Middletown, NY Homes for Sale with Acreage

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  /46

  $574,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,432 Sq Ft

  180 Mt Orange Rd, Middletown, NY 10940

  The primary suite alone tells you what kind of home this is. A vaulted cathedral ceiling overhead, a spa-style bath built around a deep soaking tub, and proportions that hold a quiet hour at the end of a long day the way a private retreat is supposed to. It is the kind of room that quietly redefines what you expect a ranch to feel like. By the time the water is running, the day has already

  

  Brian Caplicki

  KW Hudson Valley United

  180 Mt Orange Rd, Middletown, NY 10940
• Explore Middletown

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  /50

  $599,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,080 Sq Ft

  179 Reservoir Rd, Middletown, NY 10940

  Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full

  

  Dulce M Ferrera

  KW Hudson Valley United

  179 Reservoir Rd, Middletown, NY 10940
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  /50

  $895,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  411 Mt Joy Rd, Middletown, NY 10941

  Space, privacy, and thoughtful design come together at this well-maintained 4-bedroom, 2.5-bath Colonial, built in 2005, offers 3,296 sq ft of living space on 11.7 private acres—giving you room to breathe while staying conveniently close to everything Middletown has to offer.Step inside and you'll immediately notice the 9-foot ceilings that elevate every room with an airy, open feel. The main

  

  Donna Reese

  KW Hudson Valley United

  411 Mt Joy Rd, Middletown, NY 10941
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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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  /44

  $435,000

  $40K PRICE DROP

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

  57 Boorman Rd, Middletown, NY 10940

  Renovated Dutch Colonial on 5+ private acres in the Minisink school district, just minutes from Middletown!Updated kitchen features quartz countertops, ceramic tile flooring, subway tile backsplash, new cabinetry, and stainless steel appliances. First floor offers a full bath, spacious living room, dining room, and a cozy wood stove for supplemental heat. Upstairs includes 3 bedrooms and a

  

  Lynelle Alessi

  KW Hudson Valley United

  57 Boorman Rd, Middletown, NY 10940
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  /9

  $499,000

  • Land
  • 39.9 Acres
  • $12,506 per Acre

  700 van Burenville Rd, Middletown, NY 10940

  Discover your own 40-acre sanctuary in the Hudson Valley, a landscape of rolling meadows, a peaceful pond that set the stage for a truly picturesque retreat. Perfectly suited for equestrian pursuits, cattle, or recreational hunting.

  

  Joao Rodrigues

  Preferred Properties Real Esta

  700 van Burenville Rd, Middletown, NY 10940
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  /25

  $359,900

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  252 Toad Pasture Rd, Middletown, NY 10940

  Welcome home to this beautifully maintained ranch nestled on 2.2 private acres in the highly sought-after Minisink School District. Offering the perfect blend of comfort and country living, this home features 3 spacious bedrooms, 1 full bathroom, hardwood floors freshly restored. This home has a walk-out basement with endless possibilities for additional living space, a workshop, or storage.

  

  Joao Rodrigues

  Preferred Properties Real Esta

  252 Toad Pasture Rd, Middletown, NY 10940
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  /21

  $119,000

  • Land
  • 4.27 Acres
  • $27,869 per Acre

  0 Hog Mountain Cir, Middletown, NY 12430

  This is the property with a view you have been looking for. 4.27 acres of cleared, ready to build land in the Catskill Mountains just two hours from the George Washington Bridge. Whether it is a weekend retreat you have in mind or a forever home, the view is unmatched and will bring you the peace and serenity the Catskills have to offer. This property is only 10 minutes from Belleayre Ski

  

  Terence Lynch

  Century 21 New West Properties

  0 Hog Mountain Cir, Middletown, NY 12430
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  /41

  $699,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  TBD Kirbytown Rd, Middletown, NY 10940

