Litchfield County CT and Surrounding Area Homes $500k-$800k

Scroll down to find all $500,000-$800,000 homes for sale in Litchfield County, CT as well as in the surrounding communities in Dutchess County, New York. Contact us if you have questions or would like to schedule a private showing.

Search Smarter - Register with us to save favorite listings and be notified when new listings match your search criteria.

Dutchess & Columbia County NY Listings

75 Cunningham Warren CT 06754

Warren, CT75 Cunningham Road

Price$799,900

Est. Mortgage: $/month

MLS Number 170343475

  • Single Family
  • Square Feet 5,760
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2007

Custom colonial in the perfect country setting !!!! This incredible home was built by the builder for the builder and no expense was spared!!! From the moment you pull in the gravel driveway, you will get a sense of peace and privacy. With over 4,000 sqft of living space above grade and over 1700 sqft of living space below grade situated on 10+ acres to include a 40x60 steel workshop and a private pond, this is home you may never want to leave!!! The custom gourmet kitchen will surely blow your mind with plenty of room for multiple chefs, maple cabinets, granite countertops, all stainless appliances, double ovens, 2 dishwashers, a 20 ft center island, and a HUGE butlers pantry with prep sink and refrigerator. The open floor plan on the main level is an entertainer's dream with a formal dining room, living room with a fireplace, and a beautiful sunroom. A much-needed home office is on the first level and can also double as first-floor bedroom with access to the half bath. Upstairs you will fall in love with the perfect master suite complete with a walk-in closet, spa-like bathroom, and even a private sunroom! This floor also has 3 additional bedrooms and a full hall bath. The party continues downstairs in the walkout basement with your own private movie theatre and plenty of room for entertaining! Unplug and get back in touch with nature on 10.6 acres where you can make your own trails for countless days of outdoor fun!!

Listed by Heather Crabtree of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

103 Sharon Valley Sharon CT 06069

MLS Number 170313779

  • Single Family
  • Square Feet 4,165
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1870

Time to get away from it all & relax describes this updated farmhouse with addition, historic barn & located on 123 acres. Sit on the deck and enjoy the Webutuck Creek intersecting the land with thousands of feet of frontage and host to large trout and a plethora of wildlife. The home features a first floor master, suite, family room with fireplace, formal dining/living room with fireplace,home office, spacious bedrooms for the entire family and guests, hardwood flooring throughout, 1st floor laundry and stone patio. The farmhouse has the charm of yesteryear with tastefully done updates including 2 separate heating systems. Enjoy complete privacy with the open land and trail system. Take the bridge over the Webutuck to take advantage of endless possibilities including hiking, mountain biking,hunting, fishing, atv, dirt biking or just good old fashioned camping. Turn your dreams into reality and get out and see this special property today.

Listed by Michael H Barnes of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

711 West Wakefield Winchester CT 06098

MLS Number 170368687

  • Single Family
  • Square Feet 2,660
  • Bedrooms 3
  • Bathroom 4
  • Year Built 2021

Our plan or yours Large lot for the lake, 50 feet on the water, Easy access from forest ave. Plenty room to park andd party!!

Listed by Peter C Kores of Turning Point Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

168 Bentley Goshen CT 06756

MLS Number 170393974

  • Single Family
  • Square Feet 3,828
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2004

Charming home built by owner/contractor. Spacious rooms, high ceilings, and loads of natural light. Open floor plan offers great flow for entertaining and a real chef's kitchen with all the bells and whistles. Custom millwork, architectural detail, and sited a short walk from the lake / beaches. A truly grand home with private stone patio and sunny yard with specimen plantings.

