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The Matthews Group

Our Litchfield County CT Real Estate Listings

Browse our current Litchfield County real estate listings below. Contact The Matthews Group at 860-868-0511 with any questions or to schedule a private tour.

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132 Curtiss Road Warren CT 06777

Warren, CT132 Curtiss Road

Price$10,000,000

Est. Mortgage: $/month

MLS Number 170418353

  • Single Family
  • Square Feet 3,372
  • Year Built 1820
  • Bathroom 4
  • Property Style Antique, Farm House

Step back in time at Lost Acre Farm to one of the last great opportunities to own over 100 acres of unencumbered land overlooking Lake Waramaug, CT's most beautiful and protected lake. The property is located at one of the highest spots in the area and along a dead end road abutting state land and major estates. The 3 bedroom existing main house has exquisite southwestern lake views, terraces, gardens, mature fruit/specimen trees, multiple guest houses, large equestrian barn, pool with pool house and a pond with waterfall. The 3 charming guest cottages can be restored for living while the main house undergoes renovation or you build anew. The total acreage is 114.64 acres currently divided into 4 parcels. Further subdivision and conservation potential is possible as there is significant road frontage. Percolation testing would need to be done by buyers. Under 2 hours to NYC. 10 minutes to chic village centers of New Preston, Washington, Kent, Litchfield, Warren. Access to Lake Waramaug at the Warren Town beach just a 2 minute drive down the street. Nearby country clubs offer golf, beach and tennis. 20 minutes to Mohawk Mountain for skiing. Taxes reflect all 4 parcels, much of land in PA 490.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 Arrow Point Road Warren CT 06777

Warren, CT7 Arrow Point Road

Price$5,000,000

Est. Mortgage: $/month

MLS Number 170436422

  • Single Family
  • Square Feet 6,974
  • Bathroom 6
  • Bedrooms 4
  • Year Built 2006

Unique opportunity to own fabulous shingle style house with direct frontage on Lake Waramaug with private dock and walk in beach area. Generous yard in both front and rear of house. Mature landscaping with fruit trees and lake irrigation system. Built to very high standards in 2006-7 with 4 en-suite bedrooms, open kitchen, dining and living rooms all with lake views. First floor guest room, office, screened porch with fireplace, mudroom, laundry and outdoor shower. Bluestone patio with built in grill. Second level includes 2 room primary suite with lake views, walk in closet, fireplace and balcony, two additional en-suite bedrooms and game room. Finished attic flex space on third floor. Walk out lower level includes gym, wine cellar, storage and unfinished area ready for your imagination. Both an attached 2 car garage and separate stand alone 2 bay barn with walk up space above. Generator and basketball complete this incredibly rare offering.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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9 Bristol Road Middlebury CT 06762

Middlebury, CT9 Bristol Road

Price$3,995,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170373397

  • Single Family
  • Square Feet 6,554
  • Bedrooms 5
  • Bathroom 5
  • Year Built 1962

https://youtu.be/mrrIdghSV14Lake living at its finest! Custom Greek Revival built from foundation up by current owners. An entertainers dream, this 5 bedroom, 4.5 bath home has 6 acres of direct frontage on Lake Quassapaug with its own drive in boathouse with power lift and private beach. Lake facing pool with separate spa and pool house with kitchen. Lakeside terrace with stone firepit. Stunning public spaces on main level including an enormous eat in kitchen with fireplace and entertainment area with projection video system. Commercial grade appliances include Traulsen refrigerator and freezer and 48" Viking range. Luxurious primary bedroom suite includes fireplace, office and its own gym with stunning lake views! An en-suite guest room, and 3 additional bedrooms with shared bath and laundry complete the second floor. 1200 square feet of heated garage space for 4 cars. Many smart home features, geothermal heat, generator, slate roof, random width hardwood flooring, just a few of the custom finishes. Room for tennis court if desired. Do not miss your chance to make this your own ultimate lake compound. Easy access from I-84, under 2 hours from NYC, 2.5 hours from Boston.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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50 Painter Ridge Road Washington CT 06793

Washington, CT50 Painter Ridge Road

Price$3,495,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170394971

  • Single Family
  • Square Feet 6,374
  • Bedrooms 6
  • Bathroom 6
  • Year Built 1988

Located at the highest point on Painter Ridge sits this fully renovated shingle style/barn style home in move-in condition. Huge gourmet kitchen with concrete counters, top of the line appliances, 2 dishwashers, walk-in-pantry. Open floor plan with 2 seating areas, lots of sunlight, screened porch with new UV heater, dining room seats up to 25. Current master bedroom has gas fireplace and gorgeous marble bath with expansive walk-in-closet and private deck. Adjoining room for office, yoga or 6th bedroom. Two additional 2nd floor bedrooms share a bath but there is room to add another if needed. Two main floor bedrooms are great for guests or could be connected into main level master if needed. Excellent Washington location, private yet minutes to the Mayflower Inn, organic market and all area amenities. Game room with pool table, foos ball, ping pong. Gym with treadmill, bike, rower and tv. Brand new spa like bath services game room and gym. Professional landscaping, perennial cutting gardens, irrigation system, plenty of flat lawn. Wine Cellar can fit 1000s of bottles. Gunite heated pool and Jacuzzi with waterfall and Nature 2 system to reduce chlorine use by 70%. Brand new full house generator and garbage shed. Walk to land trust trails. Owner/Broker

