Pine Plains NY Real Estate & Homes for Rent

Spectacular Views From New Renovation - A long driveway approach brings you to this beautifully renovated home with gorgeous distant southern views. Features include a new Kitchen with soapstone counters, Pantry, large Living Room/Dining Room with propane fireplace and vaulted ceiling, 3 bedrooms and 2 Full Baths, and 2 front Porches facing the view. Single-floor living in a fabulous location just a short hop to the Village of Millerton, NY, the Wassaic Train Station, and Lakeville and Sharon, CT. Be sure to see this outstanding rental!

Utterly charming country home on a lovely road only minutes from the villages of Lakeville, CT and Millerton, NY. This home is filled with character, sleeps 8 and offers central air conditioning. A large lawn, patio, gazebo and sunset views complete the package. Utilities included except trash removal, tv is streaming. Tenant pays a one time cleaning fee of $600. Available for August only 8/1/24 -9/3/24.

Recently built private Litchfield county retreat. Imagine spending your summer in this beautiful home with stunning hillside distant views. Enjoy watching the sunset with family and friends on this gorgeous wrap around deck. As you enter the home the first thing you notice is the sunshine flooding the entire open concept main level. The living room provides lots of space for gathering with two full size sofas. Friends and family can gather at the large dining table which is adjacent to the chef's kitchen. The kitchen provides new stainless steel appliances, and plenty of counter space for preparing meals. You will notice that almost every room in the house has a stunning view of the landscape that surrounds the house. This home features plenty of room to host guests. The primary suite is on the first level featuring a beautiful en suite bathroom. The ground level floor has two additional bedrooms with a shared living room as well as full bathroom. The upstairs level features a spacious office as well as an additional sunny bedroom and a large full bathroom. This home is nestled in a private location but is moments from both Lakeville and Millerton for shopping and restaurants. All utilities included. Tenant is responsible only for liability insurance, lake pass & credit check. Join us this summer in the Litchfield Hills and you can understand why people instantly fall in love with the quiet corner. AVAILABLE JULY $14/m & AUGUST (through 9/3) $15.5k/m ONLY.

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 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, 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.

Salisbury Summer Rental with Pool - This private summer retreat with a heated pool and spa is ideally located on 4 park-like acres with stately trees and a level lawn at the end of a private lane for ultimate relaxation. This modern-feeling home offers open-concept spaces enhanced by high-end finishes, expansive windows, and extraordinary craftsmanship. Infused with natural light the airy gourmet kitchen joins the inviting living and dining rooms, both with wood-burning fireplaces, and invites you outdoors to a bluestone patio area and separate screened-in porch overlooking the pool area. The 1st-floor bedroom suite, office/study, and greeting room complete the first floor. The second floor has a fabulous primary suite and offers two abundantly spacious walk-in closets and a stunning primary bathroom with radiant heated floors. In addition, there are two additional bedrooms with a shared bath and a generous laundry room. Located within minutes of the villages of Salisbury, Lakeville, and Millerton. Enjoy summer 2024 in the Litchfield Hills!

Affordable summer rental, in a cozy and meticulously maintained three-bedroom, two-bathroom cottage. A quiet country lane midway between Salisbury and Millerton village centers. Well-maintained yard with mature plantings, patio. Walking distance to town beach. Short drive to theater, restaurants, farm markets, shopping. An abundance of outdoor activities, including boating, fishing, tennis, pickleball, golf, basketball, swimming, hiking. Available from Memorial Day weekend through Labor Day weekend for $15,000; or $5,000 monthly for June, July, August.

Elegant Historic Home with Fireplaces for Winter Rental - Available January 1 -June 30, 2024. - A very special renovated Historic Colonial is offered with 3 Bedrooms, one on the Main Floor, 2 Full Baths, a large Living Room with a fireplace, and a separate TV Room or Den/Office. The Main House is offered for $4,500 per month thru May 2024. Additionally available is the 2-bedroom Cottage with a Great Room, Kitchenette and Full Bath. The Main House and the Cottage may be rented together for a total of $5,750 per month thru May 2024. The Main House is available for month of June 2024 for $6000. Close to private schools, Lakeville Lake, the Villages of Salisbury, Lakeville, Sharon CT, and Millerton, NY, the Wassaic Train Station with trains to NYC, and winter ski slopes. Fabulous!

