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The Matthews Team

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 Team 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
  • Bathroom 11
  • Property Style Contemporary, Modern
  • Bedrooms 5

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: 3.56% last updated on Jan 20, 2022
* 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: 3.56% last updated on Jan 20, 2022
* 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: 3.56% last updated on Jan 20, 2022
* 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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19 Golden Harvest Road Roxbury CT 06783

Roxbury, CT19 Golden Harvest Road

Price$5,700,000

Est. Mortgage: $/month

MLS Number 170459831

  • Single Family
  • Square Feet 5,808
  • Property Style Colonial, Barn
  • Bedrooms 4
  • Bathroom 6

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.

Listing Courtesy of Compass Connecticut,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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

The Ultimate Country Retreat 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 estate combining old world charm with 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 facing sunporch. Spacious kitchen and breakfast room with 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). 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. 8 stall horse barn, second barn with car lift, and 3rd antique barn with many possibilities. Guest House above 7 car garage, greenhouse, tennis court, orchards, gardens and riding paths. Stately and magical setting just minutes to town and under 2 hours to NYC. Private schools, Sharon Playhouse and Lime Rock Park just up the road.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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
  • Bathroom 5
  • Property Style Georgian Colonial
  • 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: 3.56% last updated on Jan 20, 2022
* 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
  • Year Built 1860
  • Bathroom 5

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: 3.56% last updated on Jan 20, 2022
* 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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7 E. Farm Road Middlebury CT 06762

Middlebury, CT7 E. Farm Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 170453155

  • Single Family
  • Square Feet 9,478
  • Bathroom 7
  • Bedrooms 4
  • Property Style Colonial, European

Old-world elegance with dynamic views of Atwater Pond. This estate includes 3 building lots acquired to buffer and provide seclusion, along with a bordering land trust. This European Inspired Country Manor is designed with artful detail and a grand size similar to distinguished French and English manors. Enter into the grand sweeping foyer with 20' ceilings, marble and porcelain floors, and the impressive custom curved stairway. Continue and find outstanding details everywhere. With the authentic French stone floor reproduction and other French and English influences, this marvelous home is art that surrounds you. The splendid living room boasts a circa 1776 antique French chestnut mantel accenting a hand-built limestone fireplace. The 12' ceilings with hand sculptured beams magnify the exhilarating sense of space felt throughout this stunning manor. The striking conservatory encompassed by a dynamic amount of glass illuminates the bluestone floors and brick trim. A focus point of the elegant dining room is the double-tier octagonal tray ceiling along with the custom hand-painted stencils continued from the living room through to the kitchen. The flow of the living space extends out onto the wide bluestone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The three lots can be used to add more gardens, add a pool and pool guest house, all while providing exquisite views of Atwood Pond ... continued in the addendum

Listing Courtesy of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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
  • Property Style Barn
  • Bathroom 6
  • Year Built 1990

Waterfront Country Compound - This Mudge Pond Waterfront Converted Dairy Barn is brilliantly renovated. The heart of the house is a Great Room with exposed wooden barn beams and a soaring ceiling, wide board flooring, and a wood-burning fireplace. Enter the stone-columned gate, drive up the allée of weeping cherry trees that leads into this 8.48-acre property. Cherry trees transition to a Concord grape arbor at the entranceway. Abutting Sharon Land Trust guarantees permanent privacy. Main house: 4-5 bedrooms, 4 full bath and 2 half bath, plenty of space for office, exercise or media center, a fabulous indoor swimming pool and Pond views from the kitchen, the Great Room, and 3 bedrooms. Ground-floor Master Suite with fireplace and double French doors to a private patio overlooking the Pond. Huge walk-in closet and master bath with radiant floor heating. Professional Wolf stove with two ovens awaits culinary efforts in the kitchen with its huge seating area and patio. Screened backyard Gazebo, with views in all directions. 100' private lake frontage. 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: 3.56% last updated on Jan 20, 2022
* 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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1 Tuccio Court New Milford CT 06776

MLS Number 170416003

  • Single Family
  • Square Feet 5,259
  • Year Built 2004
  • Property Style Colonial
  • Bedrooms 4

Your secluded & serene compound awaits! While resting at the end of a cul-de-sac & on the Lake Lillinonah, your new estate offers stunningly lush & vibrant year-round views providing cascading privacy over your 6.15 total acres all seen by your exterior multi-tiered balconies! Double lot offers the ability to build a guest house or 2, install a pool or a 2nd house. Permitted for private dock as motorboats are allowed. The proximity of this location makes your options endless w/NY just over an hr away! Your front lot proudly holds the most elegant of estates! This custom Colonial showcases exquisite master craftsmanship & masonry that have this home standing out from the rest! Meticulous landscaping curls around the home & draws you in as the breathtaking 2 story marble grand foyer welcomes you in past the leaded glass double doors. A must have chef's kitchen w/center island, bar & breakfast nook. Kitchen gives way to an impressive family room w/soaring ceilings, carved limestone & crowned w/a mantled fireplace. 1st flr also hosts a masterful office, master suite retreat guarded by French doors & a luxurious spa-like master marble bath. 2nd flr hosts 3 generous bedrooms w/walk-ins closets, lrg. bonus room. Lower level is pre-plumbed for additional bathroom. Whole house surround sound, 3 heating/cooling zones & whole house humidifier. 4th flr offers an additional 843sqft w/original plans for home theater. Master electrical control pad w/automatic lifts & 1 touch house control.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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1030 Main Street North Southbury CT 06488

Southbury, CT1030 Main Street North

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170409016

  • Single Family
  • Square Feet 6,372
  • Year Built 1787
  • Property Style Colonial
  • Bedrooms 5

The stately Rochambeau House is a Connecticut classic estate. This early Federal center hall colonial was attached by portico to a carriage house in the early 20thc. which incorporates an office and apartment. Many possibilities exist for multi-generational living and efficient professional space. An expanded kitchen with formal and informal living areas make this beautiful estate well suited to today's living. There is a barn with loft and an additional guest house outbuilding. House sits on 2.09 acres with an adjacent 14.75 acre lot including road frontage. Square footage includes outbuildings.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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167 Toddy Hill Road Newtown CT 06482

MLS Number 170389072

  • Single Family
  • Square Feet 974
  • Year Built 1935
  • Bathroom 1
  • Bedrooms 2

Beautiful 18 +/- Private acres in Newtown. This can be a great getaway home with two bedrooms, one bath cape, 794 square feet. Land has open field, rolling meadows and forest, several locations have long views. Close to I-84, Merritt Parkway and I-684, less than 2 hours to New York. You can build your home and keep the current home for a guest house. Great horse property, recent boundary survey map available. Lots of nature and wildlife here, this is a property you must see to appreciate! There are several possible home sites. See land listing 170394321

Listing Courtesy of Stone Crest Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 2022 SmartMLS, Inc.