The Matthews TeamWilliam Raveis

The Matthews Team

CT Family Compounds in Litchfield County

View the latest family compounds for sale in Connecticut's Litchfield County.

Family Compounds for Sale in CT

Contact The Matthews Team 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.

You may also be interested in browsing country estates.

141 5 1/2 Mile Road Cornwall CT 06753

MLS Number 170403678

  • Single Family
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 12,373
  • Acreage 550

Villa Catarina - A grand Tuscan-style estate spectacularly situated on 550+ acres in the heart of Litchfield County offers unparalleled privacy and security as well as magnificent tri-state views of MA, CT and NY. Approached by a long scenic driveway meandering through fields and forests, this unique country compound is introduced by a granite cobbled courtyard, framed by copper beech and fragrant linden trees. The exquisite limestone and stucco Palladian-inspired villa by award-winning architect Thomas Beeby offers superior, commercial grade construction with 5 bedrooms, 4.3 baths and 6 fireplaces. Opening from a dramatic 2-story foyer showcasing a double staircase, the main floor encompasses a formal living and dining room, reception rooms/galleries, a spacious kitchen, library, and study. Gorgeous reclaimed cherry wood floors with radiant heating and 9+ ft high ceilings provide distinctive details. Upstairs, 5 luxurious bedrooms each offer stunning views of the surrounding wooded hillsides. Inviting terraces and formal gardens with dramatic westerly views, along with a Har-Tru tennis court and 6-stall horse barn complete this enchanting property. Peace and tranquility abound with this rare and exceptional offering. Additional acreage available.

Listed by Joseph Barbieri and Diana Bisselle of Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

24 Pitch Road Litchfield CT 06759

Litchfield, CT24 Pitch Road

Price$6,250,000

Est. Mortgage: $/month

MLS Number 170494362

  • Single Family
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 5,470
  • Acreage 30

Oak Tor: An exceptionally private compound abutting White Memorial's 4,000 acres of conservation land and the Arethusa Dairy Farm. Beautifully restored 1897 Colonial Revival house full of period detail and charm set in an Olmstead designed landscape surrounded by stonewalls on 30 plus acres with two-bay barn with workshop, sauna and playroom; 20x40 gunite pool and poolhouse; heated Lord & Burnham greenhouse; and outdoor fieldstone fireplace. Main house has 7 bedrooms, large master bedroom suite with tower and dressing room, 4 full baths and 2 half baths, 5 fireplaces, restored eat-in kitchen, butler's pantry, spacious screened-in porch and bluestone terrace overlooking private park-like setting. This property includes the Donahue Cottage with 2 bedrooms & 2 baths, the Webster Cottage with 2 bedrooms & 1 1/2 baths & the Caretakers Cottage with 3 bedrooms & 2 baths, Total income from these cottages is $108,000. One-of-a-kind estate.

Listed by Ted Murphy of E.J. Murphy Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

333 Montevideo Road Avon CT 06001

Avon, CT333 Montevideo Road

Price$5,995,000

Est. Mortgage: $/month

MLS Number 170441863

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6,964
  • Acreage 115

This historic 115-acre estate has a private 12-acre lake entirely on the property and sits on Talcott Mountain at the highest point in Avon CT. With sweeping majestic views of the Farmington Valley and the foothills of the Berkshire Mountains, Montevideo is simply magnificent! The main residence, rebuilt in 1991, is situated around mature trees and affords eastern views of the lake and western views of the valley. In addition to the 7900 square foot main residence, the property has three houses ranging in size from 1,000 - 2,000 square feet, three Victorian-era barns, a boathouse, a dock, and a floating wood raft. Originally established in the early 19th century, the property has been home to only three families since 1890. Daniel Wadsworth, a well-known arts patron, originally developed the property. Many historic figures have enjoyed Montevideo. Hudson River Valley School artist Thomas Cole created several paintings from the estate. Mark Twain enjoyed swimming in the property's lake. Teddy Roosevelt would stop by for visits on his way to nearby Hueblein Tower. Today the same beauty that attracted some of history's luminaries still exists. Montevideo easily could function as a personal vacation property, a corporate retreat, or a recreational compound with a private music and art studio.

