Middletown, NY Homes for Sale

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  /42

  $639,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  481 Dosen Rd, Middletown, NY 10940

  ABSOLUTELY GORGEOUS!!! MUST SEE!! QUALITY BUILT WITH BRAND NEW ADDITION AND BRAND NEW DETACHED POLE BARN!!! OVER 7 ACRES !!! 481 Dosen Road offers a rare combination of quality construction, privacy, and usable space, set on 7.4 peaceful acres. This custom-built Lok-N-Logs log home was thoughtfully designed to blend the character of a true log cabin with the comforts needed for everyday living.

  Frank Muccari Cronin & Company Real Estate

  481 Dosen Rd, Middletown, NY 10940
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  /33

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft

  718 Mountain Rd, Middletown, NY 10940

  Welcome to a timeless 1821 farmhouse set on more than five private acres in the heart of Sullivan County, where historic character meets effortless modern living. Surrounded by mature gardens, handcrafted stone walls, and sweeping mountain views, this is Upstate living at its finest. Offering more than 2,800 square feet, the home features four bedrooms, three and a half bathrooms, including two

  Davina Thomasula Four Seasons Sotheby's Int'l-K

  718 Mountain Rd, Middletown, NY 10940
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  /35

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  153 Ridgewood Ave Unit 155, Middletown, NY 10940

  Welcome to 153 Ridgewood Avenue, a beautifully maintained 2021 built ranch offering the ease and comfort of modern single level living. Vaulted ceilings, an open concept layout, stylish finishes, and abundant natural light create a warm and inviting feel from the moment you enter. With more than 1,500 square feet, the home features a spacious kitchen with stone countertops, generous prep space,

  Isaiah Lopez KW Hudson Valley United

  153 Ridgewood Ave Unit 155, Middletown, NY 10940
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  /2

  $424,999

  Coming Soon

  • 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 space,

  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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  /36

  $479,000

  $6K 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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  /46

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  18 Hickory Place, Middletown, NY 10941

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath bi-level home, built in 2010 and offering 2,225 square feet of comfortable living space. Designed with an open-concept layout, this impressive residence features a well-appointed kitchen with granite countertops, abundant cabinetry, and a seamless flow into the dining and living areas—ideal for both everyday living and

  Anita S. Cristiano HomeSmart Homes & Estates

  18 Hickory Place, Middletown, NY 10941
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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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  /34

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  158 Cottage St, Middletown, NY 10940

  Step inside this classic 3-bedroom, 2-bath Colonial and imagine the possibilities. Offering approximately 1,610 square feet, the home features a traditional layout with a living room, formal dining room, spacious kitchen, and a flexible first-floor bonus room that can serve as a den, home office, or recreation space. A dedicated laundry area adds everyday convenience, while the covered front

  Derek Greene Greene Realty Group

  158 Cottage St, Middletown, NY 10940
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  /32

  $579,000

  $20K PRICE DROP

  • 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 is

  Marie Altieri Howard Hanna Rand Realty

  1 Parkview Dr, Middletown, NY 10940
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  /36

  $585,000

  $15K PRICE DROP

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

  669 Mountain Rd, Middletown, NY 10940

  Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city lifeA grand foyer opens to a bright, airy layout with high ceilings, large windows,

  Michelle Gruberger Real Estate Circuit Inc

  669 Mountain Rd, Middletown, NY 10940
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  /50

  $498,000

  • 4 Beds
  • 3 Baths
  • 1,716 Sq Ft

  9 Ashland Ave Unit 11, Middletown, NY 10940

  Welcome to this well-maintained 4-bedroom, 3-full-bath home offering a functional layout and comfortable living spaces. The welcoming entry features an elegant chandelier and a large arched window that fills the home with natural light. The main level offers hardwood floors, vaulted ceilings, recessed lighting, a comfortable living room, and a separate dining area overlooking the backyard. The

  Jie Liu KW Hudson Valley United

  9 Ashland Ave Unit 11, Middletown, NY 10940
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  /30

  $839,000

  $10K 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 District This 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 throughout.

  Linda VanDeWeert BHG Real Estate Green Team

  238 S Centerville Rd, Middletown, NY 10940
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  /23

  $134,999

  Open Sat 12PM - 2PM $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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  /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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  /27

  $245,000

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

  49 Jimal Dr, Middletown, NY 10940

  Welcome home to this beautifully maintained 2-bedroom, 1.5-bath condo offering the perfect blend of comfort and convenience! Featuring gorgeous wood flooring on the first level, new carpeting in the second level with spacious primary bedroom, walk-in closets in both bedrooms, updated bathrooms with beautiful vanities and tiles. Enjoy a functional layout in a location that's hard to beat—just

  Anita S. Cristiano HomeSmart Homes & Estates

  49 Jimal Dr, Middletown, NY 10940
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  /36

  $379,000

  • 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

  $899,000

  • 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

  Open Sat 12PM - 2PM

  • 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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  /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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  /33

  $635,000

  $40K 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
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  /13

  $275,000

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

  11 Jordan Ln, Middletown, NY 10940

  Welcome to 11 Jordan Lane, Middletown, NY. This 2-bedroom, 2-bathroom condo offers a practical floor plan and a convenient location close to shopping, dining, schools, healthcare facilities, and major commuter routes.With strong potential and a desirable location, the property presents an excellent opportunity for investors seeking immediate rental income or buyers looking to add value