  Welcome to your brand-new home, located on a 2.4 acre wooded lot in the Minisink Valley school district. The Reese model colonial was thoughtfully designed, offering 4 bedrooms and 2.5 baths with plenty of space to grow and make memories. On the first floor, you’ll find a bright and inviting living room with beautiful hardwood floors and a cozy fireplace—perfect for movie nights or gathering with

  

  Chris Ogden

  Realty Promotions Inc

  TBD Kirbytown Rd, Middletown, NY 10940
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  /49

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,253 Sq Ft

  1652 Thompson Hollow Rd, Middletown, NY 12459

  Set in the heart of the picturesque New Kingston Valley, this enchanting two-bedroom, two-bath cottage is privately situated on 20 remarkable acres, offering an increasingly rare combination of complete seclusion, stunning natural beauty, and endless potential. Surrounded by forest and breathtaking mountain views, the property is a sanctuary where the sounds of a year-round stream and the beauty

  Jeffrey Ashton Listing by Coldwell Banker Timberland Properties

  

  1652 Thompson Hollow Rd, Middletown, NY 12459
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  /15

  $259,999

  • 4 Beds
  • 1 Bath
  • 1,140 Sq Ft

  29 Parsons Ln, Middletown, NY 10940

  Endless Potential - Discover the possibilities at 29 Parsons Lane — a private country property offering space, privacy, and opportunity on approximately 6.4 acres. Offering an additional 4.6 acres for a total of 11 acres. This single-family ranch-style home features 4 bedrooms (currently lives as a 2 bedroom & a laundry room), 1 full bathroom, and approximately 1,140 square feet of living space.

  Camelia Pena-Rivera RE/MAX Distinguished Hms.&Prop

  29 Parsons Ln, Middletown, NY 10940
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  /38

  $549,900

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft

  181 Stony Ford Rd, Middletown, NY 10941

  Set on 6.7 private acres in Middletown, this 3-bedroom, 2-bath, 1,694 sq ft home offers the perfect blend of comfort and outdoor living. Enjoy your own private retreat featuring quad trails, river access ideal for fishing, and abundant wildlife for hunting or nature watching. The outdoor space is designed for entertaining and relaxation with a fire pit area and a spacious two-tier deck complete

  Rana Ali eXp Realty

  181 Stony Ford Rd, Middletown, NY 10941
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  /50

  $2,250,000

  $445K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 20,730 Sq Ft

  285 Hill Rd, Middletown, NY 10940

  For your consideration is 285 Hill Road, a premier equine boarding, training and showing facility formerly known as Hilltop Equestrian Center and Seven Meadows Farm. Designed for function and beauty, it's a welcoming destination for both clients and guests. Numerous shows and clinics have been successfully hosted here over the years. The property includes a professional indoor arena complex, 2

  Michelle Genatempo Howard Hanna Rand Realty

  285 Hill Rd, Middletown, NY 10940
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  /4

  $1,650,000

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

  32 Gibbs Ct, Middletown, NY 10940

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

  Peter Janis Berkshire Hathaway HS NE Prop.

  32 Gibbs Ct, Middletown, NY 10940
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  /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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  /36

  $599,900

  • 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 life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and

  Michelle Gruberger Real Estate Circuit Inc

  669 Mountain Rd, Middletown, NY 10940
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  /48

  $849,900

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

  21 Lincoln Terrace Unit 19, Middletown, NY 10940

  A rare opportunity to own an architectural masterpiece designed and personally occupied by renowned local architect Dennis Jurow. Privately nestled on a beautifully wooded one-acre setting in Middletown, this iconic mid-century modern residence offers over 4,000 square feet of thoughtfully curated living space where architecture, art, and nature exist in perfect harmony. From the moment you

  Patricia Sassi RE/MAX Benchmark Realty Group

  21 Lincoln Terrace Unit 19, Middletown, NY 10940
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  /30

  $844,000

  $5K 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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  /15

  $95,000

  $10K PRICE DROP

  • Land
  • 5.1 Acres
  • $18,627 per Acre

  Lot 11 Meadow Brook Dr, Middletown, NY 12455

  Tucked away in the pastoral rolling hills, just a short drive from down town Margaretville, this very special 5 acre parcel is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views and rolling open meadows backed by magical woods to explore. With several possible building sites this parcels offers what most are looking for. Easy access, and close to

