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Litchfield County CT Luxury Homes

Search the latest luxury homes for sale in Litchfield County, CT. The Matthews Group has the knowledge and expertise to help you find the right property. Discover a variety of listings in towns including: Washington, Kent, Woodbury, & more more!

Contact us for more information and to schedule a showing for any real estate below. Save your favorite listings when you create an account with us, and you can get email updates when similar properties are posted.

134 Sherry, New Milford, CT 06776

MLS Number 170143035

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.37

Enjoy Candlewood Lake comfort and the quintessential getaway in this updated, open concept, Western exposure home. Lake views abound from just about every luxurious room. The large chef's kitchen complete with granite countertops & professional grade stainless steel appliances flows freely into the dining room, as well as spacious living room, featuring a Fieldstone fireplace, floor-to-ceiling windows, and vaulted ceilings. A full, house-length deck with hottub, and plenty of space to entertain leads to the lake. A short hallway ushers you into the private main level master suite whose spotlights include Western sunset views and a walk-in closet. A two car garage, mudroom, & a three season enclosed porch are also found on the main level. The second level features two oversized bedrooms, each with walk-in closets, vaulted ceilings, and full bathrooms. One of the bedrooms walks out onto a private and spacious rooftop deck, the perfect place to enjoy the evening or morning coffee. The waterfront boasts a large dock, lakeside patio, well-landscaped yard, steps to sandy area, & of course, wide lake views with magnificent sunsets. This one-of-a-kind home also comes with a separate and private finished space that contains two individual offices sharing a double-sided fireplace. Countless other modern amenities include an updated propane furnace, Nest temperature control, & custom outdoor lighting. Come experience lake living year-round in this exquisite waterfront retreat.

Listing Courtesy of Advanced Real Estate LLC

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$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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370 Tucker Hill, Middlebury, CT 06762

Price$1,495,000

Est. Mortgage: $/month

MLS Number 170141985

  • Single Family
  • Property Style Antique, Tudor
  • Bedrooms 7
  • Bathroom 8
  • Acreage 48

Authentic in every way! Circa 1930's Topsfield is one of Middlebury's grand estates situated on 48+/- acres in the heart of town. Sited at the end of a long private driveway with majestic trees, mature landscaping, an expansive lawn, pastures, and views to the south. Being offered by the original family at a fraction of its replacement value and waiting for the next generation of ownership. Incredible potential to live in the home of ones dreams. Potential conservation easements or subdivision possible as well.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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271 South, Roxbury, CT 06783

Price$1,595,000

Est. Mortgage: $/month

MLS Number 170140845

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5
  • Acreage 12.26

Fabulous Gated Compound comprised of 2 Residences, 2 stables with 12 stalls and equipment barn all on 12+ beautiful, level, fenced in acres. The main house is an 1850's antique that has been lovingly restored. Master bedroom on the main level as well as one on the upper level. The gourmet eat in kitchen features custom cabinets and hi-end appliances. There are beautiful hardwood floors and 2 fireplaces, 1 in the living/dining room and 1 in the office adjacent to the main floor master. The family room overlooks a beautiful in ground pool. There is a room once a wine cellar in the basement. Many sets of french doors open to the lovely landscaped property, right out of a Currier & Ives painting. The 2800 sq ft guest house has 4 bedrooms, 2.5 baths and a lovely living/dining room, kitchen, office, family room, sun room and deck. There is 400 amp service with full house back up generators for both houses. The 12+ acre property is fenced for horses, (or other animals) with open pastures and an illuminated riding ring. Enjoy all the art and culture the area has to offer as well as many thousands of acres of land trust for your hiking and out door activities. Roxbury Falls is an old fashioned swimming hole close by for Roxbury residents use only. Enjoy the town centers of Woodbury, Washington, New Preston and Kent which are all close by with antique shops, boutiques, art galleries and great restaurants. 90 minutes to Manhattan makes this a great weekend as well as a full time home!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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484 River, New Milford, CT 06755

MLS Number 170140026

  • Single Family
  • Property Style Cape Cod, Log
  • Bedrooms 3
  • Bathroom 5
  • Acreage 25.43

Tranquility & Privacy with this extraordinary property sitting on 25+ Acres in Litchfield County. This Compound offers 4 properties! Main house is a Custom built log home, open concept floor plan & dramatic great room w/massive stone firepl. Chef's kit features top of the line SS appliances, gas stove & hood, food warmer, granite counter, center island & prepping sink. Main floor Master Bdrm, a true retreat w/steam shower, jet tub & walk-in custom closet. Two spacious Bedrooms, full bath & office complete upper level with a spectacular view over-looking the Great Room. LL has your family room, half bath, sauna & walk-in shower! Mudroom, first flr laundry, half bath, 3 car heated attached garage with loft above garage finishes the main level. Radiant heat on all floors! Guest/Staff house is 2,300 sq ft contemporary w/4 Bdrms, 2 full/1 half bath Beautiful 8 box stall barn w/tack rm & loft(can store up to 5,000 bales of hay), riding ring, 3 turn outs & a separate septic ready for hookup. This home is designed to allow you to experience indoor & outdoor living in a glorious natural setting. Minutes from the quaint towns of Kent & New Milford filled w/antiques shops, restaurants, stores & more. Close to Metro North Train station & 1-1/2 hrs to NYC. Endless possibilities on this private 25 acres, events venue, family retreat, Airbnb get away. Ultimate freedom to breathe, play, live and explore endless recreational opportunities within & surrounding this property!!

