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More details for 5-9 Rock City Rd, Woodstock, NY - Retail for Sale

5-9 Rock City Rd

Woodstock, NY 12498

  • Airbnb Property
  • Retail for Sale
  • $5,427,630 CAD
  • 8,625 SF

Woodstock Retail for Sale

Welcome to 9 Rock City Rd, a rare opportunity to acquire a turnkey; high-income mixed-use building located directly in the heart of Woodstock, NY. The property offers immediate cash flow for the next owner from day one. The building consists of 12 total units, including eight residential units and four retail units with an option to utilize the separate cottage as a residential unit currently used as retail. All retail tenants are in place under leases, providing stable and predictable income, while the residential component is split between five units currently operated as short-term rentals and three units leased to annual tenants. With an opportunity to convert the remaining leased units to STRs presents a compelling value-add opportunity. This property already holds the proper license for Short Term Rental and is zoned to operate as a boutique hotel, giving it a significant competitive advantage in a market where short-term rental supply is limited complete is its own parking for up to 10 cars. Rock City Road is the premier mixed-use investment in one of HudsonValley's most sought-after destinations. With Woodstock's bustling art and cultural scene, Rock City Rd places you in the center of one of the most beloved communities in the Hudson Valley. The perfect opportunity to launch a business venture, this property truly delivers space, style, location and endless potential.

Contact:

Compass Greater New York, Llc

Property Subtype:

Storefront Retail/Residential

Date on Market:

2026-02-20

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More details for 8 Tannery Brook Rd, Woodstock, NY - Specialty for Sale

Sweetheart Gallery - 8 Tannery Brook Rd

Woodstock, NY 12498

  • Airbnb Property
  • Specialty for Sale
  • $1,342,991 CAD
  • 2,496 SF

Woodstock Specialty for Sale

8 Tannery Brook Rd Woodstock, NY 12498 Estimated payment $7,216/month Total Views 7,542 3 Beds 2 Baths 1,776 Sq Ft $676 Price per Sq Ft Highlights River Front Deck Private Yard Woodstock Elementary School Rated A- Wood Flooring 1-minute walk to Woodstock Waterfall Park About This Home Large shade trees filter dappled sunlight across this property's private waterside retreat, where the ancient stone wall of the streambed tells the story of millennia, smoothed by the eternal passage of water. Just steps from the vibrant rhythm of Tinker Street and the creative heartbeat of Woodstock, this nearly 2,500 square foot mixed-use property is more than a home or an investment, it is a rare experience. With Hamlet Commercial zoning, three distinct enclosed spaces, and versatile layouts, the possibilities extend from live/work retreat to boutique inn to entirely new ventures envisioned by its next owner. At the heart of the property is the Tannery Brook Waterfall, an in-town oasis that defines daily life here. The rushing water is constant and soothing, carrying through open windows, drifting across private decks, and enlivening the riverside lawn. Outdoors, picnic seating invites you to linger at the water's edge. Indoors, oversized UV-protected windows frame the cascade as if it were living art. Few properties offer such natural drama in the very center of a village. The main residential level is a beautifully renovated two bedroom home with comfort and flow at its core. A cook's kitchen anchors the open plan layout, connecting seamlessly to dining and living spaces where the waterfall becomes the backdrop. A spa-inspired bath with steam shower and central air adds modern ease, while a private deck offers an immersive view of Woodstock's most famous falls. Above, ''A Woodstock Waterfall Hideaway'' serves as a fully permitted short-term rental with glowing five star reviews. This one bedroom apartment features its own kitchen, living area, and workspace, and offers guests the unforgettable experience of sleeping beside the sound of water, all within moments of Woodstock's celebrated cafes, shops, and galleries. Additional features include a separately rented street-level commercial studio and a detached office, originally a garage, creating even more flexibility and income potential. There is no need for a car, as the bus stop from New York City is only steps away. With its central walkable location, multiple revenue streams, and rare position directly on the falls, this property offers both natural beauty and cultural vitality. It is not just a home or an investment, but a lifestyle, and an unparalleled opportunity in the heart of Woodstock. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Contact:

Rawspace Group, Inc

Property Subtype:

Residential Income

Date on Market:

2025-12-10

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Airbnb Properties for Sale within 50 kilometers of Woodstock, NY, USA

More details for 33 Cuomos Cv, Windham, NY - Hospitality for Sale

Haüs Windham Vacation Rentals - 33 Cuomos Cv

Windham, NY 12496

  • Airbnb Property
  • Hospitality for Sale
  • $3,479,249 CAD
  • 5,100 SF
  • Fitness Center

