Pleasant Valley NY Real Estate & Homes for Rent

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.

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

Embrace the art of living well at Poetess Place, a haven designed for writers, birders, and nature lovers, tucked away on a private riverfront perch in the heart of picturesque Kent, CT. This lovingly remodeled 3-bedroom cottage, each room adorned with queen-sized comfort, invites you into a world of warmth and serenity. Wake up to the soothing melody of the Housatonic River and be captivated by the breathtaking westerly sunsets visible from your very own wraparound Alaskan cedar deck. Immerse yourself in the tranquil ambiance, where a gentle fountain adds a melodic touch to the air, and sculpted gardens invite you to explore and connect with nature. Unwind on the cozy sleeping porch or let the Yamaha baby grand be your muse, inspiring creativity and joy. Feel the warmth of a gourmet kitchen, inviting you to create culinary delights and share moments with loved ones. Poetess Place isn't just a cottage; it's a warm embrace of luxury and nature. Nestled at the end of a rustic lane downtown Kent, the cottage offers easy access to the town's charming restaurants, unique shops, and Kent School.

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!

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.

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.

Charming colonial cottage with a rich history! Rumor has it that George Washington may have hoisted a pint of ale or two in the house when it was a Tavern in the 1700s. With a location across the street from the Housatonic River, the house offers a pleasant and scenic environment. The thoughtful and complete remodel of the home makes it move-in ready. The all-electronic package in the kitchen, including a glass-front refrigerator, adds a modern touch to the property. The addition of 3 brand new "mini split" HVAC units for heating and cooling ensures comfort throughout the house. The upstairs of the cottage has some delightful features, such as a generous primary bedroom with vaulted ceilings, sliding barn door, and hardwood floors, creating a warm and inviting space. The primary bathroom adds a touch of luxury with a soaking tub, separate shower, and even an in-wall fireplace, offering a relaxing retreat. Just a 90 minute drive from NYC & accessible by train. Walking distance from a local tavern and deli. Less than 10 mins to Sherman and Kent. 15/20 mins to New Milford and Pawling. 30 mins to Washington and Cornwall. Local stunning scenic hikes & drives. Pets will be considered Available August 1, 2024 Includes 2x/month cleaning service (clean sheets, towels, lite cleaning) Note: Studio above the garage and the garage are not available for lease.

Beautifully updated 1700's Colonial in Gaylordsville. Enjoy easy access to the shops and restaurants of Kent or the New Milford Green. This incredibly tasteful house combines antique charm with a modern flair. The house is great for entertaining or relaxing by the pool. Currently set up as a 4 bedroom with 5th private office space. Rental terms are flexible. $17,000 for any month or months desired.

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.

Available July or August at $29k per month. Gorgeous Barn Style Home that is both stylishly decorated and cozy. Metro North Wassaic train station is just 15 minutes away for great access to NYC! Quiet and private 10 acre setting with heated gunite pool, level land for play, just minutes from both Kent and Sharon Centers in the highly desirable Ellsworth area of Sharon. Open Floor Plan with high ceiling, bright and airy rooms. Patio for great entertaining. Game Room with pool table. 30 ft Granite Fireplace with Beamed ceiling in Living Room. Gourmet Kitchen, 6 bedrooms, one on the first level, 4 En suite. 2 half baths. Private guest or in law apartment. Separate children's playground, large wooden deck ideal for relaxing. Beautiful Pastoral Area... The ultimate in Vacation Homes!

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.

Available $25k/month summer. Lilac Cottage is the perfect country rental and close to town. All new bathrooms just completed. Perfect and private rental all on one level. 3 bedrooms, 3.5 baths. Primary suite with french doors leading to blue stone patio and Jacuzzi tub with separate shower and double sink. Guest bedroom with new, en-suite bath. Additional bedroom with it's own new bath. Large living room with flat-screen. Dining room with french doors to patio. Newly renovated chef's kitchen with breakfast bar and 1/2 bath and new, four season sunroom overlooking the private gardens and pool. 2 car attached garage. One level living with great flow. Fire pit and generator complete the package. Minutes to town with gourmet grocery, shops and dining. Enjoy Mudge Pond as well. Quintessential New England at it's best!...

