The Matthews GroupWilliam Raveis

The Matthews Group

CT Homes with a Guest House

Explore current listings for homes with a guest house in Connecticut's Litchfield County. You may also be interested in viewing homes with a finished basement.

Homes with Guest House for Sale in CT

Contact The Matthews Group at 860-868-0511 or online with any questions or to schedule a private tour.

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46C Senff Road Washington CT 06793

Washington, CT46C Senff Road

Price$11,950,000

Est. Mortgage: $/month

MLS Number 170391895

  • Single Family
  • Square Feet 18,811
  • Bedrooms 5
  • Bathroom 11
  • Year Built 2002

Designed by architectural firm Gray Organschi - Il Poggio delivers on a vision many desire, few will accomplish. As you enter from a quiet country road, a modernist form rises from the hillside as the promise of serene relaxation, active endeavours, intimate gatherings, and memorable events unfolds. Walls of glass enhanced by the natural beauty of wood and stone frame unobstructed views of the landscape from every room. One level down you'll find the indoor activity center with a saltwater pool, hot tub, sauna, showers, squash court, movie theatre, family room, and game room. Venture outdoors to clip herbs from the kitchen garden, start seedlings in the greenhouse, practice yoga on the balconies. Follow the custom crafted foot bridge to the private spring fed pond. Swim or paddle a canoe on the pond, play tennis on the lighted courts, or tinker in the hobby barn. Stroll to the edge of the hillside to “the folly” - reminiscent of a Roman amphitheatre where family and renowned musicians have performed. Explore 106+ acres of Il Poggio before retiring with a glass of wine from the cellar in front of one of many fireplaces. Enjoy gatherings in the grand kitchen overlooking views of the pond or relax in one of five en-suite bedrooms with spa inspired baths in the main house - four with a wood burning fireplace. With a three bedroom guest house, and bunks for four in the grass-roofed tennis house there's room for many to stay in this enclave unlike any other in the Litchfield Hills.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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132 Curtiss Road Warren CT 06777

Warren, CT132 Curtiss Road

Price$10,000,000

Est. Mortgage: $/month

MLS Number 170418353

  • Single Family
  • Square Feet 3,372
  • Bedrooms 3
  • Bathroom 4
  • Year Built 1820

Step back in time at Lost Acre Farm to one of the last great opportunities to own over 100 acres of unencumbered land overlooking Lake Waramaug, CT's most beautiful and protected lake. The property is located at one of the highest spots in the area and along a dead end road abutting state land and major estates. The 3 bedroom existing main house has exquisite southwestern lake views, terraces, gardens, mature fruit/specimen trees, multiple guest houses, large equestrian barn, pool with pool house and a pond with waterfall. The 3 charming guest cottages can be restored for living while the main house undergoes renovation or you build anew. The total acreage is 114.64 acres currently divided into 4 parcels. Further subdivision and conservation potential is possible as there is significant road frontage. Percolation testing would need to be done by buyers. Under 2 hours to NYC. 10 minutes to chic village centers of New Preston, Washington, Kent, Litchfield, Warren. Access to Lake Waramaug at the Warren Town beach just a 2 minute drive down the street. Nearby country clubs offer golf, beach and tennis. 20 minutes to Mohawk Mountain for skiing. Taxes reflect all 4 parcels, much of land in PA 490.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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46 Senff Road Washington CT 06793

Washington, CT46 Senff Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number 170406828

  • Single Family
  • Square Feet 18,811
  • Bedrooms 5
  • Bathroom 11
  • Year Built 2002

Designed by architectural firm Gray Organschi - Il Poggio delivers on a vision many desire, few will accomplish. As you enter from a quiet country road, a modernist form rises from the hillside as the promise of serene relaxation, active endeavours, intimate gatherings, and memorable events unfolds. Walls of glass enhanced by the natural beauty of wood and stone frame unobstructed views of the landscape from every room. One level down you'll find the indoor activity center with a saltwater pool, hot tub, sauna, showers, squash court, movie theatre, family room, and game room. Venture outdoors to clip herbs from the kitchen garden, start seedlings in the greenhouse, practice yoga on the balconies. Follow the custom crafted foot bridge to the private spring fed pond. Swim or paddle a canoe on the pond, play tennis on the lighted courts, or tinker in the hobby barn. Stroll to the edge of the hillside to “the folly” - reminiscent of a Roman amphitheatre where family and renowned musicians have performed. Explore 70 acres of Il Poggio before retiring with a glass of wine from the cellar in front of one of many fireplaces. Enjoy gatherings in the grand kitchen overlooking views of the pond or relax in one of five en-suite bedrooms with spa inspired baths in the main house - four with a wood burning fireplace. With a three bedroom guest house, and bunks for four in the grass-roofed tennis house there's room for many to stay in this enclave unlike any other in the Litchfield Hills.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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184 Fern Avenue Litchfield CT 06759

