CT Homes with a Guest House

MLS Number 170517236

• Single Family
• Bedrooms 10
• Bathroom 12
• Square Feet 7,528
• Acreage 232

A once in a lifetime opportunity to own over 230 acres overlooking Lake Waramaug. Nestled high in the hills overlooking the pristine beauty of the lake, this offering comprises six parcels of open fields and forest with exceptional views. Owned by the same family for the last 70 years, dignitaries from the worlds of art, politics, and industry have been entertained here while the stables, paddocks and trails have been home to thoroughbred race horses and generations of equestrians. This property includes two vintage main houses, a guest house, a guest cottage, an in-ground pool with pool house, and staff quarters attached to a twelve stall stable and carriage barn. Miles of footpaths and trails lead to natural springs, a seasonal pond and streams, and a rocky outcropping archaeologists believe was used as a shelter by native settlers. Located in the heart of Litchfield County, within two hours of Boston and Manhattan, this is the ideal opportunity for those that appreciate the history and grandeur of a property of this caliber.

Listed by William Pitt Sotheby's Int'l

MLS Number 170542863

• Single Family
• Bedrooms 10
• Bathroom 18
• Square Feet 17,735
• Acreage 3

This magnificent estate was designed by renowned architect Roger Ferris and boasts 6 levels of living with spectacular water vistas of Southport Harbor. Entry to the main level is through an imposing 2 story limestone portico into the embrace of a soaring space that is the Gallery with its mesmerizing marmalade marble floor and stunning floating wrought iron circular staircase. From this point, all major rooms on the floor emanate in a logical clockwise progression: Living Room, Library, Family Room, Eat in Kitchen and Dining Room. Fabulous floor to ceiling windows and French doors open to take full advantage of Southport Village & Harbor, Country Club of Fairfield, Long Island Sound and the Manhattan skyline. The gracious Master Bedroom Suite has a sitting room with fireplace, his & hers full baths, dressing areas and private studies. Below the Master Suite are 6 en-suite bathrooms and media/playroom area. Below the main level is a Cabana Room with kitchenette, elaborate bath complex, sauna, exercise room, office and wine cellar which leads to an outdoor pool and limestone patio. Progressing down, the next level brings you to the indoor sports facility including a squash/basketball court and dance studio. The lowest level of this home has a 75 foot long Italian marble lined indoor pool with a glass skylight roof. Included on this stunning property is an outdoor heated gunite pool with spa. The Guest House has a Living Room, Kitchen, 2 Bedrooms, 2 Full Baths & 2 Bay Garage.

Listed by Higgins Group Bedford Square

MLS Number 170562786

• Single Family
• Bedrooms 4
• Bathroom 6
• Square Feet 8,184
• Acreage 101

Unsurpassed Washington, CT Estate on 104? magical acres featuring open meadows, stone walls, mature garden, ponds & distant views situated off a scenic dirt road. The main house complex is a series of converted antique barns with exposed posts & beams throughout. The centerpiece of the main house is the stunning living room, which is an antique barn with vaulted ceiling, floor to ceiling wood burning fireplace & French doors overlooking one of the ponds. Dining room with fireplace. Eat-in country kitchen. Four en-suite bedrooms with bathrooms. Screened (glass in winter) porch with fireplace. Stone terrace with dining pavilion and outdoor fireplace. Swimming pool. 3-car attached garage. Separate two-bedroom guest house. While proximate to the villages of Washington Depot & New Preston, the property is surrounded by land trust offering ultimate privacy and enjoys only the sounds of nature. Long driveway. 5 deeded parcels with no easements. Property has been featured in Architectural Digest. Rare.