Enjoy this Lakeville retreat perched on top of a private road for the academic year. This home is sophisticated, yet comfortable. No expense was spared in the recent renovation. The new kitchen features all new appliances including a five burner Bertazzoni gas range. The kitchen features both a breakfast nook and dining table so multiple entertaining options. Off the kitchen is a laundry room and powder room featuring chic Cole & Sons wallpaper. A convenient floor plan the living room is located off the kitchen and is is flooded with sunlight. Head upstairs to four bedrooms, two full baths, and an office. The primary offers an en suite bathroom with both a soaking tub and separate shower, and a smart mirror featuring time and temperature. The lawn is level great for entertaining or a game of catch. Off the front door is a deck where you can relax and read a book at your own private oasis. Out back features another expansive deck great for entertaining. Minutes from Lakeville, Salisbury, Millerton. Close to shops, schools, Sharon Playhouse, Lime Rock and skiing. Rate is based on academic year rental.

Available early September 2024 to early June 2025 @ $4250 per month. Shorter terms considered. Fabulous 4 bedroom contemporary waterfront home with amazing lake views, kitchen/family room combo (FP not to be used), dining/living room combo with fireplace, sunroom, and 3 full and 1 half baths. About 25 minutes to skiing at Mohawk Mountain, about 30 minutes to Catamount ski area in Hillsdale NY and about 45 minutes to Butternut ski area in Great Barrington, Mass. Minutes to the villages of Lakeville and Salisbury and about 20 minutes to train service to NYC. Guest cottage not included. Will be winterized and not in use. Use of one bay in detached garage.

June $8k; July $8,500; August $8,500. Annually $5,900/month. Well Located 5 Bedroom/2.5 Bath Colonial. Fresh & Clean & Ready! Totally Private & Quiet Near Villages of Salisbury & Lakeville. Great Eat-In Kitchen Tricked Out with Appliances. Main floor Guest Bed or Den. Generous Living Room with Fireplace & TV. Multi-Zone Efficient Central AC. Main Floor Cozy Den or Office with TV. Primary Bedroom with Full Bath. Lovely Screened Porch & Stone Terrace Overlook the Private Grounds. 2-Car Attached Garage. Easy Access to Area Hiking, Lakes & Summer Fun

Annual Furnished Rental: $5,900/month. Well Located 5 Bedroom/2.5 Bath Colonial. Fresh & Clean & Ready! Totally Private & Quiet Near Villages of Salisbury & Lakeville. Proximate to Hotchkiss; Salisbury, Indian Mountain & other Area Schools. Great Eat-In Kitchen Tricked Out with Appliances. Main floor Guest Bed or Den. Generous Living Room with Fireplace & TV. Multi-Zone Efficient Central AC. Main Floor Cozy Den or Office with TV. Primary Bedroom with Full Bath. Lovely Screened Porch & Stone Terrace Overlook the Private Grounds. 2-Car Attached Garage. Easy Access to Area Hiking, Lakes & All Season Fun

JULY RENTAL WITH DAZZLING VIEWS - $18,000/month: June 30 - July 30, 2024 - This 4-Bedroom, 4-Bath light-filled home will immerse you in the heart of Litchfield County this summer. Conveniently located to the villages of Lakeville and Salisbury, yet the benefit of beautiful countryside views and privacy. A back deck is ideally suited for indoor-outdoor living. Nearby Amenities include: Lakeville Lake; Millerton, NY; Twin Lakes; Catamount Aerial Park; Appalachian Train Hiking; Sharon Audubon

Spend a season in Salisbury CT in this completely renovated 3 bedroom/3.5 bath home. Available for up to four months (minimum of three) between September 2024 - June 2025. This turn-key home -- flooded with light, tastefully furnished, and surrounded by nature - does not have a bad angle. The property has a large side porch, over-looking Pettee Brook which provides a serene setting to relax in the freshest of air. Spend your time exploring the Litchfield Hills surrounded by inspiring art and classic touches. The floorplan, while open and airy, also gives everyone space to be independent in the home, and enjoy the privacy of en-suite bathrooms. Close to skiing - Butternut, Mohawk, Catamount. Close to IMS, Salisbury School, Hotchkiss, Berkshire. Spend the fall surrounded by the changing colors of New England. Come in the winter for ice skating, skiing, and holiday festivals. Or the spring, when the northwest corner comes alive with the yellows of forsythia and green rolling meadows. The hardest part will be choosing which season to stay.