Windham Hospitality for Sale - Greene County

Property Overview Rare opportunity to acquire a fully renovated, income-producing luxury short-term rental property in the heart of the Catskill Mountains. Located at 33 Cuomos Cove Road in Windham, New York, this five-unit boutique property sits on 2.7 acres in Greene County and delivers proven, institutional-quality cash flow in one of the Northeast’s premier four-season resort markets. The building underwent a complete gut renovation in 2023, transforming it into a modern, design-forward hospitality asset with premium finishes throughout. Each of the five distinctively named suites—the Jefferson, Hamilton, Washington, Franklin, and Madison—offers a curated guest experience that commands top-of-market nightly rates and drives repeat bookings year-round. All the units in the building can also be connected via an internal hallway, currently used by staff, to create a single massive chalet for group bookings or family compound. Financial Highlights The property generates approximately $335,000 in gross annual revenue with roughly $110,000 in total operating expenses, producing a net operating income of approximately $225,000. With a proven operating history and strong demand fundamentals driven by proximity to Windham Mountain Resort, this asset offers an attractive yield profile for investors seeking passive, cash-flowing hospitality real estate. Unit Mix & Configuration The property comprises five individually appointed suites totaling 5,100 square feet across two stories, offering a diversified unit mix that captures demand across multiple guest segments: The Franklin — 2 Bedrooms / 2 Bathrooms | Full Kitchen | Private Deck with Hot Tub The Washington — 2 Bedrooms / 2 Bathrooms | Private Deck with Hot Tub The Jefferson — 1 Bedroom / 1 Bathroom | Full Kitchen | Private Deck with Hot Tub The Madison — 1 Bedroom / 1 Bathroom | Full Kitchen | Private Deck with Hot Tub The Hamilton — Studio | 2 full beds Four of the five suites feature full kitchens and private decks with hot tubs, delivering the elevated amenity package that today’s short-term rental guests demand and are willing to pay a premium for. Property & Location Highlights Built in 1986 and completely gut-renovated in 2023, the property benefits from modern mechanical systems, updated plumbing and electrical, and contemporary interior finishes while maintaining the architectural character that guests seek in a mountain retreat. The 2.7-acre parcel provides ample privacy and a serene natural setting, with mature landscaping framing the property. Windham, New York is a premier four-season destination located less than 2.5 hours from New York City, offering direct access to Windham Mountain Resort for skiing, mountain biking, and year-round recreation. The region has experienced significant growth in short-term rental demand, driven by the post-pandemic shift toward experiential travel and nature-based getaways. Greene County’s tourism economy continues to expand, creating favorable tailwinds for well-positioned hospitality assets. Investment Thesis This property represents a compelling acquisition for an investor or operator seeking a stabilized, cash-flowing hospitality asset with immediate income and potential for further optimization. The 2023 gut renovation eliminates near-term capital expenditure risk, while the diversified five-unit configuration provides income resilience and operational flexibility. The property’s strong revenue performance validates its premium market positioning, and an experienced operator may identify additional upside through ancillary revenue streams not currently offered and further upgrades.

Contact:

Atelier WM LLC

Property Subtype:

Hotel

Date on Market:

2026-01-15

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More details for 64 Highlands Drive, Hunter, NY - Specialty for Sale

CASH FLOW CONDOS HUNTER MOUNTAIN CATSKILLS. - 64 Highlands Drive

Hunter, NY 12442

  • Airbnb Property
  • Flex for Sale
  • $1,322,115 CAD
  • 1,875 SF
  • 1 Unit Available

