The agencies at Sherman
These agencies offer a selection of luxury properties location at Sherman. Feel free to contact them for personalized assistance.
Adorable 3-bedroom, 2-bath furnished cottage in sought-after Candlewood Lake community, offering an inviting open floor plan, main-level primary bedroom, and wood flooring throughout. The spacious screened porch - accessed from both the kitchen and living room - is the perfect place to relax and overlooks a private, level lawn and garden area. A detached shed includes a separate insulated room, offering flexible space for a studio, office, or retreat. Set on a quiet, level country road with little traffic, the property is ideal for walking and cycling. Enjoy access to Candlewood Lake from the town beach, along with an array of town amenities including kayak and canoe racks, a half-mile walking/jogging track, pavilion, playground, basketball court, and three tennis/pickleball courts. Sherman offers an exceptional blend of small-town charm and amenities, including a playhouse, expanded library, historical society museums, JCC community center, and local winery. Ideally located for commuting, the property is less than 90 minutes from Manhattan and is available for rent now through July 2027.
…By William Pitt Sotheby's International Realty
Stylishly renovated Contemporary Ranch with stunning lake views and direct frontage on Candlewood Lake - available to rent September 9, 2026 through May 1, 2027 for $6,500 per month. The beautiful level lot offers a captivating setting and has its own private beach, with easy access to the house and lake from the level driveway. The home's open floor plan - completely renovated in 2020 - offers all main living areas on one level and encompasses a chef's kitchen, dining area, living room, two bedrooms and two baths, with the primary bedroom suite featuring a sleeping loft above for overflow. The spacious chef's kitchen highlights an oversized granite island w/counter seating and top-of-the-line appliances. A finished lower level is accessed via a spiral staircase and offers a large recreation room with billiards and ping pong, a full kitchen and bath, and plenty of further overflow sleeping spaces. All rooms but one feature lake views and sliders to the home's multiple decks and patios. For added comfort, there is a whole house generator, central heating and A/C, and radiant heating in the lower level plus primary bath. Kayaks, paddle boards and life jackets are available for added enjoyment. Located in the highly desirable lake community of Atchison Cove where tenants can also enjoy the community clubhouse, beach and picnic areas. Just 90 minutes to Manhattan and 15 minutes to Metro North trains.
…By William Pitt Sotheby's International Realty
Your private retreat awaits. Situated to capture breathtaking, panoramic views of Candlewood Lake and the lush surrounding hills, this elegant estate offers the ultimate in privacy and peace. The expansive deck provides a flawless setting for sunset entertaining, while the interior layout-featuring 5 bedrooms and six bathrooms-offers flexible, well-designed space for any lifestyle. With the added luxury of 5 garage bays and grounds that promise total seclusion, this property represents the perfect harmony of nature and architectural refinement. Available furnished on a month-to-month basis, for the summer, or longer!
…By William Pitt Sotheby's International Realty
Beautifully restored and updated antique farmhouse with inground pool, cabana, guest house, tennis court and pond. Available to rent for the 2025 summer season or by summer month. Scenic distant views frame this private 15-acre compound. Elegantly presented interiors, with extensive renovations supervised by an AIA architect specializing in historic preservation. Attention to detail and quality is evident throughout the home. The main level offers a warm and welcoming country kitchen/dining room with oversized island, high end appliances and finishes. There is also a charming living room, spacious family room (each with fireplace), a small office and a partially-screened wraparound porch. Four bedrooms and 2.5 Baths are offered on the upper level, including a wonderful primary bedroom suite with fireplace, full bath and dressing room. Additional accommodation is available in the newly finished guest house encompassing a living area, plus bedroom, kitchen and bath. Outside are patios, terraces, stunning gardens, stone walls and chickens (!) along with an inground gunite pool and hardcourt tennis court. Beyond the property's large private pond are the distant country views that help to create this most peaceful country setting. Available for the month of June for $18,000 or July at $20,000 per month.
…By William Pitt Sotheby's International Realty
Available September 1st for yearly rental. Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Do you enjoy hiking or cross country skiing? Explore the homes 142 acres. Fall foliage is right around the corner followed by ski season. Mohawk Mountain a short distance away, or ski The Berkshires in a hour. 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 or Winter Rental pricing. Minimum 24 hour notice to view.
