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The Matthews Group

Litchfield CT Luxury Homes for Sale

Find the latest luxury homes for sale in Litchfield. Search through a variety of residential listings to find your new property. Save your favorite listings when you register with us, and you can receive email notifications when new properties match your criteria. You may also be interested in viewing luxury real estate listings in Litchfield County.

Luxury Homes in Litchfield Connecticut

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184 Fern Litchfield CT 06759

Litchfield, CT184 Fern

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170361462

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

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

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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257 Milton Road Litchfield CT 06759

Litchfield, CT257 Milton Road

Price$2,750,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number L10049256

  • Single Family
  • Square Feet 2,985
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1961

CHECK CTMLS # L10049231 This is Stonybrook Golf Course. Call agent for all the details. This beautiful property has the potential to be one of Litchfield Counties most stunning compounds/sanctuary. Land to build your dream home, maintain several holes for a private club, start a vineyard (full irrigation), option for horses. 2 ponds, stream, multiple buildings including 2 residential rentals.

Listing Courtesy of Gooseboro Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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178 Chestnut Hill Litchfield CT 06759

MLS Number 170376236

  • Single Family
  • Square Feet 6,621
  • Bedrooms 4
  • Bathroom 5
  • Year Built 2006

This custom built brick colonial is ideally suited for buyers who appreciate fine craftsmanship and exquisitely constructed millwork. The details of this home were meticulously planned and thoughtfully executed with top quality finishes throughout. Gourmet kitchen with large island opens to breakfast nook. Family room walks out to the spacious enclosed sun room and takes in views of the expansive back yard with its stone waterfall and pond. Office/library with fireplace Main level master with his/hers walk in closets. 3 bedrooms 2 baths on upper level. Office/Library. 8 zones. Generator. Lower level game room with bath and full kitchen. Wine cellar and wine/beer making studio. Barn with studio/workshop and addl 3 car garage. There are trails for walking/riding bikes at the end of this road with go on for miles. Just 5 minutes to the charming village of Litchfield and to the Litchfield Country Club. 2 hours to NYC.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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214 East Litchfield Road Litchfield CT 06759

Litchfield, CT214 East Litchfield Road

Price$2,195,000

Est. Mortgage: $/month

MLS Number 170391319

  • Single Family
  • Square Feet 5,229
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2007

This European country estate sits atop its own Litchfield Hill exuding craftsmenship throughout. Built for entertaining, a chef's kitchen sits at the heart of the home ...just off the kitchen, an atrium dining room overlooks manicured gardens and a stunning eight acre field. As meals are prepared, family and guests can join the chef in the gathering room warmed by one of four fireplaces. The living room hosts a cathedral ceiling, antique barn beams, and floor to ceiling window. Magnificent sunsets are enjoyed in the serene screened porch warmed by its massive stone fireplace. Unique spaces include a library landing off master, wine cellar, dance studio, hobby room, and gym. Owners are currently completely two bedrooms and bath... the guest suite will be ready for an au pair, in-laws, or visitors with its private entrance and kitchenette. Custom finishes include copper gutters, custom millwork throughout, and hand crafted cabinetry. The fully finished 2,200 sq ft barn has its own private bath, balcony, heat, septic, and water. The front has an expanse of French doors w/a covered porch overlooking the field. The back houses its large garden shed and a three bay garage. This versatile space could be a guest cottage, car collector showroom, studio, host equestrian pursuits, or grand entertaining! A private retreat moments away from the Litchfield Green, Route 8, and boundless Connecticut charm. A rare opportunity to own a one of a kind property.

Listing Courtesy of Mirabilio Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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44 South Street Litchfield CT 06759

Litchfield, CT44 South Street

Price$1,750,000

Est. Mortgage: $/month

MLS Number 170400250

  • Single Family
  • Square Feet 5,448
  • Bedrooms 5
  • Bathroom 7
  • Year Built 1855

Set on picturesque South Street, is one of Litchfield's few outstanding examples of an Italianate villa. Woodruff House was built in 1855 for George Morris Woodruff, a well-known resident of Litchfield at the time. This handsome, well-preserved home has a shallow hip roof with 3 wide bays. The front verandah is set with distinctive columns and there are two-story octagonal-ended bays and a double-tiered gallery. The 5448sf of living, includes a formal entrance, a Living Room, Dining Room, Den, well-appointed Kitchen, Family Room, Laundry, Mud Room and Office. Step up the grand staircase to a second floor with five bedrooms, two bedrooms are en-suite and the primary, en-suite bedroom has its own laundry and walk-in closets. There are four full and three half-baths. Enjoy a quiet moment in the rooftop cupola with distant western views. There is an underneath 2-car garage. Enjoy entertaining al fresco on the deck off the Sun Room. Step downstairs to the beautifully landscaped one acre of grounds with two additional patios. Have a swim in the heated pool. Extra features include an elevator, generator & five fireplaces. The property has a 985+sf , two-story, heated barn with electricity and room for two vehicles. Walk to town for shopping & dining. Close to White Memorial and hiking, fishing, skiing & horseback riding. 2 hrs. from NYC. Come view this truly extraordinary home!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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107 Clark Road Litchfield CT 06759

