The agencies at Litchfield
These agencies offer a selection of luxury properties location at Litchfield. Feel free to contact them for personalized assistance.
Experience the ultimate hilltop retreat in this stunning contemporary home, perfectly positioned for privacy. Set back at the end of a winding, tree-lined driveway, this sun-drenched residence offers a seamless blend of modern design and serene nature. The expansive main living area features high ceilings and French doors that open directly to a spacious deck-ideal for indoor-outdoor entertaining, alfresco dining, or quiet evenings overlooking the countryside. A large kitchen serves as the heart of the home, while oversized windows throughout frame picturesque views of the Connecticut landscape. The primary bedroom suite serves as a true sanctuary, complete with its own attached sunroom. The layout offers incredible flexibility, including a lower-level office or media room and a massive multi-purpose space perfect for a home gym, studio, or recreation room. Located just minutes from the historic Litchfield town center's premier dining, boutique shopping, and culture, you have easy access to top-tier outdoor recreation, parks, and nature reserves. Enjoy complete peace and tranquility while remaining an easy, scenic drive under two hours from Manhattan from nearby transit routes. Available as an annual unfurnished rental for the lifestyle upgrade you always wanted. Field card reads two bedrooms. Lower level office can be used as third bedroom or the multi-purpose room also.
…By William Pitt Sotheby's International Realty
Discover this unmatched mid-century contemporary marvel, a unique estate in the beauiful Westledge neighborhood that perfectly blends architectural sophistication with modern comfort. Designed with elegant, professionally curated interiors and featuring signature walls of glass, the home frames stunning, sweeping views while flooding every space with natural light. Nestled on 6.6 private acres of breathtaking beauty just minutes from the charm of Litchfield, Bantam, and the shops of Torrington, this peaceful retreat invites you to unwind and reconnect, offering vibrant outdoor gardens, ample space to explore, and even your own private 3-pin golf course. Whether you are looking for a turn-key luxury furnished residence or the flexibility of a separate, well-appointed in-law apartment, this unique property offers an unparalleled lifestyle where exquisite design, nature, and functionality integrate seamlessly. Unique & Flexible Rental Opportunity! This stunning property offers incredible versatility with two distinct living spaces. The owner is offering either the spacious main house OR the private, fully-equipped in-law apartment for rent. Whichever exceptional unit is not rented will be reserved for periodic use by the owner. Enjoy premium living tailored to your needs-whether you require the full layout of the main residence or the cozy, independent setup of the in-law suite. Inquire for specific pricing and configuration details for each unit! Minimum 3 month lease required
…By William Pitt Sotheby's International Realty
Welcome to 250 Westledge Drive, a stunning Torrington property offering a rare and uplifting lifestyle. Nestled on over 6 acres of park-like grounds, this beautiful estate is surrounded by mature trees, gorgeous gardens, and exceptional outdoor amenities, including a private 3-pin golf course, croquet, and a soccer penalty shootout area. It's the ultimate setting for relaxation and recreation, with plenty of space to easily set up your favorite outdoor games. The crown jewel of this estate is the beautiful, independent apartment attached to the main house. Recently renovated by an interior architect/designer, this sophisticated space features its own private keypad entrance, offering true autonomy and style for multi-generational living or guests. Conveniently and centrally located just 5 minutes from Route 8, this property blends peaceful privacy with easy accessibility. You are just minutes away from local shops, the historic Warner Theatre, and multiple charming nearby villages. Don't miss this rare opportunity to rent a versatile, turnkey property that offers so much more than just a place to stay-it's a true lifestyle retreat. Schedule your private tour today! Laundry is shared with main home
…By William Pitt Sotheby's International Realty
Newly renovated contemporary home in the heart of Washington is now available to rent for upcoming academic year: September 1, 2026-May 31, 2027. Drenched in natural light, this home is located on Wykeham Road, minutes from the Washington Green, Washington Depot and the Frederick Gunn School. The Leicht kitchen is a showstopper with superior European-designed cabinetry and white marble countertop boasting seamless, modern lines. High-end appliances compliment the sleek construction, including a Wolf wall oven, Gaggenau stove and oversized Thermador stainless fridge. White oak, wide plank flooring throughout adds to the crisp, clean style of the home. The open floor plan and designer lighting (Flos, Tom Dixon, Menu and Gobi) honors the simple but elegant character of this home. The en-suite primary bedroom graces the main level, with the second level offering 2 additional bedrooms and an office. Towering evergreen trees and mature perennial gardens envelop this home and give it a warm, country feel, while still being close to town center. Beautiful outdoor space and decks complete the picture for the perfect country home. Weekly housekeeping required at renter's expense required. Excellent credit score required.
