Middletown, NY Homes for Sale under $500,000

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  /44

  $435,000

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  35 Pinto Rd E, Middletown, NY 10941

  Welcome to 35 Pinto Rd E! This is am immaculate townhouse in a prime, community location---Liberty Commons. This 2+Bedroom, 3 Bath is the perfect combination of contemporary luxury living with convenience. This end unit features , open concept first floor, natural light galore, custom blinds, plenty of storage, spacious bedrooms with large closets, and 2 car tandem garage. Need more.... There is

  

  Tiffany Megna

  Howard Hanna Rand Realty

  35 Pinto Rd E, Middletown, NY 10941
• Explore Middletown

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  /31

  $299,900

  • 3 Beds
  • 1 Bath
  • 860 Sq Ft

  256 Cottage St Unit 258, Middletown, NY 10940

  The first thing you will do here is walk out into that lawn and start deciding where everything goes, the garden along the sunny side, the fire pit set well back, the patch under the old shade tree that stays empty because that is the coolest spot on the property and you are going to want it for yourself. The lot is 0.28 acres, flat and open, and every bit of it comes with the keys. Not many city

  

  Brian Caplicki

  KW Hudson Valley United

  256 Cottage St Unit 258, Middletown, NY 10940
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  /45

  $464,999

  • 3 Beds
  • 2.5 Baths
  • 1,966 Sq Ft

  45 Brola Rd, Middletown, NY 10940

  Welcome to this inviting bilevel home situated on 1.2 level acres in the Minisink School District. The property offers a wonderful combination of space, comfort, and outdoor enjoyment, featuring a fully fenced backyard, spacious deck, and above-ground pool, perfect for relaxing or entertaining.Inside, hardwood flooring runs throughout the main living areas, creating a warm and inviting feel.

  

  Chativa Bowen

  Keller Williams Realty

  45 Brola Rd, Middletown, NY 10940
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  /3

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,019 Sq Ft

  16 Earle St Unit 14 1/2, Middletown, NY 10940

  Prime opportunity for investors, renovators, or savvy buyers looking to build instant sweat equity. With some TLC and modern updates, you can bring your vision to life and transform this house into a standout primary residence or high-yield rental investment.Unbeatable Location & Convenience:Walkable: Walking distance to SUNY Orange campus, downtown amenities, and local

  

  Joao Rodrigues

  Preferred Properties Real Esta

  16 Earle St Unit 14 1/2, Middletown, NY 10940
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  /48

  $425,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,074 Sq Ft

  57 Boorman Rd, Middletown, NY 10940

  Seller is willing to contribute towards closing costs. Welcome home to this fully renovated Dutch Colonial set on 5+ private acres in the desirable Minisink Valley Central School District, located just minutes from Middletown!Step inside to a beautifully updated kitchen featuring sleek quartz countertops, ceramic tile flooring, a subway tile backsplash, new cabinetry, and stainless steel

  

  Lynelle Alessi

  KW Hudson Valley United

  57 Boorman Rd, Middletown, NY 10940
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  /33

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,328 Sq Ft

  3 Allerton Ave, Middletown, NY 10940

  Welcome to 3 Allerton Ave, a charming and well-maintained Ranch-style home nestled in one of Middletown’s sought-after neighborhoods. Set on a private 0.20-acre lot, this inviting property offers a peaceful suburban setting with shopping, dining, public transportation, and commuter routes just minutes away. A welcoming front porch leads into a bright foyer and semi-open living space connecting

  

  Erin Connolly-Frontino

  Artisan Realty

  3 Allerton Ave, Middletown, NY 10940
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  /17

  $294,990

  $5K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  50 Hampton Ct, Middletown, NY 10941

  Welcome to 50 Hampton Court, Middletown, NY 10941! This inviting 3-bedroom, 1.5-bath home offers a comfortable layout with plenty of space to relax, entertain, and make your own. Step inside to a bright entryway that opens to a spacious living room featuring attractive wood-look flooring, recessed lighting, a dramatic accent wall, and a fireplace that creates a warm focal point. The kitchen