Listed by Karen Newton and Stephen M Drezen of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1 North Sawyer Hill Washington CT 06777

MLS Number 170397911

  • Multi Family Multi-Family For Sale
  • Square Feet 4,983
  • Bedrooms 11
  • Bathroom 8
  • Year Built 1930

6 Units-4 Buildings B-3/R-1 Zones. Main House/Building 1-2016 sq. ft.- Built in 1930 4 Bed/2.5BA enclosed porch, oil heat, tank in basement. Building 2-3 Family Complex-1737 sq. ft.- Built in 1940 5BD/3BA oil heat/tank in basement. Building 3-Cottage-Built in 1930-1BD/1BA 630 sq. ft. Propane heat-outside. Building 4-Cottage-Built in 1930 1 BD/1BA 600 sq. ft. Oil heat tank outside. Proof of funds required prior to showing.

Listed by Kathleen A Harrison of Fazzone & Harrison

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

68 Gaylord New Milford CT 06776

MLS Number 170366805

  • Land
  • MLS Status Active
  • Acreage 57.1
  • Other Amenities Waterfront
  • Zoning R80

57.10 acres of undeveloped R-80 zoned land in picturesque Litchfield County. Build your dream estate. Or, builders create your desired residential community. 68 miles to the George Washington Bridge in NYC. Close to Danbury Line commuter train on Metro North. Close to Candlewood Lake, Mohawk Ski Mountain, hiking any many other outdoor and cultural activities.

Listed by Nalini Hage of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

72 Herb Sharon CT 06069

Sharon, CT72 Herb Road

Price$799,000

Est. Mortgage: $/month

MLS Number 170391179

  • Single Family
  • Square Feet 1,140
  • Bedrooms 1
  • Bathroom 2
  • Year Built 2006

Panoramic views of the Housatonic Valley overlooking 4 Towns! One bedroom 1 1/2 bath country home in a very private location bordering thousands of acres of preserved land including the Appalachian Trail Corridor. On a Town-designated scenic road. 16.2 acres of lightly wooded and meadow rolling land. Radiant heated 30' x 30' (11 ft. ceilings) first level garage. White oak 3",5",7" width flooring and lots of windows. 10' x 20' deck to enjoy the seasons and sunrises/sunsets. Full bath upstairs and half bath in garage area. Economical propane heat and cooktop. Potential for horses and livestock in meadows. Several potential sites for construction of the main house while using the existing house as a guest home. Underground 400 amp service and 4 bedroom existing septic system.

Listed by Ira Goldspiel and Stephen Pener of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

72 Herb Sharon CT 06069

Sharon, CT72 Herb Road

Price$799,000

Est. Mortgage: $/month

MLS Number 170395457

  • Land
  • MLS Status Active
  • Acreage 16.29
  • Zoning Res

Panoramic views of the Housatonic Valley overlooking 4 Towns! One bedroom 1 1/2 bath country home in a very private location bordering thousands of acres of preserved land including the Appalachian Trail Corridor. On a Town-designated scenic road. 16.2 acres of lightly wooded and meadow rolling land. Radiant heated 30' x 30' (11 ft. ceilings) first level garage. White oak 3",5",7" width flooring and lots of windows. 10' x 20' deck to enjoy the seasons and sunrises/sunsets. Full bath upstairs and half bath in garage area. Economical propane heat and cooktop. Potential for horses and livestock in meadows. Several potential sites for construction of the main house while using the existing house as a guest home. Underground 400 amp service and 4 bedroom existing septic system.

Listed by Ira Goldspiel and Stephen Pener of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

4 Mia Bella Drive New Milford CT 06776

MLS Number 170396123

  • Single Family
  • Square Feet 4,050
  • Bedrooms 4
  • Bathroom 3
  • Year Built 2005