…By William Pitt Sotheby's International Realty
Situated in an idyllic location this single family rental was renovated this summer. The house has many new features including a new kitchen, bathrooms, thermostats, lighting, windows, doors, siding, roof, and garage doors. There is even an auto-on generator, full basement and attached 2 car garage. The 3 bedroom, 1 1/2 bathroom one level home is privately sited and close to beautiful Lake Waramaug. One year lease required. Credit check, references, and security deposit. No pets please.
…By William Pitt Sotheby's International Realty
This lovely three bedroom two bathroom ranch style home sits on a portion of Sunny Valley Preserve. Enjoy the bucolic setting with easy access to hiking trails. Full basement. Southern New Milford location for an easy commute! Good credit required.
…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
Available for Academic or Annual Rental! This New Preston gem is just 2 hours from NYC and has been newly renovated to perfection. A 1910 Washington Lake Cottage offers a rare opportunity to enjoy New Preston Village and Lake Waramaug with it's great shopping and dining just a short walk away! High design and a Perfect combination of Old and New, the open concept layout with a combined living room/dining room and vaulted ceiling make a comfortable place to entertain guests with a grand picture window, overlooking the center of New Preston. The home offers a high end kitchen with soapstone counters, custom cabinetry with hidden appliances, and waterfall-edge island open on to a bluestone terrace for plein air dining. The primary bedroom with vaulted ceiling and an elegant classic marble and tile bath with a step in shower create a quiet respite from everyday life. The chic, cozy great room with small den or office and full bath allows for easy work from home or comfortable space for guests. A stone path and tiered stonewalls grace the grounds.
…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
Available September 1st, 2025- June 1st, 2026. This historic Victorian home in the New Preston section of Washington is now available for rent after being tastefully renovated from top to bottom. The main level is highlighted by the expansive kitchen with soapstone counters, a butler's pantry, and French doors leading to a rear patio area. The remainder of the first floor features a living room, spacious great room, dining room, and an office with a full bath that could be used as a 5th bedroom. Upstairs are 4 bedrooms, each named after prior owners who have called The Humphrey's House home over the past 127 years, including a nephew of Mark Twain. The bright and sunny primary bedroom has a stylish walk in closet, and an en suite bathroom with a steam shower and radiant heat flooring. A brand new bathroom in the second en suite bedroom features the same top of the line upgrades. Two additional cozy bedrooms sit across the hall, with a third second level bath serving the two rooms. Well known British designer Graham Robert Moore has transformed this Victorian gem into a marvelous display of the modern day aesthetic without abandoning the history of the home. The 40x18 heated saltwater pool features an electric cover and 8 person attached hot tub. This home is just a short stroll to swimming and boating at Lake Waramaug, shopping in the New Preston town center, 30 minutes to skiing at Mohawk Mtn. & Metro North trains, and 90 minutes from Manhattan!
…By William Pitt Sotheby's International Realty
Hard-to-find short-term furnished 2 bedroom spacious rental now available through end of November in the Old Farms complex with wonderful views in New Milford. This rental offers a spacious primary suite with full bath and walk-in closet with slider access to the sun-drenched 3-season room. There is a 2nd bedroom with access to the second full bath. The Living Room with dining area also has access to 3-season room via sliders. Tastefully updated with fully equipped kitchen with stainless steel appliances, Corian countertop, with brand new flooring throughout the entire home! Enjoy lots of extra space for recreation, office and storage in the finished lower level (also furnished) and convenient laundry area. One of the only ranch units to have an expanded patio for grilling, a convenient parking space and end unit carport. Perfect location near everything New Milford has to offer along with surrounding New England towns and recreation.
