The Matthews Team

William Raveis Lifestyles Realty

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 William Raveis Lifestyles Team at 860-868-0511 or online with any questions or to schedule a private tour.

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Warren CT 06777

Warren, CT

Price$16,000,000

Est. Mortgage: $/month

MLS Number 170517236

  • Single Family
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 7,528
  • Acreage 231.85

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 Pat Lahoud of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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130 Taconic Road Salisbury CT 06068

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 - pending sub-division approval. Adjusted Assessment and Taxes TBD

Listed by Juliet Moore and Elyse Harney Morris of Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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46C Senff Road Washington CT 06793

Washington, CT46C Senff Road

Price$8,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170496156

  • Single Family
  • Bedrooms 5
  • Bathroom 11
  • Square Feet 18,811
  • Acreage 106

$1,700,000 Price Adjustment with 106+/- Acres! Designed by Gray Organschi Architecture - 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 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 wood burning fireplaces and spa inspired baths. Along 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.

Listed by Kathryn Clair and Kathryn C Bassett of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 170464720

  • Single Family
  • Bedrooms 8
  • Bathroom 13
  • Square Feet 12,016
  • 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.

Listed by Lisa Fagan of eXp Realty

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%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 Bristol Road Middlebury CT 06762

Middlebury, CT1 Bristol Road

Price$5,750,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170509609

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,409
  • Acreage 5.94

Stunning, turn-key, waterfront compound on 5.94 acres! Exceptionally rare opportunity to own an estate on Lake Quassapaug being sold with all furnishings inside and out, a double-decker pontoon boat, and much more to make this an incredibly easy move. Built by Beaver Mountain Log Homes of NY, there are 7 structures. The main residence; a 2 bedroom guest house; pool house w kitchenette & full bath; boathouse w office, 3 car garage w guest room, full bath, cigar and wine room; two story barn w full bath & loft; heated & cooled dog house w dog run. Main house features open living for easy entertaining, soaring vaulted ceilings & large windows to enjoy the incredible view. The chefs' kitchen has a large island, top of the line appliances, & side by side dining area. The primary bedroom is conveniently on the main level w full bath, walk-in closet and sliding doors to the covered rear porch. On the upper floor, there are 4 additional generously sized bedrooms, 2 full baths, an office/sitting room and loft space. The lower level boasts a media room, wet bar, rec room, full bath and 2 laundry rooms. The outdoor entertaining space has a Gunite infinity pool and spa and a covered rear porch overlooking the lake. There are patios, stonewalls, professionally landscaped gardens, and large dock for boating, fishing, swimming all at your own private lakeside lodge. This is a property you have to see to believe-words cannot describe all it has to offer!

Listed by Jill Sloane of Brown Harris Stevens

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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207 Southeast Road New Hartford CT 06057

New Hartford, CT207 Southeast Road

Price$4,750,000

Est. Mortgage: $/month

MLS Number 170423749

  • Single Family
  • Bedrooms 7
  • Bathroom 11
  • Square Feet 11,581
  • Acreage 64.06

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, 5miles to shopping, 15 to Weha !

Listed by Great Estates,CT

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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36 Whitford Road Sharon CT 06069

Sharon, CT36 Whitford Road

Price$4,675,000

Est. Mortgage: $/month

MLS Number 170506671

  • Single Family
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,070
  • Acreage 11.65

Exceptional home on 11.65 private acres with breathtaking western views. Large windows take full advantage of the view in the living room and kitchen. Enjoy the Chef's Kitchen with sophisticated design, a Marble-topped center island, stainless steel appliances, both gas and induction cooktops, an extra-wide sink, double ovens, and dishwashers for easy cleanup. Enjoy multiple dining options, al fresco on the deck, casual in the kitchen, or formal in the main dining room, each with its own appeal. Next to the kitchen, is a rustic and casual living space with a wood plank vaulted ceiling, stone hearth, and chimney. Other first-floor rooms include a library/office with built-in bookcases and a main floor bedroom with a shared full-sized bath. On the second floor, you'll find the primary suite with large windows, a walk-in closet, and a full bath. The lower level has great entertaining space with a mini-kitchen, wine storage, gathering space, large bedroom, changing rooms, and full bath. A french door provides quick access to the lounge area and pool. The attached guest house has a covered breezy-way and includes a gym/studio, full bath, bedroom, and private entrance. Professionally landscaped this property is truly special with beautiful plantings and specimen Pear trees. The heated gunite pool has a lovely grass surround and a pool house with an outdoor kitchen. Other features include a gated entry, a pond with a fountain, and cascading water feature.

Listed by Elyse Harney Morris and Tracy Macgowan of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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187 Wykeham Road Washington CT 06793

Washington, CT187 Wykeham Road

Price$4,295,000

Est. Mortgage: $/month

MLS Number 170482363

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,340
  • Acreage 11.13

One of the Most Admired Homes in Washington CT. Ultra Top Location on Quiet Secondary Town Road. Picture Perfect Estate with Meticulous Main House, Converted Barn Guest House, Pool & Pool House. Set on 11+ Flat, Useable & Manicured Acres Dotted with Fruit Trees & Mature Gardens. First Time to the Market in Over 30 Years. Finely Detailed 4 Bedroom, 5 Bath Main House Complimented by 3 Fireplaces, Gracious Room Proportions & Ubiquitous Natural Light. Welcoming Entry Foyer with Fireplace & Vaulted Ceiling; Enviable Paneled Library; Primary Bedroom Suite Enjoys Views Over Lush Grounds; Sun Room Offers Access to Gardens & Pool, Fourth Bedroom on Lower Level Includes Sitting Room, Full Bath & Roughed-in Area for Kitchen - These are Just a Few of the Special Features of this Fully Renovated Period Home. The Chic Guest Barn Offers 2-3 Bedrooms, Kitchen & Cavernous Living Room with Two-sided Fireplace. Timeless Gunite Pool/Spa & Pool House with Full Bath. This is a Special Offering in Coveted Location.

Listed by Graham Klemm and Carolyn Klemm of Klemm Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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95 Roxbury Road Washington CT 06793

Washington, CT95 Roxbury Road

Price$3,999,000

Est. Mortgage: $/month

MLS Number 170485710

  • Single Family
  • Bedrooms 6
  • Bathroom 9
  • Square Feet 8,888
  • Acreage 20.14

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, pool 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 Maria Taylor and Carolyn Klemm of Klemm Real Estate Inc

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 6,719
  • 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.

Listed by Thomas McGowan of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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
  • Bedrooms 9
  • Bathroom 14
  • Square Feet 12,759
  • Acreage 23.95

The Ultimate Country Compound sited on 23+ park-like acres with stunning western views. This exceptional property (main house circa mid-1800s) was transformed into a magnificent estate combining old world charm with modern amenities. 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, sunken 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, Guest House, greenhouse, tennis court, orchards, gardens and riding paths. Ideal for the car enthusiast/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.

Listed by Diana Bisselle of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 9,478
  • Acreage 7.99

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

Listed by Deborah A Laemmerhirt of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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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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.