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.

Time Saving Tip: Create a free account to save your favorite listings and get notified when new properties match your criteria.

46C Senff Washington CT 06793

Washington, CT46C Senff Road

Price$11,950,000

Est. Mortgage: $/month

MLS Number 170391895

  • Single Family
  • Property Style Modern
  • Bedrooms 5
  • Bathroom 11
  • Acreage 106

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: 2.93% last updated on Jun 17, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

46 Senff Road Washington CT 06793

Washington, CT46 Senff Road Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number 170406828

  • Single Family
  • Property Style Contemporary, Modern
  • Bedrooms 5
  • Bathroom 11
  • Acreage 70.7

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: 2.93% last updated on Jun 17, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

184 Fern Litchfield CT 06759

Litchfield, CT184 Fern Avenue

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170361462

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 8
  • Bathroom 13
  • Acreage 29.5

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: 2.93% last updated on Jun 17, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

93 Amenia Union Road Sharon CT 06069

MLS Number 170403476

  • Single Family
  • Property Style Colonial, Barn
  • Bedrooms 9
  • Bathroom 14
  • Acreage 23.95

Iconic Sharon Estate sited on 24+/- 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: 2.93% last updated on Jun 17, 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

12 East Goshen CT 06756

Goshen, CT12 East Street North

Price$3,995,000

Est. Mortgage: $/month

MLS Number 170168838

  • Single Family
  • Property Style Georgian Colonial
  • Bedrooms 6
  • Bathroom 5
  • Acreage 74.32

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: 2.93% last updated on Jun 17, 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

113 Interlaken Salisbury CT 06039

MLS Number 170386255

  • Single Family
  • Property Style Cottage
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.05

Lakeville Lake Waterfront Residence -Peace and tranquility with unobstructed views over the lake to the Taconic Range. This private Lakeville waterfront lake retreat has 100' of direct frontage accessed by a sweeping lawn to your potential site for dock and potential swim platform. The main house has 3 bedrooms and 2 full bathrooms, 2 wood-burning fireplaces with a separate guest house with an additional bedroom and bathroom that make this feel like your own private compound. With vaulted ceilings, and several French doors to a large bluestone patio you will enjoy countless summer evenings.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

144 East Shore Washington CT 06777

MLS Number 170280303

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 4
  • Acreage 8.2

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: 2.93% last updated on Jun 17, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

69 Mudge Pond Sharon CT 06069

Sharon, CT69 Mudge Pond Road

Price$2,545,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170359039

  • Single Family
  • Property Style Barn
  • Bedrooms 5
  • Bathroom 6
  • Acreage 8.48

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: 2.93% last updated on Jun 17, 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

397 2nd Hill Falls Bridgewater CT 06752

Bridgewater, CT397 2nd Hill Falls Lane

Price$2,400,000

Est. Mortgage: $/month

MLS Number 170311976

  • Single Family
  • Property Style Colonial, European
  • Bedrooms 4
  • Bathroom 5
  • Acreage 44.18

Architecturally Designed European Style Country Estate, beautifully sited on 44+ acres w/wonderful gardens, amazing stone work, heated front walkway, landscape lighting & sweeping lawns. Fabulous craftsmanship & attention to detail. Lovely grand entry, paneled living room w/French doors to covered porch, formal dining room, cozy paneled library w/fireplace. Gourmet country kitchen, spacious family room w/cathedral ceilings & stone fireplace, fantastic game room, sun filled solarium that over looks the L shaped heated gunite pool, blue stone terracing and outdoor kitchen. 1st floor master w/cathedral ceiling and glass door to covered porch, upper level has 3 additional bedrooms and sitting area. This property also boasts an amazing 1 bedroom stone guest house w/kitchen, living room w/stone fireplace, dining area and loft, 3 bay garage, propane heating, generator and separate septic system Enjoy total tranquil privacy!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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

206 Hattertown Newtown CT 06470

MLS Number 170332337

  • Single Family
  • Property Style Colonial
  • Bedrooms 8
  • Bathroom 8
  • Acreage 7.07

