Dover Plains NY Real Estate & Homes for Rent

This beautifully renovated Revolutionary War Era home is a rare find in Dutchess County. It is a cherished gem from the Georgian period and is highly regarded in the Millbrook region. Situated on a spacious, manicured and private 120-acre property overlooking a pond, the updated home offers all the amenities needed for a perfect summer vacation in upstate New York. An oversized family room makes for memorable gatherings, the expansive eat-in kitchen opens up to a covered porch, gardens (enhanced with recent plantings), and an inviting inground saltwater pool; perfect for cooling off in the summer heat. Additionally, there is a gym for those who enjoy staying active. Enjoy a large primary suite and four well-appointed guest bedrooms and 5.5 bathrooms. For those who love to entertain, the formal dining room and library are perfect spaces for hosting summer gatherings, as is the outdoor patio for entertaining and al-fresco dining. Upon request, there is also a newly refurbished apartment available. The downtown area of Millbrook and the Dover Plains train station are just a short distance away, adding to the convenience and charm of this exceptional property.

Spacious one bedroom accessory apartment located off a quiet country road in a beautiful setting. Great natural light, new windows, new bamboo floors. Sliding doors off the living room lead to a deck and fantastic yard. The primary bedroom has a large en-suite full bathroom. Nice sized kitchen, separate laundry room with washer and dryer and half bath complete the unit. Heat is included in the monthly rent. Pets are welcome. The unit has 200 amperage service and central air conditioning. Storage available in the attic. Ideal location, five minutes to Metro North, restaurants, and shopping in Wassaic and Amenia. Less than 15 minutes to Kent, CT another chic fabulous town with shopping, stores, and restaurants.

Academic rental. Inquire for summer pricing. Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate on 389 acres, straddles Kent, CT and Amenia, NY. Experience this truly magnificent classic stone and shingle manor house sited perfectly to experience lush sunsets and fairytale mists with the upmost in privacy. Only eight minutes from the center of Kent and less than two hours from New York City, access is via a private gated road that winds through trees, past old stonewalls with glimpses of open meadow and a serene pond. Spacious rooms perfect for entertaining include a large great room with a soaring peaked ceiling and a 20' stone fireplace, a sun-filled formal dining room with three exposures and a huge chef's kitchen with a massive stone fireplace and adjoining catering kitchen, a marble paneled powder room and mud room. Beautiful reclaimed chestnut floors, exquisite detailing and numerous banks of windows and French doors make this an unparalleled home. The master bedroom suite--which includes paneled library, separate office workspace and large bathroom and dressing areas--is located on the first floor in a private wing of the house. Of course, there is a billiard room, complete with mini-kitchen and bar, full bath and adjoining guest bedroom/office area. A second-floor master-sized guest room has a beautiful bath with soaking tub and deck that faces the amazing mountain views. Two bedroom suites with ensuite bathrooms, a charming peaked children's bedroom and a well-appointed office area complete this floor. The extensive and recently renovated lower level contains a media room with 9' screen, half bath, wine tasting room and wine cellar with adjoining prep kitchen for large gatherings. In addition, there is a sunny laundry room, craft room and gym with ground level access. Beautiful stone steps lead down to a stunning natural stone pool and a tennis court. There is also a two-story pool house with spiral staircase, full kitchen and full bath. The expansive two building maintenance court also contains a pumping system for irrigating the lawns and gardens.

SEASONAL RENTAL. Straight out of a storybook is this enchanted log cabin secluded in the forest overlooking the Webatuck Creek. The primary bedroom with its own fireplace overlooks the waterfall and gardens. There are two additional bedrooms, one with a queen bed overlooking the creek and the other reached by its own staircase has twin beds. There are two baths, one with an adjoining a room just for a soaking tub. This period home, built in 1933, affords a rustic allure with classic furnishings and original hardware yet many conveniences of the modern world. So many charming spaces to enjoy, from the elegant great room with soaring ceilings and stone fireplace, to the delightful porch where one would want to curl up for a nap to the sounds of cascading water. This magical setting of 8.2 acres, is located directly on the creek overlooking a waterfall. Enjoy fly fishing or a cool dip in the summer. The property exudes peace and tranquility while located just five minutes from the Metro North train and convenient to Kent and Sharon, CT as well as Millbrook. Nearby amenities include Harlem Valley Rail Trail, Silo Ridge Field Club, Millbrook Hunt Club, Mashomack Club, the drive-in movie theater, Lakeville Lake, Troutbeck, and all of the area's incredible outdoor recreation, restaurants and shops. No pets. References & credit check required.