  

  Haakim Byrd

  HomeSmart Homes & Estates

  50 Hampton Ct, Middletown, NY 10941
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  /45

  $489,000

  Pre-Foreclosure

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

  50 Scott Dr, Middletown, NY 10941

  Welcome to this spacious four-bedroom, two-bathroom corner-lot home in the desirable Scotchtown area of Orange County. The updated kitchen features stainless steel appliances, while hardwood floors flow throughout the main level. A distinctive sloped ceiling enhances the living room’s open, airy feel and abundant natural light. Sliding glass doors from the dining room lead to a large rear

  

  Dulce M Ferrera

  KW Hudson Valley United

  50 Scott Dr, Middletown, NY 10941
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  /43

  $399,900

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,919 Sq Ft

  83 Deer Ct Dr, Middletown, NY 10940

  Beautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located in the highly desirable Deer Run complex. This move-in-ready home features laminate flooring throughout, with tile flooring in the kitchen and bathrooms. The kitchen was tastefully updated in 2020, along with the heating and cooling system, which is electronically controlled and offers a high-efficiency SEER

  

  Dulce M Ferrera

  KW Hudson Valley United

  83 Deer Ct Dr, Middletown, NY 10940
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  /26

  $339,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  101 N Beacon St, Middletown, NY 10940

  Move in ready 3 bedrooms, 2 bathroom home. Clean and freshly painted. Updated kitchen and bathrooms. Located on a dead end street. Private Fenced-in yard. Conveniently located minutes from local shops, restaurants, Galleria Mall, Garnet Health and close proximity to I86 and I84. Very easy to show. Call today for your own private viewing.

  

  Dulce M Ferrera

  KW Hudson Valley United

  101 N Beacon St, Middletown, NY 10940
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  /9

  $399,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,799 Sq Ft

  12 Todd Dr, Middletown, NY 10941

  Conveniently located in Pine Bush schools and close to ammenities is the 3 bedroom two bath split level on a cul-de-sac

  

  Lynelle Alessi

  KW Hudson Valley United

  12 Todd Dr, Middletown, NY 10941
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  /49

  $455,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft

  168 Shawangunk Rd, Middletown, NY 10940

  Discover the perfect blend of historic charm, modern comfort, and peaceful country living in this utterly delightful home, beautifully situated on 2.2 wooded acres. Rich in character, the residence showcases timeless architectural details while benefiting from a comprehensive renovation. Prior to renovation, the home was thoroughly gutted and fully foam insulated, with all-new plumbing and

  

  Jason Kerwar

  William Raveis Real Estate

  168 Shawangunk Rd, Middletown, NY 10940
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  /33

  $475,000

  Open Sun 12PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  8 Pine St, Middletown, NY 10940

  Come view this beautifully appointed Raised Ranch in a commuter-friendly area of Middletown . This 4 bedroom two bath home boasts an open kitchen concept with 4 generous sized bedrooms upstairs an open downstairs area that can become anything you desire. It comes fully equipped with all appliances. You will also enjoy the spacious canopied deck and pool. Act now and you can bein this wonderful

  Robin White KW Hudson Valley United

  8 Pine St, Middletown, NY 10940
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  /28

  $399,000

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

  19 Putters Way Unit 6, Middletown, NY 10940

  Beautiful Townhouse in Fairways at Wallkill! Enjoy maintenance-free living in this desirable Fairways community townhouse. Conveniently located near major highways, shopping, and Orange Regional Medical Center, this home features 2 bedrooms, 2.5 bathrooms, a spacious living room, and a bright private balcony overlooking the pool.Residents have access to outstanding amenities including a

  Xiaohui Cui KW Hudson Valley United

  19 Putters Way Unit 6, Middletown, NY 10940
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  /31

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  21 Black Stallion Ct, Middletown, NY 10940

