5-Bedroom Homes for Sale in Ulster County NY

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  /25

  $1,299,000

  • 10 Beds
  • 12 Baths
  • 4,448 Sq Ft

  57 Samsonville Rd, Kerhonkson, NY 12446

  This is a great investment opportunity all apartments are currently rented. All appartments are in good condition. Possible owner financing to qualified buyer. For appointments 24 hr notice due to tenants. This property is well maintained.

  Frank Tangredi Frank Tangredi Realty Company

  57 Samsonville Rd, Kerhonkson, NY 12446
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• 

  

  

  /24

  $565,000

  • 6 Beds
  • 6 Baths
  • 1,025 Sq Ft

  2 Mountain Valley Rd, Boiceville, NY 12412

  Welcome to this exquisite two-family home nestled in the picturesque town of Olive. The upstairs apartment boasts charming cathedral ceilings and skylights, bathing the space in natural light and offering a sense of openness and serenity. Each of the spacious three-bedroom apartments, complete with a well-appointed bathroom, comes with its own garage for added convenience. Washer and dryer

  Barry Creagan Howard Hanna Rand Realty

  2 Mountain Valley Rd, Boiceville, NY 12412
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  /25

  $575,000

  • 5 Beds
  • 2 Baths
  • 1,532 Sq Ft

  66 Spook Hole Rd, Ellenville, NY 12428

  Unleash your inner adventurer and escape the ordinary at 66-68 Spook Hole! Nestled on a sprawling 62.6-acre canvas of serene seclusion, just two hours from NYC's hustle and bustle, this expansive estate is your invitation to a life less ordinary. Imagine waking up to sun-dappled mornings and the symphony of nature in your private paradise. This property offers not just one, but two charming

  Kerri Stretch Howard Hanna Rand Realty

  66 Spook Hole Rd, Ellenville, NY 12428
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  /50

  $819,900

  • 5 Beds
  • 4.5 Baths
  • 4,545 Sq Ft

  67 Latham Cir, Saugerties, NY 12477

  67 Latham Circle blends modern comfort, style, and convenience in an unbeatable location. Sunlight fills every room, highlighting a smartly designed layout with spaces to relax, entertain, and recharge. Enjoy fireside evenings in the living room, cooking in the smart kitchen, soaking in the five-person hot tub, or unwinding in the three-person infrared sauna.The first-floor primary suite

  Peter Sisca Real Broker NY LLC

  67 Latham Cir, Saugerties, NY 12477
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  /16

  $589,999

  • 6 Beds
  • 3 Baths
  • 3,189 Sq Ft

  11 High St, Kingston, NY 12401

  **Investment Opportunity in Kingston, NY: Two-Family Property with Rental Income Potential**Are you looking for a promising investment opportunity in Kingston? This former restaurant, now transformed into a two-family residence, is ready for your vision! With 85% of the work already completed, this property offers a unique chance to step into a project with significant potential. This is

  Darnell Williams R New York

  11 High St, Kingston, NY 12401
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  /50

  $459,000

  • 5 Beds
  • 2.5 Baths
  • 4,022 Sq Ft

  5 Burma Rd, Marlboro, NY 12542

  5-Bedroom Farmhouse on Over 2 Acres with Endless Possibilities!Welcome to this spacious and versatile 4000+ sq. ft. farmhouse, perfectly situated on 2.2 private acres, offering the ideal blend of classic charm and modern functionality. Whether you're dreaming of a multi-purpose residence, home business, or entertainment haven, this property delivers on all fronts.Key

  BRIDGET CAPAWANA Exit Realty Connections

  5 Burma Rd, Marlboro, NY 12542
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  /45

  $1,799,500

  • 6 Beds
  • 6 Baths
  • 6,164 Sq Ft

  174 Bristol Hill Rd, Glenford, NY 12433

  Secluded 6-Bedroom Estate with Seasonal Reservoir Views and Stunning Sunrises !sauna, reservoir view, Woodstock, luxury kitchen, elevator shaft, accessibility and grand staircase Nestled on a quiet, picturesque road just 4 miles from the heart of Woodstock, this extraordinary 6-bedroom, 6-bathroom estate offers privacy, craftsmanship, and timeless character on nearly 2 acres of lush,