…By William Pitt Sotheby's International Realty
Olive Farm will soon feature a 38' x 20' in-ground saltwater pool - just in time for summer! The home sits on 6 fully-fenced acres and is positioned for long-range Western sunset views of the Housatonic River Valley. Hardwood flooring, built-ins, and great natural light are present throughout. Enter into the kitchen equipped with black walnut countertops, a gas range stove and breakfast bar area. The adjacent dining room features plenty of built-in storage and an 8 person table. Sunlight fills the living room through a glass door leading to the screened-in porch, and through a large row of windows offering amazing views of the surrounding mountains. A cozy den with a pull-out sofa for guests connects the living room and main level en-suite bedroom, complete with a recently remodeled full bath. The second floor consists of a large primary bedroom with the same stunning Western views, a 10x8 room that could function as closet space or an office, and an additional bedroom with two full sized beds. A full hallway bathroom accommodates the upper level. The tranquility of Cornwall, CT can be from the 60 ft. long wrap around porch, and the beautiful new bluestone patio and saltwater pool. Shopping and dining in nearby Kent, Sharon, Litchfield, and New Preston can be reached in 20 minutes or less. Only 30 minutes to Metro North trains and 2 hours by car to Manhattan! Available June 1st - August 31st. June offered at $12,500, July & August at $15,000 per month. Pool installation beginning in April and will be ready by Memorial Day weekend. Renderings of the project available upon request.
…By William Pitt Sotheby's International Realty
Embrace the quintessential New England lifestyle in this beautifully presented one-level home, ideally situated in the heart of New Preston Village. Designed for effortless living, the home centers around a bright, well-appointed kitchen and dining area that flows seamlessly into a welcoming living room. A charming stone fireplace anchors the space, which is generously sized to accommodate a baby grand piano and perfect for gathering with family and friends. Glass doors lead to a private patio, offering a peaceful setting to relax or entertain while enjoying breathtaking sunset views over the valley. The thoughtfully designed floor plan includes three bedrooms: two connected by a convenient Jack-and-Jill half bath, and a third smaller bedroom ideal as a home office, guest room, or daybed space. A full bath completes the layout, providing comfort and functionality for both everyday living and weekend escapes. Set on a level lot with beautifully established perennial gardens, this property offers a tranquil outdoor setting ideal for bird watching and quiet mornings. Just a short stroll to town, you'll enjoy easy access to New Preston's charming shops and acclaimed dining. Perfect as a weekend retreat or full-time residence, this home places you close to Lake Waramaug, Washington, Litchfield, and the many outdoor pursuits of the Litchfield Hills-including hiking, skiing, state parks, and watersports-making it a true four-season destination.