Litchfield, CT184 Fern Avenue

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170361462

  • Single Family
  • Square Feet 12,016
  • Bedrooms 8
  • Bathroom 13
  • Year Built 1992

One of Litchfield's largest estates, on almost thirty acres, this 12,000sf Center Hall Colonial is perched on your own sprawling park w/stonewalls, heated saltwater Gunite pool, bluestone patios and decks. This estate boasts an oversized two bedroom guest house, renovated greenhouse. Land backs up to Topsmead State Forest & Land Trust for more seclusion. Inside find high ceilings, a two-story balcony, grand foyer, cascading staircase. Eat-in gourmet kitchen w/ x-large island. Treat guests to the inviting formal dining room bathed in sunlight and a fireplace, also in the heart of the home a big bright family room, a private library with custom built-ins, a private 3 rm suite, giant mudroom, 13 baths, 8+ bedrms, a master suite w/FP, sitting area, sunrm & luxurious spa retreat, a delight for any couple. Fully finished third floor plus fin walkout LL w/exercise-rm, wine cellar, 2-½ baths, steam spa shower, small kitchen and family room with a perfectly rustic grand stone wood fireplace. Come in after star gazing in your top of the line hot tub! For the enthusiast, a 6-car heated garage w/room for 12cars w/a lift. 7 zones, private gym, separate residence, new whole house generator. Two hours to NYC, live in Litchfield, one of Connecticut's hottest destinations in the country you crave only moments into town. Come explore life in Litchfield County w/vineyards, shops, parks, dining + more. Add a helipad for convenient and safe travel. Seller added substantial acreage this past year.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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93 Amenia Union Road Sharon CT 06069

MLS Number 170403476

  • Single Family
  • Square Feet 12,759
  • Bedrooms 9
  • Bathroom 14
  • Year Built 1983

Iconic Sharon Estate sited on 23+/- park-like acres with stunning western views on a coveted country road. This exceptional property (main house circa mid-1800s) was transformed into a magnificent country compound, combining old world charm with a plethora of modern amenities and stunning selection of newer buildings and barns. The main residence reflects the grandeur of its original vintage, with a collection of gracious rooms, period details and 7 fireplaces. A circular drive leads to a gracious entry with fireplace. Impressive living room with fireplace and large windows. Formal dining room showcases an elegant marble fireplace and French doors, leading to an enclosed east and south facing sunporch. Spacious kitchen and breakfast room include a large hearth, antique beams and flooring. Elegant wood paneled study with fireplace and bar connects to adjoining guest and entertainment building. 5 BDRs and 9 Baths in the main house (primary with fireplace, en-suite). 3 BDRs and 2 kitchens in the adjoining residence featuring cathedral wood-beam ceilings, large fieldstone fireplace, indoor pool & spa with enclosed terrace. Wine cellar, gym, sauna, and pistol range on lower levels. This ultimate country retreat also features an 8 stall horse barn, second barn with car lift, and third antique barn with many possibilities. Guest House above garage, greenhouse, tennis court, orchards, gardens and riding paths. Stately and magical setting just minutes to town and under 2 hours to NYC.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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207 Southeast Road New Hartford CT 06057

New Hartford, CT207 Southeast Road

Price$4,750,000

Est. Mortgage: $/month

MLS Number 170423749

  • Single Family
  • Square Feet 11,581
  • Bedrooms 7
  • Bathroom 11
  • Year Built 2003