  Rosalie Glauser Listing by Frank Lumia Real Estate Plus!, LLC

  

  Lot 11 Meadow Brook Dr, Middletown, NY 12455
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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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  /49

  $589,900

  • 3 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  311 New Vernon Rd, Middletown, NY 10940

  Nestled well off the road amid mature landscaping and expansive lawn, this custom Colonial offers a rare combination of privacy, space, and pride of ownership. Built and meticulously maintained by its original owners, the home reflects years of thoughtful updates and careful stewardship. Inside, hardwood floors extend throughout the home, creating warmth and continuity from room to room. Custom

  Patricia Sassi RE/MAX Benchmark Realty Group

  311 New Vernon Rd, 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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  /17

  $629,000

  • 4 Beds
  • 3 Baths
  • 2,600 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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  /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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  /3

  $350,000

  • Land
  • 1.42 Acres
  • $245,752 per Acre

  65 James P Kelly Way, Middletown, NY 10940

  Great location for a business. C-3 Zoning allows for any business, commercial or residential mix use. 262 feet frontage. Annual Average Daily Traffic (AADT) for 2023 is 10,569. There was a pre-approved building plan for a doctor's office building. The land is in the city of Middletown. The city will provide water and sewer. C-3 allow for 6 story mix-use business and residential building with the

  Jonathon Lee KW Hudson Valley United

  65 James P Kelly Way, Middletown, NY 10940
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  /35

  $200,000

  • Land
  • 51.7 Acres
  • $3,868 per Acre

  Tbd Hall Rd, Middletown, NY 12455

  Hike up to see this spectacular 51.7 acres of prime Real Estate. This property has everything except a road which will have to be built. A previous right of way was moved years ago due to flooding. The walk in does require waterproof boots and a lot of good energy. The parcel has every kind of topography you could imagine. Mouch of it is a large lightly wooded plateau. The southeastern boundary

  William Chris St. John Win Morrison Realty

  Tbd Hall Rd, Middletown, NY 12455
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  /38

  $699,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  168 Pine Grove Rd, Middletown, NY 10940

  Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the

  Leeshai Lemish Panorama Realty

  168 Pine Grove Rd, Middletown, NY 10940
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  /5

  $300,000

  • Land
  • 6 Acres
  • $50,000 per Acre

  0 Mount Hope Rd, Middletown, NY

  Looking to build? Land available in prime location. Situated directly between Middletown and Town of Mount Hope with easy access to all major roadways. Zoned for residential and agriculture. Buyer/builder to subdivide 5-6 acres from this 37+ acre parcel as agreeable to seller and proposed in contract. Flat, open, cleared land may be suitable for 1-3 building lots. Land to purchase provides

  Amanda Ferrantello Hudson Valley Griffith

  0 Mount Hope Rd, Middletown, NY
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  /11

  $1,475,000

  • Land
  • 92.31 Acres
  • $15,979 per Acre

  0 Red Kill Rd, Middletown, NY 12430

  92.30 acres for sale in the Catskill Mountains New York.This secluded and versatile property is now for sale for the first time since 1996. Set above the charming Village of Fleischmanns and just 0.6 miles from Main Street, this 92-acre parcel offers the privacy of a wilderness retreat with the convenience of a village doorstep.-Interior roadways.-A large man-made spring-fed pond and

  peter neumann Listing by Keller Williams Upstate NY Properties

  

  0 Red Kill Rd, Middletown, NY 12430
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  /44

  $799,999

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  TBD Brook Rd, Middletown, NY 10941

  New Construction LUXURY HOME in Valley Central Schools outside of SCOTCHTOWN! "Choose Your Finishes" on this Stunning 3,000 sq. ft. modern Colonial privately set atop a scenic 5-acre wooded lot offering privacy and natural beauty. Conveniently located 5-10 minutes to Middletown, Pine Bush, and Montgomery. The main level features a spacious open-concept floor plan with 9-foot ceilings, hardwood