Hunter Specialty for Sale - Greene County

Rare Turnkey Investment Opportunity: Portfolio of Three Ski-In/Ski-Out Condominiums at Hunter Highlands, Hunter Mountain Nestled in the heart of the Catskills at the premier Hunter Highlands community—true slopeside living adjacent to Vail Resorts' Hunter Mountain—this exclusive portfolio offers three meticulously renovated 1-bedroom condominiums (Units B4, D6, and E2). Each unit is a proven performer, delivering approximately $60,000 in annual gross rental income with a documented three-year history, for a combined portfolio revenue of around $180,000 per year. These cozy, modern retreats sleep 4 comfortably and feature: • King bed in the bedroom with hotel-quality linens and blackout shades • Queen pull-out sofa in the living room, plus rollaway bed option • Fully equipped kitchens with full-size appliances, dishwasher, coffee station, and essentials • In-unit washer/dryer for ultimate convenience • High-speed 500 MB WiFi, smart TVs with streaming services • Private patios with mountain views, perfect for morning coffee or evening relaxation • Cozy fireplaces and open-concept layouts blending mountain-lodge charm with contemporary finishes Recent renovations elevate the appeal: Unit B4 boasts a brand-new kitchen and bathroom, Unit D6 a refreshed kitchen, and Unit E2 a complete gut renovation. All units include installed security cameras, noise/occupancy monitors, and benefit from hundreds of five-star reviews across booking platforms. Step directly onto the slopes for ski-in/ski-out access in winter, or enjoy year-round adventures: ziplining, hiking trails, Kaaterskill Club & Spa, Dolan's Lake, and the vibrant village of Tannersville with dining, breweries, and nightlife—all just minutes away. This is a fully turnkey business acquisition, including: • The real estate • Established short-term rental operation and intellectual property • All furnishings, systems, and vendor relationships • Personal onboarding: Seller will add buyer as co-host on platforms, introduce cleaners/maintenance teams, and provide hands-on support for months post-closing Financial highlights: Low overhead with ~$250/month maintenance and ~$1,500/year taxes/insurance per unit, yielding strong cash flow and a projected cap rate in the high-teens to low-20% range—with significant upside potential. Ideal for an investor seeking immediate income, seamless transition, and growth in one of New York's most desirable four-season destinations. Don't miss this exceptional, hands-off opportunity to own a thriving slopeside portfolio. Contact for financials.

Contact:

Win Morrison Realty

Date on Market:

2026-02-09

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More details for 4494-4496 Route 209, Stone Ridge, NY - Hospitality for Sale

ElmRock Inn - 4494-4496 Route 209

Stone Ridge, NY 12484

  • Airbnb Property
  • Hospitality for Sale
  • $2,080,592 CAD
  • 2,996 SF

Stone Ridge Hospitality for Sale

Welcome to Elmrock Inn, an elegant boutique estate in Stone Ridge, where 19th-century Dutch Colonial architecture meets modern country elegance. Set on five acres framed by towering Locust trees, this historic brick estate has long been a sought-after destination for weddings, private events, and unforgettable Hudson Valley getaways. Inside, soaring ceilings, antique-inspired furnishings, and a welcoming great room and grand dining hall with fireplace flow seamlessly. Head upstairs to a second-story bar lounge and expansive deck overlooking the grounds. Below, the bluestone patio under the elevated deck, organic herb gardens, and outdoor firepit create the perfect backdrop for gatherings or quiet retreat. The expansive property lends itself perfectly for badminton and frisbee. Five beautifully appointed suites in the main house feature private baths and luxurious details. On the main level there are two large suites and a separate office, and upstairs are three more suites and a storage closet. The property also includes ample parking and a professional-grade kitchen, ideal for both intimate breakfasts and large-scale catering. Completing the compound is a picturesque post-and-beam guest cottage, equally suited as an owner's residence, artist's studio, or rental opportunity. Its rustic craftsmanship, open floor plan, exposed beams, and abundant light highlight the region's timeless character, with an upstairs suite adding flexibility. Just under two hours from New York City and nestled near Mohonk, Minnewaska, and Stone Ridge, Elmrock Inn offers both lifestyle and income potential: keep it as a thriving bed-and-breakfast, enjoy it as a grand private estate, or reimagine it as a creative retreat or Airbnb. Impeccably maintained and steeped in Catskill charm, this turn-key boutique farmhouse compound is ready for its next chapter. Property consists of 2 buildings: 4494 Route 209, Marbletown (69.4.-1-1.200) 4496 Route 209, Route 209, Rochester (69.4-2-1.320) A 3D Walkthrough Tour is available in the digital Lookbook or by request.

Contact:

Coldwell Banker Village Green Realty - WD

Property Subtype:

Bed and Breakfast

Date on Market:

2025-12-17

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More details for 705 Warren St, Hudson, NY - Retail for Sale

705 Warren Street - 705 Warren St

Hudson, NY 12534

  • Airbnb Property
  • Retail for Sale
  • $3,270,495 CAD
  • 5,750 SF
  • Air Conditioning
  • Security System
  • Smoke Detector