Welcome to Bee Mountain Farm. This stunning, private 64 acre estate with gated access awaits you. Your own private hiking trails surround you and your almost 1 mile private driveway leads you to your breathtaking 11,500+ square foot shingle style, English country manor home, designed by architect Jack Kemper with inspiration from the beautiful Mayflower Inn located in Washington Depot, CT. As you enter the main residence the level of craftsmanship is unparalleled, with coffered ceilings, exquisite crown molding, oversized arched doorways, exposed wood beams, custom stonework throughout, wide plank floors, and a custom open concept kitchen/living room with oversized island that is sure to wow ! Cozy, and extremely well architected, this estate size home leaves you feeling inspired, relaxed and most important comfortable. A master suite with his and her baths 2 walk in closets, 5 additional bedrooms all with ensuite baths, yoga/media/playroom make up the second floor. Third floor includes a bedroom and bath, cedar closets for storage, and media room. The finished lower level makes you feel that you have stepped into a true English Pub experience! Custom bar with all the highest level of finishes! Magnificent coffered tin ceilings, copper sinks, concrete countertops, kegerator taps, temperature controlled wine room and gym with sauna! This is truly a must see in person property. Guest house, Two full home generators, 4 approved building lots, 5miles to shopping, 15 to Weha !

Listing Courtesy of Great Estates,CT

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12 East Street North Goshen CT 06756

Goshen, CT12 East Street North

Price$3,995,000

Est. Mortgage: $/month

MLS Number 170168838

  • Single Family
  • Square Feet 6,719
  • Bedrooms 6
  • Bathroom 5
  • Year Built 1802

CATHERINE HALL 1802 Classic Brick Federal Georgian on a 74-acre estate offering stunning period detail throughout the main house with over 6000sq.ft. 6 bedrooms, 8 fireplaces, grand private and public rooms with high ceilings in beautifully restored condition. A guest house with a garden overlooks endless views of water company land. A second guest house is a converted barn with 5 bedrooms, 2 kitchens, terrace, deck, and views. There is also a 1773 garrison-style homestead with 4 bedrooms and 4 fireplaces. The estate offers tennis courts, inground pool, stone walls, horse paddocks, formal gardens, sweeping lawns, and views. Perfect private or corporate country retreat, horse property, family compound, reception venue all with endless possibilities.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

36 Clover Knolls Roxbury CT 06783

Roxbury, CT36 Clover Knolls

Price$3,300,000

Est. Mortgage: $/month

MLS Number 170418676

  • Single Family
  • Square Feet 3,050
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1987

Clover Knolls - 129 acres of natural beauty in one of Roxbury's most storied and treasured corners. Offering a variety of Connecticut's best landscapes including sun-kissed farm pastures with distant views, lovingly tended mature forest, a sparkling spring-fed pond and open sweeping lawn around the contemporary home, few locations in Litchfield County evoke such emotion, inspiration and sense of place. Offered for the first time in nearly forty years, this special property is ready for its next chapter and presents a multitude of possibilities. There are multiple building parcels allowing for the construction of a larger main residence, separate dwellings for a single-owner compound, or for subdivision. The current 2BR residence is set on a perfect spot with views to the pond and further distant views beyond and was built with a beautifully warm and simple design aesthetic reminiscent of Frank Lloyd Wright. Construction of a larger, main residence at a higher elevation could leave the existing home as a guest house, pool/tennis house, etc. The property is largely held in tax-benefitting status and the forest is under a forestry management plan which keeps the woods healthy and maximizes their attractiveness for humans and wildlife alike. This truly magical land sits in the heart of Litchfield County's desirable Roxbury/Washington region, less than two hours from Manhattan but a world away. Taxes and assessment listed are for all five parcels.

Listing Courtesy of Compass Connecticut,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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102 North Street Roxbury CT 06783

Roxbury, CT102 North Street

Price$2,895,000

Est. Mortgage: $/month

MLS Number 170422197

  • Single Family
  • Square Feet 5,204
  • Bedrooms 6
  • Bathroom 5
  • Year Built 1860

Magnificent Compound. "Four Stone Chimneys" of Edgehill Farm, updated by noted NYC designer, the late Burt Wayne, is located just 90 minutes from NYC. Set on over 21 acres of open meadow, gardens and stone terraces in the historic town of Roxbury where Arthur Miller, Marilyn Monroe, Walter Mathau, Alexander Calder, William Styron, among many other artists and writers perfected their craft, is the perfect getaway! This 1860's Colonial Revival Estate with 6 bedrooms in the Main house, 4.5 baths and 4 fireplaces, has been lovingly maintained and updated with the finest materials. Enjoy your guests with a 3 bedroom carriage house and an additional 2 bedroom guest house surrounding a natural shaped in-ground pool, sumptuous gardens and brick terrace. The rooms are a generous size with high ceilings and detailed moldings throughout. A dramatic columned front porch runs the entire length of the main house. The guest houses, each with 1450 feet, have 4 season porches and overlook Orchard, Christmas Tree Farm and Pine grove. The barns and silos are noted on the Connecticut State Registry of Historic Farm Buildings. A stone walled driveway leads you into the heart of the this stunning "Gentleman or Gentlewomans' farm" and is the perfect residence for an equestrian, artist or writer!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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144 East Shore Washington CT 06777