Superior Colonial Style Home with Sunset Views on Nearly 2 Acres. Nestled in a quiet and desirable enclave in the charming town of New Milford, the gateway to New England. Explore the Town Green Farmer's Market, shops, cafes and delightful surrounding villages, each with their own character. End your days with sunset views from this immaculately maintained property. Inside, the light filled main floor flows easily for gracious entertaining. A spacious eat-in kitchen w/ garden views features a large island, granite countertops, Sub-Zero fridge, Wolf oven and induction range. Breakfast nook opens to terraced patio w/ outdoor kitchen and multiple seating areas. A stone fireplace is the focal point of the bright, airy living room. Double French doors open to the stunning formal dining room w/ tray ceiling. Crown molding and wainscoting details compliment inlayed hardwood floors. Across the two-story foyer is a home office. Main floor also contains powder room, full laundry, garage and basement access. Upper-level features Master Suite bathed in daylight, w/ walk-in closet, travertine bath w/ double sinks, jetted tub, walk-in shower. There are 3 additional spacious bedrooms and a full bath w/ double vanity. Large media room provides hang out space for games, movies w/ a Bose Home Audio system. A full unfinished basement contains utilities, plenty of storage. Oversized 3 car garage with epoxy floor and work area. This beautiful home offers the perfect balance of Town and Country

Listed by Travis A Given of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

279A Kent Road Kent CT 06757

Kent, CT279A Kent Road Road

Price$797,500

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170394280

  • Single Family
  • Square Feet 2,309
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1923

Originally built in 1923, this early mid-century home is set on 9+ private acres with an in-ground pool. The first floor features the kitchen, with butcher block counters and cozy eating area, that opens to the outdoor deck. The light-filled living room, anchored by a fireplace, is highlighted by a vaulted ceiling and access to a covered porch. The formal dining room includes an additional fireplace and opens to a lovely sunroom. A main level bedroom, currently used as a den, rounds out the first floor. Up a level, one finds the primary bedroom, which includes the home's third fireplace and sunny overflow space with vaulted ceiling, plus an additional bedroom that both share a full bath. Situated minutes to the village of Kent with easy access to Metro-North & NYC, this chic country escape awaits in the heart of of the Litchfield Hills.

Listed by Ira Goldspiel and Stephen Pener of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

College Hill North Canaan CT 06018

MLS Number 170339844

  • Land
  • MLS Status Active
  • Acreage 78.48
  • Other Amenities Golf, Waterfront
  • Waterfront

78.48 acres of farm land and forest on both sides of College Hill Rd. This is made up of 3 parcels. This beautiful property has been used for organic farming. The north side of College Hill has views to the Catskills! The Whiting River runs along the western boundary of the lot on the south side of College Hill. The best trout fishing in Ct. If you are looking for a large parcel to farm, build your dream home on, hunt, fish or as an investment, it is here waiting for you! Could be a major estate location! Taxes reflect 490 farming designation. Has to be used for agriculture. Development rights sold to the state years ago. Homes in photos are neighbors! Call for surveys.

Listed by Sharon McGuire of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

24 Dolldorf Kent CT 06757

Kent, CT24 Dolldorf Road

Price$795,000

Est. Mortgage: $/month

MLS Number 170398218

  • Single Family
  • Square Feet 1,848
  • Bedrooms 2
  • Bathroom 3
  • Year Built 2014

Modern Eyebrow Colonial custom designed and built in 2014 on 1.5 private acres off a scenic country road close to Macedonia State Park and the Appalachian Trail. Entering from the covered front porch into the foyer, one is drawn into the open concept main living space that anchors the home. A spacious kitchen with a center island is open to a large seating area as well as a dining area with sidebar and built-in wine fridge. Through a set of French doors, this living area opens to an expansive back patio. Rounding out the first floor is a den/guest room with a wood burning fireplace as well as a powder room. The upper level features the light-filled primary bedroom with vaulted ceiling, walk-in closet, and spa-like bathroom. In addition, a spacious second bedroom, with its own private bath, plus upper level laundry. All bathrooms include radiant heated floors. The lower level of the home has been finished and is currently used as a home office. The property includes a two car attached garage as well as a new custom 16' tall shed. Located in the heart of the Litchfield Hills near Kent's vibrant village center with many shops, art galleries and restaurants, this perfect country retreat is less than two hours from NYC and minutes to Metro-North.

Listed by Stephen Pener of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.93% last updated on Jun 17, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.