Lakefront Summer Rental- Available: July & August @ $20,000/month. Enjoy lakefront living from this ideally situated 3-bedroom, 3-bath home on Lakeville Lake. The stunning architecture of this home is thoughtfully designed to frame the lake views from both the upper and lower levels, giving nearly every room a water view! The first floor includes an open-concept Living Room with a fireplace and a Dining Room - both of which are open to the raised deck overlooking Lakeville Lake. The Kitchen opens to a back courtyard for grilling and more intimate settings. The Primary Suite and another Bedroom and Full Bath off the hall complete the main living level. The Lower Level opens to a Family Room with sliding doors out to the yard and lake. Three additional Rooms and a Bath off the Hall on this lower level create space for everyone! Minutes to the villages of Lakeville and Salisbury, a stone's throw to the Lakeville Town Grove (beach), nearby the Salisbury Railroad Ramble biking and walking path, and all of the area's local restaurants and shops. 20 minutes to Wassaic Station.

Winter Furnished Rental - Available: Nov. 1, 2024 - April 30, 2025 - This beautifully restored antique is on a sweet side street in Lakeville, CT. Features include 3 lovely Bedrooms, 2 full baths, a Living Room with a gas fireplace, a Library, a marble-countered Kitchen, central air-conditioning, and a lovely Terrace and lawn to the Brook, which runs along the back of the property. The Bike Path entrance, just down the street, connects with the shops, library, and restaurants in the village area of Salisbury and with the Town ballfield and tennis courts - and then, it is only a short way to Lakeville Lake. Also, close to Millerton, NY, and the Wassaic Train Station with Metro-North to Grand Central.

LAKEVILLE VILLAGE RENTAL - Available: July 2024 - Located in the village of Salisbury within walking distance to restaurants, galleries, and Lakeville Lake is this well-designed fun summer village rental. New Chef's Kitchen with marble island, separate Dining, and Living Rooms, and additional Study with wood-burning fireplace on the first floor. Four Bedrooms including the Master Suite are on the second level and a modern loft is on the upper level. Great, fun house to enjoy and within minutes to Hotchkiss, Indian Mountain, and Salisbury Schools.

Welcome to your new home in the picturesque town of Sharon, Connecticut! This charming two bedroom, one bathroom apartment is the epitome of comfort and style, offering a perfect blend of modern amenities and New England charm. Upon entering, you'll be greeted by a spacious kitchen that boasts both functionality and style. The living area is equally inviting, providing a generous space for relaxation and socializing. Large windows flood the room with natural light, creating a warm and inviting atmosphere. Whether you're unwinding after a long day or hosting friends for a cozy get-together, this living space is sure to become the heart of your new home. The two bedrooms offer a peaceful retreat, each designed with comfort in mind. With ample space, these bedrooms are the perfect escape for restful nights and lazy Sunday mornings. Beyond the comforts of your new home, Sharon, Connecticut, offers a wealth of recreational activities to enhance your lifestyle. Embrace the natural beauty of the area with hiking and biking trails that showcase the stunning landscapes. Take a leisurely stroll down the town's charming green, enjoy the cafes, and cultural attractions. In Sharon, you'll find beautiful landscapes and endless hikes just moments away.

