The Matthews GroupWilliam Raveis

The Matthews Group

CT Weekend Houses

Browse weekend homes for sale in Connecticut's Litchfield County. If you're looking for a weekend escape from Brooklyn, NYC, or the surrounding areas, Connecticut is just a couple hours away and is a beautiful place to go and relax! Our team of experts can help you find the perfect vacation home or weekend getaway. You may also be interested in viewing vacation homes.

Weekend Homes for Sale in CT

Contact The Matthews Group at 860-868-0511 or online with any questions or to schedule a private tour.

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40 A Nettleton Hollow Washington CT 06793

MLS Number 170384938

  • Single Family
  • Square Feet 5,162
  • Bedrooms 4
  • Bathroom 5
  • Year Built 2021

To Be Built. Hobi Award Winning, Shingle Style home built by fine home builder, Corbo Associates, set on spectacular 8.69 acres of open and lightly wooded private approved building lot with pond and stream in Estate area of Washington, next to the Historic District. Crushed stone driveway, mature trees and stone walls make it a perfect place to enjoy full time or weekends. *See other listing for parcel 170382611. Allowance for Pool. Close to the Mayflower Inn, Great hiking trails with Lake Waramaug Town Beach Access and area restaurants in both Washington and the Bantam/Litchfield area. Nettleton Hollow Road is a great level road for walking or biking and just 5 minutes from Washington Depot!

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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11 Tory Lane Newtown CT 06470

Newtown, CT11 Tory Lane, Taunton

Price$1,400,000

Est. Mortgage: $/month

MLS Number 170415500

  • Single Family
  • Square Feet 2,850
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1840

Updated vintage colonial 9-room home, large flexible use outbuilding, and barn nestled in an enchanting 5-acre setting within the quintessentially bucolic New England community of Newtown. A magical escape from Manhattan. The main house, like the town itself, respects tradition while also embracing modernity. Two renovations, expansions and updates preserved 19th century period details, including exposed hand-hewn beams, plaster walls and two brick fireplaces, while moving the 2,850 sf, 4-bedroom, 3-bath house into the modern era. The 1,214 sf outbuilding, added in 1920, features studio space, an outdoor shower, a cabana area with a full bath, and income-producing Airbnb opportunities. The barn provides space for rustically elegant entertaining, dining, relaxation, yoga, and meditation; like living in the pages of a Ralph Lauren catalogue. Nature at its finest; the property boasts a botanical bounty of open meadows with a profusion of wildflowers. The pollinator pathway gives way to secret gardens, an abundance of edible wild berry bushes, large fenced vegetable garden and canopies of trees with restful shade. Walking paths wind passed a custom in-ground swimming pool and fire pit with log stump seats. Conveniently located minutes from shops and eateries in the center of Newtown with its iconic flagpole. Proximity to I-84, and Routes 6 and 25. Close enough for a daily commute if necessary, perfect as a year-round home or weekend retreat.

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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137 Minortown Road Woodbury CT 06798

MLS Number 170407805

  • Single Family
  • Square Feet 4,214
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2000

Spectacular, Unique and Private! A gated drive brings you to this very unique home that gives you the feel of a ski lodge in the mountains. The land is beautifully landscaped and has about 1000' of frontage on the Nonnewaug River a short hike through the woods. There is a small sandy beach in one area and great fishing. A gunite pool with a water fall is right off the great room. The interior has an open floor plan with kitchen, dining and the great room easily accessed. The great room has a vaulted ceiling and a stunning 2 story river stone fireplace. 2 sets of sliders lead to the deck which leads to the pool area. The kitchen has granite counter tops, double ovens, a gas cook top and stainless steel appliances. The main floor master has a walk in closet, a fireplace, sliders to the deck and a master bath with a whirlpool tub and a separate stall shower. There is a main floor laundry room and another full bath on this level. The upper level has 3 additional bedrooms and a full hall bath. There is a finished den in the lower level with a gas fireplace and sliders to the out doors. For the car enthusiast/hobbyist, there is a 24X40 detached barn with 12' insulated doors and 2x6 construction. Bring all your toys! Under 2 hours to NYC makes this a great weekend getaway as well as a full time home. First time on the market! Taxes reflect 8 acres in 490 status