Listed by Klemm Real Estate Inc

MLS Number 170565068

• Single Family
• Bedrooms 6
• Bathroom 9
• Square Feet 7,800
• Acreage 28

Hedgelawn Farm - Incomparable country compound on 28 acres overlooking hundreds of acres of Steep Rock Land Trust. Three distinct residences: The Barn House, set on one of Washington's highest elevations with forever views, is a 4,500SF luxury penthouse carefully plucked from the top of Manhattan's newest highrise and placed on one of Litchfield County's most bucolic hilltops. 3BR/4.5BA with walls of glass, grand open living on the main floor, sumptuous baths, a wellness level and a staircase designed by an internationally renowned architect. The 2,800SF Guest House has 2BR/2.5BA in the original farmhouse - transformed into a California modern experience within a historic structure. The Cottage is a 1BR studio with kitchen, bath and perfect for au pair or an artist in residence. Unlike any other estate offered at this price point, everything is brand new - all new mechanicals, all new kitchens and baths - all three residences rebuilt from the ground up in the last 5 years. All construction to the highest level: all copper plumbing, all new wiring, heavy handsplit cedar roofing, lightning protection, whole property generator, ecobatt insulation. Post and beam structures of Cottage + Guest House rebuilt by Ed Cady. Kevin Cady rebuilt Barn House structure and Dan Keys did interior finish. 2 ponds, flat open pastures, 5 vehicle barn, outbuildings and more. Over 10 years in the making, the transformation is complete and Hedgelawn Farm is ready for its next steward. Owner Agent.

Listed by Compass Connecticut,LLC

MLS Number 170557625

• Single Family
• Bedrooms 7
• Bathroom 9
• Square Feet 9,720
• Acreage 41

Impeccably designed for the sophisticated owner, this enchanting country estate is a serenely private retreat on 40.95 acres. The exquisite manor home offers contemporary flair and stunning natural beauty in nearly 10,000 square feet: luxurious first-floor master suite, chef's kitchen with commercial-grade appliances, 6 upper-level bedrooms surrounding a central family room and gym, lower-level entertaining area plus attached cabana with shower/changing room as well as 3-car attached garage and detached 2-car garage with loft apartment. Outdoor living is sublime with in-ground pool, double-sided stone fireplace, built-in outdoor barbeque stations, stone patios, and alfresco dining, plus tennis court w/hut, 3-acre stocked pond with boathouse, 4-stall horse stable and riding ring w/4 paddocks. Also included:antique 3-BR guest house and a spectacular rustic-chic acoustic party barn w/a double-height stone fireplace, zinc-top bar, reclaimed barn-wood walls and loft with Murphy beds. Don't miss this unparalleled opportunity for refined living, entertaining and?recreation. Bucolic Redding with its wooded acres, state parks, hiking trails, rivers, ponds, hundreds of acres of open space and conservation lands.The New York Times has referred to Redding as "An Upscale Town with Upcountry Style". Maple Hill Country Estate is a fabulous weekend haven and a superlative full-time residence-lifestyle, location, convenient to commute routes, Danbury airport, trains, shopping and restaurants.

Listed by William Pitt Sotheby's Int'l

MLS Number 170487337

• Single Family
• Bedrooms 5
• Bathroom 11
• Square Feet 11,224
• Acreage 41

Exceptional Estate with Western Views, Pool, and Pond - An outstanding Twin Lakes area home privately sited on one of the premiere roads in Salisbury, CT with a legacy property designed by the World-Renowned Landscape Architect Dan Kiley. Gorgeous Main House suited for entertaining with 5 Bedrooms, 6 Full Baths and 3 Half Baths, soaring Living Room ceiling, formal Dining Room, Library, Eat-in Kitchen, Family Room, Playroom with Kitchen, Gym, Indoor Pool, central air conditioning, generator, Pond with dock, Har-tru Tennis Court, Basketball Half-Court - all facing magnificent western Views. On +/-41 gorgeous acres. Additionally featured is a beautiful, newly renovated 2-Bedroom 2-Full Bath Guest House with central air and a private stone Terrace and Garden, and a Gate House with a spectacular Office with fireplace, a multi-car Garage, and one-Bedroom Apartment. A magnificent Estate in the Northwest Corner of Connecticut just minutes from The White Hart Inn, and the lakes, hiking, restaurants, and shopping of Salisbury, CT, Millerton, NY, and the Southern Berkshires. Spectacular! Property being offered on +/-41 acres. Adjusted Assessment and Taxes TBD

Listed by Elyse Harney Real Estate

MLS Number 409973

• Residential Single Family Detached
• Bedrooms 5
• Bathroom 9
• Square Feet 11,224
• Acreage 41