Hudson Retail for Sale - Columbia County

Stunning live-work opportunity on prime Warren Street, overlooking the 7th St Park and fast-growing Upper Depot District. One of the very few fully renovated and modernized buildings of its kind, offering approx. 5,750 sf of finished space across 4 floors plus a basement. The spacious residential upper level extends over 3 floors covering approx. 2,800 sf of modern, light-filled contemporary living in the heart of thriving Hudson, NY. These floors are currently configured as a luxurious 3rd/4th floor 2-bedroom duplex for the owner, and a successful 2nd floor 2-bedroom rental/Airbnb apartment. Enjoy the income from the current layout or combine both apartments to create one of the grandest triplex apartments in Hudson. Both apartments have been completely remodeled, including a new sprinkler system in the 3rd and 4th floors and newly insulated roof, as well as new kitchens and bathrooms. The upper floors in particular enjoy fabulous Catskill / sunset views to the west, and the entire front-facing windows have unencumbered easterly views across the open grass and trees of the park, and it's soon to be renovated Fountain of Venus. The ground floor is currently a successful design showroom covering approx. 2,400 sf of open plan space, and a further approx. 500 sf used as a garage / storage space. The latter could easily be repurposed as art or design studios, or a workshop. The front of the showroom includes a full chef's kitchen, previously used for cooking classes, along with a large powder room, and an additional storage parlor. The rear of the showroom is flooded with light from both 2 large industrial steel-framed windows and 2 huge skylights added with the new roof in 2018. Moreover, an unfinished basement below offers an additional approx. 1,200 sf of storage. The live/work zoning of Warren Street allows flexibility of use and means an array of possibilities to transform the space's current retail footprint to bar/restaurant, gallery, maker space, or whatever your heart desires! The current owner has undertaken extensive renovations to the entire building over the last 10+ years to create its now pristine condition. Major improvements include, but are not limited to, all new electrical and plumbing, new Spilt units for AC and heating throughout, a new rear roof, new windows front and back in the apartments, new 3rd floor balcony, adding the sprinkler system to legalize the 4th floor (formerly attic), and most recently, a new GAF asphalt shingle main roof and brand new water heater. There is even a heated sidewalk to allow safe entry / exit during the depths of winter! Finally, structural steel was added early in the remodeling to create both the ground floor's open plan and to ensure a structural solidity to the entire building and the floors above; uncommon in a building of this age in Hudson. Warren Street is the main artery of the historic City of Hudson, where stunning town houses co-exist with architecturally significant mixed use (commercial / residential) buildings, exemplified by 705 Warren. This remarkable turnkey property sits in an enviable position. While close to great restaurants, boutique stores, galleries and the historic Park Theater, 705 also sits across the park from the fast-growing Upper Depot District which will be anchored by the soon to be opened Pocketbook Factory hotel and arts center. Hudson itself sits at the heart of the Hudson Valley, 2 hours by car or Amtrak from NYC

Contact:

Tri-Hudson Realty LLC

Property Subtype:

Storefront Retail/Residential

Date on Market:

2025-04-16

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More details for 54 Parkwood Blvd, Hudson, NY - Multifamily for Sale

54 Parkwood Blvd

Hudson, NY 12534

  • Airbnb Property
  • Multifamily for Sale
  • $1,384,742 CAD
  • 3,925 SF
  • Kitchen

Hudson Multifamily for Sale - Columbia County

“ A wonderful example of one of the most beloved of all American architectural styles, this shingle style, coastal-inspired home mixes beautifully restored cedar shake details with a picturesque multi-gabled roof, stunning interior woodwork and a gorgeous array of original multi-paned and intricately mullioned windows. Shingle style homes are known for blending timeless natural materials with a relaxed, informal aesthetic perfect for modern living. Substantial work has been completed to painstakingly restore this lovely property, carefully preserving its detailed millwork and original oak floors while adding important upgrades such as a new roof and gutters, boiler, 400-amp electric service, new front porch foundation, and roughed-in bathrooms. Further amenities include a 520 sq ft barn with amazing potential, just minutes from the Hudson River. Although currently being presented as a partially converted 8-unit charmer, this property would make a gracious single-family home with short-term rental potential if converted back to the grand home it once was. Spacious and filled with character, its sun-filled porches and lovely architectural details beckon! If you’re looking for that perfect home or investment property, only 2.5 hours from NYC, close to shops, restaurants, and scenic state parks, this property is ideal! “ | 3% Agent Commission |

Contact:

Kristal Heinz

Property Subtype:

Apartment

Date on Market:

2025-09-10

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More details for 76 Prince St, Kingston, NY - Retail for Sale