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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67 Taagan Point Road Danbury CT 06811
Pending Continue to Show

MLS Number 170416810

  • Single Family
  • Square Feet 3,044
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1934

Savour the rich rewards of life on the lake. Peace and tranquility, unobstructed views, western exposure and beautiful sunsets... This private Candlewood Lake waterfront retreat is a must see. The expansive, secluded outdoor space features 242' of direct frontage, two sandy beaches, lakeside patio, a private boat launch area, and a jetty, creating a protected swim area. There is potential for 2 docks and a swim platform. The gently rolling lawn and the thoughtfully designed English Gardens offer stunning displays of seasonal color as well as many private areas to sit and reflect. Nurture your mind, body & soul in this private, soul-soothing sanctuary. Custom designed by the homeowner, this 3000+ sf home awaits your personal touch. Home features 9' ceilings, 3 bdrms, 3 full baths, fieldstone fireplace and expansive deck, perfect for entertaining. The master retreat encompasses the entire upper level. With vaulted ceilings, skylights, arched windows and french doors to the Juliette balcony. Enjoy summer sunsets or the peacefulness of the majestic winter snow. The eclectic charm of the home reflects 30 years of love by the homeowners. With some updating and your creative perspective, this home can have a fresh, modern look that will reflect your own personal lifestyle. Whether enjoying this property as a year-round residence or weekend retreat, the possibilities are endless...

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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501 Litchfield Road Norfolk CT 06058

MLS Number 170348945

  • Single Family
  • Square Feet 3,756
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1956

EDGEHILL-A Country Compound A private estate outside the historic village of Norfolk CT, EDGEHILL fulfills the promise of the finest of country living and is equally perfect for a weekend getaway, year-round living, a family compound, or corporate retreat. Entering through a picturesque stone wall, the grounds consist of the Main House, a Guest House, a Cottage and Gatehouse/Caretaker's Apartment, a pool, pond, with open and forested land on 22.33 acres. The Main House presents a stunning and spacious Great Room overlooking the pool and upper terrace, a ground floor master suite, and 2 additional bedrooms. The year-round enclosed and heated porch offers 4 season wildlife watching as does the breakfast room. Cocktails or dinner for a few or many on the terrace or under the pergola adds to the charm. There are 4 fireplaces, multiple upgrades, and detail throughout. The house boasts central air-conditioning, a centralized music system on the first floor, and a generator. The refurbished Guest House, also centrally air-conditioned, is close to the Main House and encourages family and guest participation while maintaining privacy. EDGEHILL is just a short drive to the Norfolk village center offering country dining, entertainment, historic buildings, and its globally acknowledged treasure, the Yale Summer School of Music and Art. It is near Tanglewood, theater, great hiking, and ski slopes. Norfolk enjoys an unrivaled reputation in Connecticut's Northwest corner.

Listing Courtesy of Elyse Harney 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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65 Painter Ridge Road Roxbury CT 06783

MLS Number 170402214

  • Single Family
  • Square Feet 3,447
  • Bedrooms 4
  • Bathroom 3
  • Year Built 2001

Located on the most picturesque ridge in Roxbury is this gorgeous 7.33 acre country home. Known for its tranquil seasons and stunning westerly views. A residence boasting a combination of spaces for formal and informal entertaining. Perfectly proportioned rooms and sophisticated color palette. Special features include heated gunite pool, home office, rec room with gym equipment and pool table, fireplace, patio, hardwood flooring throughout, mudroom with access to oversized 2 bay garage off kitchen. A wonderful opportunity to live here all year around or use as a weekend getaway. Enjoy the surrounding cultural treasures, vineyards, ski resorts, parks, nature reserves, trendy restaurants and shops. Country splendor and convenient living all within 2 hours of NYC. On the market for the first time. Truly a pleasure to show.