Listed by Paula F Ostop and Ellyn M Marshall of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

500-508 Twin Lakes Road Salisbury CT 06068

Salisbury, CT500-508 Twin Lakes Road

Price$4,385,000

Est. Mortgage: $/month

MLS Number 170490291

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 6,002
  • Acreage 8.29

Summer Fun on Twin Lakes Salisbury, Ct. - Exceptional Twin Lakes compound for the discerning buyer consisting of two gently sloping lots on over 8 acres with 490' of southerly exposed waterfront on Lake Washinee. The Main house has been tastefully renovated and upgraded while maintaining its vintage charm. Relax by the impressive stone fireplace in the Lodge room which opens to the kitchen and dining areas. In the summertime, the wide and comfortable screened-in Porch will be your own private oasis while you enjoy magnificent long unobstructed views over the lake. Two en suite bedrooms on the main level with one being a spacious primary suite leads you to the lower level with an additional bedroom, bathroom, gym, and entertainment rooms. Formerly a boys summer camp in 1940 the property has three additional fully winterized guest houses. Additional residences are Guesthouse (1) four bedrooms with three bathrooms; Guesthouse (2) four bedrooms and two and one-half bathrooms; Guesthouse (3) two bedrooms and one bathroom ( all per town of Salisbury Tax cards). Close to the Twin Lakes Beach Club and O'Hara's landing.

Listed by Elyse Harney Morris and Thomas Callahan of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

30 Mark Twain Lane Redding CT 06896

MLS Number 170478047

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 6,300
  • Acreage 28.53

"Stormfield" - the iconic mansion built in Redding for author Samuel Clemens, best known as Mark Twain, who lived there from 1908 until his death in 1910. Upon surveying the countryside from his new home, Clemens exclaimed “How beautiful it all is. I did not think it could be as beautiful as this.” He stipulated the house should be built in the style of a Tuscan villa, after having enjoyed time in Italy, and derived the property's name from his short story "Captain Stormfield's Visit to Heaven." After a fire in 1923, the current estate was re-built in 1925 on the same foundation, retaining the original terraces, stone walls, stone pillars, and formal gardens. The home is sited on 28.53 private acres and adjoins 161 acres of Redding Land Trust. This magnificent country compound includes the 6,300 sf main residence with 4-5 bedrooms, 5/1 baths, and 3 fireplaces, plus the detached pool/carriage house offering heated gunite pool, 3 garage bays, as well as the 2nd floor guest/caretaker cottage with 2 bedrooms, full bath, living room and kitchen. Feel like you've stepped back in time where exquisitely appointed period details artfully blend with today's modern amenities. Grand formal rooms include the elegant dining room overlooking the stone terrace and rolling lawn, plus the formal living room with striking hand painted coffered ceiling and adjoining library. One of Redding's signature properties and a rare opportunity to own a piece of American History, just 58 miles to Midtown.

Listed by Laura J Freed Ancona of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

102 North Street Roxbury CT 06783

Roxbury, CT102 North Street

Price$2,695,000

Est. Mortgage: $/month

MLS Number 170422197

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 5,204
  • Acreage 21.66

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 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!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

36 Clover Knolls Roxbury CT 06783

Roxbury, CT36 Clover Knolls

Price$2,675,000

Est. Mortgage: $/month

MLS Number 170484416

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 3,050
  • Acreage 129.04

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 3BR 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.

Listed by Rick Distel and Jeffrey Phillips of Compass Connecticut,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

22 River Road Sharon CT 06069

Sharon, CT22 River Road

Price$2,675,000

Est. Mortgage: $/month

Open House

MLS Number 170465512

  • Single Family
  • Next Open House: Sun 06/26 1:00 pm. to 3:00 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,516