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.

Welcome to a timeless piece of history, the Ezra Clark House, believed to be the oldest home in the village of Millerton. Built in 1780, this remarkable estate stands as a testament to centuries of architectural craftsmanship and refined elegance. The main house and guest house are a combined 3,825 square feet of living space. With 5 bedrooms, 3.5 bathrooms. The main house has two inviting living areas, this home effortlessly combines historic charm with modern comfort. Whether you're unwinding by the fireplace or entertaining guests on the spacious outdoor patio or by the gunite pool, this property offers the most discerning renters with a little bit of everything. Need a quiet space to work or study? The private office provides the perfect retreat. Step outside onto the beautiful brick patio or second-floor balcony, where you can savor tranquil moments overlooking your own private pond. Adjacent to the main house, discover a charming 1,264 square foot guest house, complete with 2 bedrooms, 1 bathroom, rec room and kitchen. Outside, an oasis awaits. Lounge by the shimmering gunite pool, surrounded by lush greenery and framed by panoramic views of the countryside. Challenge friends to a friendly match on the tennis court, or simply bask in the serenity of your expansive 8-acre estate. This property is offered from July 15 - August 25 from $20,000. Should you wish to rent the property through Labor Day weekend, you can do so for an additional $5,000.

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.

Luxurious Apartment A on Sharon Green - Newly Renovated Luxurious One Bedroom with Loft - Unfurnished, 2nd Floor Apartment on the Sharon Green with lots of natural light and central air. Washer, dryer in unit. Low monthly tenant additional costs for heat/ac,electricity, cable & internet. Landlord covers cost for water, plowing,mowing,landscaping and trash removal. Garage available for additional $150 monthly

Summer 2024 Rental - $10k/Month: June/July/August. Uber Stylish 4 Bed/3.5 Bath Cabin. Quiet & Private Setting Tucked Back from Low-Traveled Town Road. Open Floor Plan with Fireplace & Vaulted Ceiling. Elevator. 1st Floor Primary Suite with Luxurious Bath. Upstairs En Suite First Class Bedroom Plus 2 Others with Shared Bath. Wonderful, Large Screened-in Porch. 3 Min to Village; 12 Min to Metro North; Proximate to Lakes & Area Attractions.

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)

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!

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

Amazing Academic Year 2024-25 rental opportunity - This modern masterpiece enjoys spectacular sunset views that stretch to the Catskill Mountains in the distance. Entering the home, one is greeted by a floating steel and glass staircase and is drawn to the living room highlighted by a two-story wall of glass as well as handsome exposed beams. The sleek kitchen with island opens to an eating area as well as a wonderfully spacious covered porch that overlooks the pool area. A formal dining room, den with fireplace, main floor bedroom with private bath, powder room, and mudroom round out this level. Up one, you will find the primary bedroom suite with private bath, two ensuite bedrooms, and a dedicated laundry room. The third floor of the home is finished and includes a sitting area, kitchenette, half bath and bedroom. Available for the 2024-25 Academic Year for $10,000/month.

Modern in the Litchfield Hills - This modern masterpiece enjoys spectacular sunset views that stretch to the Catskill Mountains in the distance. Entering the home, one is greeted by a floating steel and glass staircase and is drawn to the living room highlighted by a two-story wall of glass as well as handsome exposed beams. The sleek kitchen with island opens to an eating area as well as a wonderfully spacious covered porch that overlooks the pool area. A formal dining room, den with fireplace, main floor bedroom with private bath, powder room, and mudroom round out this level. Up one, you will find the primary bedroom suite with private bath, two ensuite bedrooms, and a dedicated laundry room. The third floor of the home is finished and includes a sitting area, kitchenette, half bath and bedroom. Available Summer 2024 for $25,000 for June, $35,000/month for July and August, as well as on a weekly basis for $10,000.