This fabulous, converted barn is the guest house on the owners 40-acre property. Located on a quiet dead-end road within walking distance to the lovely village of Sharon. With approximately 2,500 square feet of beautifully-appointed living space and an expansive open floor plan, everything (from the construction of the living space to the furnishings) is new. In addition to a modern kitchen with counter seating for four, a spacious dining area, a very large living/great room and a gas fireplace, two bedrooms and 2.5 bathrooms with radiant heat in the floors & a sizable mud room, there is a laundry room, pantry, garage space for 1 car, and full-house generator. Tenants are welcome to enjoy the in-ground, gunite, salt water pool. A unique luxurious rental it is conveniently located at the center of all that Litchfield, Dutchess and the surrounding Counties have to offer; just minutes to some of the areas most lovely towns including Millbrook, Millerton, Lakeville, Salisbury, Kent, Washington and Great Barrington. A lovely drive to Rhinebeck, an easy 2 hour drive to Manhattan and 10 minutes to Metro North trains to Manhattan. Landlord is responsible for wifi, mowing/landscaping, garbage disposal Tenant is responsible for electric. propane, cable tv and house cleaning No pets allowed Candidates must have excellent references & credit

This fabulous, converted barn is the guest house on the owners 40-acre property. Located on a quiet dead-end road within walking distance to the lovely village of Sharon. With approximately 2,500 square feet of beautifully-appointed living space and an expansive open floor plan, everything (from the construction of the living space to the furnishings) is new. In addition to a modern kitchen with counter seating for four, a spacious dining area, a very large living/great room and a gas fireplace, two bedrooms and 2.5 bathrooms with radiant heat in the floors & a sizable mud room, there is a laundry room, pantry, garage space for 1 car, and full-house generator. Tenants are welcome to enjoy the in-ground, gunite, salt water pool. A unique luxurious rental it is conveniently located at the center of all that Litchfield, Dutchess, Columbia and Berkshire Counties have to offer; just minutes to some of the areas most lovely towns including Millbrook, Millerton, Lakeville, Salisbury, Kent, Washington and Great Barrington. A lovely drive to Rhinebeck or Hudson, an easy 2 hour drive to Manhattan and 10 minutes to Metro North trains to Manhattan. Landlord is responsible for wifi, mowing/landscaping, garbage disposal Tenant is responsible for electric. propane, cable tv and house cleaning No pets allowed Candidates must have excellent references & credit

5-BR Salisbury Village Home - Available: $8000/month for June & $12,500/month of July - This newly renovated 5-bedroom, 3.5-Bath home brings you to the heart of Salisbury for an ideal country retreat. A gorgeous Chef's Kitchen sits at the heart of the home, joining the Dining Room that opens to the Screened Porch and fenced yard. A Living Room with a Fireplace, Library, and spacious Mudroom entry complete the first floor of this home. The second floor features the Master Suite, two additional bedrooms that share a Hall Bath, and a Laundry that is filled with sunlight. The Third Floor boasts two additional bedrooms and a full bath with a clawfoot soaking tub. Enjoy in-town activities, the Salisbury Bike Path, Lakeville town Beach, Twin Lakes boating, and the quintessential charm of a summer home right in the village center. Short distance to White Hart Restaurant, Provision Cafe, Sweet Williams Bakery and Cafe, Labonne's Market, boutiques, Scoville Memorial Library, Lakeville Town Grove, Appalachian Trail hiking, Lion's Head hiking Also Nearby: Millerton, NY; Great Barrington, MA; Sharon, CT.

5-BR Salisbury Village Home - This newly renovated 5-Bedroom, 3.5-Bath home brings you to the heart of Salisbury for an ideal country retreat. A gorgeous Chef's Kitchen sits at the heart of the home, joining the Dining Room that opens to the Screened Porch and fenced yard. A Living Room with a Fireplace, Library, and spacious Mudroom entry complete the first floor of this home. The second floor features the Master Suite, two additional bedrooms that share a Hall Bath, and Laundry that is filled with sunlight. The Third Floor boasts two additional bedrooms and a full bath with a clawfoot soaking tub. Enjoy in-town activities, the Salisbury Bike Path, Lakeville town Beach, Twin Lakes boating, and the quintessential the charm of a summer home right in the village center. Short distance to White Hart Restaurant, Provision Cafe, Sweet Williams Bakery and Cafe, Labonne's Market, boutiques, Scoville Memorial Library, Lakeville Town Grove, Appalachian Trail hiking, Lion's Head hiking Also Nearby: Millerton, NY; Great Barrington, MA; Sharon, CT.

