Middletown, NY Homes for Sale with Acreage

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  /32

  $1,799,000

  • 5 Beds
  • 9 Baths
  • 7,794 Sq Ft

  3 Bristol Dr, Middletown, NY 10941

  Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 square feet of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 8.55-bathroom residence features expansive, light-filled interiors and estate-scale proportions ideal for both entertaining and everyday

  

  Mohamed Elgoarany

  All American Realty Management

  (329) 215-0309

  3 Bristol Dr, Middletown, NY 10941
• Explore Middletown

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  /50

  $829,000

  • 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

  (329) 208-2931

  3 Kings Dr, Middletown, NY 10941
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  /41

  $699,900

  • 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

  (329) 209-9962

  TBD Kirbytown Rd, Middletown, NY 10940
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  /50

  $620,000

  • 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

  Keller Williams Hudson Valley

  (329) 207-0914

  179 Reservoir Rd, Middletown, NY 10940
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  /44

  $475,000

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

  57 Boorman Rd, Middletown, NY 10940

  This nicely renovated Dutch Colonial is located on 5+ acres surrounded by mature trees just minutes from Middletown and in Minisink schools. Renovated kitchen has Quartz counters, ceramic tile floor, subway tile back splash, new cabinets and stainless appliances. Wood stove for additional source of heat, first floor full bath and livingroom, diningroom with wood floors rounds out the first floor.

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 212-0455

  57 Boorman Rd, Middletown, NY 10940
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  /49

  $749,000

  • 5 Beds
  • 3 Baths
  • 2,828 Sq Ft

  482 Scotchtown Ave, Middletown, NY 10941

  Classic 1863 Farmhouse in Mint Condition – Riverfront Property in Goshen School District. Step into timeless elegance with this beautifully restored 1863 farmhouse, set on 10 picturesque acres in the highly desirable Goshen School District. This 5-bedroom, 3-bath home offers the perfect blend of historic charm and modern convenience, featuring original hardwood floors, a brick fireplace,

  Pamela Henning Keller Williams Hudson Valley

  482 Scotchtown Ave, Middletown, NY 10941
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  /50

  $2,695,000

  • 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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  /34

  $640,000 Pre-Foreclosure

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  235 Maples Rd, Middletown, NY 10940

  This well-maintained spacious Colonial Home is ideally situated on a 2 Acre Lot in the Town of Wallkill Countryside. Lovely Kitchen W/Breakfast nook overlooks a Large Level Backyard & Private Rear Entertainment Deck. An entry foyer greets you when you arrive at this home, that features a Formal Dining Room, Living Room, Family Room, Powder Room, & mud Room/Laundry to complete the 1st Floor. The

  Shernette Hall VYLLA Home

  235 Maples 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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  /24

  $439,900 Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,905 Sq Ft

  566 County Route 49, Middletown, NY 10940

  For Sale – 566 County Route 46, Middletown, NY 10940 Welcome to this spacious 3-bedroom, 4-bath colonial-style condo located in a quiet country setting in Middletown. This home is the largest unit in the 4-unit condo complex, offering generous living space and a comfortable layout. The first floor features a bright and inviting large living room with sliding doors leading to a rear deck, perfect

  Jonathon Lee Keller Williams Hudson Valley

  566 County Route 49, Middletown, NY 10940
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  /24

  $579,990

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  30 Daly Rd, Middletown, NY 10940

  New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft

  Jonathon Lee Keller Williams Hudson Valley

  30 Daly Rd, Middletown, NY 10940
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  /35

  $999,999

  • 3 Beds
  • 2.5 Baths
  • 3,315 Sq Ft

  535 County Route 22, Middletown, NY 10940

  Looking to Enjoy Life? Experience 535 Ct Rt 22 in the Minisink School District. Unique Handcrafted Home that is surrounded by Nature and Privacy. This Amazing property is backed up to a NYS Protected Conservation in addition to the existing 21 1/2 Acres of Privacy. Gorgeous Breath-taking views can be seen from almost every window of the home. Enjoy the Dramatic, Sundrenched, Eye Popping Open

  John Biasi Howard Hanna Rand Realty

  535 County Route 22, Middletown, NY 10940
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  /26

  $599,990

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

  2078 Route 6, Middletown, NY 10940

  Unique bi-level house with spectacular 9-foot ceilings , from the moment you step inside , the grand entryway and soaring ceilings set the tone , complemented by abundant natural light and stunning views, just off entry the heart of the home awaits- beautiful granite countertop in kitchen with stainless appliances , hardwood floors flows seamlessly through the cozy living room anchored by a

  Steve Ruiz-Esparza eRealty Advisors, Inc

  2078 Route 6, Middletown, NY 10940
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  /35

  $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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  /3