Listing Courtesy of The Brokerage of New England

$
$
%
$/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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215 Belgo Road Salisbury CT 06039

Salisbury, CT215 Belgo Road, Lakeville

Price$1,095,000

Est. Mortgage: $/month

MLS Number 170417129

  • Single Family
  • Square Feet 2,160
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1965

“Contemporary Feel” and exceptional attention to detail are the magic behind this newly renovated, warm and inviting 3-bedroom and 3 bath home with a versatile floorplan. Located on a quiet country road in Lakeville, Ct. , enjoy amazing sunsets and fabulous western views from the spacious deck and living room with fireplace. Prepare delightful meals in the new kitchen with custom cabinetry, upscale appliances, center island, and gorgeous marble countertops. The tastefully appointed dining room transitions to the large screened-in porch and blue-stone patio, perfect for entertaining. The large media/family room offers many options to suit your lifestyle. The many enhancements, include hardwood floors throughout, all new electric, heating/central air systems, thermo-pane windows and entry door, and full-house generator, make this a great full-time country home or weekend retreat. Located just a short drive from The Hotchkiss School, The Salisbury School, and Indian Mountain School, this home is 2-hours from NYC and minutes from the train and the Mohawk, Catamount, and Butternut Ski Areas, as well as from Music Mountain, Tanglewood, Infinity Hall, and all the many cultural activities the Northwest Corner has to offer.

Listing Courtesy of Elyse Harney 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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170 Lower North Canaan CT 06024

MLS Number 170395161

  • Single Family
  • Square Feet 3,324
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1752

IDYLLIC COUNTRY HOUSE WITH RIVERSIDE CABIN Magnificently set, basking in the beauty of Canaan Mountain. A 1752 restored farm house with American Craftsman details constructed from timbers harvested off the property is now available for sale. Nestled between a classic New England 19th century church and the Blackberry River the main house, in pristine condition, with 3 Bedrooms, 3 Baths, is complete with a country chef's kitchen, 3 fireplaces and a wrap-around bluestone porch with beautiful unobstructed views of Canaan Mountain. Set on 12 acres with two large barns containing horse stalls, a chicken coop, a greenhouse, a workroom, 5 bays of garage with utility doors as well as a charming former country store with full bath, this picturesque estate could serve as a peaceful weekend retreat or as a horse property. A short hike through meticulously kept gardens, orchards, and bucolic pastures reveals the perfect country cabin set on 2000 feet of river frontage. Only 2.5 hours from New York City. Close to Berkshire school, Salisbury school, Hotchkiss school, Campbell Falls, Appalachian Trail, and Tanglewood. Near Salisbury CT, Norfolk CT, Great Barrington MA, and all that beautiful Litchfield County and the Berkshires have to offer.

Listing Courtesy of Elyse Harney 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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429 Mirey Dam Middlebury CT 06762

Middlebury, CT429 Mirey Dam

Price$859,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170404354

  • Single Family
  • Square Feet 5,312
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2000

Outdoor Oasis!! *HEATED POOL*PATIO*GAZEBO*4 SEASON SUNROOM*LEVEL YARD*FINISHED LL (exercise, media room) * Fenced & Private* Vacation at home while enjoying spectacular pool & setting! Perfect home for entertaining with great flow inside & out! STUNNING Brick Col (3662sf PLUS 1650sf LL = 5312 TOTAL) surrounded by Land Trust. OPEN SPACE & PRIVACY! 10ft ceilings & oversized custom doors 1st floor! Arched entry to dramatic 2 story marble foyer w/curved staircase, Palladium window & archways. DR w/tray ceiling, elaborate trim & alcove w/special accent lights; LR w/vaulted ceiling, Palladium window. Steps down to the sunken 2 story FR w/2 story windows streaming natural light, impressive flr to ceiling stone fpl, open balcony & built-ins! Gourmet custom kitchen with granite counters, two Wolfe Ovens, custom built hood vent, tile backsplash, Subzero refrigerator & wine cooler. French doors to a fabulous 4season sunrm w vaulted ceiling, skylights & glass sliders to heated inground pool, patio & expansive LEVEL yard w/firepit! Main flr MBR suite w/2 walk in closets, gas fpl, tray ceiling & bath with his & her vanities, tub & separate shower. Upstairs includes 3 add'l BRs:(2 BRs w/walk in closets & Jack/Jill bathroom, plus 3rd BR & full bath. PLUS 1650sf finished lower level Recreation Room, Exercise Rm, Media & Office w/walk in closet. Possible IN-LAW Suite! 3 car garage! Cul de sac. Award winning Region 15 Schools, 90 min/NYC & 120 min/Boston. Year round or summer weekend getaway!

