Middletown, NY Homes for Sale

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  /30

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  25 Fairways Dr Unit 1, Middletown, NY 10940

  Step into this fully updated, move-in ready luxury condo located in one of the area’s most sought-after gated communities. This stunning first-floor residence has been meticulously upgraded from top to bottom—featuring designer finishes, fresh modern paint tones, and premium luxury flooring throughout. The custom kitchen is outfitted with elegant cabinetry, granite countertops, and stylish

  

  Randolph Rogers

  eXp Realty

  (845) 299-8068

  25 Fairways Dr Unit 1, Middletown, NY 10940
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  /25

  $420,000

  • 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

  (845) 436-3953

  71 Commonwealth Ave, Middletown, NY 10940
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  /42

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,542 Sq Ft

  138 Reinhardt Rd, Middletown, NY 10940

  Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (845) 447-9473

  138 Reinhardt Rd, Middletown, NY 10940
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  /2

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  13 Smith St, Middletown, NY 10940

  Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 299-0839

  13 Smith St, Middletown, NY 10940
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  /50

  $889,000

  • 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
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  /26

  $410,000

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  31 Beattie Ave, Middletown, NY 10940

  Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 286-4605

  31 Beattie Ave, Middletown, NY 10940
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  /24

  $380,000

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

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

  For investors or anyone interested in taking on tenants until 9/30/26 and at that time can take possession of the unit. Tenants have a lease expiration date of 9/30/26 and must remain there until that time. Tenants pay $2850 a month and pay for oil and electric. They are excellent tenants. New townhouse on right side (Unit 2C) available in the Minisink Valley School District. This home

  

  Hazel Cello

  Keller Williams Hudson Valley

  (845) 328-4272

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

  $380,000

  • 5 Beds
  • 2 Baths
  • 2,440 Sq Ft

  44 Houston Ave, Middletown, NY 10940

  Excellent opportunity to own a 2 family house whether you are an investor or want to live in one of the units and rent the second one. Spacious apartments. First floor apartment has 3 bedrooms and 1 bathroom, second floor apartment has 2 bedrooms and 1 bath. Conveniently located, walking distance to Touro College where students are always looking for close by rentals. Minutes to I86 and I84,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 497-6793

  44 Houston Ave, Middletown, NY 10940
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  /50

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft

  166 Hilly's Ln, Middletown, NY 12455

  Escape to your own private retreat on 13.2 acres in the charming community of New Kingston. This updated cedar sided chalet offers 3 bedrooms plus a cozy sleeping nook, 2 beautifully renovated baths, and a long list of thoughtful upgrades within the past 24 months. A Tuli Kivi soapstone stove fireplace insert brings warmth and charm, but the true showstopper is the 18’ x 18’ screened

  Susan Doig Listing by Coldwell Banker Timberland Properties

  

  166 Hilly's Ln, Middletown, NY 12455
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  /21

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,552 Sq Ft

  125 Whipple Rd, Middletown, NY 10940

  Discover the perfect blend of serenity and comfort in this stunning 4-bedroom, 3-bathroom raised ranch nestled on a sprawling 1.5-acre lot in the heart of Middletown, NY. As you step inside, the heart of the residence, a spacious and sunlit living area, invites family gatherings and effortless entertaining. Culinary enthusiasts will delight in the modern kitchen, boasting sleek appliances and

  Eboni Navas Julia B Fee Sothebys Int. Rlty

  125 Whipple Rd, Middletown, NY 10940
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  /36

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,760 Sq Ft

  214 Phillips St, Middletown, NY 10940

  Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 sqft layout across three levels of living space. The gourmet kitchen features an island with a breakfast bar and flows seamlessly into a large dining area. The luxurious primary suite includes a full ensuite bath with dual vanities, a shower, and a separate soaking tub, all highlighted by expansive windows.

  Donna Gray Redfin Real Estate

  214 Phillips St, Middletown, NY 10940
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  /28

  $649,900

  • 3 Beds
  • 3 Baths
  • 3,021 Sq Ft

  34 Feiertag Rd, Middletown, NY 10941

  Let your dreams begin with large colonial home located on a Cul-de-Sac in the Pine Bush School District. Step inside to a large and open foyer with high ceilings which creates a welcoming atmosphere. The main level features a formal dining room, den/office, cozy family room with woodburning fireplace, open eat in kitchen with breakfast area, full bath and enclosed screened deck overlooking the