…By William Pitt Sotheby's International Realty
Experience the ultimate August retreat at 16 Anderson Acres Road, a contemporary masterpiece perched in the heart of Kent. This architectural gem is designed to blur the lines between luxury and nature, offering unrivaled panoramic views that stretch for miles from nearly every room in the house. Whether you are sipping your morning coffee in the open-concept living space or unwinding by the stunning pool, the breathtaking vistas of the Litchfield Hills serve as your constant, serene backdrop. The location offers a perfect balance of secluded tranquility and vibrant summer activity. You are within walking or biking distance to Lake Waramaug, where the best of lake life-from kayaking to sunset strolls awaits. Nature enthusiasts will also appreciate being minutes away from the lush trails and scenic beauty of Kent Falls State Park. When you're ready for a change of pace, the charming village of Kent is just a short 10-minute drive away, providing instant access to world-class art galleries, museums, boutique shopping, and a renowned culinary scene. Secure your private slice of paradise for the month of August and enjoy the very best of Connecticut summer living.
…By William Pitt Sotheby's International Realty
The House by the Brook - Fully furnished, charming house overlooking a stream available for a school-year rental mid-August 16, 2026 through May 31, 2027. Three bedroom, 2 1/2 bath home is on Cream Hill, the most desirable area of Cornwall. Gracious home features large rooms, many windows, and wood floors throughout. Downstairs are living room, dining room, office or bedroom, kitchen, and pantry. Upstairs are two bedrooms and 2 full baths. House is bordered by protected forest and farmland. Garage with one parking space available. W/D in home. Oil heat. Very local to several private schools. Pets considered on case by case basis. 24 hours notice to view.
…By William Pitt Sotheby's International Realty
STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a comfortable and chic look. Long distant views and rolling, verdant lawns add to the magic of this property. Close to top restaurants, art galleries, shopping and outdoor recreation. Only 90 minutes to NYC. Note: Field card indicates that there are 3 bedrooms but the house has 4 bedrooms and a 1250 tank.
…By William Pitt Sotheby's International Realty
ANNUAL RENTAL: Cozy and super charming 3 BDR, 2 BATH country cape offering a peaceful retreat on beautifully maintained estate grounds. The serene property boasts a lovely yard, complete with mature plantings that provide a picturesque setting for this idyllic home. A light-filled, well-appointed interior exudes warmth and comfort with a layout that flows effortlessly. Lovely dining room opens into both a large kitchen and light-filled living room. Bedroom and full bath on the main level. Primary bedroom and 3rd bedroom upstairs with full bath. Enjoy relaxing on the wood deck amidst the beauty of the pines and natural surroundings. Ample parking in driveway or under covered garage. Located near the charming and historic Cornwall Covered Bridge, this home combines the tranquility of country living with the subtle touch of historical significance that is found in the Northwest Corner. Enjoy this special sanctuary where every day feels like a peaceful escape. Close to area private schools (Hotchkiss, Kent, Salisbury & Berkshire Schools). Hike the Appalachian Trail, swim in area lakes, and dine at farm to table restaurants. 2+ hours to NYC.
…By William Pitt Sotheby's International Realty
Sharon, CT - Nature is your neighbor in this welcoming 3BR/1.5BA home tucked among tall trees and rolling hills for tranquil, picture-perfect living. Enter via an open kitchen with ample cabinets and counter space, plus a brand-new energy-efficient wood-burning stove. Adjacent is the airy living room with cathedral ceiling and skylights that flood the space with natural light. Beside the Livingroom, the first-floor primary bedroom enjoys its own private outdoor entrance. The main level also includes a full bath with linen closet, a laundry room, and a storage room. Upstairs are two generous bedrooms with large closets and a spacious half bath with linen closet. Propane utilities and the wood stove help keep heating costs low. Live peacefully in Sharon with hiking minutes away at Sharon Land Trust and the Sharon Audubon Center, and performances at the Sharon Playhouse. Swim at Mudge Pond; shop local at Sharon Market; enjoy meals at Troutbeck, Le Gamin, Pigs Fly South, or light fare at JP Giffords. Engage the community at Hotchkiss Library. You're ~10 minutes to Sharon center and ~5 minutes to Cornwall Bridge, with a hospital in town. Nearby villages-Millerton, Cornwall, Kent, Lakeville, and Salisbury-offer charming cafes, antiques, waterfalls, trails, private schools, and Lime Rock Park (Millerton is within 10 miles). Explore art at Standard Space (Sharon), Geary Contemporary (Millerton), and the Wassaic Project. Your new home awaits!