  Richu Saj Kerala Realty, LLC

  11 Jordan Ln, Middletown, NY 10940
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  /50

  $899,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,894 Sq Ft

  114 Last Rd, Middletown, NY 10941

  Distinctive 11-Acre Country Retreat - More than a home, this property delivers a lifestyle defined by space, privacy, and ease. Set across two parcels totaling 11.1 acres, this distinctive Cape Cod combines thoughtful design and easy, everyday living. From the expansive covered front porch to the farmhouse-style entry, the home immediately feels airy and inviting. Inside, the home balances warmth

  Michelle Genatempo Howard Hanna Rand Realty

  114 Last Rd, Middletown, NY 10941
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  /32

  $740,000

  • 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 is

  Cecilia Lewis Century 21 Elite Realty

  210 Howells Turnpike, Middletown, NY 10940
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  /17

  $629,000

  • 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
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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 garage

  Doreen Crowther Howard Hanna Rand Realty

  58 Cobblestone Ln, Middletown, NY 10940
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  /35

  $415,000

  • 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 the moment

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
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  /22

  $399,000

  Open Sun 1PM - 3PM $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
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  /18

  $55,000

  • Land
  • 5.26 Acres
  • $10,456 per Acre

  0 Joe Todd Rd Unit R1680388, Middletown, NY 10940

  Near the end of a quiet town-maintained dead-end road, you’ll find this ideal building lot in the town of Fleischmanns. This parcel has a mix of evergreens, deciduous trees, open clearings, and a seasonal stream, most of which is on level terrain ideal for a driveway and building site. Enjoy the peace and tranquility of a wooded sanctuary just minutes up the hill from the happening main street of

  Peter Kleeman Listing by Jewett and Jewett LLC

  

  0 Joe Todd Rd Unit R1680388, Middletown, NY 10940
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  /12

  $65,000

  $10K PRICE INCREASE

  • Land
  • 7,875 Sq Ft
  • $359,513 per Acre

  538 E Main St, Middletown, NY 10940

  Residential land avaiable on East Main Street, close to the Crystal Medical center, close to NYS HWY 17, close to the Galleria Mall, close to the new Resorts and Casino about 30 milles away, close to the Poconos, come built you new home here.Attached to this listing are documents from the building dept to help you, Make sure to see the documents attached.

  Frank Rivera Hudson Valley Home Connection

  538 E Main St, Middletown, NY 10940
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  /50

  $310,000

  • 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
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  /58

  $575,000

  • 12 Beds
  • 10 Baths
  • 5,004 Sq Ft

  5 Wawayanda Place, Middletown, NY 10940

  CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

  Jamie Sittner Find Advisors

  5 Wawayanda Place, Middletown, NY 10940
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  /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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  /49

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,912 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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  /3

  $179,900

  • Land
  • 3.15 Acres
  • $57,111 per Acre

  182 Pocatello Rd, Middletown, NY 10940

  Build your dream home on this fully engineered and Town of Wallkill-approved 3+ acre parcel, located within the desirable Middletown School District. This ready-to-build lot offers the perfect combination of privacy and convenience, with a peaceful setting while remaining just minutes from major highways, shopping, dining, and everyday amenities. A rare opportunity to own a fully approved

  Jonathon Lee KW Hudson Valley United

  182 Pocatello Rd, Middletown, NY 10940
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  /49

  $370,000

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

  15 Old Anvil Ln, Middletown, NY 10940

  Welcome to 15 Old Anvil Ln, Middletown, a lovingly cared for end unit townhouse in the sought after "The Meadows" community. This unit has been lived in and cared for by the same owners for approximately 40 years. The owner is a builder so he has not skipped on his own improvements and care. The unit offers 3 bedrooms and 2.5 bathrooms, a kitchen and formal dining room with a slider to a

  Valeria Rios KW Hudson Valley United

  15 Old Anvil Ln, Middletown, NY 10940
• 

  

  /13

  $85,000

  • Land
  • 5.1 Acres
  • $16,667 per Acre

  Lot 11 Meadowbrook Dr, Middletown, NY 12455

  Just a short drive from down town Margaretville, tucked away in the pastoral rolling hills, sits this very special 5 acre parcel with lovely open views. What this parcel has to offer is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views, rolling open meadows backed by magical woods to explore, surrounded by the sounds of nature. With several

  Rosalie Glauser Frank Lumia Real Estate Plus

  Lot 11 Meadowbrook Dr, Middletown, NY 12455
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  /33

  $400,000

  • 4 Beds
  • 2 Baths
  • 2,241 Sq Ft

  34 Spring St, Middletown, NY 10940

  Welcome to 34 Spring Street, a spacious multi-family property offering a total of 4 bedrooms and 2 full bathrooms. This versatile home presents an excellent opportunity for investors, owner-occupants, or buyers seeking a flexible living arrangement for extended family. Live in one unit while renting the other, or add both residences to your investment portfolio for potential rental income. Each

  Kerri Stretch Howard Hanna Rand Realty

  34 Spring St, Middletown, NY 10940
• 

  

  /44

  $339,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,830 Sq Ft

  122 Castle High Rd, Middletown, NY 10940

  Set on approximately 2 acres, this 1920’s unique multi-level home provides plenty of room to enjoy the outdoors. A standout feature is the property's unique location, offering road frontage on two separate roads, Castle High Road and Eatontown Road and both Agricultural and Residential zoning. Whether you've dreamed of creating your own homestead, raising chickens or other livestock, planting

  Denise Clancy Curasi Realty, Inc.

  122 Castle High Rd, Middletown, NY 10940

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