An outstanding Twin Lakes area home privately sited on one of the premier roads in Salisbury, CT with a legacy property designed by the World-Renowned Landscape Architect Dan Kiley. Gorgeous Main House suited for entertaining with 5 Bedrooms, 8 Full Baths, and 3 Half Baths, soaring Living Room ceiling, formal Dining Room, Library, Eat-in Kitchen, Family Room, Playroom with Kitchen, Gym, Indoor Pool, central air conditioning, generator, Pond with dock, Har-Tru Tennis Court, Basketball Half-Court - all facing magnificent western Views. On +/-41 gorgeous acres. Additionally featured is a beautiful, newly renovated 2-Bedroom 2-Full Bath Guest House with central air and a private stone Terrace and Garden, and a GateHouse with a spectacular Office with fireplace, a multi-car garage, and a one-Bedroom Apartment. A magnificent Estate in the Northwest Corner of Connecticut just minutes from The White Hart Inn, and the lakes, hiking, restaurants, and shopping of Salisbury, Ct, Millerton, Ny, and the Southern Berkshires. Spectacular! Taxes TBD. The villages of Millerton, NY & Sharon, Lakeville & Salisbury, CT are only minutes away. Nearby amenities include several private & public schools, hiking, tennis, Mohawk Mountain, and Catamount Ski Area & Aerial Park.

Listed by ELYSE HARNEY REAL ESTATE CT

MLS Number 170561021

• Single Family
• Bedrooms 9
• Bathroom 14
• Square Feet 12,759
• Acreage 35

Iconic Sharon showcase estate now available on ~35 park-like acres with stunning panoramic views. (This listing now includes additional 10+ acres with 2 BDR house, pond, and building site). This enchanting property (main house c. 1870) was transformed into a magnificent country compound, combining old world charm with modern amenities. The 5 BDR, 6.5 Bath main house reflects the grandeur of its original vintage - gracious rooms and 7 fireplaces. A circular drive leads to a grand entry with fireplace, living room with fireplace and large windows. Formal dining room features an elegant marble fireplace and French doors, leading to an enclosed east-facing sunporch. Spacious kitchen and breakfast room with large hearth and antique beams. Elegant wood paneled study with fireplace & bar connects to adjoining pool house with 3 BDR, 3 Bath guest quarters and entertainment space. Impressive field stone fireplace, cathedral wood-beam ceilings, and enclosed terrace. Gym, sauna, and pistol range on lower level. Beyond the gardens and apple orchard: 8 stall horse barn with attached car barn with lift, large equipment barn, antique storage barn, riding paths, guest house, greenhouse, and tennis court. Across from 70+ acres of Sharon Land Trust (Benton Hill Preserve) with fabulous hiking trails. Ideal for the car collector with space for 20+ cars. 15 minutes to Lime Rock Park! Stately setting, minutes to town and under 2 hours to NYC. Close to area Private Schools, Troutbeck and Train.

Listed by William Pitt Sotheby's Int'l

MLS Number 170558416

• Single Family
• Bedrooms 6
• Bathroom 6
• Square Feet 5,500

Fantastic waterfront home with separate guest house located on the coveted FAIRFIELD BEACH (near Penfield Beach) - with 5500 SF of living space, 6 car garage and 70 feet of beach frontage with panoramic views of Long Island Sound & Penfield Lighthouse. Main house boasts tons of windows & sliding french doors that provide sunlight & ocean breezes. The main level has an open floor plan w/wrap around covered porch (and just a few steps to oversized patio), living room w/gas fireplace, dining area, breakfast area, eat in kitchen, walk in pantry, powder room, mudroom, laundry room & two car garage. The rear staircase brings you to the 500SF family room w/soaring ceiling. The primary suite has luxurious spa-like bathroom, spacious walk in closet, office/sitting room & sliders to covered porch. This level also includes an ensuite bedroom w/sliders to covered porch, two additional bedrooms & hall bath. The finished walk up 3rd floor is unheated and serves as an incredible playroom with tons of storage and a peacefully located inset balcony overlooking the beach & water. The second building on property has an additional four car garage with a nearly 1000SF, 4 room, 2 bedroom, 1 bath apartment perfect for AuPair, In-Law or rental income potential. Add'l characteristics include exterior access only bathroom with shower for beach guests, solar panels, two level 2 EV chargers, whole house gas generator, security system, vinyl shingle siding & trim. Best deal in the Fairfield Beach area.