  Thomas Pignone Green Ventures Realty

  174 Bristol Hill Rd, Glenford, NY 12433
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  /45

  $925,000 Open Sat 12PM - 2PM

  • 6 Beds
  • 4.5 Baths
  • 3,112 Sq Ft

  628 Lattintown Rd, Marlboro, NY 12542

  HGTV Farmhouse with Historic Charm on 5 Acres with CreekWelcome to 628 Lattintown Road, an HGTV-featured 1800s farmhouse that's been beautifully reimagined for modern living while keeping every ounce of its historic soul intact. Tucked away down a long driveway on five lush acres, this Marlboro retreat feels like stepping into your own private sanctuary, where the gently winding

  Bree Chambers Compass Greater NY, LLC

  628 Lattintown Rd, Marlboro, NY 12542
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  /71

  $1,395,000

  • 5 Beds
  • 6 Baths
  • 3,500 Sq Ft

  71 Stony Kill Rd, Accord, NY 12404

  Welcome to this enchanting 20-acre Hudson Valley retreat—an organic homestead and income-generating compound nestled along the Stony Kill Creek, just under 2 hours from NYC.Lovingly stewarded by the same family for over 40 years, the land has been organically farmed and is rich with natural loam and nutrients. This versatile property offers a rare mix of privacy, rental income, and rural

  Megan Rios Berardi Realty

  71 Stony Kill Rd, Accord, NY 12404
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  /52

  $1,299,000

  • 6 Beds
  • 5 Baths
  • 2,746 Sq Ft

  199 Echo Hill Rd, Saugerties, NY 12477

  36 bucolic acres with two houses for the price of one. The property features a seasonal waterfall and a couple of small streams and plenty of trails to enjoy all from your own backyard. The property is within 15 minutes from the heart of Woodstock and Saugerties. The main house features a fully finished basement with three separate rooms including a dry bar and a crafting room with a half bath.

  Michael Barros Win Morrison Realty

  199 Echo Hill Rd, Saugerties, NY 12477
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  /30

  $675,000

  • 13 Beds
  • 13 Baths
  • 1,960 Sq Ft

  66-84 Katzman Rd, Wawarsing, NY 12428

  Welcome to your own private oasis! Set on over 33 acres, this unique property features 8 bungalows with year-round permitted use, making it perfect for families seeking a peaceful getaway or investors exploring rental income opportunities.(5, two bedroom bungalows and 3, one bedroom bungalows). All have new roofs, buried water lines and their own septic clean outs. Some bungalows require

  Joe Stoeckeler Century 21 Stoeckeler R.E.

  66-84 Katzman Rd, Wawarsing, NY 12428
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  /21

  $675,000

  • 15 Beds
  • 15 Baths
  • 10,130 Sq Ft

  288-292 Main St, Pine Hill, NY 12465

  The Pine Hill Arms - a Catskills classic, ready for revival! Built in 1882 and set on nearly 2 acres in the heart of Pine Hill, this historic 15-bedroom inn with full-service restaurant, bar, and cafe offers a rare opportunity to reimagine a beloved Catskills institution. With a total interior square footage of over 10,000 sq ft, the property features a spacious lobby, commercial kitchen,

  Laura Warren Coldwell Banker Village Green

  288-292 Main St, Pine Hill, NY 12465
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  /30

  $1,100,000

  • 5 Beds
  • 1 Bath
  • 2,091 Sq Ft

  2018 Beaverkill Rd, Livingston Manor, NY 12758

  Sportsman’s Paradise in the Beaverkill Valley!This rare 18+ acre offering in the heart of the Beaverkill Valley includes the historic Turnwood General Store, an original 5-bedroom, 2-bath farmhouse, a 4+ car detached garage, and a scenic 2+ acre hay field with direct river frontage.The historic barn / general store spans over 4,800 sq ft across two floors and offers tremendous