  Welcome to inviting, freshly painted, updated 3-bedroom, 1.5-bathroom home in The Meadows community~Main floor offers kitchen-with brand new cabinets, new stainless steel appliances, granite countertops, roomy dining area, bright and expansive living room with large bay window and half bathroom~Door from the kitchen leads to the large deck perfect for relaxing and entertaining your guests

  Liene Kasparsons Keller Williams Realty

  21 Black Stallion Ct, Middletown, NY 10940
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  /5

  $345,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,380 Sq Ft

  8 Budd Ave, Middletown, NY 10940

  Step into the warmth and charm of this beautifully maintained Colonial, where classic character meets comfortable modern living. Gleaming hardwood floors flow throughout much of the home, complementing the inviting architectural details found throughout.The spacious, sun-filled Living Room features an arched doorway leading to the Formal Dining Room—perfect for entertaining or enjoying

  Richard Froehlich RE/MAX Benchmark Realty Group

  8 Budd Ave, Middletown, NY 10940
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  /23

  $349,000

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft

  15 Kendal Ln, Middletown, NY 10940

  Beautifully maintained end-unit townhouse in the highly desirable Water's Edge community! This move-in-ready 2-bedroom, 2.5-bath home offers a bright, open layout with a spacious foyer, updated kitchen featuring newer appliances, a large living room with new sliding glass doors leading to a private patio, and a convenient first-floor powder room. Upstairs, the primary suite features cathedral

  Jonathon Lee KW Hudson Valley United

  15 Kendal Ln, Middletown, NY 10940
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  /20

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 2,097 Sq Ft

  4 Kless Ct, Middletown, NY 10940

  Welcome to Maple Fields! This well-maintained 3-bedroom, 2.5-bath townhouse with a versatile finished loft offers a functional layout designed for today's lifestyle.The main level features an open-concept living area, a dedicated dining space, and a bright kitchen with stainless steel appliances, a pantry, tile backsplash, and ample counter space. Sliding glass doors open to a private

  Bryant Moran YourHomeSold Guaranteed Realty

  4 Kless Ct, Middletown, NY 10940
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  /42

  $215,000

  • 1 Bed
  • 1 Bath
  • 879 Sq Ft

  11 Brittany Dr, Middletown, NY 10940

  Welcome to a low-maintenance lifestyle, minimal utilities, included heat and hot water, generous storage, and a commuter-friendly setting. This condominium is an excellent opportunity for buyers looking for comfort and convenience . Located in a quiet, peaceful neighborhood, this second-floor condo offers a welcome retreat while still being close to varied amenities and transportation options

  Amanda Ferrantello Hudson Valley Griffith

  11 Brittany Dr, Middletown, NY 10940
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  /47

  $420,500

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft

  34 Adams Ave, Middletown, NY 10940

  Welcome to this charming 3-bedroom, 1.5-bath Colonial nestled on a level, fenced lot in the heart of Middletown. Built in 1941, this well-maintained home beautifully blends timeless character with everyday functionality, showcasing original hardwood floors, classic woodwork, detailed moldings, and elegant arched doorways throughout.The inviting first floor features a spacious living room,

  Linda Potyak Iron Valley RE Tri-State

  34 Adams Ave, Middletown, NY 10940
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  /49

  $394,000

  $25K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,928 Sq Ft

  48-50 Mountain Ave, Middletown, NY 10940

  Welcome to 48-50 Mountain Avenue, where timeless Cape Cod charm meets modern comfort in one of Middletown's most convenient locations. Beautifully updated and meticulously maintained, this inviting 3-bedroom, 1.5-bath home offers approximately 1,928 square feet of warm, light-filled living space on a beautifully landscaped 0.36-acre lot tucked away on a quiet cul-de-sac. From the moment you

  Amanda Brehm KW Hudson Valley United

  48-50 Mountain Ave, Middletown, NY 10940
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  /46