…By William Pitt Sotheby's International Realty
TIME TO PLAN YOUR SUMMER VACATION! OR RENT YEARLY! Available June and July. Call for Summer Pricing! Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Swim in the heated gunfire pool. Explore the homes 142 acres. Plenty of room for family and friends who want to experience the beauty of Litchfield County. There is a 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. There is easy access to Litchfield County's many private schools. Enjoy the hiking trails at local land trust, canoeing or kayaking on the Housatonic river or Lake Waramaug. There are country fairs, art shows, local theatre, great restaurants and many fine shops to explore. Available starting September $12k per month for yearly lease. Call for Summer Rental pricing. Minimum 24 hour notice to view.
…By William Pitt Sotheby's International Realty
Comfortable 3+ bedroom, 2 bath Sharon rental minutes to the center of town. Enjoy a true mid-century modern house on a quiet country road. Once inside, stairs lead up to a spacious living room with a pleasant circular flow into the dining room and kitchen. Primary bedroom with full bath and 2 other bedrooms on the main floor and additional bedroom with twin beds upstairs. Just up the road from the Sharon Audubon Center, hiking trails and many farm to table restaurants. Enjoy the Sharon Playhouse during the summer months, Mudge Pond for swimming and easy access to surrounding towns for dining and shopping. Close to area private schools: Hotchkiss, Millbrook School, Kent School and Indian Mountain School.
…By William Pitt Sotheby's International Realty
A Regal Sanctuary with recent key upgrades! Seize the opportunity to own a piece of majesty with this unparalleled castle perched atop a hill, commanding 60+ acres of pristine land. Surrounded by conservancy property, this estate promises uninterrupted tranquility and privacy. As you ascend the private road, the castle's imposing silhouette against the horizon is a prelude to the grandeur within. Boasting expansive living spaces, this 7,000+ sq ft residence offers endless potential for luxury and craftsmanship. The property's elevated position on the ridgeline affords breathtaking panoramic views stretching all the way to the Berkshires, ensuring every sunset is a spectacular event. The surrounding acreage, a mix of open spaces, ponds, woods and wild beauty, provides a serene retreat from the world. With nature as your neighbor, the possibilities are endless. There are trails for miles, an old mill, enjoy the local flora and fauna or simply bask in the peace that only such a secluded estate can offer. Incredible opportunity for development - plans available with a proposal to create a subdivision of lots with views (currently 2 lots). Recent improvements to the driveway & new 6 bed septic system. Located in the charming town of Sharon with great restaurants and the playhouse theater. Also close to Cornwall & Millerton, NY. This is more than a home; it's a kingdom where life is lived on a grand scale. Don't miss this incredible opportunity to create your castle in the sky!
…By William Pitt Sotheby's International Realty
Available at $16,500 for Aug. 17 - Sept 7, Labor Day. 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 playground, large wooden deck ideal for relaxing. Beautiful Pastoral Area.... The ultimate in Vacation Homes!
…By William Pitt Sotheby's International Realty
Welcome to your contemporary retreat in the heart of Goshen, CT. This modern home, nestled within the tranquil surroundings of Litchfield County embodies a perfect blend of luxury and comfort for your short-term getaway. Sleek lines, expansive windows, and a minimalist aesthetic define this stunning property. Situated amidst lush greenery, with serene outdoor views that promise a peaceful stay. The home's spacious interior is designed for flow and functionality, featuring high ceilings and an open-plan layout. Equipped with top-of-the-line appliances, perfect for culinary enthusiasts. Boasting multiple bedrooms, each thoughtfully appointed to ensure restful nights. A private deck and outdoor seating areas allow guests to immerse themselves in nature's beauty. Just moments away from Dog Pond and the charming town centers of Goshen and Litchfield, one can enjoy a variety of dining and shopping options. Whether you're seeking a peaceful retreat or an active escape, this home is the perfect base for exploring all that the Litchfield Hills is known for. Indulge in a stay that promises relaxation and rejuvenation. Summer (Jun-Aug) $11,000 per month. Please see listing agent for fall and winter availability and pricing.