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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26 Greenwood, New Milford, CT 06776

MLS Number 170140396

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.08

Enhance your life! Imagine feeling like you're on vacation every day in a setting that boasts an active outdoor lifestyle Enter through the prestigious Ferris Estates to find this Lake Oasis on beautiful Echo Point w/ 150 Ft of Picture Perfect Lakefront built w/ no expense spared. This 4500 Sq Ft 4 Lvl abode has it all. From the Game Room & Media Center to the Gym & Library, the list goes on. This property sports a stunning luxury kitch, MBR Suite w/ magnificent bath, and an upgraded security system. Venture outside to find extravagant stone structures, boat dock, & waterside cottage for guest retreat. Multiple patios provide a variety of uses from entertaining family & friends to enjoying some quiet time soaking in the breathtaking views. Be sure to check out the video of the property to get a better understanding of what this incredible property has to offer.

Listing Courtesy of Re/Max Right Choice

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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170 Lower, North Canaan, CT 06024

Price$1,399,000

Est. Mortgage: $/month

MLS Number 170140001

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 13.54
  • Square Feet 3,324

This quality builder's home has endless possibilities on it's 12+ acres. Completely fenced in pasture land, and over 2,000 feet of river frontage, compliments the back of this property. The outer parts of land boarder beautiful pine trees and forestry, the state forest, and the Canaan mountains. The stately manor with it's 3 fire places adds to the charm with plenty of seating in the library or one of the two family rooms. The large out buildings consist of an art studio, workshop, stable perfect for the horse lover, green house, and a care takers's guest house. For the gardner's dream, an extravagant garden and mature fruit trees add to the country living found at this property. Blackberry River opens up to a beautiful swimming area and canoeing just along the property lines. Step inside to a charming, quaint, and cozy home that makes you want to stay in and warm up by one of the three fireplaces. This is not only the perfect home for owner occupant but for someone who sees the beauty of the historic church adjacent to the property for a wedding venue, winery, or a creative idea for the farm land. Ideal location 20-30 minutes from major ski resorts. Also located near private schooling including Berkshires, Hotchkiss, and Kent. Schedule your showing today, a unique property like this won't last!!

Listing Courtesy of Better Living Realty, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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150 East Hyerdale, Goshen, CT 06756

Price$1,650,000

Est. Mortgage: $/month

MLS Number 170138268

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 6
  • Acreage 0.92

Located on the East Side of pristine Woodridge Lake, is a one of a kind custom home. Real wood beams, open floor plan with high cathedral ceilings, massive stone fireplace, wide board floors, twin screened in porches. The kitchen is open to the main living area with granite counts, six burner Viking range, stainless steel appliances and a pantry. The master bedroom suite is located on the first floor with a walk in closet and a private bath. Four additional bedrooms and two baths are on the upper floor plus an open large lounge area that joins all four bedrooms. The lower level walks out to the lawn and lake and has a large recreation room with a fireplace and a full bath. A large bunk room w a half bath is above the 3 car garage. The large main floor deck has an outdoor spa and a staircase leading to the lawn. The private waterfront space has a dock and beach area.This classic style post and bream home is a must see. Call, text email to set up an appointment. Enjoy Country Club living at its best! Four sandy beaches; marina; boating and fishing; 8 tennis courts; (4 Har-Tru courts) a 12,500 sf clubhouse w/ Wi-Fi internet access, meeting rooms, library, fitness center, locker rooms; heated Jr. Olympic pool; playground; organized activities and much more. Woodridge Lake is a private community set on 1320 ac. The finished sf of the home is 5,193. The lower level sf is not included in the total calculated Heat & A/C space Lower level is 1,300 sf.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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79 Lake, New Fairfield, CT 06812

Price$1,595,000

Est. Mortgage: $/month

MLS Number 170139584

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.68
  • Square Feet 3,351

Enchanting and Eclectic Candlewood Isle expanded waterfront cottage is the focal point of this idyllic lake retreat with a rare Candlewood Isle in- ground , oval Wagner Pool, guest cottage and expansive lake views that envelope this unique property. The desirable open plan showcases a vaulted great room with beams, random, wide plank floors, floor to ceiling stone fireplace and French doors to an expansive, vaulted sunroom surrounded by pristine lake views from every angle. Updated kitchen hosts raised panel maple cabinetry, granite counters, gas cooktop, double ovens, L-shaped island and enticing lake views. An adjacent are ables as den or larger eat in kitchen area. An adjacent, grand dining room offers panel trim & views from all angles. Five spacious bedrooms, offer wood floors, a main level master & 3 baths in main house. The charming guest house with stone fireplace includes living room , kitchen, bedroom and full bath with deck overlooking the pool and lake. Room for expansion in the walk-up attic and full basement currently used for storage. Scenic perennial gardens, mature plantings including specimen trees and shrubs, stone walks, walls, wrap deck, dock and much more from this one of kind Candlewood Isle find.

