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
  • Property Style Cape Cod, Other
  • Bedrooms 4
  • Bathroom 5
  • Acreage 8.69

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: 2.96% last updated on May 6, 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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27 Bell Hill Washington CT 06793

Washington, CT27 Bell Hill Road

Price$2,600,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170384193

  • Single Family
  • Property Style Contemporary, Modern
  • Bedrooms 3
  • Bathroom 3
  • Acreage 4.11

TOP OF THE HILL One of the most desirable areas in Washington. Accessed by a quiet road leading to the top of Bell Hill overlooking the town of Washington, this 2,600+ sq/ft mid-century modern home sits among the stars, and offers jaw-dropping long views to the West while delivering complete privacy. Meticulously renovated, this flexible 3-4-bed/3-bath home is equipped with an array of modern amenities and designed with grand-scale windows that capture the surrounding vista. Boasting a bright, open living space with high beamed ceilings, hardwood flooring throughout, gourmet kitchen with french doors opening to patio/pool, two river rock wood-burning fireplaces, floor to ceiling windows, Master suite on main level, and dramatic views from every room. Outdoor features include a beautiful flagstone wrapped heated gunite pool, flagstone patio off the dining room, screened sunset porch, full-size paddleball court, sprawling lawn, and a gravel drive accented by a stone wall. Square footage listed does not include completely finished lower level. The perfect weekend retreat or fulltime haven in an area surrounded by the best estate properties. Minutes to the Washington Town Green, and Mayflower Grace Hotel. Llower level features french doors, walkout to patio area and views. Attached two car garage with detached 3 car. Whole house generator. Tenant occupied, showings by appointment only. Renovated in 2015. Conditioned space is 3539 sqft per Architectural drawings.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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43 Squire Roxbury CT 06783

Roxbury, CT43 Squire Road

Price$2,295,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170350542

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 3
  • Acreage 8.83

Spectacular and one of a kind estate and setting in Litchfield County offers views over Tierney Land Trust with a private walking path to cascading waterfall, "Mo Cuishle" or My Love is just under 80 minutes from NYC. Magnificently sited, private 8+ acres with Pool, updated and freshly painted 1940's 4 bedroom Cape Cod, with an Open concept floor plan make if a great weekend retreat of full time easy living home. A heated gunite pool, blue stone terrace with steps leading down to the pool and overlook of Tierney Land Preserve and Jack's Brook with a long driveway which leads you through an allee of hemlocks and out to level and rolling lawn with a fruit orchard and protected views. There is a walking trail that wraps around the property and gives an overlook of rushing Jack's brook and the cascading waterfall, abutting nearby hiking trails for great walks which make this a one of a kind estate property!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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 Norfolk CT 06058

MLS Number 170348945

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 4
  • Acreage 22.33

EDGEHILL 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 and great hiking in the summer and ski slopes in the winter. 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: 2.96% last updated on May 6, 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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2 Petersons Danbury CT 06811
Pending Continue to Show

MLS Number 170384511

  • Single Family
  • Property Style Colonial, European
  • Bedrooms 4
  • Bathroom 5
  • Acreage 1.86

Elegantly appointed, Colonial Estate Home, in West Danbury, less than 70 min to NY city, offers the ideal weekend/summer retreat or full-time getaway. Escape the confines of city life & surround yourself with beauty. Curb appeal beyond compare, professional landscape framed by stone walks, walls, patios, deck & outdoor fireplace, with an ideal site & design for a future pool & pool house. The gracious entry, with a sweeping staircase & open balcony, greets you! An elegantly appointed dining & living room are ideal for grand entertaining. French doors lead from the living room to a main level office & an expansive sunroom to use as a music room, game room or additional entertaining space surrounded by walls of windows. A Chef's kitchen showcases island bar, Viking appliances, gas range & butler's pantry. Four large bedrooms on the second level include an owner's suite with dual closets & marble bath with frameless shower, double vanities & jetted tub. A vaulted guest ste includes TV room & private bath. Two additional bedrooms plus a Hollywood style bath & fully appointed laundry room complete this floor. More room to grow or excellent storage space is found in the walk-up attic. The walk-out, lower level offers game & exercise room, full bath plus excessive storage with shelving. Three car garage, whole house generator, solar panels reduce electric, level yard, lush landscape, fountain & specimen plantings create an ideal escape to CT country just min to NY border!

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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lot Squire Roxbury CT 06783

Roxbury, CTlot Squire Road

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170388623

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3.05
  • Square Feet 3,500

Would you like to escape for the weekend to one of the most beautiful Towns in Litchfield county,let me introduce this unique opportunity to build your dream weekend home in Roxbury Ct,own this exquisite energy eficient new construction with high end finishes ,state of art first floor master bedroom suite with luxurious bath,gourmet kitchen open floor plan ,this is a perfect blend of modern and traditional architecture and style. designed for modern life style .Home Built By Corbo,call for floor plans and detail info.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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92 Hemlock Roxbury CT 06783

MLS Number 170394711

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3.03
  • Square Feet 3,500

Would you like to escape for the weekend to one of the most beautiful Towns in Litchfield county,build your dream home in Roxbury Ct,own this exquisite energy eficient new construction with high end finishes ,this is a perfect blend of modern and traditional architecture and style, truly once in the lifetime opportunity. This country cottage is designed for a modern life style offering the perfect blend of elegance,comfort,exceptional craftsmanship and today's technologies,spectacular gourmet kitchen open to specious family room,formal dining room,2 story foyer,fabulous ,state of art 1st floor master bedroom suite with hers and his walk in closets, luxurious master bath. Home Built by Corbo.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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329 Old Turnpike Bridgewater CT 06752