…By William Pitt Sotheby's International Realty
Experience the ultimate country retreat with this charming, fully furnished 3-bedroom, 3-bathroom cottage set on 13+ private acres. Available for the Academic year or Winter rental, this inviting property features a heated saltwater gunite pool, a separate guest cottage, beautifully maintained grounds, and perennial gardens. The main residence boasts a sun-filled kitchen with an eat-in area, a spacious living room with a fireplace, and a primary bedroom suite on the main floor. An additional bedroom is located on the main level, with a third bedroom upstairs. Ideally situated for convenience and tranquility, this home offers easy access to NYC via Metro-North, is moments from Bulls Bridge Golf Club, Mohawk Mountain Ski Area and close to the shops and restaurants of Kent and New Preston village centers. Available 8/16 through Labor Day, Academic Term, Annual Rental.
…By William Pitt Sotheby's International Realty
This recently remodeled 3 bedroom, 1.5 bath ranch is set in the rolling hills of Kent and offers sweeping mountain views. Enter through the spacious mudroom equipped with a washer/dryer and half bath. Sitting adjacent is a beautiful room with brick floors and vaulted ceilings, providing a perfect space for a family room, home office, or creative studio. The kitchen has been completely refreshed with all new appliances and opens seamlessly to the dining room, where a bay window overlooks the backyard and covered bluestone patio. Natural light fills the well-sized living room, featuring hardwood floors and a wood burning fireplace. Three comfortable bedrooms and a remodeled bathroom complete the living space. Ideally located just minutes from downtown Kent, as well as Macedonia Brook and Kent Falls State Parks, this home offers easy access to some of the area's most beloved attractions. Metro North trains are just a 20 minute drive away and Manhattan can be reached by car in under 2 hours. Whether you're searching for a weekend escape or a full-time residence, this is a wonderful opportunity to enjoy all that one of Litchfield County's most charming towns has to offer.
…By William Pitt Sotheby's International Realty
Over forty private wooded acres, a mountain stream, and hiking trails that lead to your own waterfall. This three-bedroom rustic stone cottage in the heart of the Litchfield Hills is the kind of country rental that's hard to find and harder to leave. A screen porch overlooks the running water, the living room has handsome exposed beams and opens to a covered porch, and wood-burning fireplaces make evenings in the formal dining room feel exactly right. One bedroom on the main level; the primary and third bedrooms up a level. The setting is quintessential Connecticut, located off a scenic country roads lined with antique homes. Macedonia Brook State Park at your doorstep, the village of Kent just minutes away, Metro-North is close by, and New York City just two hours away.
…By William Pitt Sotheby's International Realty
Academic Year Rental. Nestled in the wooded canopy of the Litchfield Hills, this cozy 2 bedroom garage/barn offers the perfect blend of charm and serenity. Inside, the kitchen welcomes you with a cheerful atmosphere, while an inviting living room features a spacious living arrangement. Step outside onto the deck to enjoy an ideal spot for summer grilling or to take in the lovely, elevated views toward the Housatonic River and experience spectacular evening sunsets. The property features softly rolling lawns inviting you to relax in your own quiet, private sanctuary. Listen to the tranquil chorus of native birdlife and the soothing sounds of the surrounding forest. Just minutes from the historic Cornwall Covered Bridge, this captivating property delivers the ultimate New England country escape.
…By William Pitt Sotheby's International Realty
Beautiful one bedroom rental in pristine condition. Hardwood floors throughout. Bedroom has a deck with amazing views! Excellent credit a must. Absolutely no smoking/vaping or pets.