AVAILABLE: July 1, 2024 - August 30, 2024 4-BR SALISBURY VILLAGE HOME - This newly renovated 4-Bedroom, 4-Bath home brings you to the heart of Salisbury for an ideal summer retreat. A renovated Kitchen, Living Room with Fireplace, Family Room, Dining Room, Sun Porch, and First Floor Bedroom with Bath complete this home's first floor. 3 Large Upper-Level Bedrooms, each with its own Bath, offer enough space for everyone! Pets are considered on a case-by-case basis. Enjoy in-town activities, the Salisbury Bike Path, Lakeville town Beach, Twin Lakes boating, and the quintessential charm of a summer home right in the village center. Short distance to White Hart Restaurant, Provision Cafe, Sweet Williams Bakery and Cafe, Labonne's Market, boutiques, Scoville Memorial Library, Lakeville Town Grove, Appalachian Trail hiking, Lion's Head hiking.

Spend your summer in this amazingly elegant home perched in natures wonderland minutes from the center of picturesque Salisbury. No expense was spared in this carefully curated home of design enthusiasts dreams. This homes light and airy nature is welcoming and comfortable. The large floor to ceiling windows provide amazing light and give you the sense that you are residing in a tree house. Plenty of rooms for guests: three bedrooms with King beds (one of them can be converted to two twins), as well as a portable crib. The house features 3 full bathrooms, one on each floor. The chefs kitchen featuring a gas range will make entertaining a breeze. Host your guests at the large dining table, outside on the wrap around deck or on the expansive lawn. Roast marshmallows in the evenings at the firepit. The lower level provides an additional entertaining space that could be used as a playroom, media room or additional guest quarters (with a pull out bed). As a summer resident of Salisbury, you have access to Lakeville Lake including swimming, basketball, playground. Spend your days exploring nearby Great Barrington, Sharon, Salisbury, and Millerton. Head to Tanglewood on the weekends for unbelievable live performances or to nearby Sharon Playhouse for local theatre. All utilities included. Tenant is responsible only for liability insurance, lake pass & credit check. Available: 6/28-9/3 ($15k per 4 weeks)

Fabulous Summer or Short-term Rental. Enjoy this ultra-private French Country-inspired home approached by a long winding drive through the woods. Ideal as a short-term rental and only 2 minutes to the center of Sharon! Lovely hilltop home has a gracious entry leading to a living room with fireplace, and dining room. Open concept kitchen and breakfast room make for easy conversation while cooking. 3 sunny bedrooms with large picture windows, 2.5 baths, and cozy study complete this comfortable one-level layout. Bluestone patio is perfectly positioned for outdoor dining to capture sunsets across the level and expansive backyard. Close to Hotchkiss, Salisbury School, Millbrook School and Indian Mountain School. Easy drive to Dutchess County. Less than 15 minutes to Wassaic train and only 2 hours to NYC. Ideal country retreat! Available for various time periods all year round! WiFi and Internet.

Fabulous winter/ski weekend retreat or short-term rental. Enjoy this ultra-private French Country-inspired home approached by a long winding drive through the woods. Ideal as a short-term rental and only 2 minutes to the center of Sharon! Lovely hilltop home has a gracious entry leading to a living room with fireplace, and dining room. Open concept kitchen and breakfast room make for easy conversation while cooking. 3 sunny bedrooms with large picture windows, 2.5 baths, and cozy study complete this comfortable one-level layout. Bluestone patio is perfectly positioned for outdoor dining to capture sunsets across the level and expansive backyard. Close to Hotchkiss, Salisbury School, Millbrook School and Indian Mountain School. Easy drive to ski areas including Mohawk, Catamount and Butternut as well as Dutchess County. Less than 15 minutes to Wassaic train and only 2 hours to NYC. Ideal country retreat! Available for various time periods all year round! ($8,000/mo for June, July or August 2024)