76 Prince St

Kingston, NY 12401

  • Airbnb Property
  • Retail for Sale
  • $3,479,250 CAD
  • 7,297 SF

Kingston Retail for Sale - Downtown Kingston

Welcome to 76 Prince Street —a creative sanctuary in the heart of Kingston, NY. This one-of-a-kind, mixed-use property offers over 7,000 square feet of fully renovated space, stylish and functional to support your business and creative ambitions. Located in the Midtown Kingston Arts District, the building has undergone a complete transformation under the expert vision of an accomplished photographer. The ground floor currently serves as an art gallery, studio, production space and event venue, with elements of a commercial kitchen in place. The flexible T5F zoning that allows for a wide range of uses — including the potential for full residential conversion. Upstairs, a stunning two-bedroom loft is bathed in natural light, with soaring ceilings, original wood floors, an open-concept kitchen, and private access to rear parking. Currently operating as a successful short-term rental, it also presents an ideal opportunity for an owner-occupied live/work lifestyle. Surrounded by Kingston's thriving creative community, you'll find inspiration in every direction — from local galleries and eclectic dining to cultural events that make this neighborhood so dynamic. No detail was overlooked in the recent renovations, which preserved the building's historic charm while introducing modern comforts. One of the property's many standout features is its private rear parking lot with space for 10+ vehicles. Additional municipal parking across the street easily supports the building's 200-person capacity. Just minutes from the NYS Thruway, Uptown Kingston, and the Rondout waterfront, this is more than a property — it's a rare chance to be the steward of something extraordinary. 90 miles from the GWB and only 20 minutes to Amtrak/Metro North stations

Contact:

TKG The Kinderhook Group Hudson

Property Subtype:

Storefront Retail/Office

Date on Market:

2025-05-12

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More details for 4028 County Route 26, Greenville, NY - Multifamily for Sale

Stevens Hill Farm - 4028 County Route 26

Greenville, NY 12083

  • Airbnb Property
  • Multifamily for Sale
  • $3,618,420 CAD
  • 7,159 SF

Greenville Multifamily for Sale - Greene County

Catskills Estate + Proven Income + Endless Possibility 4 Parcels | 3 Homes | 2 Massive Barns | Dozens of Uses | 1 Private Lake This is your once-in-a-generation opportunity to own a legacy compound in the Catskills, where every acre has possibility and positioned for future growth. Spanning over 24 acres across four separate tax parcels, this remarkable offering includes three unique residences—two of which are profitable, established Airbnbs - plus a 6-bedroom personal residence (yet to be restored), two massive barns, a brand-new private pond, and multiple sheds, garages, and outbuildings, including a project tiny house known affectionately as The Museum. The site is ideally suited for a boutique hospitality business, event venue, creative compound, wellness retreat, or multi-family homestead. The question isn't if it can happen here - it's how big you want to go. Property Overview 4082 County Route 26 - The Heart of the Compound Your personal base of operations or a flagship home for guests. This 6-bedroom, 3-bath home sits on just shy of 10 acres with mountain views, four outbuildings, and a newly dug, 2-acre private pond that reaches 20 feet deep. The property includes a large barn, carriage house, garage, and a project tiny house that was designed to sleep six - renderings and architect plans included. There's flexibility here to complete the project, expand further, or simply enjoy the privacy and scale of the setting. 4050 County Route 26 - The Saltbox A stunning 19th-century home that has been taken down to the studs and rebuilt with modern systems and timeless style. 3 bedrooms, 2 full baths, all new plumbing, electric, heating, and wide plank floors throughout. The kitchen stuns with granite counters, oversized island with wine cooler, and custom cabinetry. French oak flooring and a wood-burning fireplace add warmth and character. Outside is a versatile outbuilding that could easily become two duplex hotel-style suites. Currently operating as a profitable 5-star Airbnb. 4028 County Route 26 - The Other White House This 6-bedroom, 3-bath home has undergone a full interior restoration, including new septic and plumbing. Clean, spacious, and ideal for larger group rentals or a dedicated innkeeper's house. Out back are two barns, including a towering, historic dairy barn perfect for conversion into an event space, retreat hall, or large-scale creative workshop. Also a current 5-star Airbnb with proven revenue. Additional Parcel - 8.85 Acres Across the Road Prime open land with mountain views, dual access points, and clear potential for subdivision or a full glamping buildout. This is the infrastructure and logistical support that turns a boutique dream into a scalable operation. The town is open to creative, responsible development. Lifestyle + Location Minutes from Windham and Hunter Mountains, Island Green Golf Club, farm-to-table restaurants, antique shops, and endless hiking trails. This is a high-traffic region for weddings, retreats, STRs, and weekenders—making it as much a lifestyle decision as it is a smart investment. Additional Assets - Option to transfer a 501(c)(3) nonprofit built around the property's historic legacy - Full architectural plans and renderings for The Greenhouse (tiny house) - Branding & original business plan from prior venue concept (The Jaye/Stevens Hill Farm) - Existing bookings and STR income (approx. 30K in current pipeline) - Seller is open to bundling or splitting parcels, with preferred groupings for the Airbnb homes

Contact:

Dugo Realty

Property Subtype:

Multi Family

Date on Market:

2025-05-31

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