Litchfield, CT107 Clark Road

Price$1,695,000

Est. Mortgage: $/month

MLS Number 170328482

  • Single Family
  • Square Feet 3,934
  • Bedrooms 6
  • Bathroom 6
  • Year Built 1970

The warmth of summer invites you sit on the expansive deck and feel the gentle breezes. This architecturally designed Contemporary has been beautifully and thoughtfully updated. Bright and airy with expansive windows and wrap around deck. The river rock and slate walkways add a Zen like quality with the crisp stonewalls and landscaping. The present owners have done extensive renovations with the finest materials yet keeping the unique Chalet feeling of the house. The Kitchen has a wall of windows, granite counters, Wolf range, Subzero refrigerator, freezer, fireplace and door to the deck for outdoor grilling. Living room with built-in book case, fireplace and access to the deck. The Dining room has two story windows and pocket doors to the kitchen. Off the kitchen is the den - great spot to relax after dinner. Two bedrooms, one full and 2 half bathrooms complete this floor. The Primary suite is on the upper level with a fireplace and large walk in closet, beautiful custom bathroom. There are 2 more bedrooms and bath. The lower level has a bedroom, kitchen, dining room/living room combination, gym with mirrors, fireplace and door to the outside. Short walk through the winding river stone and slate path you arrive at the heated in ground pool and cabana. Many rooms for all sorts of activities - Minutes from the center of Litchfield. Lots of outdoor activities in Litchfield with great restaurants, walking trails, fishing, nearby golf. Come and enjoy!!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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571 Torrington Road Litchfield CT 06759

Litchfield, CT571 Torrington Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 170392324

  • Single Family
  • Square Feet 11,850
  • Bedrooms 21
  • Bathroom 25
  • Year Built 1990

Don't miss this unique opportunity to own the Iconic Tollgate Hill Inn -- This is a special property with many uses including a charming Restaurant with a large well equipped commercial kitchen, an Inn with 20 guest rooms with private full bathrooms and many with fireplaces, an 120 seat Banquet facility/ Conference Center, Wedding venue with plenty of rooms to accommodate guests, a Family Compound -- The possibilities are endless!! - The History of the buildings is amazing -- The 1745 Captain William Bull Tavern (on the National Register of Historic Places- No restrictions on the Building) houses the Restaurant and Bar along with 6 Guest rooms and has tremendous character throughout - The Schoolhouse Building was moved here in 1928 from Berlin, Ct. where it was the oldest Schoolhouse and has 4 Guest rooms - The Tavern and Schoolhouse are connected by a really cool tunnel that goes under the driveway -- The last building was constructed in 1991 and houses the Banquet / Conference Room with a very nice Lobby/Office area and 11 spacious Guest rooms with a large deck and patio overlooking a beautiful yard. This is one you must see to appreciate - Don't pass up this Spectacular Property!!

Listing Courtesy of The Washington Agency

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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158 Fern Avenue Litchfield CT 06759

Litchfield, CT158 Fern Avenue

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170358579

  • Single Family
  • Square Feet 4,351
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1995

Set on 8, beautifully maintained acres, lies this stunning, Country French Manor. Prominently situated, there are, manicured border gardens, stone walls and remarkable distant views to the east. On the south side is the Hauser Nature Preserve. Enter the two story, light-filled foyer with winding staircase. The first floor has a formal Living and Dining Room, a Kitchen with Family Room added in 2002 and with views to the terrace and eastern hills beyond. Adjacent to the Kitchen is a Sitting Area with fireplace. The first floor Master Suite has a dressing area, full bath and bedroom, also with views to the east. Enjoy cocktails on the stone terrace off the Family Room or on the deck. A side hallway provides additional storage, a serving bar with access to the Dining Room, making for easy entertaining, a Pantry, Laundry Room and half bath. There is an attached 3-car garage with above storage. The second floor has three bedrooms and a full bath, one bedroom, makes an excellent office. The Lower level is equipped with a generous amount of storage and a dedicated recreation/exercise area. The grounds are equipped with a sprinkler system and two storage sheds. New SEPTIC tank installed, May 2021!This property includes an on demand generator. Just two hours from Manhattan, close to the village of Litchfield for shops and dining, horseback riding, skiing, long walks and hiking. Come view this impressive, home and all that it has to offer!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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180 South Street Litchfield CT 06759