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 Road Litchfield CT 06759

MLS Number 170376236

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

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: 3.11% last updated on Dec 2, 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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Beebe Hill Road Canaan CT 06018

Canaan, CTBeebe Hill Road, Beebe Hill

Price$1,890,000

Est. Mortgage: $/month

MLS Number 170419970

  • Land
  • MLS Status Active
  • Acreage 72.46
  • Other Amenities Waterfront
  • Subdividable

Beebe Hill Road 72.5 SPECTACULAR Acres in Falls Village. Beautiful Farmland and meadow with wide unparalleled views of the Berkshires. The land is in 490 Farmland, but otherwise unrestricted. All the acres have gorgeous distant panoramic views. One of the best building site is near the top of the parcel at an elevation of about 1.000 ' which overlook all the surrounding countryside and valleys. The morning light is spectacular as it rakes across the hayfields and the sunsets are equally beautiful. POTENTIAL FOR GUEST HOUSES, CONSERVATION RESTRICTIONS OR SUB-DIVISION. PERC TESTS AND SUGGESTED ENGINEERING PLANS AVAILABLE. #1637 A must see ! Fantastic potential.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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

135 Crest Road Middlebury CT 06762

Middlebury, CT135 Crest Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 170453401

  • Single Family
  • Square Feet 3,864
  • Property Style Contemporary
  • Bathroom 6
  • Bedrooms 4

Remarkable mid-century style in the heart of Middlebury. Many recent upgrades. 4 bedrooms, 3 en-suite, one with hall bath. Chef's eat in kitchen, open living room/dining room, den, powder room, laundry/mudroom and 4 bedrooms all on main level. Gym, game room, darkroom, cedar closet and full bath in mostly finished lower level. Fabulous deck looking into the western tree canopy. Pool and pool house along with back up generator. Very close to town, Lake Quassapaug, I-84 and Oxford Airport (but not so close you can hear either). Fresh and fun!

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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

5 Bristol Road Middlebury CT 06762

Middlebury, CT5 Bristol Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 170415685

  • Single Family
  • Square Feet 1,680
  • Year Built 1928
  • Bathroom 2
  • Property Style Cottage

First time on market in over 100 years. 5+ acres of direct frontage on Lake Quassapaug with 1928 Cottage in need of renovation or build your dream home. Shares a private cove with its own drive in boathouse. Fabulous western sunsets across the lake with gentle sloping lawn and mature plantings and trees. Very special setting. Surrounded by multimillion dollar estates. 2 hours to NYC, 3 hours to Boston, less than 1 hour to Hartford or New Haven. 10 minutes to Oxford Airport.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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

530 Milton Road Litchfield CT 06759

Litchfield, CT530 Milton Road, Milton

Price$1,690,000

Est. Mortgage: $/month

MLS Number 170432292

  • Single Family
  • Square Feet 4,347
  • Bathroom 4
  • Bedrooms 5
  • Year Built 1756

Spectacular. Turn key. Authentic Salt Box circa 1756. One of the largest in Connecticut. In mint condition, with many recent updates. New mechanical systems, new kitchen and baths. A large generator is also a recent addition. A beautifully restored barn and a garage are an additional bonus. The landscaped beds and garden, enhanced with stone walls add to the charm and value of this unique propert. It is set in on historic Milton Green. It is over 4,347 sq,ft, on a 4.37 acres lot with 5 bedrooms, 4 bathrooms. Antique charm with all the modern convenience.The additional barn add another 2.000 s/f if needed... Truly an architectural Gem!... The house and the garden have being published in the Rizzoli book by Annie Kelly & Tim Street Porter" Rooms to Inspire in the Country".

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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

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
  • Year Built 1782
  • Property Style Colonial

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: 3.11% last updated on Dec 2, 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

MLS Number 170260841

  • Commercial
  • Square Feet 4,021
  • MLS Status Active
  • Year Built 1782
  • Acreage 0.5

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: 3.11% last updated on Dec 2, 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

1461 Bunker Hill Road Watertown CT 06795

Watertown, CT1461 Bunker Hill Road

Price$799,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170425217

  • Single Family
  • Square Feet 4,353
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2008

This Custom built Colonial greets you with beautiful Brazilian Cherry Floors throughout the main level. Formal living / sitting room with wonderful natural light. Formal dining room, again with great natural light, butler panty/bar w/dishwasher. Chef's kitchen w/high end appliances, room here to entertain your guests, open to family room w/ fireplace, or step out the French doors to enjoy morning coffee on the stone patio overlooking private back yard. 1st Floor Primary bedroom en-suite with private balcony, 3 guest bedrooms, upper level with views, 2 full baths. Wonderful Game room with deck & full wet bar. Lower level has exercise room, potential for in-law suite with separate entrance. Pool Site. Set on the out skirts of Watertown. Private schools nearby. Shopping, very convenient as are the major routes for commuting. This stunning home is waiting for you, your family and friends to enjoy!

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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

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.