  Julianna Cotthaus 1st Independent Realty Grp

  34 Feiertag Rd, Middletown, NY 10941
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  /35

  $589,000

  • 4 Beds
  • 3 Baths
  • 2,732 Sq Ft

  24 3rd St, Middletown, NY 10940

  BETTER THAN NEW! SPACIOUS 4-Bedroom, 3-Full Bath Bi-Level ColonialWelcome to this meticulously maintained home offering over 2,700 sq ft of beautifully finished living space that blends modern style with timeless charm.Step into the gorgeous eat-in kitchen, thoughtfully designed with:A large center island with ample seatingGleaming hardwood floorsVaulted

  Jane Panico Realty Promotions Inc

  24 3rd St, Middletown, NY 10940
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  /38

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  7 Avoncroft Ln, Middletown, NY 10940

  Discover the perfect balance of modern design and everyday comfort in this beautifully updated 3-bedroom, 3-bath corner townhouse, ideally located in one of Middletown’s most sought-after neighborhoods. Step inside and be welcomed by a bright, open-concept living space that feels both chic and inviting. The stylishly renovated kitchen is a true standout and it is complete with sleek countertops,

  Kewin Garabito eXp Realty

  7 Avoncroft Ln, Middletown, NY 10940
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  /40

  $725,000

  • 5 Beds
  • 3.5 Baths
  • 3,358 Sq Ft

  339 Kirbytown Rd, Middletown, NY 10940

  Nestled gracefully amidst more than thirteen acres of lush, undisturbed countryside, this remarkable colonial-style residence stands as a testament to elegance, comfort, and thoughtful practicality. A rare offering in today’s market, the property invites you to experience the best of both worlds: resplendent rural seclusion and immediate access to the conveniences of modern life. Conceived as a

  Annie Hansen Howard Hanna Rand Realty

  339 Kirbytown Rd, Middletown, NY 10940
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  /27

  $665,000

  • 4 Beds
  • 2.5 Baths
  • 2,078 Sq Ft

  2 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

  2 Beyers Rd, Middletown, NY 10941
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  /31

  $480,000

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

  295 Lybolt Rd, Middletown, NY 10941

  Spacious home with large yard on a quiet street - what more could you want? This beautiful contemporary home has had many upgrades over the last few years! The main level features an open kitchen, dining room and living room with partial wrap around deck - perfect for entertaining or just extended living space. Three large bedrooms and two full bathrooms complete the upper level. Downstairs

  Britanni Gaucher Keller Williams Realty

  295 Lybolt Rd, Middletown, NY 10941
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  /30

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,633 Sq Ft

  306 S Centerville Rd, Middletown, NY 10940

  Staycation in the Country – An Entertainer’s Dream! Discover the perfect blend of comfort, beauty, and functionality in this spacious 4-bedroom, 2.5-bath colonial nestled on a serene 1.6-acre lot in Minisink School District. With room to spread out, incredible indoor and outdoor spaces, this home is your year-round getaway—without ever leaving your driveway. The heart of the home is a show

  Johan Tola Keller Williams Realty Group

  306 S Centerville Rd, Middletown, NY 10940
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  /35

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft

  30 Wilson St, Middletown, NY 10940

  MAGAZINE READY!!!! HGTV CALLED, YOUR DREAM HOME JUST HIT THE MARKET! Absolutely Stunning Newly Renovated Raised Ranch in Middletown! Prepare to be impressed by this incredible, newly renovated raised ranch, ideally situated in a quiet and peaceful Middletown neighborhood. Thoughtfully redesigned with impeccable taste and high end, on-trend finishes, this home offers both style and substance in

  Frank Muccari Cronin & Company Real Estate

  30 Wilson St, Middletown, NY 10940
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  /32

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,994 Sq Ft

  43 Last Rd, Middletown, NY 10941

  Stunning large ranch zoned 215 - 1 Family Res w/Apt, many updates set up for extended family...two kitchens! Come see this beautifully maintained home features master bedroom with bath, walking closet, sunken living room, large open kitchen featuring dining area with sliding door to huge deck overlooking a fenced in level yard and shed. This cedar sided home has been meticulously maintained,

  Mary Jo Coleman Curasi Realty, Inc.

  43 Last Rd, Middletown, NY 10941
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  /17

  $309,900

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

  71 Jordan Ln, Middletown, NY 10940

  Welcome to this sought-after 2-bedroom, 2.5-bath townhouse in Mountainside Hills Condominium. The main level has hardwood floors, a kitchen dining area, a spacious living room with access to your private deck, a powder room, and an in-unit laundry room. Upstairs, you'll find the primary bedroom with an ensuite bathroom and walk-in closet, plus an additional bedroom and a full bath. The home also

  Jonathon Lee Keller Williams Hudson Valley

  71 Jordan Ln, Middletown, NY 10940
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  /32

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  1 Parkview Dr, Middletown, NY 10940