  $485,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  172 Mt Joy Rd, Middletown, NY 10941

  Tranquil Goshen Colonial with Beautiful Grounds & Sunset Views. Welcome to your own peaceful retreat in the heart of the Hudson Valley! Set on a beautifully maintained, level one-acre lot in the Goshen School District, this charming 3-bedroom, 1.5-bath Colonial offers the perfect blend of comfort, character and country living—just minutes from the heart of the Village of Goshen.Step

  Susanne Dermigny Howard Hanna Rand Realty

  172 Mt Joy Rd, Middletown, NY 10941
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  /27

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  41 Irwin Ave, Middletown, NY 10940

  The covered front porch, hardwood floors, and separate rooms give this home the kind of simple, straightforward layout that has worked for generations and still works today. Step inside and you'll find plenty of natural light, along with distinct living and dining rooms that each have their own purpose without making the home feel disconnected.The kitchen is practical and well equipped,

  Joshua Papka Keller Williams Realty HV Nort

  41 Irwin Ave, 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

  $499,000

  • 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

  $319,000

  • 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

  $474,995

  $10K 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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  /27

  $399,900

  $50K PRICE DROP

  • 5 Beds
  • 3 Baths

  37 Monhagen Ave, Middletown, NY 10940

  Welcome to an opportunity that is becoming harder and harder to find. This multi-family property sits on a nearly half-acre lot in the City of Middletown and offers investors, contractors, and ambitious buyers the chance to create significant value. With 2,151 square feet, five bedrooms, three full bathrooms, and income-producing potential, this is the type of property that rewards vision and

  Isaiah Lopez KW Hudson Valley United

  37 Monhagen Ave, 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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  /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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  /37

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,246 Sq Ft

  293 Highland Ave Extension, Middletown, NY 10940

  Offering over 1,200 square feet of one-level living, this home still has some of the fun details that made the 1950’s so memorable. A classic Dutch door? Check. Original woodwork? Absolutely. Hardwood floors hiding beneath the carpeting? They’re just waiting to make their comeback. And that fabulous pink-tiled bathroom? We say embrace it! The enclosed porch is another favorite—a cozy little spot

  Patricia Sassi RE/MAX Benchmark Realty Group

  293 Highland Ave Extension, Middletown, NY 10940
• 

  /2

  $324,999

  Coming Soon

  • 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

  $320,000

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

  18 Deer Ct Dr Unit Building 19 unit 18, Middletown, NY 10940

  Well-maintained 2-bedroom, 2 bathroom condo in the Deer Run Community with a 53-foot garage. Hardwood floors are throughout the open-concept living/dining room. The kitchen features stainless steel appliances. Recently updated washer, dryer (2025) and water heater (2025) and new windows. Primary bedroom features an en-suite bathroom and a walk-in closet.Conveniently located on the Dolson

  David Wilson Hudson Premium Realty

  18 Deer Ct Dr Unit Building 19 unit 18, Middletown, NY 10940
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  /49

  $495,000

  • 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
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  /35

  $399,999

  $15K 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
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  /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
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  /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
• 

  

  /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
• 

  

  /50

  $299,000

  $11K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  4 Lincoln St, Middletown, NY 10940

  This 3-bedroom, 2-bath Colonial offers 1,398 square feet of comfortable living space on a 0.11-acre lot. Built in 1890, the home blends timeless style with thoughtful upgrades while keeping its original charm. Enjoy bright mornings with natural light, cozy evenings at home, and a neighborhood close to shopping, restaurants, parks, schools, and local services. All utilities are available, making

  Matthew Gibbs KW Hudson Valley United

  4 Lincoln St, Middletown, NY 10940
• 

  

  /19

  $333,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  23 Harrison St Unit 25, Middletown, NY 10940

  Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c

  Pedro Garcia Curasi Realty, Inc.

  23 Harrison St Unit 25, Middletown, NY 10940

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