  Chip Parrish Keller Williams Prestige Prop

  2018 Beaverkill Rd, Livingston Manor, NY 12758
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  /35

  $835,000

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

  405 Vista Maria Rd, Cragsmoor, NY 12420

  Vintage charm meets modern convenience in this circa 1900 Cragsmoor home. Situated on a 1.46-acre corner lot at the top of the hill, this property is located in the picturesque hamlet of Cragsmoor—known for its sweeping vistas and access to over 5,000 acres of protected land perfect for hiking, exploring, and enjoying nature’s serenity.A short distance to the post office and library, the

  Carolyn Peters-Baker Keller Williams Hudson Valley

  405 Vista Maria Rd, Cragsmoor, NY 12420
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  /89

  $8,350,000

  • 6 Beds
  • 7 Baths
  • 6,900 Sq Ft

  290 Ulster Landing Rd, Kingston, NY 12401

  Ulster Landing is a storied & magnificent former Livingston estate established in the early 1800s, perched on 34 acres above the Hudson River with far-reaching views & more than half a mile of river frontage.Down a long, winding driveway lies the historic and remarkably well-preserved main house.On the 1st floor, the formal living & dining rooms have exquisite views of the river & are

  Raj Kumar Four Seasons Sotheby's Int.

  290 Ulster Landing Rd, Kingston, NY 12401
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  /50

  $2,595,000

  • 5 Beds
  • 3 Baths
  • 3,566 Sq Ft

  169 Baker Rd, West Hurley, NY 12491

  Set at the end of a long, private driveway, Eagle Ridge Estate sits high above the Ashokan Reservoir on over nine secluded acres, offering rare peace, unbroken mountain views, and the quiet grace of a home rooted deeply in history. Surrounded by century-old lilacs and a broad open lawn, this 5-bedroom, 3-bathroom residence spans 3,566 square feet across three floors, with timeless design and

  Jake Garay Serhant LLC

  169 Baker Rd, West Hurley, NY 12491
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  /9

  $1,485,000

  • 15 Beds
  • 15 Baths
  • 6,688 Sq Ft

  95 Green St, Kingston, NY 12401

  Located in one of the most walkable and vibrant corners of the Hudson Valley, 95 Green Street is a rare opportunity to own a fully rented, 14-unit multifamily asset in the cultural and commercial core of Kingston. Built circa 1900, the building retains classic Hudson Valley charm and solid construction, with all units recently renovated. The units are 7 studios, including one oversized, and one

  Sheneur Menaker Hudson Modern

  95 Green St, Kingston, NY 12401
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  /16

  $2,000,000

  • 16 Beds
  • 16 Baths
  • 6,055 Sq Ft

  58 St James St, Kingston, NY 12401

  Own a piece of Kingston's storied charm with this fully stabilized, income-generating 17-unit apartment complex in the heart of Uptown. Featuring old-world architectural details like stamped tin ceilings, original hardwood floors, crown moldings, and restored trim work, this property offers historic character, modern upgrades, and ready to underwrite cashflow. The complex consists of a 14-unit

  Sheneur Menaker Hudson Modern

  58 St James St, Kingston, NY 12401
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  /16

  $799,000

  • 6 Beds
  • 6 Baths
  • 3,100 Sq Ft

  104 North Rd, Highland, NY 12528

  Come explore this once in a lifetime oppurtunity! New construction duplex/2 family home located right in Highland on North Road. Will be a great investment property, rent both sides or live in one and rent the other. Both units include 3 bedrooms, 2 1/2 baths, full unfinished basement and approximately 1550 sq. ft. This home features stone front with large windows, lots of natural light, upgraded

  Marisa Bellacicco Century 21 Alliance Rlty Group

  104 North Rd, Highland, NY 12528
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  /37

  $1,100,000

  • 12 Beds
  • 12 Baths
  • 4,860 Sq Ft

  996 Dominican Ln, Saugerties, NY 12477

  Create Your Hudson River Legacy Estate at 996 Dominican Lane.Discover the rare opportunity to establish a multi-generational legacy property on one of the Hudson Valley's most coveted riverfront parcels. This exceptional 8.7-acre estate offers discerning buyers the chance to craft their family's forever home while building lasting wealth through strategic property development. Transform