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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365 South Street Litchfield CT 06759

Litchfield, CT365 South Street

Price$825,000

Est. Mortgage: $/month

MLS Number 170413440

  • Single Family
  • Square Feet 2,220
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1825

Located in the Litchfield Historic District, and less than a mile from the Village Green, this 1825 Colonial has just been updated to become your perfect full-time or weekend home. The main floor has a formal living room with gas fireplace, a dining room, a family room with fireplace that opens to the terrace, a generous recently updated kitchen, a laundry room and a full bath. The second floor now has a master bedroom with a new master bath en suite, two guest bedrooms and a new full bath. The beautiful wide board floors and beamed ceilings add charm and character. The house is equipped with central air. Recent improvements include the roof and double hung windows. The two-car garage is attached by a breezeway and is equipped with an electric car charger. The grounds are exceptional with mature perennial gardens, fruit trees and distant eastern views. Convenient to shopping, restaurants, skiing, hiking and Bantam Lake. Excellent private and public schools in the area including Hotchkiss, Forman, Frederick Gunn, Rumsey Hall and Taft. Approx 2 hours to NYC.

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

14 Minor Bridge Road Roxbury CT 06783

MLS Number 170414824

  • Single Family
  • Square Feet 3,906
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1961

Park Like Setting with room for a pool! This 5 bedroom colonial has room for all. It is spacious and open and has a first floor main bedroom with vaulted ceiling and walk in closet. The large kitchen is for the serious chef! There is a 60" Viking gas range with 6 burners and 2 ovens. A subzero refrigerator keep all your beverages cool and there are 2 dishwashers. The new quartz counter tops are lovely. There is plenty of space to work with the island. French doors walk out to a large rear deck for the barbeque. Both the large living room and family room have fireplaces and there is a lovely formal dining room. The chandelier in the living room is excluded. Wood floors complete the main level. On the upper level are 4 additional bedrooms and a full bath. The lower level features a laundry room and den plus a 2 car garage and storage. You can stroll across the road to Roxbury Falls and access to Lake Lillinonah is close by also. Enjoy all the summer fairs, art shows, land trust for hiking, swimming, fishing and so much more. The local Farmers Markets are open on Saturdays and there are many farm to table restaurants. The Antique capital of Ct, Woodbury is close by with many shops. Located 1.5 hours from NYC would make this a great weekend escape as well as a full time 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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62 Lakeview Road Winchester CT 06098
Pending Continue to Show

MLS Number 170394530

  • Single Family
  • Square Feet 4,709
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1958

Whether you are looking for a weekend retreat or a place to call home year round, this fabulous Craftsman Colonial offers the perfect blend of tranquil country living and convenience. Architecturally designed addition over $800k in 2003. Beautiful handcrafted millwork featuring masterful stairways, cabinetry, paneled walls and furniture grade built-ins, sun washed interiors and oversized windows. Dramatic Great room with spectacular floor-to-ceiling stone fireplace is truly a show stopper. An Entertainer's DREAM! Formal dining room is perfect for fireside dinners and conversation. Enjoy the smart design of the well-equipped gourmet kitchen w/stainless appliances and Rainforest Green marble counters complimented by breakfast bar for two, dining area with banquette seating, and gorgeous custom built desk. Main floor includes three good sized bedrooms and master with white spa-like bath w/sliders that lead to private deck. Loft w/library overlooking great room and second floor guest suite complete the upper level. Finished lower level includes a cool home theater just perfect for movie night, an exercise room, full-bath and 23' x 16' versatile office/guest suite/family room with fireplace. Heated garage, quarter sawn white oak floors, new kitchen appliances 2019, new pool liner, new septic tank 2015. Majestic sunrises and sunsets, beautiful snowfalls, summer fun at the saltwater pool, gorgeous fall foliage. Your very own private oasis. Exceptional Experience. Exceptional 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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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.