Great one bedroom cottage in great location, close to train village of Millbrook, Wassaic, Its a great home completely redone No Pets

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open meadow, and serene pond. Spacious rooms perfect for entertaining include a great room with a soaring peaked ceiling and a 20' stone fireplace, sun-filled formal dining room with three exposures, huge Chef's kitchen with a massive stone fireplace and adjoining catering kitchen. Beautiful reclaimed chestnut floors, exquisite detailing and banks of windows and French doors. The paneled library, office and master bedroom suite are located on the first floor in a private wing of the house. Billiard room, complete with mini-kitchen, full bath and adjoining guest bedroom. Second-floor master guest room with soaking tub and deck with views. Two bedroom suites with ensuite bathrooms, charming children's bedroom and an office complete this floor. Lower level with a media room, half-bath, wine tasting room and wine cellar with adjoining prep kitchen. Laundry room, craft room and gym. Beautiful stone steps lead to a stunning pool & pool house with full kitchen & tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

2 Bedroom apartment in historic Bulls Bridge Inn. Located across the street from the Appalachian Trail with River access for outdoor enthusiasts. Close to the historic Kent Covered Bridge. Enjoy a stroll in the charming downtown of Kent or explore Kent Fall, both just a short drive away. If you're hungry, don't leave home, go downstairs and enjoy amazing food and drinks in the Bulls Bridge Inn & Tavern. All brand new appliances. Rent is $1700/mo plus a monthly fixed charge of $300/mo that includes electric, heat, hot water, laundry, refuse, snow removal and maintenance. Pets friendly.

Available for August 2024. $30,000. Adult Summer Camp. 18th Century Reproduction Colonial with smashing Guest House + Pool on 10+/- private acres in highly desirable South Kent Location. Must see!

Spend August enjoying this spectacular, light-filled, tastefully furnished, spacious, 4 bedroom, 4.5 bath modern farmhouse sitting high on a hill with breathtaking, 360-degree views and complete privacy. No matter where you look and from every room in the home, the views are stunning. The home boasts an open floor plan, 3 fireplaces and lots of glass that brings the beauty of the outside in, and outside enjoy a fabulous blue stone patio and an infinity pool, worthy of a 5-star resort. The front porch of the home offers another stunning place to sit, enjoy a meal or a drink, watch the sun set and take in the incredible views. It is located on a scenic quiet road in Duchess County, and is just minutes to Sharon and Kent, CT and other beautiful Litchfield County towns, and close to Millbrook & Millerton NY and all that the Hudson Valley has to offer. It is a truly special place and the perfect summer rental. Available August 2nd- September 2nd, 2024 for $20,000. Well-behaved dogs will be considered.

The most charming Millbrook rental, 20 Linden Court, is privately situated on .75 acres and only one mile to Franklin Avenue. This is an 1863 compound with a 3 bedroom, 1.5 bathroom main house, a pool, and a separate pool house / studio with a kitchenette, full bath, and lots of room to entertain. The main house features a stylish and functional kitchen, a powder room, a dining room with French doors leading to a beautiful outdoor deck, a living room, and separate sitting room. All rooms are chicly furnished for the most discerning tastes. There are three bedrooms plus a dressing room on the second floor including a full bath with a soaking tub. The pool house, replete with kitchenette and full bath has two rooms perfect for a home office, art studio, yoga room, or the occasional overnight guest. The pool is situated between the main house and pool house and is attractively decked. The property is fully landscaped and lighted for absolute enjoyment in outdoor entertaining. Tenant pays all utilities.