  Robert Airhart Compass Greater New York, LLC

  996 Dominican Ln, Saugerties, NY 12477
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  /51

  $925,000

  • 8 Beds
  • 3 Baths
  • 2,800 Sq Ft

  38 Plattekill Ave, New Paltz, NY 12561

  Turn-of-the-century duplex located directly across from SUNY New Paltz in the heart of the village—an exceptional opportunity to own a high-performing, income-generating property in one of the Hudson Valley's most sought-after locations. This beautifully maintained home features a spacious two bedroom apartment on the first floor, currently listed at 2,500/month, and six individual bedrooms

  Emily Benazzi VORO, LLC

  38 Plattekill Ave, New Paltz, NY 12561
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  /30

  $2,100,000

  • 9 Beds
  • 10 Baths
  • 8,452 Sq Ft

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498

  Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

  Nancy Felcetto Brown Harris Stevens Hudson

  0 Wittenberg Rd Unit 20252191, Woodstock, NY 12498
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  /33

  $2,100,000

  • 9 Beds
  • 10 Baths
  • 8,452 Sq Ft

  Unlisted Address

  Welcome to Happy Brooks , The much-loved compound for many years of Woodstock Festival co-founder and legendary music industry icon Michael Lang, this mythic Mt. Tremper property boasts true style, along with a creative pedigree that dates back to the 1920s. Originally built for the artist G. Adolph Anderson, the 17 acre estate features three architecturally significant & historic structures

  Nancy Felcetto Brown Harris Stevens HV LLC

  Unlisted Address
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  /45

  $819,000

  • 5 Beds
  • 2 Baths
  • 2,221 Sq Ft

  5813 U S 44, Kerhonkson, NY 12446

  A rare and versatile offering in the heart of the Shawangunk Mountains: two fully separate and distinct homes, each with its own pool, hot tub, and private outdoor amenities — all set on nearly 2 acres of beautifully landscaped land. Currently operated as successful Airbnb rentals with strong financials and glowing five-star reviews, this is a standout opportunity for investors, second-home

  Dylan Taft Taft Street Realty, Inc.

  5813 U S 44, Kerhonkson, NY 12446
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  /44

  $315,000

  • 6 Beds
  • 5 Baths
  • 3,885 Sq Ft

  165 Fair St, Kingston, NY 12401

  Incredibly rare opportunity in the heart of highly desirable Uptown Kingston! This fire-damaged 4-family building offers over 3,800 sq ft of potential just steps from the vibrant Stockade District. Situated on historic Fair Street, surrounded by restaurants, shops, galleries, and weekend markets, this property is primed for redevelopment. Originally configured as four residential units with

  Michael Cahill HomeSmart Homes & Estates

  165 Fair St, Kingston, NY 12401
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  /44

  $1,900,000

  • 7 Beds
  • 4.5 Baths
  • 5,015 Sq Ft

  55 Leggett Rd, Stone Ridge, NY 12484

  Clematis Cottage c1890 is a 7 Bedroom, 4.5 Bath, 8 Fireplace Historic Masterpiece located on one of the most beautiful Roads in Stone Ridge a destination known for peaceful weekends , summer escapes and more recently a haven for full time residency. This stately Gilded Age residence surrounded by 11+ acres with design by noted architect Charles Coolidge Haight, retains those rare but most

  Bill Sidoriak Flemming Realty

  55 Leggett Rd, Stone Ridge, NY 12484
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  /41

  $925,000

  • 6 Beds
  • 3.5 Baths
  • 2,610 Sq Ft

  204-208 New York 42, Shandaken, NY 12480

  Tucked away on 10 private, wooded acres in the heart of the Catskills, this unique compound offers the perfect blend of rustic charm, modern comfort, and income-generating potential. With a 4-bedroom, 2.5-bath main house and a separate 2-bedroom, 1-bath guest house, this serene escape is ideal for full-time living, weekend getaways, or as a turnkey investment property. The grounds feature a pool,

  Jason Nadeau Compass Greater NY, LLC

  204-208 New York 42, Shandaken, NY 12480
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  /36