  Philip Barnao eXp Realty

  TBD Brook Rd, Middletown, NY 10941
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  /43

  $745,000

  $670K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,395 Sq Ft

  903 Rd, Middletown, NY 12421

  Rare Catskills Investment Retreat — Pool, Views & Proven Short-Term Rental Income. One of the few properties in the Catskills with a private pool and the income to match, this turnkey 4-bedroom, 2-bath mountain retreat on 5+ acres offers a competitive edge that most area listings simply cannot. The private pool extends peak demand well beyond the winter ski season, attracting premium summer

  Ashley O'Malley Listing by Jewett and Jewett LLC

  

  903 Rd, Middletown, NY 12421
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  /13

  $45,000

  • Land
  • 1.4 Acres
  • $32,143 per Acre

  Pocatello Road Pocatello Rd, Middletown, NY 10940

  Country Living. yet just ten minutes to Middletown NY. area of nice homes. over 249 feet county road frontage. no close neighbors private. Rt 17 Rt 24 Rt 35 all close by. for easy commute to work. Orange County is a leader in population and company relocating more jobs Avalible. five minutes to Maple Hill Elementary School zoned R2 with no water and no sewer one would need 3 Acres so this

  John Melchior Howard Hanna Rand Realty

  Pocatello Road Pocatello Rd, Middletown, NY 10940
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  /41

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,906 Sq Ft

  512 County Route 49, Middletown, NY 10940

  Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtaking views, exceptional updates, and true move-in-ready condition. From the moment you enter the impressive two-story foyer, you'll appreciate the bright, open-concept design and abundance of natural light streaming through every window. The spacious main living areas are perfect for both everyday living and

  Jonathon Lee KW Hudson Valley United

  512 County Route 49, Middletown, NY 10940
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  /10

  $299,999

  • Land
  • 27.2 Acres
  • $11,029 per Acre

  328 Bloomingburg Rd, Middletown, NY 10940

  Fully Available!! Vacant Property directly across from Fair Oaks Drive in Movie theater and a gas station with plenty of road frontage!! Minutes to RT17. 27.2 ACRES!!! Electric on road at the front of the property! Possible small farm, Big enough for horses, growing crops, family compound. R2 Zoning.The owner is currently using the property to grow crops and has an Agricultural tax exemption.

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
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  /8

  $90,000

  • Land
  • 5.37 Acres
  • $16,760 per Acre

  0 Basil Todd Rd, Middletown, NY 12430

  Over five acres of meadow, woods and Mountain View’s to build your dream home. Minutes to Belleayre to enjoy the outdoors. With inventory down, there isn’t any need to settle. We have access to local builders, engineers and contractors to help guide you through the process. Looking for more?? There is an adjacent five acre parcel also available. Seller may be willing to finance too.

  Heather Martin United RE Hudson Valley Edge

  0 Basil Todd Rd, Middletown, NY 12430
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  /16

  $599,000

  $96K PRICE DROP

  • Land
  • 5.07 Acres
  • $118,146 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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  /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
• 

  

  /21

  $560,000

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

  77 Upper Rd, Middletown, NY 10940

  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 finished basement with 3 additional rooms for storage or home office, and it also has 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
• 

  

  /6

  $799,000

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

  1 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

  1 Winters Ln, Middletown, NY 10940
• 

  

  /24

  $555,000

  $24K PRICE DROP

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

  29 Murray Rd, Middletown, NY 10940

  Set on 3- private acres, this spacious residence offers refined living with a functional and versatile layout in a quiet location. This home features 5-bedrooms and 3- full bathrooms, providing ample space for a variety of needs. This well-maintained residence features a versatile multi-level layout with multiple living spaces, providing a wide range of use options. The main level includes a

  Regina Lombardo KW Hudson Valley United

  29 Murray Rd, Middletown, NY 10940

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