  Welcome to 1 Parkview Dr. in beautiful Presidential Park in Middletown, NY. Located on a corner lot, this expanded raised ranch shines. Gleaming hardwood floors and spacious room size are only some if it's great features. Eat in kitchen boasts an atrium that looks out to its lovely landscaped backyard. Spend time in this space and you'll feel like you're on vacation. Beautiful inground pool

  Marie Altieri Howard Hanna Rand Realty

  1 Parkview Dr, Middletown, NY 10940
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  /23

  $318,000

  • 2 Beds
  • 2.5 Baths
  • 1,831 Sq Ft

  12 Deer Ct Dr, Middletown, NY 10940

  Spacious Townhouse in a Prime Location!This well-located townhouse offers the perfect combination of space, comfort, and convenience. Ideal for commuters and anyone who enjoys being close to all the action. Just minutes from major highways, the home provides easy access to shopping centers, restaurants, and everyday essentials. For city bound travelers, getting around is simple. With nearby

  Beverly Huaman Howard Hanna Rand Realty

  12 Deer Ct Dr, Middletown, NY 10940
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  /37

  $510,000

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

  612 Shoddy Hollow Rd, Middletown, NY 10940

  Located on one of the most scenic and peaceful roads in Orange County, this spacious mother-daughter home offers exceptional privacy on a full acre of land, just minutes from Middletown shopping, dining, and NYC train access. Tucked away on a quiet road, the home provides a rare sense of seclusion while still being close to everyday conveniences. Inside, you’ll find two full kitchens with

  Kewin Garabito eXp Realty

  612 Shoddy Hollow Rd, Middletown, NY 10940
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  /24

  $475,000

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft

  51 Pine Ct, Middletown, NY 10941

  Beautiful Split Level home situated in one of the nicest areas of The Town Of Wallkill. This wonderful home offers an Open Airy Floor Plan, Gorgeous Harwood Floors on the First Floor, Brand New Designer Custom Kitchen with Quartz Countertops, Breakfast Bar, Stainless Steel Appliances, and Recessed Lighting. Large Sun Drenched Living Room with a Bay Window , spacious Dining Rm, Primary Bedroom

  John Biasi Howard Hanna Rand Realty

  51 Pine Ct, Middletown, NY 10941
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  /25

  $535,000

  • 1 Bed
  • 1 Bath
  • 1,088 Sq Ft

  727 Route 17m, Middletown, NY 10940

  Single Family home and mix-use property in prime location. Live on the property and have your business or use entirely for commercial purposes. This unique property offers incredible potential for various business or residential opportunities in a highly commercial area. Zoned Light Enterprise, this property provides flexibility for special uses, making it ideal for entrepreneurs,

  AnnaMarie O'Brien Curasi Realty, Inc.

  727 Route 17m, Middletown, NY 10940
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  /41

  $480,000

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

  4 Thistle Ln, Middletown, NY 10940

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

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
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  /25

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,536 Sq Ft

  208 Grahamtown Rd, Middletown, NY 10940

  PRICE REDUCTION! Welcome to 208 Grahamtown Rd, this charming estate spanning 54+ acres is a nature lover's paradise with abundance in wildlife and mature trees offering immense potential and breathtaking views. The home features beautiful hardwood floors, a wood burning stove, 4 over-sized bedrooms, 2 full bathrooms, 1st floor office/den, multiple outbuildings, and 1 car attached garage. Whether

  Steven Cabrera Resort Realty

  208 Grahamtown Rd, Middletown, NY 10940
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  /2

  $525,000

  • 5 Beds
  • 4 Baths
  • 3,140 Sq Ft

  7 Highland View Place, Middletown, NY 10940

  Welcome home to this beautifully maintained 5-bedroom, 4-bathroom raised ranch, ideally situated near the highly-rated Presidential Park Elementary School in Middletown, NY. Perfect for growing families or multi-generational living, this expansive home offers generous living space, natural light throughout, and thoughtful updates that make it move-in ready.Step inside to discover an open-concept

  Hilary Hemans-Mensah Keller Williams Realty

  7 Highland View Place, Middletown, NY 10940
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  /23

  $489,900

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  39 Brookline Ave, Middletown, NY 10940

  ***Charming 3 bedroom Home***Welcome to your dream home! Nestled in a quiet, family-friendly neighborhood, this beautifully updated 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, style, and convenience.Step inside to discover an open-concept living space filled with natural light, features a spacious dining area ideal for entertaining. The updated kitchen

  Andrea Rose Keller Williams Hudson Valley

  39 Brookline Ave, Middletown, NY 10940
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  /19

  $369,000

  • 4 Beds
  • 1.5 Baths
  • 1,272 Sq Ft

  35 Woods Place, Middletown, NY 10940

  This charming four-bedroom, one-bathroom home offers comfortable living space with a versatile layout. The layout provides plenty of room with flexible living spaces. Located in a welcoming Middletown neighborhood, you'll enjoy easy access to quality schools, convenient public transportation, and shopping options just minutes away. Whether you're starting fresh or looking to upgrade, this