Summer 2024! June $20k; July $23k, Aug $27k. Utterly Charming Colonial on Quiet Road Near Village & Metro North. Brand New High-End Eat-in Kitchen. Fabulous Pastoral & Distant Views. Cell Service! Excellent Wifi! Screened Porch. Stone Terracing. 4 Bedrooms, 3.5 Full Baths. Renovated Modern Primary Bath. Central AC. Screened-Porch. Lovely Retreat from NYC. #EscapeNYC

This two story condo is located only a few short blocks from the center of the Millbrook Village. Restaurants, shops, library, park and schools are all within walking distance. The Alden Terrace community is comprised of just 32 units set in attractively landscaped grounds. Each unit has a designated parking spot and there are ample guest spots. This unit has been completely painted and is move in ready. In addition to the kitchen, the first floor features an entry foyer, dining room/living room with fireplace, powder room and laundry. The second floor has two bedrooms and two full baths. The landlord pays the common charges which cover landscaping, snow removal and garbage collection. Tenant is responsible for electric and water/sewer. Minimum one year lease.

FOR RENT - Fabulous luxury duplex condominium rental within walking distance to Millbrook village. This spacious, approximately 1650 sq ft apartment is light-filled with vaulted ceiling and an open floor plan. Custom kitchen with granite countertops and stainless steel appliances opens up to a dining/living room area with huge windows and double height ceilings. There is also a powder room and one bedroom with a full bathroom en suite on the first floor and the primary bedroom suite on the second floor. There are built in book cases on the second floor loft area, the perfect place for an office or reading nook. Hardwood flooring throughout and a washer and dryer, as well as a small deck at back of the apartment overlooking the back yard, a detached 1 car garage and an outdoor parking space for a second car. Available immediately. $2,975/month. No pets.

Fantastic one bedroom apartment in the historic Millbrook Inn. This unit has been completely renovated with preservation of details that fill the space with character. 9' ceilings, beautiful windows and hardwood floors throughout. All rooms are light filled and there are lovely views of the neighboring horse farm and sunsets. All appliances are brand new. This unit is within walking distance of Village amenities. Ample off street parking. High efficiency heat and a/c unit.,AboveGrade:600,Cooling:Heat Pump,ExteriorFeatures:Landscaped,Outside Lighting,FLOORING:Wood,InteriorFeatures:Electric Dryer Connection,Electric Stove Connection,Washer Connection,OwnerPays:Fire Insurance,Sewer,Water,RentalTerm:MINIMUM ONE YEAR,ROOF:Asphalt Shingles

Furnished Yearly or Summer Rental. SOUTHFIELDS. This spacious and private country retreat in Millbrook is located on 24 acres with pastoral views. The home is tastefully furnished and provides an abundance of space with 4,978 square feet; and 4 bedrooms and 5 full and 2 half baths. The floor plan flows beautifully between rooms and has gorgeous wide board floors spanning the first floor. A spacious living room with a large stone fireplace is the perfect location to enjoy chilly winter nights. The eat-in country kitchen is bright and spacious with top of the line appliances, soapstone countertops, butcher block island and an office nook. Double doors lead to the patio with a 16'5" x 10'2" screened porch for enjoying the warmer seasons. A heated, gunite pool also can be enjoyed during the summer. There is a first floor primary suite that has a cozy fireplace and includes two separate primary bathrooms. An office, entry, mudroom, half bath and bar area add to the first floor. Upstairs is a great room with soaring cathedral ceilings framed by large post and beams, a game room and three additional ensuite bedrooms. Adding to the list of amenities is a large covered front porch, two car garage under, central vacuum and an automatic generator. References and credit check required. Also available Memorial Day through Labor Day for $50,000.

Begin the summer with a June retreat in Kent, CT. Both fabulously comfortable and elegantly styled this colonial home offers views, privacy and lovely outside deck space, pool area and lawn. A 4-bedroom home with the primary suite on the main floor as well as two graciously set bedrooms on the second floor served by a large bathroom. An additional suite on the lower level provides ample room. Country kitchen, formal dining room and office are all centrally located and designed to access the large western facing deck. Kick back with a cocktail, wine or coffee on this spot. The large living room has a generous screened porch for dining, napping or work in nature's virtual office. The view from the deck and hot tub is sweet, while the pool is ensconced within a secret privet garden below. The lower level of the house opens to the pool area and doubles as a comfy viewing room with a lux couches and huge screen TV. One can have so much fun here on the 2.5 acre property or go explore the area and float the Housatonic river, antique shop, walk downtown Kent and enjoy the numerous trails and restaurants Litchfield County offers. 15 minutes from Metro North train from Grand Central. Take the summer and enjoy this amazing country escape. Also available for the month of August $12,000.