  $1,995,995

  • 7 Beds
  • 6 Baths
  • 7,020 Sq Ft

  589-595 Plank Rd, Phoenicia, NY 12464

  This beautiful estate must be seen. Owned by the same family for over 40 years, the compound has been lovingly expanded and restored. It is anchored by an 1870 farmhouse with many amenities. You enter the house to a wonderful chef's kitchen with cathedral ceilings accompanied by a walk-in pantry. There are granite countertops and top appliances. The first floor includes a spacious entertaining

  Michael Shaughnessy Halter Associates Realty Inc

  589-595 Plank Rd, Phoenicia, NY 12464
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  /46

  $525,000

  • 5 Beds
  • 3 Baths
  • 2,024 Sq Ft

  191 Bedell Ave, Highland, NY 12528

  Welcome to 191 Bedell Ave in Highland, a move-in ready gem blending classic charm with modern updates! This beautifully maintained home features cathedral ceilings, hardwood floors, abundant natural light, and spacious living areas perfect for relaxing or entertaining. This sprawling raised ranch includes 5 bedrooms, 3 baths, and tons of living space on 1.46 Acres! Sit back and relax in the fully

  Michael Cahill HomeSmart Homes & Estates

  191 Bedell Ave, Highland, NY 12528
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  /42

  $875,000

  • 5 Beds
  • 4 Baths
  • 4,283 Sq Ft

  14 Clarks Ln, Milton, NY 12547

  Set on a full acre in the peaceful hamlet of Milton, this expansive 5-bedroom, 4-bathroom Colonial offers over 4,200 square feet of finished living space with opportunity to customize across three generous levels. The main floor features a recently renovated eat-in kitchen, formal dining room, multiple living areas, an office, mudroom with laundry hookups, and a spacious primary suite with en

  DARREN BARR Serhant LLC

  14 Clarks Ln, Milton, NY 12547
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  /29

  $675,000

  • 7 Beds
  • 4 Baths
  • 3,500 Sq Ft

  49 Highlands Rd, Highmount, NY 12441

  Historic Victorian Elegance with Unmatched Belleayre Mountain Views --Step into timeless grandeur at this stately Victorian estate, perched directly across from Belleayre Mountain with panoramic views of its iconic ski runs. Set on 2.65 serene acres, this 1900s home offers 3,500 square feet of refined character, featuring seven bedrooms and four bathrooms, including a versatile accessory

  Felicity Taylor Corcoran Country Living

  49 Highlands Rd, Highmount, NY 12441
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  /38

  $2,300,000

  • 13 Beds
  • 5 Baths
  • 8,000 Sq Ft

  540 New York 42, Shandaken, NY 12480

  Experience the best of Catskills living at the Mountain Brook Inn, a beautifully restored historic home in Shandaken, NY. Originally built in 1805 and extensively renovated for 2025, this remarkable residence offers nearly 8,000 square feet of living space on a picturesque 1-acre lot along the tranquil Bushnellsville Creek. The home spans three levels, featuring seven spacious bedrooms on the

  Alicia Goldman Christie's Int. Real Estate

  540 New York 42, Shandaken, NY 12480
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  /24

  $649,000

  • 9 Beds
  • 6 Baths

  14 Montross St, Saugerties, NY 12477

  Prime 3-Unit Multifamily Opportunity in the Heart of Saugerties, NY! Location, Location, Location!An Investment Dream, Just one block from the vibrant shops, restaurants, and galleries of Partition Street and Main Street, this incredible multifamily property places you right in the cultural and commercial heart of Saugerties. This rare gem offers strong income potential in one of the most

  Christopher Virtuoso Keller Williams Hudson Valley

  14 Montross St, Saugerties, NY 12477
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  /41

  $1,799,000

  • 7 Beds
  • 3.5 Baths
  • 4,514 Sq Ft

  12 Armstrong Rd, Arkville, NY 12406

  Own Paradise. At the end of a town-maintained dead-end road in the Catskills is The Odell Farm, 335 splendid acres of forest, meadows, pond, and stream adjoining thousands of acres of protected state land. This private and delightfully secluded retreat consists of the original 4BR 1.5 bath 1826 farmhouse and 1991 3BR 2BA oversized lodge along with a detached 5 bay garage and a professionally