WHITE HAWK - an impressive 1936 stone farmhouse situated at the foothills of the Berkshires on 35+ private acres. Approach this magical property through stone gates, and up a gently winding driveway past a large barn with car lift, paddock, guest cottage and cathedral pines to arrive at this beautifully situated country compound. Surrounded by expansive lawns, this stunning 4 BDR, 3.5 Bath home is the ideal retreat for outdoor enthusiasts and those who appreciate sophisticated country living. Inside the local stone-quarried home, one is greeted by a chef's kitchen and breakfast room overlooking beautiful gardens. A comfortable living room is flanked by a stone fireplace and bookshelves. A 3 season screened-in porch is off the living room and is the best vantage point to relax and watch wildlife. Cozy Study/BDR ensuite is just down the hall from the dining room. 3 large bedrooms and 2 full baths upstairs with stunning stone and wood accents. Large bonus room with wood stove, cathedral ceiling and picture windows - great for gazing at the distant mountains. Deep set windows, stone, and wood beams throughout. Step outside to enjoy a heated pool, a pond for fishing and boating, and a large stone fire pit. The soothing sound of Guinea Brook provides wonderful background noise. The perfect year-round getaway - and for gatherings big and small. Mohawk Ski area and Appalachian Trail nearby. Time stops at White Hawk but the outside world is minutes away. A truly memorable property.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

144 East Shore Road Washington CT 06777

MLS Number 170498716

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,222
  • Acreage 8.2

LAKE WARAMAUG COMPOUND, A BEAUTIFUL 8 ACRE parcel abutting Steep Rock Pinnacle Private land allows you to hike to the incredible Pinnacle lookout. The main house is tastefully appointed and recently renovated including dual pane windows on the main level, hardwood flooring and 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 BOAT HOUSE W/ dock, kitchenette, heat, seating and waterfront lights • Heated Indoor Pool • Screened Summer Room • Lavish Outdoor Entertainment Space • Two Story Guest House with Kitchenette, Gas Fireplace & extra storage Outdoor shower, propane grill and fireplace on the stone terrace

Listed by Pat Lahoud of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

13 Silver City Road Newtown CT 06470

Newtown, CT13 Silver City Road

Price$2,395,000

Est. Mortgage: $/month

MLS Number 170487336

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,989
  • Acreage 7.86

Retreat from the world in this 7.4-acre resort-like gated estate compound with guest cottage and private studio/office space. Set in the hills above Lake Lillinonah this immaculately maintained 7000 sq.ft. 5 bedroom/4.5 bath brick home is defined by serene views of nature and luxurious amenities like a dramatic front foyer with Moroccan marble tile, chef's kitchen, spa-like master suite and heated indoor Gunite pool with reclaimed stone waterfalls. A recently built elegant farmhouse style guest cottage contains living quarters on the main level, a multipurpose studio and office, half bath, and paved second driveway access. Perfect for entertaining, the main house boasts a custom bar room, theater/game room, three fireplaces and sauna. The grounds are illuminated with gas tiki torches, outdoor fireplace and extensive patios. Massive bifold door opens from the studio to the outdoors for hosting private classes, workshops or parties! Steps from miles of hiking, biking and horse trails, fishing and boating in Upper Paugussett State Forest. Additional equestrian/animal facilities include: 70 x 160 riding arena, 3 Dutch door style 10 x 12 horse stalls, 12 x 24 Dutch door stall & tack/hay room, additional sheds for housing/storage, fenced grazing pastures, 10 x 16 run-in shed, 7 by 28 ft chicken coop & netted habitat with pond and waterfall! Enjoy the best of a country lifestyle with numerous fruit trees and raised bed vegetable/herb gardens!

Listed by Chip Neumann of Houlihan Lawrence

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

141 Poverty Hollow Road Newtown CT 06470

MLS Number 170355313

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 3,657
  • Acreage 44.22

Exceptional opportunities abound for your imagination on these 44+- fabulous acres. Perfect for a secluded family compound for privacy and protection, an equestrian paradise with trails for the horse lover or just hike in all seasons and enjoy the serene and picturesque property around you. Protected lands (Aquarion Water) surrounds most of the property which provides added privacy. This is an estate area amid horse farms, prestige properties, and gentle hills. Nature has provided fabulous long distance views and picturesque terrain with a mix of cleared fields, woods and ponds. One section of the property contains a charming old colonial house built in the early 1800's, a barn, one-room schoolhouse and other outbuildings. The colonial home has been owned by the same family since the 1950's and would need a complete renovation. Situated close to Redding border on a road with an easy commute to lower Fairfield County and New York City

Listed by William Piccirillo of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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.