10941

  Welcome to this one-of-a-kind custom home tucked away at the end of a quiet cul-de-sac in the highly sought-after Pine Bush School District. Offering over 4,200 square feet of living space, this home combines quality craftsmanship, privacy, and features you simply won’t find anywhere else. Step inside to soaring cathedral ceilings, beautiful hardwood floors throughout, and a formal dining room

  Susan Giordano Hudson Premium Realty

  14 Longview Ln, Middletown, NY 10941
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  /25

  $478,000

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

  25 Independence Ave, Middletown, NY 10940

  It is located in one of Middletown's most desirable neighborhoods, where strong demand and steadily increasing home values make this an exceptional opportunity!This beautifully renovated, move-in-ready 4-bedroom home has been thoughtfully updated from top to bottom. The brand-new kitchen features modern cabinetry, a new stove, and an added pantry/storage closet, creating a stylish and

  Jin Pang Panorama Realty

  25 Independence Ave, Middletown, NY 10940
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  /14

  $393,000

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing and heating, plus with a big corner lot. Plenty of space, beautiful kitchen - come see it today.

  Safdar Mursalin eXp Realty

  1 Chestnut St, Middletown, NY 10940
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  /22

  $395,000

  $55K PRICE DROP

  • 1,450 Sq Ft

  13 Benton Ave, Middletown, NY 10940

  Beautiful Brick Mixed Use Building located in a very desirable area of Middletown. This wonderful building features 3 Units. First unit is Office SpaceThat is great for an accountant, attorney,Real Estate office. Etc. Second Level offers a Spacious 1 Bedroom apartment 3 rd level offers another large 1 bedroom Apartment. Separate Electric and Hot water heaters. Large Parking Lot Second

  John Biasi Howard Hanna Rand Realty

  13 Benton Ave, Middletown, NY 10940
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  /37

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft

  24 Beth Dr, Middletown, NY 10941

  Your home is this fully renovated 3-bedroom property that seamlessly blends modern interior elegance with an extraordinary backyard oasis! Step inside to an airy, light-filled open-concept floor plan showcasing fresh updates throughout, including sleek new flooring, modern lighting fixtures, and spa-inspired renovated bathrooms. The open gourmet kitchen serves as the heart of the home,

  Marc Cineus Howard Hanna Rand Realty

  24 Beth Dr, Middletown, NY 10941
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  /19

  $560,000

  • 4 Beds
  • 3 Baths
  • 2,162 Sq Ft

  77 Upper Rd, Middletown, NY 10940

  Accepted Offer- Continue Showing for Back up. This beautiful ranch-style property is ready to move in. Amazing upgrades were made to this home with beautiful hardwood floors, 4 bedrooms, 3 bathrooms, a huge partially finished basement with enough space for a personal gym with access to an amazing backyard that features a beautiful above-ground pool, a tennis court, volleyball court, or basketball

  Yajaira Silva Madison Allied LLC

  77 Upper Rd, Middletown, NY 10940
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  /24

  $299,999

  • 2 Beds
  • 1 Bath
  • 1,164 Sq Ft

  14 Airport Rd, Middletown, NY 10940

  14 Airport Road is ready for a little love and its next chapter. Located in the Town of Wallkill, this home offers a surprisingly spacious and flexible layout with plenty to work with for a buyer ready to roll up their sleeves and make it their own.The main level offers an open flow between the kitchen and living areas, with a brick fireplace adding character to the space. The kitchen is

  Cindy-Lee Dorcely KW Hudson Valley United

  14 Airport Rd, Middletown, NY 10940
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  /6

  $799,000

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

  76 Winters Ln, Middletown, NY 10940

  Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 1 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

  76 Winters Ln, Middletown, NY 10940
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  /33

  $499,999

  Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  678 Prosperous Valley Rd, Middletown, NY 10940

  Welcome to 678 Prosperous Valley Road, a beautifully renovated Colonial nestled on 0.80 acres in the desirable Town of Middletown. Combining timeless character with modern upgrades, this move-in-ready home offers 4 spacious bedrooms, 2 full bathrooms, and approximately 1,861 square feet of thoughtfully updated living space.Recent improvements include a stunning remodeled kitchen, fully

  Yonauris Gonzalez Then eXp Realty

  678 Prosperous Valley Rd, Middletown, NY 10940
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  /24

  $555,000

  $24K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,202 Sq Ft

  29 Murray Rd, Middletown, NY 10940

  3 PRIVATE ACRES + ULTIMATE VERSATILITY + POSSIBLE INCOME POTENTIAL = A RARE MIDDLETOWN OPPORTUNITY Set on 3 serene, wooded acres, this beautifully maintained raised ranch offers an expansive 2,202 sq. ft. of living space designed with a unique, highly adaptable layout that can help with your financial goals or adapt to your lifestyle. The main level features a bright open-concept main floor with