…By William Pitt Sotheby's International Realty
Discover the perfect balance of peaceful country living and modern comfort at this renovated, partially furnished 3-bedroom, 2-bathroom home, offering approximately 1,550+ square feet of thoughtfully designed living space. Nestled along one of Kent's most scenic country roads on sought-after Skiff Mountain, this inviting residence provides a private retreat surrounded by nature while remaining just five minutes from the charming village of Kent. Filled with natural light, the home features warm hardwood floors, spacious and welcoming living areas, and tasteful updates throughout. A wood-burning fireplace creates the perfect place to gather on crisp New England evenings, while the expansive deck extends the living space outdoors-ideal for entertaining, relaxing, or simply taking in the tranquil woodland setting. A new washer, dryer, and dishwasher have recently been installed, adding everyday convenience to this well-maintained home. Whether you're enjoying the quiet surroundings or exploring nearby hiking trails, local art galleries, boutique shopping, and acclaimed restaurants, you'll appreciate the unique lifestyle that makes Kent one of Litchfield County's most desirable destinations. Available immediately for an annual lease. Tenant is responsible for all utilities. No pets, please do not inquire.
…By William Pitt Sotheby's International Realty
Annual furnished rental in a tranquil country cottage on Lake Lillinonah. This is an extremely rare opportunity to rent with direct lake frontage with a lovely grassy area by the lake and dock. This well appointed 2 bedroom home is the perfect writer's or artist's retreat, nestled on a lightly wooded hillside overlooking CT's best kept secret lake. 90 minutes to Manhattan. Enjoy the 2 patios and deck areas among the lovely perennials and stone walls with calming lake views. Relax in the quiet country life on the lake. Great for bass fishing, too.
…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
Wonderful opportunity to live in the heart of prestigious Roxbury in Litchfield County. Well preserved antique colonial filled with charm. Updates include kitchen, baths and open living area leading to primary bedroom. Brand new septic, 4 car garage with storage above and period outbuildings including a barn. Washer and dryer are located on the main level, upstairs bedrooms offer privacy for guests. 5 bedrooms are ample size plus 2 work/study rooms. In town location with a private back yard and easy access to New York. Property is also listed for sale.
…By William Pitt Sotheby's International Realty
All inclusive Furnished rental available 9/5/2025. Escape to the serene countryside and experience the authentic charm of this beautifully renovated antique home with a refreshing, heated pool. This rental is fully equipped and all-inclusive with bi-weekly housekeeping. Step inside and discover the beauty of a historical Colonial home, thoughtfully updated with modern comforts. The rooms offer plenty of space and showcase exposed beams and vaulted ceilings. You'll appreciate the natural touch of hardwood floors and the convenience of five fireplaces for those cooler evenings. Stay comfortable all year long with central air conditioning ensuring a pleasant stay in any season. The heart of the home is a charming country kitchen, providing an ideal space for cooking up delightful meals. It opens onto a stone patio, inviting you to enjoy the outdoors with relaxed gatherings. Take in the tranquil views of the countryside as the property sits on level open land adjacent to a land trust. For moments of relaxation, take advantage of the outdoor pool, a refreshing oasis on warmer days. Annual rental $10k per month, academic term $8k per month, winter 3 month minimum $8k per month. You'll find all the local amenities you need nearby, including a variety of recreation and cultural venues, shopping and fine dining options. 60 minutes to lower Fairfield County, NYC is 90 minutes.
…By William Pitt Sotheby's International Realty
All-inclusive furnished rental. Available: Winter- 3 month min. $8000/month. Summer Season- Memorial Day thru Labor Day $65,000/season. Summer monthly- $25,000/month. Escape to the serene countryside and experience the authentic charm of this beautifully renovated antique home with a refreshing, heated pool. This rental is fully equipped and all-inclusive with bi-weekly housekeeping. Step inside and discover the beauty of a historical Colonial home, thoughtfully updated with modern comforts. The rooms offer plenty of space and showcase exposed beams and vaulted ceilings. You'll appreciate the natural touch of hardwood floors and the convenience of five fireplaces for those cooler evenings. Stay comfortable all year long with central air conditioning ensuring a pleasant stay in any season. The heart of the home is a charming country kitchen, providing an ideal space for cooking up delightful meals. It opens onto a stone patio, inviting you to enjoy the outdoors with relaxed gatherings. Take in the tranquil views of the countryside as the property sits on level open land adjacent to a land trust. You'll find all the local amenities you need nearby, including a variety of recreation and cultural venues, shopping and fine dining options. 60 minutes to lower Fairfield County, NYC is 90 minutes.
…By William Pitt Sotheby's International Realty
Available from September 15 - May 15 2027 for $8k 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 playground, large wooden deck ideal for relaxing. Beautiful Pastoral Area.... The ultimate in Vacation Homes!