MLS Number 170280303

  • Single Family
  • Square Feet 3,222
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1925

LAKE WARAMAUG COMPOUND, A BEAUTIFUL 8 ACRE parcel abuting Steep Rock Pinnacle. The main house is tastefully appointed & recently renovated including dual pane windows on the main level, hardwood flooring as well as a painted cork floor in the kitchen. The open floor plan on the main level includes a gourmet chef's kitchen with a breakfast bar, tranquil dining room, original stone fireplaces in the living room. A total of 4 bedrooms in the main house with the master bedroom suite boasting a vaulted ceiling, built-in bookshelf & includes aloft as a designated exercise room & office space with electric skylights. A meticulously maintained boathouse positioned at the best swimming & water skiing location on the lake. Walk down the steps to the water's edge with landscape lighting for your evening swim. The boathouse includes a kitchen, living area & docking for two boats. Spend the day on the lake & retreat to the main house for dinner on a beautiful stone terrace canopied by mature trees overlooking the lake; complete with a custom chic gas fire pit. AMENITIES AT THE LAKE WARAMAUG COMPOUND • Heated Indoor Pool • Screened Summer Room • Lavish Outdoor Entertainment Space • Two Story Guest House with Kitchenette, Gas Fireplace & Extra Storage

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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69 Mudge Pond Road Sharon CT 06069

Sharon, CT69 Mudge Pond Road

Price$2,295,000

Est. Mortgage: $/month

MLS Number 170359039

  • Single Family
  • Square Feet 6,000
  • Bedrooms 5
  • Bathroom 6
  • Year Built 1990

Waterfront Converted Barn - Mudge Pond Waterfront Converted Dairy Barn has been brilliantly renovated while retaining its authentic barn charm. Located on 8.48 acres abutting Sharon Land Trust. The soaring ceilings with exposed wood beams in the Great Room combined with the large wood-burning stone fireplace create a dramatic yet warm and inviting atmosphere while mesmerized by the calm waterfront. The Main house has 4-5 bedrooms and 5.5 baths, a fabulous indoor swimming pool and lake views from Kitchen, a Great Room, and 3 bedrooms. This amazing property boasts 2 Guest Houses. The Lake Side Guest House has a full kitchen, living room, bedroom, 2 full baths, and 2 patios with lake views. The Guesthouse on the Land Trust side has 2 bedrooms, a kitchen, a living room, 2 full baths, and a back porch. Convenient to Lakeville, Salisbury, Hotchkiss, IMS, and Millerton. Easy access to Metro-North.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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96 Kinney Hill Road Washington CT 06777

MLS Number 170412933

  • Single Family
  • Square Feet 5,010
  • Bathroom 5
  • Year Built 2001
  • Bedrooms 4

Private oasis in a coveted estate area with turn-key residence, in-ground pool and guest house circa 2016. Set on 10+ park-like acres, the main house includes 4 bed/4.5 baths, 3-season screened-in porch and heated pool with stone patio. The great room and eat-in kitchen flow seamlessly featuring a stone fireplace, maple floors, mahogany island, top-of-the-line appliances, dedicated pantry and comfortable breakfast nook. Doors throughout the main floor open out to a wraparound deck overlooking the landscaped grounds, herb gardens and pool. Wake to western views in the primary bedroom which features vaulted ceiling, walk-in closets and bathroom with radiant heat and soaking tub. Three additional guest bedrooms include built-in office nooks; one is en-suite. A bonus room functions perfectly as a gym or home office. Finished lower level includes a full bath, kitchenette, and bonus rooms. The side entrance via the three-bay, heated garage makes for easy living with upgraded mudroom and laundry room. The one-bedroom guest house is set privately and boasts a stone fireplace, screened porch, single-bay garage and electric vehicle charging station. The property includes an owned solar system which achieves nearly net zero electricity for the estate. Stroll the grounds via your own trails and enjoy seasonal views, stunning rock outcroppings and over 2+ acres of beautiful fenced-in lawn. Located minutes to New Preston, Washington Depot + Lake Waramaug this property truly has it all!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.