  Regina Lombardo KW Hudson Valley United

  29 Murray Rd, Middletown, NY 10940
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  /37

  $1,600,000

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  430 Kirbytown Rd, Middletown, NY 10940

  PRIVATE ONE OF A KIND RANCH!! 16 Acres! One Level Living! 4 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Master Bedroom Suite with Walk In Closet! Large Kitchen with Breakfast Bar & Ceramic Tiles! Over Sized Living Room with Gleaming Hard Wood Floors and Sliders to Double Deck! Full Basement for Endless Possibilities! Celling Fans! Recessed Lighting! Laundry Room! Wooded Lot! Lots of Parking! Plenty

  Amanda Dnistrian ARC Realty 1 in Sales

  430 Kirbytown Rd, Middletown, NY 10940
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  /16

  $329,000

  • 2 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  15 N Aspen Rd, Middletown, NY 10940

  NO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready 2-bedroom home, thoughtfully updated with modern finishes and designed for today’s lifestyle. From the moment you step inside, you’re greeted by a bright and inviting interior that feels both stylish and comfortable. The updated kitchen shines with sleek countertops, crisp cabinetry, and modern appliances,

  Carmela Lopez Borrazas Serhant LLC

  15 N Aspen Rd, Middletown, NY 10940
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  /49

  $765,000

  • 4 Beds
  • 3 Baths
  • 3,064 Sq Ft

  118 Ridge Dr, Middletown, NY 10940

  Timeless Character. Endless Possibilities.Nestled on over 12 private, wooded acres along a quiet country road, this stately brick Colonial offers the rare opportunity to own a home where history, craftsmanship, and natural beauty come together. Built circa 1900 and encompassing more than 3,000 square feet, this remarkable residence is filled with the warmth and architectural character that

  Patricia Sassi RE/MAX Benchmark Realty Group

  118 Ridge Dr, Middletown, NY 10940
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  /29

  $350,000

  $25K PRICE DROP

  • Land
  • 34.56 Acres
  • $10,127 per Acre

  0 W Hubbell Hill Rd Unit KEY1027019, Middletown, NY 12455

  Discover the possibilities with this exceptional 34+ acre land parcel nestled in a peaceful rural setting. Offering a perfect blend of open space, privacy, and natural beauty, this property provides an ideal canvas for your dream home, retreat, hobby farm, recreational getaway, or future investment.Surrounded by scenic countryside and abundant wildlife, the land offers plenty of room for

  Amanda Ferrantello Hudson Valley Griffith

  0 W Hubbell Hill Rd Unit KEY1027019, Middletown, NY 12455
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  /39

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  1630 Goshen Turnpike, Middletown, NY 10941

  Turnkey 3-Bed, 1-Bath with stunning mountain views! Completely remodeled from top to bottom with a brand-new upgraded kitchen, updated bath, and cozy living space. Features a versatile indoor porch, new deck, and a large backyard patio perfect for entertaining. Ready for you to move in!

  Yehuda Lefkowits MS Realty Group USA, Inc

  1630 Goshen Turnpike, Middletown, NY 10941
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  /50

  $850,000

  • 4 Beds
  • 4.5 Baths
  • 4,522 Sq Ft

  232 Tally Ho Rd, Middletown, NY 10940

  A Rare Country Estate Rich in History, Character & Timeless Beauty. Nestled off the road and surrounded by approximately 17 private, wooded acres, this remarkable circa 1820 estate offers an extraordinary opportunity to own a piece of Hudson Valley history. Lovingly expanded over generations while preserving its original character, this one of a kind residence encompasses over 4,500 square feet

  Patricia Sassi RE/MAX Benchmark Realty Group

  232 Tally Ho Rd, Middletown, NY 10940
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  /28

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  21 Keystone Park, Middletown, NY 10940

  What you've been waiting for! Adorable and affordable 3 BR ranch on a cul de sac with lovely, private back yard! Large LR! Kitchen opens to Dining area! New walk in shower in bath! Full basement and 1 car garage. C/A! HW floors! Newer windows! Municipal services! Convenient to shopping and Route 17 for commuter!

  Linda Clark Hudson Valley Griffith

  21 Keystone Park, Middletown, NY 10940
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  /23

  $399,995

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft

  17 Last Rd, Middletown, NY 10941

  Welcome to 17 Last Rd, a unique retreat nestled on a sprawling 3.9-acre lot in the heart of Middletown. The upper level features 2 bedrooms and 1 full bathroom, while the lower level offers ground-level access with its own separate entrance, an additional bedroom, and a full bathroom. This versatile 2-bedroom, 2-full-bathroom home is designed to maximize natural light, creating a bright and airy

  Bryant Moran YourHomeSold Guaranteed Realty

  17 Last Rd, Middletown, NY 10941
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  /16

  $165,000

  $10K PRICE DROP Pre-Foreclosure

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  488 Tally Ho Rd, Middletown, NY 10940

