The agencies at Hillsdale
These agencies offer a selection of luxury properties location at Hillsdale. Feel free to contact them for personalized assistance.
Located 2.5 hours from NYC and Boston, this 4-bedroom, 3-bathroom Hillsdale summer rental offers a bright, contemporary interior with curated antiques on 8+ private acres featuring streams, a pond, and historic barns. The home includes a modern open kitchen with Caesarstone countertops and state-of-the-art appliances, which flows directly to a bluestone patio and stone terrace equipped with an outdoor grill for alfresco dining. Centrally located, the property is less than 10 minutes from the Hawthorne Valley organic market and Hillsdale's shops, farmers' market, and local brewery. Outdoor recreation is nearby at Catamount's zip line, Copake Lake, and Bash Bish Falls, while the neighboring towns of Millerton and Hudson provide easy access to the Harlem Valley Rail Trail, fine dining, and Amtrak. This residence serves as a perfectly positioned seasonal retreat combining rural privacy with convenient access to the best of the Hudson Valley and Berkshires. Flexible, month-to-month or for the entire summer. Fully equipped, all utilities, Wifi, and ground maintenance included. Tenant required to carry liability and renter's insurance. Property also listed on One Key MLS service #989409
…By William Pitt Sotheby's International Realty
August 2023 - Hip 1820 country home with Scandinavian interior design touches. The living room and the den with fireplace have both an abundance of natrual light from south facing windows. Dining room leads to a brick patio from where your eyes can wander the land. Large eat in kitchen with ample pantry and laundry. Fantastic screened in porch overlooks a large pool with bountiful vegetable gardens. Lovingly cared for property offers lavish space with 3 more guest bedrooms, office area and two full baths upstairs. Mainly wood flooring and lots of natrual light fill this gracious home. Truly a Berkshire retreat for everyone to enjoy.
…By William Pitt Sotheby's International Realty
Fully renovated two-bedroom cottage in the hamlet of Pine Plains, offering the convenience of in-town living just steps from the center of this charming Hudson Valley community. The home features a bright, welcoming interior with an updated kitchen and bath, two well-proportioned bedrooms, and the convenience of an in-home washer and dryer. Modern updates throughout blend cottage charm with contemporary finishes. From this central location, enjoy a short walk to some of Pine Plains' favorite destinations, including the acclaimed Stissing House restaurant and performances and events at the Stissing Center for Arts & Culture. Hiking at Stissing Mountain and the trails of Thompson Pond Preserve are just minutes away. Nearby farm stands and dairies, including Chaseholm Farm and Ronnybrook Farm Dairy, highlight the region's agricultural heritage. Conveniently located within easy driving distance of Rhinebeck, Hudson, Millbrook, Amenia, and Millerton, offering access to some of the Hudson Valley's best dining, shopping, and cultural destinations.
…By Four Seasons Sotheby's International Realty
This classic picture-perfect contemporary home features an open floor plan, cathedral ceilings, updated everything, and an in-ground heated pool. In addition, this outstanding Alford property is located on 5.46 acres, and it is less than a 10 minute drive to the center of Great Barrington with all of that town's fabulous restaurants, shops and food stores. The screened porch overlooks a recently constructed stone patio and deck with a built-in top-of-the-line gas grill and an easy access to the fabulous in-ground heated pool. If you are looking to escape to the ideal rental home, this listing should be Option #1. The famous real estate saying about location, location, location could have this property as its photography definition. Already rented for July/August 2025 at much higher rates.
…By William Pitt Sotheby's International Realty
Beautifully and completely renovated, second floor, light filled, two-bedroom apartment with hardwood floors, air conditioning, new kitchen and tiled bathroom. Up the stairs into the open living space with high vaulted ceilings. A wonderful kitchen with tiled floor, backsplash and counters, an extra-large sink in front of windows overlooking the garden. Brand new appliances including a dishwasher. Dining area with built in additional storage and more windows. Step out onto the balcony, facing southwest for wonderful light and sunsets. Perfect spot to relax, dine or work remotely. New windows, extra insulation along with very energy efficient heating/air conditioning system and LED lighting. In unit washer and dryer, spacious closets, wired for internet, off street parking and garden space in back. Locked storage space for each apartment in the dry basement. A short walk to Amtrak and two blocks to Warren Street shops, cafes and restaurants. Or a quick stroll to the Hudson River Waterfront Park or the fabulous weekly Farmers Market. Tenant pays heat and electric. Rental application, satisfactory credit report and references. No smoking on property. One dog with landlord approval. Renter's insurance required.
…By William Pitt Sotheby's International Realty
Millerton, NY — Fresh, modern ground-floor living with village convenience Be the first to enjoy this gut-renovated (2023-2024) ground-floor, walk-out apartment set on a one-acre village lot. Oriented toward a beautiful ridgeline just above the Harlem Valley Rail Trail, the home captures year-round sunset views. A covered porch/mudroom entrance keeps rain and snow outside, while a second entry opens to a central hallway that connects the kitchen, living room, and bedroom for an easy, practical flow. The kitchen is crisp and functional with a brand-new gas range and vent hood, new flooring, and ample cabinetry for pantry and storage needs. The fully rebuilt bathroom features a vanity with integrated storage, new lighting, and a sleek glass corner shower. In the bedroom, you'll find brand-new floors and windows, newly installed heating, and a double-insulated exterior door to enhance comfort and efficiency throughout the seasons. A detached garage is included and is perfect for bicycles, seasonal gear, or an outdoor maker space. From the property, it's an easy three-minute walk to Millerton's corner amenities—a diner, pizzeria, tea house, Chinese restaurant, florist, and consignment shop—and just a few more minutes to boutiques, additional restaurants, art galleries, a coffee shop, movie theater, library, CVS, bank, and a gas/convenience store. This is a strictly non-smoking property, ideal for one or two occupants seeking a turnkey home with storage, sunsets, and an effortless village lifestyle.