MLS Number 170336740

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 3
  • Acreage 30.94

Exceptional Views and an Extraordinary 30 plus acres surround this renovated contemporary with privacy plus! Spacious and bright, a two story entry greets you with an indoor Koi pond and waterfall, updated white Kingswood Kitchen with tile floor and granite counters, spacious great room with stone fireplace surrounded by nature views, lawns & gardens. Living and dining room plus 4 spacious bedrooms including a master suite with private bath and balcony offer room for family and guests. A separate bonus area, over the 3 car attached garage, is ideal for in home office. Exercise room and game room occupy the finished lower level. The new Azek wrap decking affords ultimate views of the property and distant hills. Ideal land for a horse farm includes a brook, lightly wooded area for trails and an additional 3 car detached, heated garage with epoxy floor and truck lifts (100 volt, 240 amp service)for 6 garages in total is perfect for trucks, tractors and equipment or for the car enthusiast. House has 2 attics and 400 amp service The ultimate in relaxation is found at the in-ground gunite pool with waterfall & views, surrounded by rock gardens and mature plantings. The ultimate escape from the confinement of the city in one of Litchfield's prime locations. Close to New Milford town center, shopping, theater & more! Special features A fabulous weekend /seasonal retreat or full time resiidence! Interior photos to follow.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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
  • Property Style Farm House
  • Bedrooms 3
  • Bathroom 3
  • Acreage 12.02

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: 2.96% last updated on May 6, 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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5 Shepards New Fairfield CT 06812

New Fairfield, CT5 Shepards Way

Price$899,000

Est. Mortgage: $/month

MLS Number 170388906

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.23
  • Square Feet 4,823

Resort-style living with heated in-ground salt water pool, huge patio, stone outdoor cooking and close to Candlewood Lake - An entertaining home for you to share and enjoy, only 60 miles from NYC! This spectacular home offers +4,000 sf of finished living space with plenty of space for company to stay for the weekend. The dramatic open two-story entry foyer is flanked by French doors to an office with built-ins and custom millwork, crown moldings and wainscoting throughout the home. The formal living and dining rooms are spacious with hardwood floors and open to the gourmet kitchen with center island, granite counters, propane cooking, SubZero, walk-in pantry and dining area with tile floor. The second front entrance has hardwood floors, opens to the beautiful family room with stone fireplace and sunroom with built-in desks, perfect for in-home learning. Upper level bedrooms include the master bedroom suite with hardwood floors, fireplace, dual walk-in-closets and full bath with jet tub and shower, three additional bedrooms with carpet and full hall bath. The lower level has custom built cubbies at the entrance, hardwood floors, large rec room/media room/exercise, full bathroom with shower and additional room, perfect for a second office, etc. French doors to the stamped concrete covered patio and pool area provides a top-notch entertaining space. Located close to town, hiking trails, shopping, MetroNorth trains - Vacation Living at its best - WELCOME HOME!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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13 Chelsea Danbury CT 06811

MLS Number 170390663

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.39

Elegant architectural detail exudes the comfortable living and entertaining this beautiful Westville Estates home will provide. This totally renovated Smart home is surrounded by a beautifully landscaped setting. The dramatic two-story foyer boasts a striking chandelier, an overlook & the ceramic mosaic porcelain tile flooring continuing into the elegant kitchen. There you'll find custom cabinets & upscale appliances, surrounding a uniquely designed island. All deliver the perfect milieu for a chef's dream. Beyond the counter height breakfast bar is the great room w/gas fireplace, beautiful hardwood floors & a custom entertainment center. The main floor is completed with the formal dining room emphasized with a tray ceiling, leading through swish columns to the living room & a den. The second floor has a fabulous master en suite featuring an exceptional bath with a distinctive vanity, sleek soaking tub, glass shower all w/unique fixtures, two walk-in closets & a sizable exercise room. Also on this level are three additional spacious bedrooms & the hall bathroom touting a “spa” feel w/a teak vanity & hanging glass shower dividers. The lower level has a huge L-shaped game/family room, an office with a wall fireplace & a shelved storage room. There is a deluxe outside environment great for daily use, entertaining & as a weekend escape. This SMART home has a great location for an easy down county & NYS commute. Don't miss this one - Call or text TODAY. See Addendum for more info.

Listing Courtesy of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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20 Brinsmaid Washington CT 06794

MLS Number 170396576

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 3.77

Light and bright define this three bedroom 2 1/2 bathroom center-hall Colonial located in bucolic Washington Depot. Stand on the expansive back deck overlooking four level acres complete with mature fruit trees. Inside you will find a NEWELY RENOVATED open concept kitchen, living and dining area. The kitchen is complete with stainless steel appliances granite countertops and soft close cabinetry. Upstairs you will find a spacious master bedroom with en-suite bath, two well appointed guest rooms and another full bath. A finished basement guides you to a screened-in, ground level patio with hot tub. Less than two hours from New York City this is the perfect weekend retreat. Move quick it won't last long!

Listing Courtesy of Regency Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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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 2021 Smart MLS, Inc. All rights reserved.