…By William Pitt Sotheby's International Realty
SEASONAL RENTAL - LAKEVILLE ESTATE - September 15th - April 1st Experience the timeless elegance of this 1827 antique home on a spectacular 22-acre private estate. This sensational property blends historic charm with modern convenience in the coveted Lakeville/Lime Rock area. Throughout, you'll find ample windows providing radiant natural sunlight, and stunning, wide-plank hardwood floors that speaks to the home's rich heritage. There is a cozy sitting room in the open country kitchen area, modern appliances, and an adjacent formal dining room as well as a downstairs 1/2 bath. Upstairs are 4 generous bedrooms including a primary suite with fireplace & full bath offering both a stand alone shower & antique tub. Three additional spacious bedrooms share a full bath, & there is an office area upstairs. The well situated fireplaces create warmth and ambiance perfect for the seasonal months. The expansive grounds include multiple barns and a beautiful pond seen from the magnificent sun room. This rural sanctuary provides seclusion while maintaining easy access to area amenities, ski resorts, restaurants and many entertainment options, as well as several prestigious private schools close-by. The perfect retreat for those seeking authentic New England charm and serenity for the winter months.
…By William Pitt Sotheby's International Realty
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. Additional 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 island with bar seating. The formal dining room and outside deck area with BBQ grill are accessible from the kitchen. A feature fireplace in the spacious living room and attached 3 car garage complete this home. The fenced in rear yard with expansive patio area, waterfall and custom-built infinity pool designed and constructed by premier area designer, Dobson Pool Company. Available academic term September 2026-2027 $7500/mth plus utilities. Also available summer term 2027, $20,000/mth plus utilities.
…By William Pitt Sotheby's International Realty
French Country Storybook Estate ~ a rare opportunity to reside in one of Sharon's most distinguished estates blending old world charm with modern comforts. Shrouded in privacy in the heart of town, a sweeping private drive leads to a magnificent pea stone courtyard, serving as a stately prelude to a home framed by rolling fields and manicured lawns with breathtaking western views over the historic Sharon Green. Inside, the home boasts a voluminous family wing with soaring cathedral ceilings, great stone fireplace, and rustic beams; a recently updated galley kitchen that opens into a formal dining room; and a refined layout featuring 3 main-level bedrooms and 3 full baths, plus a secluded study. Ascend the central circular staircase to find a private lofted sanctuary also with a full bath. The exterior invites you to savor the seasons-whether enjoying an alfresco breakfast on the terrace or enjoying the sunset on the western patio. A pleasant stroll to the Hotchkiss Library, coffee shop, food store and other local shops. ANNUAL or ACADEMIC: $6,000/mo. Also available for the SUMMER: June/July/August at $12,000/mo.
…By William Pitt Sotheby's International Realty
Welcome to 137 Knowles Ave in Southington, where this beautifully renovated duplex unit offers a rare blend of modern updates, generous space, and thoughtful accessibility. Hardwood floors run throughout the home, creating a warm and cohesive feel, while a gas fireplace provides a comfortable focal point in the main living area. The updated kitchen showcases a sleek, modern design with granite countertops, newer appliances including a refrigerator, and ample cabinetry-ideal for both everyday living and entertaining. Two generously sized bedrooms feature large closets, offering excellent storage and comfort. All televisions in the unit are included, making this home truly move-in ready. Designed with convenience in mind, the home includes a handicap-accessible full bathroom and a chairlift from the attached one-car garage, allowing for ease of access throughout the living space. The fully insulated basement provides plenty of storage and features updated mechanicals, offering both efficiency and peace of mind. Outside, tenants can enjoy a private patio-perfect for relaxing, dining, or enjoying warmer weather. With modern finishes, abundant storage, accessible features, and inviting outdoor space, this thoughtfully updated unit offers comfort, functionality, and quality living in a convenient Plantsville location.
…By William Pitt Sotheby's International Realty
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These agencies offer a selection of luxury properties location at Litchfield. Feel free to contact them for personalized assistance.