  A charming 1940 bungalow located in the highly desirable Minisink Valley School District, this home sits on a quiet 0.23-acre lot and makes an excellent starter home with low taxes. The front door opens into a spacious living area filled with natural light. The main level offers one bedroom plus an office that can serve as a second bedroom if needed. The full basement—not included in the listed

  Jason Schobert eXp Realty

  488 Tally Ho Rd, Middletown, NY 10940
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  /40

  $354,900

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  41 Roosevelt Ave Unit 39, Middletown, NY 10940

  Welcome home to this beautifully maintained 3-bedroom, 1-bath Colonial in the City of Middletown. Conveniently located near shopping, restaurants, parks, schools, and major commuter routes, this home blends classic charm with practical everyday living. From the moment you arrive, you'll be drawn to the expansive wraparound front porch—the perfect place to enjoy your morning coffee or unwind at

  Patricia Sassi RE/MAX Benchmark Realty Group

  41 Roosevelt Ave Unit 39, Middletown, NY 10940
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  /29

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  30 Chestnut Ave, Middletown, NY 10940

  Tucked into one of Middletown's established neighborhoods, 30 Chestnut Avenue is a home that effortlessly blends comfort, style, and convenience. From the moment you step inside, you'll appreciate the bright, open floor plan where natural light pours through the windows, creating inviting spaces designed for both everyday living and memorable gatherings.The heart of the home is the

  Lauren Iacono Corcoran Baer & McIntosh

  30 Chestnut Ave, Middletown, NY 10940
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  /22

  $530,000

  Open Sat 12PM - 2PM $55K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,332 Sq Ft

  2078 Route 6, Middletown, NY 10940

  Welcome to this beautifully maintained contemporary bi-level home set on 2.2 private acres in the scenic countryside of Orange County. Built in 2015, this exceptional residence combines modern comfort with peaceful surroundings, offering the perfect balance of privacy and convenience. The impressive entryway welcomes you with soaring cathedral ceilings, abundant natural light, and an open, airy

  Shiva Kalipersad Anthony Napolitano Homes

  2078 Route 6, Middletown, NY 10940
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  /50

  $549,900

  $50K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 3,280 Sq Ft

  22 Camp Orange Rd, Middletown, NY 10941

  Cherished through generations and lovingly maintained by its owners, this remarkable circa home is ready for its next chapter. Set on 3.6 beautifully level acres in the Valley Central School District, the property offers the perfect blend of historic character, functional space, and country charm. As you approach, the care and pride of ownership are immediately evident. A welcoming front porch

  Rosalie Cook Weichert Realtors

  22 Camp Orange Rd, Middletown, NY 10941
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  /42

  $430,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  11 Columbia Ave, Middletown, NY 10940

  BEAUTIFULLY maintain old style home in the heart of Middletown with low PROPERTY taxes. A must-see home to appreciate it quality and charm. Located near Davidge Park. Commuter Friendly location easy access to Route 17 and interstate highway 84 to Penn and Conn. NJ Transit and a 15 min walk to the Shortline Bus to Midtown Manhattan with Plenty of Parking should you choose to drive to the bus

  Norberto Tirado N Tirado Realty LLC

  11 Columbia Ave, Middletown, NY 10940
• 

  

  /28

  $399,999

  Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  70 Peach Place, Middletown, NY 10940

  Welcome to 70 Peach Place, a beautifully maintained townhouse nestled in the desirable Peach Hills subdivision. This spacious home offers the perfect blend of comfort, convenience, and value with no HOA fees and low taxes.Step inside to discover newly updated bathrooms, new appliances, and a brand-new hot water heater, providing peace of mind for years to come. The generous primary suite

  Virginia Corbett eXp Realty

  70 Peach Place, Middletown, NY 10940
• 

  

  /45

  $795,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,276 Sq Ft

  34 Stapleton Ct, Middletown, NY 10940

  Seller ready to go! This stunning four-bedroom Colonial is nestled on 1.3 acres at the end of a peaceful cul-de-sac, backing up to the scenic Hunter Nature Preserve. Solar panels owned, utility bills less than $25/month. Enjoy relaxing evenings on the spacious rocking chair front porch. The updated kitchen features beautiful granite countertops and a custom backsplash, perfect for culinary

  Annie Hansen Howard Hanna Rand Realty

  34 Stapleton Ct, Middletown, NY 10940
• 

  

  /20

  $146,900

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  394 Concord Ln, Middletown, NY 10940

  A fantastic opportunity for first time home buyers, downsizers or investors. Step into this freshly painted, well maintained 1 bedroom condo and experience easy living, low maintenance and community perks including pool and clubhouse. Stainless steel stove and dishwasher are only 3 years old, heating unit 7-8 years old. This complex is conveniently located near major highways and shopping. Enjoy

  Carol Scully Keller Williams Realty

  394 Concord Ln, Middletown, NY 10940

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