Litchfield, CT180 South Street

Price$1,200,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170269218

  • Single Family
  • Square Feet 5,521
  • Bedrooms 6
  • Bathroom 8
  • Year Built 1856

This architecturally significant home is located in Litchfield's historic district on South Street. Originally built as a boys boarding school for Oliver Wolcott's son, this residence is one of the fine examples of the mid-late 19th century homes that graced Litchfield's center. Situated on 2.6 acres, the property has sweeping, level lawns, a south side pergola and terrace and a heated in-ground lap pool. Step inside the foyer to grandness that includes a formal Living Room and Library with 9' ceilings, five fireplaces, a formal Dining Room, complete Chef's Kitchen, butler's pantry, a seating area with fireplace and French doors to a large exterior deck for entertaining. There is a paneled, cozy den off the Living Room with fireplace and powder room. The second floor has six bedrooms including a grand Master Suite with 9' ceilings, fireplace, three closets, full bath & dressing area. Two en-suite bedrooms, nursery, large laundry area & linen closets, the children's bunk room and hall bath complete the second floor. Enjoy gracious living with all the modern amenities. Truly an outstanding village residence! Less than 1/2 mile to the village center. Several points of interest including the Library, Tapping Reeve House, Law School and Meadow are along the way. Enjoy the village green with shops and restaurants. Just 2 hrs. from NYC, close to White Memorial, skiing, horseback riding.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 East Street Litchfield CT 06759

Litchfield, CT7 East Street

Price$1,049,000

Est. Mortgage: $/month

MLS Number 170258659

  • Single Family
  • Square Feet 4,021
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1782

This historic home w/ separate commercial bldg is a unique opportunity in the center of the uber charming village of Litchfield. Both buildings have been restored by the current owner while retaining their character incl: wide board flrs, wainscoting, paneling, & 7 frplces. Main house kitchen leads to a keeping room for gatherings around the large hearth fireplace. The show stopper is a spacious Tavern room, used as game room w/ its original bar. The 2nd fl features 4 beds w/ 2 full baths (there is room to add an addl bath). 3rd floor has 2 beds w/ a shared bath. Beautiful gardens, specimen trees, stone walls & patios surround the house & integrate the bldgs. The commercial bldg is used as a dr's office & can be configured to other specs. It includes an attached main floor bedroom apartment w/ full bath, kitchenette & terrace. A sep. entrance opens to a lobby/waiting rm, offices, 2 half baths (one w/ handicap access), kitchenette & a fully finished 2nd fl w/ 2 offices & storage. Signage facing rte 202 & the Village Green is grandfathered. For history buffs, this is the Rev Timothy Collins house & his son added the Tavern in 1770. The commercial bldg was built in 1781 & moved to its current location in 1812. It remains the oldest continuously occupied commercial bldg in CT. Main house & the office apartment currently active Air B&B w/ proven income & rave reviews. Easy walk to town restaurants & shops.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

15 Bigos Road Litchfield CT 06759

Litchfield, CT15 Bigos Road

Price$1,045,000

Est. Mortgage: $/month

MLS Number 170316513

  • Single Family
  • Square Feet 4,463
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2001

" WESTOVER " One of Litchfield Connecticut's finest homes. Long private drive flanked by open lawn leads to circular driveway with center garden and fountain. Covered entry welcomes you. Foyer offers a sweeping staircase, tile floors and Juliet balcony with French doors. Formal dining with hardwood floors, built-in hutch. Open Kitchen offers, granite counters, center island, pantry area. Great for entertains. Living area with granite wet bar, French doors to Garden Room overlooking back yard. Family room with wood floors, gas fireplace and French doors to tiled sun room. Second floor. Master suite affords a formal sitting room with gas fireplace, hardwood floors. The full bath offers granite tops vanity with double sinks, water closet, whirlpool tub. Guest suite with French doors and Juliet Balcony, tile bath and hardwood floors. Two additional spacious bedrooms offer side rooms and share a marble hall bath. Plus a finished third floor room 34'x25'. The basement can be finished for additional space and offers the finest in mechanicals. There is zoned central air. Combination of baseboard and radiant heat. Viessman boiler plus horicell Oil/hot water holding tank. 400-amp electrical service. An abundant of additional amenities. A three bay 36'x26' garage is finished, cooled and heated. There is also a brick floored and walled patio off the sun room. Raised garden offering specimen plantings, garden space, long vistas, open sky & Numerous amenities are to be seen upon viewing.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

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