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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120 East, Sharon, CT 06069

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170138331

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 2
  • Bathroom 1
  • Acreage 87.26

Sharon Mountain Cottage & Barn This 87+ acres parcel of pristine Sharon CT farmland offers a rolling landscape surrounded by a quintessential New England backdrop. The 2-Bedroom, 1-Bath Cottage and charming Barn located at the other end of the property boasts endless possibilities for your country retreat or comfortable provisions while you build your own forever home. This Sharon Mountain setting brings you to the heart of one of Litchfield County's premier locations. Minutes from Hotchkiss School, Wassaic Station, local skiing, lakes, and restaurants. Land Size: 87.26 acres Map: 11; Lots: 5 (76.73 ac.), 6 (2 ac.), 7-1 (8.53 ac.) Also available as: 170058935, 170058935, 170138304, 170138372, 170138384

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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104 East Street, Sharon, CT 06069

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170138304

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.23

A unique offering of this prestigious family estate in Sharon, CT. An original 200-year-old farmhouse, situated on Sharon Mountain, an area boasting large tracts of land and much conserved property. This 4-Bedroom, 3-Bath home with a renovation that includes the addition of the Master Bedroom Suite with private Bath, and Family Room with vaulted ceiling, hewn beams and wood burning fireplace. The property includes an in-ground swimming pool and barn. Bucolic pastoral view surround and additional land is available. This home is a short scenic drive from the Sharon town center and the area's amenities, including: Hotchkiss School, Salisbury School, Lakeville Lake, Sharon Beach, Millbrook School, Kildonan, and the villages of Great Barrington, MA and Millerton, NY. Enjoy the quintessential charm of New England from this year-round retreat in the heart of the Litchfield Hills. Also available as: 170058935, 170138304, 170138372, 170138384

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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109 Mountain, Kent, CT 06757

Price$3,950,000

Est. Mortgage: $/month

MLS Number 170134485

  • Single Family
  • Property Style Colonial
  • Bedrooms 7
  • Bathroom 7
  • Acreage 125

Spectacular Mountaintop Retreat with 270 degree views of CT, NY, and MA that are unrivaled in Litchfield County. Sited on 124+/- acres down a long driveway with gated entry. This property offers complete privacy with an extensive trail system, mature woodlands, flat playing fields, treehouse, vineyards, and an expansive lawn perfect for viewing the nightly SUNSETS. Truly exquisite landscaping with meticulously kept cutting, vegetable and berry gardens. Pool, pergola, outdoor dining pavilion, tennis. The interior features an open kitchen/family room area as well as a breakfast room with circular windows out to the view. There is also formal dining with bar and formal living room. Two main floor guest rooms could be combined to form main level master if needed. Large naturally cooled wine room where you can store the wine made with your own vineyards! If you are looking for a country estate with privacy and western views just 1 hour 45 minutes from NYC, this property should not be missed.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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15 Evans Hill, Sherman, CT 06784

Price$1,125,000

Est. Mortgage: $/month

MLS Number 170133519

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Acreage 4
  • Square Feet 4,887

Welcome to this idyllic country escape! Quality construction Colonial has a sophisticated contemporary flare with handcrafted details throughout the home. This wonderful gathering place has a main level open floor plan where the kitchen & breakfast nook share a fireplace with the large living room, and transitions to a raised sitting room at the center of the front entrance. The formal dining room with its see through fireplace, french doors and trey ceilings has the versatility to be a game room, and connects to a comfortable den with a vaulted wood ceiling. Rounding out the main level is an exquisite master bedroom suite with french doors leading to an enclosed porch, a see though fireplace connecting the master bathroom, walk in closet, and access to a large office with another gas fireplace. On the upper level, there are 4 bedrooms, 3 full bathrooms, exercise room, laundry room, and a second staircase leading back to the kitchen. Beyond the luxurious living space is the outdoor oasis! Inground heated gunite pool, relaxing hot tub, outdoor kitchen and patio area are the perfect summer retreat. Four acres offer privacy without isolation and is a golf cart ride away from the prestigious River Oaks Country Club. Close proximity to the train station make this a perfect weekend or full time home!

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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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Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.