Idyllic August retreat in Kent, CT. Both fabulously comfortable and elegantly styled this colonial home offers views, privacy and lovely outside deck space, pool area and lawn. A 4-bedroom home with the primary suite on the main floor as well as two graciously set bedrooms on the second floor served by a large bathroom. An additional suite on the lower level provides ample room. Country kitchen, formal dining room and office are all centrally located and designed to access the large western facing deck. Kick back with a cocktail, wine or coffee on this spot. The large living room has a generous screened porch for dining, napping or work in nature's virtual office. The view from the deck and hot tub is sweet, while the pool is ensconced within a secret privet garden below. The lower level of the house opens to the pool area and doubles as a comfy viewing room with a lux couches and huge screen TV. One can have so much fun here on the 2.5 acre property or go explore the area and float the Housatonic river, antique shop, walk downtown Kent and enjoy the numerous trails and restaurants Litchfield County offers. 15 minutes from Metro North train from Grand Central. Take the summer and enjoy this amazing country escape. Also available for the month of June $10,000.

Second floor apartment has both front and back entrances, one level living, Large bedroom/living room, Spacious Eat in Kitchen, new renovated Bathroom with light up vanity mirror, deck. Building equipped with back up generator in case of power outage. Heat, hot water, garbage and snow removal of parking lot included in rent. Tenant pays electric, cable (optimum), internet, and phone. No Smoking. Tenant to fill out Rental Application, provide pay stubs(Proof of Income) and Credit Report. Conveniently located to shopping and walking distance to Harlem Valley - Wingdale Train Station. Tenant to pay: First month rent, one month security and one month rental fee.

AVAILABLE JUNE 2024 @ $8,500k/month. Modern Country home filled with stylish designer furniture and art. Fabulous AAA South Kent location with expansive lawn and western exposures. 4-5 bedrooms, fabulous outdoor entertainment areas, pond and brook. Close to Lake Waramaug, Appalachian Trail, Mohawk Mtn skiing, Kent and New Preston. Not far from NYC metro north train. 90 min drive to Midtown. Inquire about flexible rental terms.

Magnolia Cottage is nestled within a luxurious country retreat in eastern Dutchess County, offering a concierge-style experience. Just minutes from the train, it's an easy 90-minute journey to Manhattan and 75 minutes to Albany. This charming 3-bedroom retreat boasts a sunlit living room, a versatile den/bedroom with ample storage, a well-appointed kitchen, and a generous bath with a clawfoot tub and separate tiled shower. Two bedrooms feature queen-sized beds, while the third offers a cozy twin bed. Step onto the private deck to grill and unwind, or explore the wooded trails, with the expansive saltwater pool and its surrounding cabanas, gardens, patios, and screened pavilion inviting relaxation and recreation. Your rental package includes weekly maid service, along with pool and personal linens, utilities, wifi, cable, reserved parking, and full access to resort amenities. Beyond the retreat's borders, discover a wealth of experiences, from visits to wineries, distilleries, and breweries to exploring farmers markets, enjoying polo matches and theater, savoring farm-to-table dining, indulging in shooting clubs, and much more.