…By William Pitt Sotheby's International Realty
A Sweet and Sunny antique available for the Spring (mid-May thru July 1) and/or Academic Term - Set on 1.4 acres along a desirable road in Lakeville, this 1700s home perfectly blends modern comforts with historic character. Step inside to find three bedrooms and two bathrooms across two floors. The living room, anchored by a massive hearth, is the center of the home. The galley kitchen, with an adjoining mudroom, offers plenty of storage and opens to the outdoor deck- perfect for dining and entertaining. A cozy den and the option for a first-floor primary suite with an en-suite bathroom complete the main level. Upstairs are 2 light-filled bedrooms and a spacious full bathroom. The original details and hardwood floors throughout the home add warm and rustic charm to this bright and airy home. Conveniently located minutes from local private schools and easy access to Salisbury, 30 Indian Mountain Road is the epitome of effortless country living.
…By William Pitt Sotheby's International Realty
A Sweet and Sunny antique available for the Academic Term - Set on 1.4 acres along a desirable road in Lakeville, this 1700s home perfectly blends modern comforts with historic character. Step inside to find three bedrooms and two bathrooms across two floors. The living room, anchored by a massive hearth, is the center of the home. The galley kitchen, with an adjoining mudroom, offers plenty of storage and opens to the outdoor deck- perfect for dining and entertaining. A cozy den and the option for a first-floor bedroom with an en-suite bathroom complete the main level. Upstairs are 2 light-filled bedrooms and a spacious full bathroom. The original details and hardwood floors throughout the home add warm, rustic charm to this bright, airy home. Conveniently located minutes from local private schools, the center of Salisbury, and all that Litchfield County has to offer.
…By William Pitt Sotheby's International Realty
Rustic Chic Barn, renovated as an energy efficient home, consisting of 2 large open floors w/ a Queen Bed on 1st floor, and 2 more Queen Beds on the 2nd Floor. A group, or two couples should be comfortable sharing this unique space. Fully equipped kitchen w/gas stove, washer & dryer. There is a separate toilet with sink, and a single shower with sink. Radiant floor heating throughout. Full music set up w/instruments & PA on 2nd floor. 1GB Wifi, smart thermostat, smart lighting, AC window units on each floor, 2x 42' TV w/firestick & cable. There is also a full house Auto-Backup Generator. Ambient light moves through the building during the day & no artificial lighting is needed. Excellent star gazing, with spectacular views of the Milky Way on a clear night. Circular driveway lined with Apple Trees leads to a large stone patio w/BBQ as well as an above ground fire pit. Summer guests have access to a canoe, blueberry, peach and apple groves, as well as a Lakeville lake facility and parking pass. The Hotchkiss 9 hole golf course is 1 mile away. Winter guests have 3 local ski resorts 30-45 minutes away plus a ski jump in Salisbury. Hotchkiss, Indian Mountain, Salisbury private schools, Lime Rock Park Racetrack & cultural activities & shopping in Millerton, NY are all within a 5 mile radius. Privacy, amazing marsh views w/abundant bird watching, wildlife, country living, comfort & convenience awaits you. Field Card states 1 Bedroom, there is a Bed on the first floor & 2 Beds on the 2nd floor - open floor plan
…By William Pitt Sotheby's International Realty
Phenomenal spacious contemporary. Freshly renovated with detail to light and open space. First floor bedroom with bath. Two living areas. Large eat-in kitchen. Spacious back deck and front porch. Upstairs has 4 more bedrooms. Primary suite has soaking tub. Beautiful pasture views in a sweet neighborhood on dead end street. Minutes from downtown Great Barrington. Close to all your favorite Berkshire attractions.
…By William Pitt Sotheby's International Realty
This stunning mid-century 3-bedroom, 3.5-bathroom house is indeed a hidden gem nestled in the sought-after village of Mill River. Offering a harmonious blend of tranquility, luxury, and convenience, this property promises an unparalleled living experience. Upon entering the grounds, you'll immediately be captivated by the picturesque setting. Sunlight filtering through the woodlands casts a gentle glow over the meticulously manicured gardens, creating an oasis of complete privacy and serenity. The home itself is a masterpiece of modern design, exuding elegance and sophistication at every turn. Each of the three spacious bedrooms boasts its own newly renovated en-suite bath, ensuring comfort and privacy for residents and guests alike. Additionally, a versatile sunroom offers the flexibility to serve as additional guest space or a cozy retreat for relaxation. At the heart of the home lies a double-sided stone fireplace, which serves as both a focal point and a source of warmth and comfort for cooler evenings in the open-plan kitchen, living, and dining area. This seamless integration of spaces fosters an inviting ambiance, perfect for gatherings with loved ones or simply unwinding after a long day. Moreover, the property boasts additional amenities such as a Steamshower, outdoor sauna, high-speed internet and is pet-friendly, enhancing the overall living experience. In summary, this exceptional property offers a rare combination of elegance, comfort, and convenience, making it the ultimate retreat for enjoying the summer months in the idyllic village of Mill River. Whether you seek a peaceful sanctuary or a stylish space for entertaining, this home is sure to exceed your expectations and provide an unforgettable living experience.
…By William Pitt Sotheby's International Realty
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These agencies offer a selection of luxury properties location at Hillsdale. Feel free to contact them for personalized assistance.