  $69,000

  • Land
  • 6.5 Acres
  • $10,615 per Acre

  0 County Road 49, Middletown, NY 10940

  6 Acres of Raw Land! Prime Middletown parcel with potential for residential development or investment. Quiet lot with easy access to main roads and nearby amenities. Drive-by 409 County Route 49Middletown, NY 10940 to see property. this address if the neighboring lot

  Bryant Moran YourHomeSold Guaranteed Realty

  0 County Road 49, Middletown, NY 10940
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  /28

  $849,000

  • 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

  $99,000

  • Land
  • 5.1 Acres
  • $19,412 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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  /5

  $495,000

  • Land
  • 3.8 Acres
  • $130,297 per Acre

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940

  Attention Builders and Developers: Presenting a rare, fully-approved 3-lot subdivision on Silverlake Scotchtown Road in the desirable Town of Wallkill, ready for the construction of three new two-family homes. Each lot is designed to accomodate a 32x80 structure which is large enough for each unit to include 3 bedrooms, 2 baths and a 1 car garage. Seller does not have architectural plans so

  Jason McGovern Keller Williams Hudson Valley

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940
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  /27

  $574,999

  • 4 Beds
  • 2.5 Baths
  • 2,255 Sq Ft

  53 Daly Rd, Middletown, NY 10940

  Say hello to the best of both worlds! A peaceful residence located in Middletown, NY! This beautifully designed residence offers a seamless flow for modern living. The heart of the home is an expansive kitchen, connected to a generous dining area—ideal for hosting dinner parties or holiday gatherings. Step outside through the sliding doors to your private oasis: an extra large refinished deck

  Michelle Pepe Curasi Realty, Inc.

  53 Daly Rd, Middletown, NY 10940
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  /17

  $259,999

  • 4 Beds
  • 1 Bath
  • 1,140 Sq Ft

  29 Parsons Ln, Middletown, NY 10940

  Fantastic opportunity at 29 Parsons! This property is being offered as a cornerstone of a 3-parcel investment package. While individually the 4 bedroom home on 6+ acres of land the complete 3-property bundle—including an additional 5+ acres of land—is available for a package. The home is a 4 bedroom & lives as a 2 large bedrooms and a laundry room. Perfect for developers or those looking for a

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

  29 Parsons Ln, Middletown, NY 10940
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  /37

  $159,000

  • Land
  • 14.61 Acres
  • $10,883 per Acre

  Lots 2 / 3 Quail Ridge Rd, Middletown, NY 12455

  Two scenic parcels totaling 14.61 acres with sweeping mountain views offer the perfect canvas for an inspiring Catskills retreat. Ideally situated between the charming towns of Margaretville and Roxbury, this location provides convenient access to grocery stores, art galleries, cafés, and quaint local shops—while still feeling worlds away from the hectic life of more developed areas. An excellent

  James Karpowicz Coldwell Banker Timberland Pro

  Lots 2 / 3 Quail Ridge Rd, Middletown, NY 12455
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  /36

  $509,999

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

  612 Shoddy Hollow Rd, Middletown, NY 10940

  Welcome to 612 Shoddy Hollow Road, a beautifully maintained 4 bedroom, 3 full bathroom raised ranch tucked away in sought after Mount Hope. This inviting home offers the perfect blend of comfort, space, and functionality. Upon entry, you’re greeted by a bright, open concept living room that seamlessly flows to a spacious deck overlooking the property ideal for relaxing or entertaining. The cozy

  Alexander Fayn Prominent Properties Sotheby's

  612 Shoddy Hollow Rd, Middletown, NY 10940
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  /2

  $40,000

  • 550 Sq Ft

  40 Ivory Ln, Middletown, NY 10940

  SPACIOUS LAND AVAILABLE FOR SALE IN DESIRABLE AREA OF MIDDLETOWN NY

  ALISON NIXON eXp Realty

  40 Ivory Ln, Middletown, NY 10940
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  /12

  $269,000

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft

  11 Philcox Rd, Middletown, NY 10940

  Rare opportunity to own two homes next door to each other in the Pine Bush School District. Single family home 2 bed, 1 bath, recently updated. Quiet road with only two homes, both originally owned by the same family, offering privacy and flexibility. Conveniently located near shopping, dining, train service, Resorts World Catskills, Kartrite Waterpark, and Bethel Woods Center for the Arts. Easy

  Joseph Rubeo Keller Williams Hudson Valley

  11 Philcox Rd, 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 Keller Williams Hudson Valley

  65 James P Kelly Way, 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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  /43

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  50 Brola Rd, Middletown, NY 10940