  Kevin Sanabria eRealty Advisors, Inc

  35 Woods Place, Middletown, NY 10940
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  /16

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,584 Sq Ft

  35 Harrison St, Middletown, NY 10940

  Discover exceptional rental income potential with this spacious six-bedroom, two-bathroom multi-family property in the heart of Middletown. This investment opportunity offers generous living spaces. Located near Middletown Mini Market for daily essentials and close to Beattie Hill Park for outdoor recreation. The property sits conveniently near Middletown High School and public transportation via

  Kevin Sanabria eRealty Advisors, Inc

  35 Harrison St, Middletown, NY 10940
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  /29

  $329,000

  • 4 Beds
  • 2 Baths
  • 2,460 Sq Ft

  9 Albert St, Middletown, NY 10940

  3 FINISHED FLOORS! Welcome to this exceptional income generating multi-residential property! Ideally situated near Middletown’s restaurants, shopping malls, public transportation to NYC, major highways, and hospital facilities. This property offers unmatched convenience. Each apartment boasts two spacious bedrooms, an over-sized living room perfect for your largest furniture set, and an

  Robert 'Bob' & Frances 'Fran' Murray Howard Hanna Rand Realty

  9 Albert St, Middletown, NY 10940
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  /24

  $459,900

  • 1 Bed
  • 1 Bath
  • 2,400 Sq Ft

  652 New York 211 Unit 650, Middletown, NY 10940

  FOR SALE: Versatile Mixed-Use Building – Ideal for Owner-Operator | 650-652 Route 211 W, Middletown, NY 10940A rare opportunity to own a fully updated 2-unit standalone building in a prime high-visibility corner location at Route 211 West and California Drive in the Town of Wallkill.Property Overview:Total Building Size: Approx. 2,400 sq ftLot Size: Generous lot with

  Jonathon Lee Keller Williams Hudson Valley

  652 New York 211 Unit 650, Middletown, NY 10940
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  /30

  $399,999

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  5 Mills Ave, Middletown, NY 10940

  LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

  Richard Baxter Keller Williams Realty

  5 Mills Ave, Middletown, NY 10940
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  /5

  $399,900

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  7 Bartlett Dr, Middletown, NY 10941

  None

  Vital Desvarieux All Century Realty

  7 Bartlett Dr, Middletown, NY 10941
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  /27

  $430,000

  • 5 Beds
  • 2 Baths
  • 2,447 Sq Ft

  2 Mountain Ave, Middletown, NY 10940

  Step into this spacious and versatile raised-ranch style two-family home, perfectly located in the quiet neighborhood of Middletown!This well-maintained property offers a total of 5 bedrooms, 2 full bathrooms, and a bonus room ideal for a home office, playroom, gym, or guest space tailored to fit your lifestyle.The upper-level unit features a bright and open layout with a spacious living

  Jeaneth Pino-Bartchak RE/MAX Benchmark Realty Group

  2 Mountain Ave, Middletown, NY 10940
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  /50

  $645,000

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

  8 Green Ct, Middletown, NY 10940

  This well-maintained 3-level townhome sits within a luxury gated community of The Fairways, right next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, and restaurants. The home offers a 2-car garage, a finished basement with garage-level entry, and a practical layout designed for comfortable living. Hardwood floors span the main level, which features

  Jie Liu Keller Williams Hudson Valley

  8 Green Ct, Middletown, NY 10940
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  /27

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  105 Sheffield Dr, Middletown, NY 10940

  Town of Wallkill Townhouse - Low Taxes - Great InvestmentThis charming 3-bedroom, 1.5-bath home is your perfect mix of space, location, and value. Nestled on a generous lot with a large yard, there's plenty of room for play, gardening, or entertaining under the stars. Step out from your primary bedroom onto a balcony—the ideal spot for morning coffee or winding down with a book while

  Cindy-Lee Dorcely Keller Williams Hudson Valley

  105 Sheffield Dr, Middletown, NY 10940
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  /21

  $519,000

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

  6 Broad St, Middletown, NY 10940

  Great two family duplex located in the City of Middletown. It's conveniently located walking distance to Touro College , I84 and I86, and also close to local shops and restaurants . Located approximately 70 miles North of New York City this property has a strong income potential with long term upside . At one time this was a triplex and is now a legal duplex. The 2nd floor apartment has 2

  Neal Kolze Curasi Realty, Inc.

  6 Broad St, Middletown, NY 10940

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