  Dara Barr Keller Williams Upstate NYProp

  12 Armstrong Rd, Arkville, NY 12406
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  /35

  $599,900

  • 6 Beds
  • 3 Baths
  • 3,059 Sq Ft

  1441 County Road 2, Olivebridge, NY 12461

  Welcome to 1441 County Road 2 in Olivebridge, NY—a beautifully renovated 6-bedroom, 3-bathroom home nestled on 2.32 acres in the heart of the Catskills. This spacious 3,059 sq ft retreat features a brand-new kitchen, three cozy fireplaces, a sun-drenched great room, and a primary en suite on the main floor. With three bedrooms on each level, a full walk-out basement, and a large deck over the

  Nicholas Cuomo Keller Williams Realty

  1441 County Road 2, Olivebridge, NY 12461
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  /36

  $579,900

  • 7 Beds
  • 5 Baths
  • 3,464 Sq Ft

  651 Glasco Turnpike, Saugerties, NY 12477

  Rare opportunity to own two distinct homes on a single lot, both overlooking the Esopus Creek. Whether you're seeking an investment property, a multi-generational living setup, or a private retreat, this dual home offering provides endless potential! The stone home, formally known as the Lanigan House, was built as a fort and originally constructed around 1700. This historic beauty sits on the

  Megan Rios Berardi Realty

  651 Glasco Turnpike, Saugerties, NY 12477
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  /44

  $1,100,000

  • 5 Beds
  • 3 Baths
  • 5,216 Sq Ft

  370 Forest Rd, Wallkill, NY 12589

  DESIGNED AND BUILT FOR ENTERTAINING...This residence is a raised ranch with over 5200 square feet of living space on 2 floors. The house has 5/6 bedrooms, 3 full baths, a master bath with a large walk-in shower, a 32x33 great room with high ceilings and a lot of glass, a wine cellar, a unique vestibule / foyer entrance, a 188 KW diesel generator, a 3 car garage and approx. 1140 square feet of

  Dennis Barr John J Lease REALTORS Inc

  370 Forest Rd, Wallkill, NY 12589
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  /32

  $599,000

  • 5 Beds
  • 5 Baths
  • 2,100 Sq Ft

  393 Main St, Kingston, NY 12401

  393 Main Street is a fully occupied five-unit property offering strong cash flow and excellent rental history in one of Ulster County's most in-demand markets. With a current Net Operating Income (NOI) of 64k, this turnkey asset is a great fit for both new investors and seasoned professionals seeking dependable returns.393 Main is being sold as part of a rare portfolio with 296 and 385

  Savannah Miceli Century 21 Alliance-NP

  393 Main St, Kingston, NY 12401
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  /23

  $450,000

  • 5 Beds
  • 3 Baths
  • 1,900 Sq Ft

  385 Main St, Rosendale, NY 12472

  Don't miss this opportunity to own a well-located, high-potential three-family property in the vibrant hamlet of Rosendale. With a projected Net Operating Income (NOI) of 45k, this property is ideal for first-time investors or seasoned buyers looking to expand their portfolio.Being sold as part of a rare three-property portfolio with neighboring 296 and 393 Main Street, this is a chance

  Savannah Miceli Century 21 Alliance-NP

  385 Main St, Rosendale, NY 12472
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  /29

  $1,600,000

  • 13 Beds
  • 13 Baths
  • 4,802 Sq Ft

  669-671 Broadway Rt 9w, Esopus, NY 12429

  Prime Hospitality Investment Opportunity on Mirror Lake - 10-Unit Motel & 2-Family HomeLocated on the banks of Mirror Lake, this 1.2-acre hospitality-zoned property offers a unique investment opportunity just 5 minutes from Downtown Kingston's waterfront and 90 miles from NYC. Formerly operating as the Lake Motel, the property consists of two adjacent parcels: a 10-unit motel and a

  Greg Berardi Berardi Realty

  669-671 Broadway Rt 9w, Esopus, NY 12429

Showing Results 41 - 80, Page 2 of 3