…By William Pitt Sotheby's International Realty
JUST REDUCED TO $1500 PER MONTH.. Amazing location, just across from Land Trust for hiking. Annual Unfurnished Studio Apartment above the garage at Red Studio Farm. Located in the scenic and historic Nettleton Hollow area of Washington and just 90 minutes from NYC! Wonderful western exposure for sunsets and views over nearby meadows and pond. The apartment has Great room with Cathedral ceiling, sleeping loft, full bath and kitchen on over 5 acres of secluded and lightly wooded land with stone walls and towering oak trees, along with a balcony which overlooks the Litchfield Hills. Small kitchen and full bath with a loft above.
…By William Pitt Sotheby's International Realty
Perched to capture breathtaking, unobstructed vistas, this ultra-private 3 BDR, 3 Bath home offers a front-row seat to spectacular western sunsets rolling all the way out to the dramatic silhouette of the Catskill Mountains. Golden-hour light floods the expansive living room through a wide bank of picture windows, framing the painterly horizon and creating an unforgettable backdrop for entertaining against sweeping lawns and open fields. 2 main-level bedrooms (one en-suite) and an upper-level bedroom all drink in the surrounding green countryside, while the dining room and eat-in kitchen keep you connected to the scenery. A writer's haven surrounded by hiking trails and ponds nearby, this scenic escape is minutes from farm-to-table dining, local cultural assets like the Sharon Playhouse, The Hotchkiss Library and the Audubon Center. Easy access to local private schools (Hotchkiss, Kent, and Millbrook Schools) - 2 hours via car or train to NYC. Available September 18, 2026.
…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
Available for lease from September 15, 2026 through Memorial Day 2027, this direct waterfront home on Candlewood Lake offers a rare opportunity to experience luxurious lakeside living. Spanning over 3,000 square feet with 3 bedrooms plus a potential fourth bedroom or office and 3 full baths, the home provides generous space for comfort and entertaining. Nestled in a serene no-wake zone at the Lattins Cove end of southern Candlewood Lake, the property boasts 110 feet of direct lakefront with stunning, uninterrupted views. Inside, the beautifully updated interior features a modern kitchen with granite counters and stainless steel appliances, opening via sliding doors to a porch. The living room impresses with vaulted ceilings, a striking stone fireplace, and a wall of windows framing breathtaking lake views. The primary suite serves as a private retreat, complete with vaulted ceilings, exposed beams, a generous walk-in closet, and a spa-like bath with soaking tub and separate shower. The lower level includes another bedroom, a spacious family room with walk-out access, a full bath, and laundry facilities. Outdoor living is exceptional, with a large deck overlooking the lake and a lakeside stone patio-ideal for relaxing or entertaining. Offered fully furnished, this turnkey home invites you to enjoy the ultimate in lakefront serenity and style.
…By William Pitt Sotheby's International Realty
Brand-new architecture that actually gets it right. 10+ private acres on a river in Litchfield, where cutting-edge design meets the kind of nature you thought didn't exist anymore. Single-level living done right: wide hallways, High ceilings, clean lines, polished concrete floors with radiant heat underfoot. Open concept living currently presented as a spacious dining area and two distinct living spaces leading to deck access perfect for outdoor entertaining. Well appointed Kitchen with breakfast bar seating and all the high-end touches. Two primary suites one with a separate entrance. Main primary suite features a top-tier infrared sauna. Two more bedrooms round things out. Huge storage room and garage! Large family bathroom with claw foot tub. Step outside and it's your own private playground with direct water access and views of the river. Trails run into State Land next door - effectively extending your backyard! Mohawk Mountain for winter ski weekends, access to Bantam Lake for summer days and the kind of privacy that makes you forget the world exists-yet you're minutes from refined dining and culture, quintessential New England villages, Litchfield's farm-to-table scene and Bantam's local charm. Fully furnished. Flexible rental terms available. Landlord to cover lawn maintenance, snow removal and internet. Tenant to cover electric, propane, trash removal and carry renters insurance.
…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
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These agencies offer a selection of luxury properties location at Sherman. Feel free to contact them for personalized assistance.