Reserve your spot for the 2024 Season at The Carriage House, a charming part of an exclusive country resort in eastern Dutchess County. Just minutes from Silo Ridge, Metro North, and a short drive from Manhattan and Albany, this circa 1790 two-story cottage, once a carriage storage, has been elegantly transformed into a Victorian-era lodging. Step into the spacious sunken great room with 14' ceilings and large windows overlooking lush lawns and woodlands. The updated kitchen boasts stylish stone counter tops, complementing the two generous bedrooms and modern bathroom featuring a delightful glass-enclosed shower. Relax on the private awning-covered patio with a BBQ, surrounded by extensive gardens. Explore wooded trails, take a dip in the expansive salt-water pool with cabanas, or unwind in the screened-in pavilion. Walk to nearby restaurants or cozy up by the fire pit for stargazing nights. Your rental includes weekly maid service, pool and personal towels, linens, utilities, WiFi, cable, reserved parking, full access to resort amenities, and a complimentary breakfast on your first morning. For additional luxuries, inquire about services like a personal chef, daily maid services, or private poolside parties. Dive into Dutchess County's offerings, from wineries, distilleries, and breweries to farmers' markets, polo matches, and farm-to-table dining. Minimum rental is 60 days, offering the perfect blend of serene country living and vibrant local experiences.

Welcome to The Lodge, nestled within a concierge-styled country resort in scenic Dutchess County, just minutes from the train station and a short commute to Manhattan and Albany. This charming retreat features a rocking chair front porch, a spacious vaulted living room with patio access, a gourmet kitchen with island seating, 2 full tiled bathrooms, and a sunroom. Enjoy outdoor amenities like private wooded trails, a salt-water pool surrounded by cabanas and gardens, and a screened-in pavilion. The rental includes weekly maid service, pool and personal towels, linens, utilities, wifi, cable, reserved parking, and full-use of resort amenities. Explore nearby wineries, breweries, farmers markets, farm-to-table restaurants, and shooting clubs. Experience the tranquility of country living and convenience of resort-style amenities at The Lodge.

Incredible country home with heated gunite swimming pool skillfully blended into the natural stone landscape. The perfect place for relaxing and entertaining, whilst enjoying open, sunshine views over the golf course. Views from every room! Located within the River Oaks Country Club with resort quality amenities, this large and tastefully furnished 4 bedroom (each with walk-in closets), 3 & 1/2 bath home is offered fully furnished and in mint condition. Laundry room is located on the bedroom level. Enter the master bedroom suite through double doors, featuring two walk-in closets and spacious en-suite bathroom with cast iron tub, double vanity and dressing area. Large walk-in shower with rain fall, wall jets and sitting bench. Bonus windowed room off the bathroom which could be used as an office / gym / huge closet! This well equipped home includes central air-conditioning and a superbly appointed kitchen with Viking appliances, wet bar, breakfast dining area and a large kitchen island with bar seating. The formal dining room and outside deck area with BBQ grill are both accessible from the kitchen. A feature fireplace in the spacious living room and attached 3 car garage complete this home. The outdoor area includes a circular driveway with fountain, fenced in rear yard with expansive patio area, waterfall and custom-built infinity pool. Available Summer 2024 (May 20-Sept 20) for $20,000 per month plus utilities.

Recently renovated Farmhouse set on an idyllic 39+ acres enjoying wonderful pastoral views. The main level of the home features a large eat-in kitchen with spacious pantry, formal dining room, a living room highlighted by exposed hand-hewn beams and woodstove, a cozy den, and a full bath which includes the laundry. Upstairs one finds four bedrooms, one full and one half bath, and a sitting room. Located in one of the most scenic spots of all Litchfield County and only minutes to the village of Kent, countless outdoor pursuits, as well as Metro-North. Rental offering is for the home only, fully furnished, on an annual basis. Use of the barns not being offered. No pets. Tenant responsible for utilities and renters insurance.

This is a furnished SUMMER RENTAL for $8,000 per month of July and/or August, or $14,500 for both months. Located in beautiful Litchfield County, antique lovers will delight in this absolutely charming C. 1836 renovated Colonial with original wide board flooring, 3 fireplaces, built-ins and preserved vintage detailing throughout. Tremendously appealing and sited on a beautiful 2.34-acre lot encompassing lovingly maintained gardens and a picturesque open field/yard. Many recent updates include stylish kitchen and bathroom upgrades and the addition of a beautiful screened in porch. This is a gem of an antique home in historic Gaylordsville - minutes south of the destination village of Kent, CT. Located within 90 minutes of Manhattan with convenient access to all Litchfield County amenities as well as the Berkshires and nearby areas of NY State. Minutes to Metro North trains and close to shopping and restaurants in both Kent and New Milford.