  Bring your vision to life at 50 Brola Road. Perfectly situated in the picturesque countryside within the Minisink school district you will find a tremendous opportunity. The home itself offers a spacious and open floor plan along with ample parking, fenced rear yard, plenty of storage space and room for expansion. There is a building lot to the right of the property that can be purchased for a

  Nicholas Carbone HomeSmart Homes & Estates

  50 Brola Rd, Middletown, NY 10940
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  /43

  $765,000

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

  903 Rd, Middletown, NY 12421

  Unlock the door to your newly furnished & thoughtfully renovated 4 bedroom, 2 full bath Catskill Mountain Ski Retreat! The property delivers both Upstate sanctuary & investment making it a remarkably special experience. Overlooking breathtaking Denver Vega Valley, this 5 acre property captures sweeping mountain vistas, glowing sunsets, and a peaceful seasonal stream. Private wooded acreage

  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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  /10

  $299,999

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

  328 Bloomingburg Rd, Middletown, NY 10940

  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. NO engineering

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
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  $605,000

  • 4 Beds
  • 3 Baths
  • 2,132 Sq Ft

  125 White Bridge Rd, Middletown, NY 10940

  This home offers so much more than a new build. Enjoy 2,132 square feet of well maintained, comfortable living space, topped with a brand new roof. Set on 2.6 beautiful acres in a serene country setting, the property’s signature feature is its fully owned solar array. No roof penetrations, no lease agreements — just clean energy and real savings. Electric bills as low as $28 per month speak for

  Anthony Spadaro RE/MAX Benchmark Realty Group

  125 White Bridge Rd, Middletown, NY 10940
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  /3

  $115,000

  • Land
  • 2.1 Acres
  • $54,762 per Acre

  143 Shawangunk Rd, Middletown, NY 10941

  TWO lots available for $115,000 each. Zoned Highway Commercial, suitable for several commercial uses subject to site plan approval. Lot 1 is 2.1 acres. Lot 2 is 2.3 acres. Previously engineered but needs to be updated as part of the design process. Good location between exits 116 and 118 on NYS Rt 17/Quickway/Interstate 86 providing excellent interstate and highway access. High visibility.

  Richard (RJ) Smith Rand Commercial

  143 Shawangunk Rd, Middletown, NY 10941
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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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  /46

  $674,900

  • 4 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  320 Highland Avenue Extension, Middletown, NY 10940

  Rare Gem – Like-New Home with Park-Like Setting; StunningDesign. Welcome to a truly special property—an exceptional home thatcombines style, comfort, and an unbeatable location. Homes Like thisrarely come to market. Meticulously maintained and showing Like new,this residence offers the perfect blend of elegance and convenience with a tastefully designed interior with modern

  Matthew Gibbs Keller Williams Hudson Valley

  320 Highland Avenue Extension, Middletown, NY 10940
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  /6

  $1,550,000

  • 5 Beds
  • 5.5 Baths
  • 4,365 Sq Ft

  79 Bisch Rd, Middletown, NY 10940

  Discover the allure of 89 sprawling acres in Orange County, New York, featuring a charming farm house and a tranquil pond. The farmhouse, with its rustic charm and scenic surroundings, holds immense potential as a delightful Airbnb destination or a mini vacation retreat. Its spacious interior, cozy ambiance, and proximity to nature make it an idea I spot for relaxation and rejuvenation.

  Siang Liu P R O Links Realty Inc

  79 Bisch Rd, Middletown, NY 10940
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  /6

  $99,000

  • Land
  • 6.48 Acres
  • $15,278 per Acre

  0 Fox Meadow Ln, Middletown, NY 12455

  Surveyed 6.4-Acre Hilltop Parcel with perc test, septic plans to be provided, and with electric on property. Perched atop one of the most beautiful and sought-after hills in Margaretville, this exceptional 6+ acre parcel offers a rare opportunity to own your own private slice of Catskills paradise. Located at the very end of a quiet, private road, this property features breathtaking 180-degree

  Susan Doig Listing by Coldwell Banker Timberland Properties

  

  0 Fox Meadow Ln, Middletown, NY 12455
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  /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
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  /7

  $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
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  /29

  $650,000

  • 3 Beds
  • 4 Baths
  • 2,320 Sq Ft

  33 O Brian Rd, Middletown, NY 10940

  Seeking privacy and tranquility without complete seclusion? This charming log home sits on 15 acres surrounded by natural beauty (partially wetlands) and peaceful views of a neighboring lake. The expansive deck is ideal for entertaining and summer barbecues, while the three-season porch provides a cozy retreat in any weather. Inside, the great room impresses with vaulted ceilings, exposed beams,

  Kokoshen Li Corcoran Country Living

  33 O Brian Rd, Middletown, NY 10940

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