Breathtaking private 7+ acre 3 homes on family estate! Unbelievable 1 of a kind property - room for *everyone* to move in! Perfect manicured grounds backs up to 27 acres of equestrian riding/hiking trails belonging to newtown forest assoc. No expense has been spared. Magnificent main house is a 5,412 sq ft nantucket-inspired colonial. Features 4 spacious bedrooms w/ 2 master suites & laundry on both the main & upper levels. Huge gourmet eat-in kitch, stunning formal dining rm, classic new england library w/details you will not believe. Office, formal reception/living rm, sunrm w/windows galore. Massive family rm w/cathedral/post & beam ceilings, fireplace (1 of 5). French doors open to incredible backyard patio. Barbecue, pool w/hot tub & waterfall, grotto, pergola, tennis & basketball courts. Giant sprawling yard ready for all sports, or barn, horses & more! Wait till you see the add'l 2 other custom designed/built homes! A private guest house w/post & beam constr. Kitch, fam rm, & vermont-inspired bedroom. The carriage house features attached 3 car garage w/bar, cathedral ceilings, fireplace & 3 bedrooms. Work out in the phenomenal gym below! Add'l 2 car garage is next door. Every house has its own mechanicals, c/a, septic. A standby generator backs up entire property. You will not find any other estate which offers so much for the value. One of the most beautiful homes in ffld county w/access to all major highways. Easy commute to stamford & nyc. Don't miss this one!

Listing Courtesy of CB Country to Coast Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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

129 Huntingtown Newtown CT 06470

Newtown, CT129 Huntingtown Road

Price$1,760,000

Est. Mortgage: $/month

MLS Number 170265307

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 7
  • Acreage 29.66

30 ACRE ESTATE! Helipad Allowed on the property! INDOOR HEATED POOL, YOUR OWN PRIVATE SAUNA AWAITS YOU! This majestic Newtown Estate is prominently situated on 29+ acres of lushly landscaped gated property. The Estate offers 4,153 sq.ft. of main house with a three car garage, 10 rooms with high elevated ceilings, 4 bedrooms and 4 1/2 baths and a beautiful indoor pool with sauna and hot tub/spa room. There is an additional 3,509 finished on the lower level to include the indoor heated pool. The property has a magnificent private 1 acre swim pond that is connected to the Pootatuck River. The grounds include a spacious 1800sq. ft. Guest House which offers 2 bedrooms, spacious office and 1 1/2 baths, high elevated ceilings, hardwood floors throughout with custom carved wooden doors and an additional 4-car attached garage. The Equestrian facilities offers 2 separate barns totaling 25 stalls. The first barn features 8 matted stalls with wash stall, tack room and feed room on the lower level; the upper level offers 7 matted stalls, hayloft, hay drop, bathroom and gathering room. The second barn offers 11 stalls, 2 tack rooms, feed room and storage shed; there also is a manure pad that can also be used for tractor storage when not in use. There is sand riding ring and additional grass riding ring, 13 grass paddocks, riding trails and a 4 horse run-in shed. A truly spectacular property. ABSOLUTELY A MAGNIFICENT SETTING!

Listing Courtesy of Flat Fee Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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

501 Litchfield Norfolk CT 06058

MLS Number 170348945

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 4
  • Acreage 22.33

EDGEHILL-A Country Compound A private estate outside the historic village of Norfolk CT, EDGEHILL fulfills the promise of the finest of country living and is equally perfect for a weekend getaway, year-round living, a family compound, or corporate retreat. Entering through a picturesque stone wall, the grounds consist of the Main House, a Guest House, a Cottage and Gatehouse/Caretaker's Apartment, a pool, pond, with open and forested land on 22.33 acres. The Main House presents a stunning and spacious Great Room overlooking the pool and upper terrace, a ground floor master suite, and 2 additional bedrooms. The year-round enclosed and heated porch offers 4 season wildlife watching as does the breakfast room. Cocktails or dinner for a few or many on the terrace or under the pergola adds to the charm. There are 4 fireplaces, multiple upgrades, and detail throughout. The house boasts central air-conditioning, a centralized music system on the first floor, and a generator. The refurbished Guest House, also centrally air-conditioned, is close to the Main House and encourages family and guest participation while maintaining privacy. EDGEHILL is just a short drive to the Norfolk village center offering country dining, entertainment, historic buildings, and its globally acknowledged treasure, the Yale Summer School of Music and Art. It is near Tanglewood, theater, great hiking, and ski slopes. Norfolk enjoys an unrivaled reputation in Connecticut's Northwest corner.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 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.

Save 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.