Listed by William Raveis Real Estate

MLS Number 170560982

• Single Family
• Bedrooms 4
• Bathroom 6
• Square Feet 5,808
• Acreage 27

Perched at one of Roxbury's highest elevations, with hypnotizing views, lies the Golden Harvest homestead of master builder Ed Cady. The compound sits on a 26 acre parcel personally selected for its privacy, elevation and direct adjacency to the Roxbury Land Trust's 450 acre preserve. Using antique timber barn frames from upstate New York, he constructed the buildings that stand today. The main house exudes casual comfort, with hand-hewn beams blending seamlessly with modern finishes. There are five fireplaces in the main home, antique wide-board floors, native Roxbury granite and endless bespoke details that are so distinctively Cady. The spacious kitchen has a separate eating area, pantry and sun-filled greenhouse. The public wing of the home houses the great room, with soaring ceilings, never-ending views and room for both intimate and large-scale entertaining. The upper level houses two primary bedroom suites plus an office that is easily converted to an additional BR. The lower level includes a recreation room and full bath. The 1BR/1.5BA guest house - well separated from the main house - is a jewel with all the same Cady detailing and a deck overlooking the entire Shepaug River Valley. The barn has parking for 3+ additional vehicles and an in-law apartment above. Additional outbuildings give the property a rich historic texture. The craftsmanship and quality here is at the highest level, and the opportunity to own the "King's Castle" comes up only once in a generation.

Listed by Compass Connecticut,LLC

MLS Number 170552402

• Single Family
• Bedrooms 4
• Bathroom 3
• Square Feet 3,705
• Acreage 11

This outstanding 10.96-acre waterfront compound on the majestic Washinee Lake is uniquely situated on a peninsula with 1200 feet of water frontage providing the ultimate feeling of being on vacation. The main house is perfectly sized at 2,600 sq ft on the main floor and an additional 1,100 sq ft on the lower level, There is fabulous guest space in the 2-bedroom log cabin for extended family and friends. Both homes offer plenty of room to spread out or cozy up by the fireplaces in each living room. The property has an expansive lawn with mature landscaping, a gunite pool between the main house and guest house, a blue stone patio with a firepit directly at the water's edge, and a private dock for all to relax and enjoy the serenity of its surroundings. Whether you enjoy sailing, kayaking, water skiing, swimming, fishing, or just relaxing on the porch, there is something for everyone. Ideally situated near the many private & public schools, Catamount Ski Area and Aerial Park, and the villages of Salisbury, CT, Millerton, NY, Great Barrington, MA, and Wassiac Train Station.

Listed by Elyse Harney Real Estate

MLS Number 170485710

• Single Family
• Bedrooms 6
• Bathroom 9
• Square Feet 8,888
• Acreage 20

Elegant country estate set on 20 acres that can be reconfigured in multiple ways to meet your lifestyle demands. This magnificent property includes the modern shingle style main residence, heated infinity pool and spa, bath house, 2 guest cottages, an office, 16 stall horse barn that can be converted to a party barn/car storage, etc, trout pond, two brooks, rolling lawns, pastures. There are 7 bedrooms, 6 full, 3 half baths and 8 fireplaces. The home is heated by both geothermal and oil forced hot air. Extra's also include an elevator, full house generator and an irrigation system. Pool house has a full kitchen, dining area, open living room with fireplace, 2 changing rooms/shower rooms and recreation/bedroom as well as a half bath. The charming cottage has living/dining combo with fireplace, bedroom and full bath. A guest house sits at the front of the property with living/dining combo, fireplace, kitchen, bedroom and full bath. The two story office includes 6 rooms, one bath and kitchenette. The horse barn, includes 16 stalls, bathroom, wash stall, tack room, office and full loft. There are 5 grass pastures and a riding ring. 90 minutes from NYC

Listed by Klemm Real Estate Inc