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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.

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Dutchess & Columbia County NY Listings

119 Under Mountain, Canaan, CT 06031

Price$800,000

Est. Mortgage: $/month

MLS Number L10224551

  • Single Family
  • Square Feet 3,072
  • Bedrooms 6
  • Bathroom 3
  • Year Built 1748

LIME ROCK DRIVERS: STORE YOUR CARS -- HOUSE YOUR CREW! - A tri-level 60×35 foot Barn (scroll for images) offers endless possibilities for race cars, artist's space, animals, and more. Also, within less than 5 miles of Lime Rock, in a bucolic setting with stunning mountain views, sits this cozy 1748 Homestead, totally renovated, and featuring 3 fireplaces, 6 Bedrooms and 3 Baths. A screened Porch overlooking the property adds outdoor entertaining space, and an open fenced deck surrounds the addition to the rear. The 18.42 rolling Falls Village, CT acres abut over 1,000 acres of conservation and State land and feature fruit trees, a swimmable spring-fed pond stocked with wide-mouthed bass, and a small stream. The former 19th century General Store with two-car Garage adds to the charm of this property. Located in the foothills of the Berkshire Mountains, close to all weekend activities such as race car driving, hiking, swimming, antiqueing, hunting, fishing, and skiing. On a gorgeous quiet road within close proximity to Music Mountain, the Appalachian Trail, private schools, and the Villages of Lime Rock, Lakeville and Salisbury. Set high in the Litchfield Hills, this property is priced below appraised value by motivated seller!

Listed by Eva Yxfeldt of Elyse Harney Real Estate

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Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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17 Woodin, Kent, CT 06757

Price$799,900

Est. Mortgage: $/month

MLS Number 170057020

  • Single Family
  • Square Feet 5,563
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2004

Stunning architecturally designed home on 13.5 acres protected by open space offering seclusion with trees as well as seasonal views. Two large flagstone patios and exceptional Trex deck with stainless steel cabling. When fall/winter comes enjoy the indoor pool with spa feature and the double wall gas fireplace. Master suite with gas fireplace and sitting room. two large closets (one with cedar on walls and ceiling). Breath-taking kitchen with high-end appliances, wine cooler and beautiful granite counter tops. Great room with corner gas fireplace offering an open concept allowing for an intimate flow for today's life style. Finished lower level with full bath, two exceptional bedrooms, exercise/recreational room. On the upper level is the loft which can be used for additional space for a home office. Outside is a fire pit for cool fall/winter nights. Speakers, lights, and lighting rods The Town of Kent has been recognized as the most beautiful town in Ct. PARADISE FOUND - JUST FOR YOU! Agent owner.

Listed by Rob Gansel of William Raveis Real Estate

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Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Chimney Hill, Sherman, CT 06784

Price$799,000

Est. Mortgage: $/month

MLS Number 170008246

  • Single Family
  • Square Feet 4,787
  • Bedrooms 4
  • Bathroom 5
  • Year Built 2004

1M to New York Line in total privacy on 4 ACRES find dramatic custom detail in this French Country Home w/versatile floor plan & traditional flair. Stunning cherry floors. Formal Music Room & Dining Rooms greet you. French Doors lead to Deck/Porch. Cherry Gourmet Kitchen w/breakfast bar & nook open to Vaulted Family Room w/frplc-french doors open to covered porch & terraced POOL AREA w/ Hot Tub. ML Master Suite w/frplc & french doors to Pool Area plus stunning Master Spa Bath & 2 walkin closets. 2 add ML BDRMS & full bath. Den/Library w/ frplc. UL hosts Family Room w/balcony & Full BA. 4-5 BD/3.5 BA includes FULL APARTMENT w/separate entrance. Walk In Pantry (14 x 15)/Walk In Laundry (12 x 9)/Mud Room (10 x 7). Don't miss the walk out lower level w/incredible storage & workshop area. 1 M to quaint town center, new community tennis court, pavilion and town beach on CANDLEWOOD LAKE. A wonderful home for weekend or year round.

Listed by Kathleen A Harrison of Fazzone & Harrison

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Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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195 Painter Hill, Roxbury, CT 06783

Price$799,000

Est. Mortgage: $/month

MLS Number 170021977

  • Single Family
  • Square Feet 2,432
  • Bedrooms 1
  • Bathroom 2
  • Year Built 1980

Yann Weymouth, a world-renowned architect, designed this modern retreat in 1980 using concrete block, galvanized steel, slate floors and walls of windows. The house has an open floor plan, an abundance of light and a private setting in an excellent location. A long driveway leads to a private 4.87 acre setting with mature gardens, extensive stone walls and open meadow. Perfect for entertaining! The great room spills out to a spacious patio with wisteria covered patio on the western side. The kitchen features high end appliances including Wolfe cook top, double ovens, and a spacious center island with slate counters. The great room has a wood burning fireplace, a wall of windows facing west and transom windows on the east side allowing room for art work. The current studio is a multipurpose room with high ceilings and skylights. There is an abundance of natural light throughout the house. At the far end of the house there is a spacious master bedroom with two master baths en suite and his & hers walk-in closets. There is a laundry room off the kitchen and an attached garage ready for future expansion. Unique and special. Note: the house could easily be returned to the original 2 bedroom layout.

Listed by and Bonnie Garguilo of William Pitt Sotheby's Int'l

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Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Rocky Mountain, Roxbury, CT 06783

Price$799,000

Est. Mortgage: $/month

MLS Number 170068540

  • Single Family
  • Square Feet 3,097
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1998

4/5-Bedroom Colonial on 4.15ac with possible in-law situated within walking distance to park/playground and hiking trails. Open floorplan. Hardwood floors throughout. Kitchen features granite countertops, double oven, and center island with cooktop, opens to Dining area with French doors to large deck with western seasonal views. Adjacent Great Room has Cathedral ceilings, old brick fireplace and ceiling fan. Separate Formal Dining Room. Fully finished basement features Exercise Room and Media/Guest Room with full bath. Owner/Agent. Possible short sale - may require bank approval.

Listed by Alison Lundie of William Raveis Real Estate

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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85 Curtiss, Warren, CT 06777

Price$799,000

Est. Mortgage: $/month

MLS Number 170075429

  • Single Family
  • Square Feet 850
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1939

Imagine waking up to the sound of the nearby stream and looking over vineyards and Lake Waramaug. This 10 acre-lot can potentially be divided into two building lots with sweeping views of Lake Waramaug -- within walking distance to the beautiful Warren town beach, Lake Waramaug Country Club and the historic Hopkins Inn & Vineyard. This property offers complete privacy in an estate area. If subdivided, it could support 4 or more buildings: a pool house, guest apartment, garage and main house. Conveniently located only 17 miles to the Metro North train, 6 minutes to the charming shopping village of New Preston, 90 minutes to NYC. Rustic Cottage from 1939 is sold "as is". Preliminary PERC tests have been done.

Listed by Mark Madonna and Jeffrey Phillips of William Pitt Sotheby's Int'l

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Smokey Hollow, Washington, CT 06794

Price$799,000

Est. Mortgage: $/month

Pending

MLS Number L10168186

  • Single Family
  • Square Feet 2,860
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1991

Magical Setting. Beautifully designed Colonial complete with in ground pool and seasonal views! Set on a quiet private lane and just minutes from Washington Depot, Bantam and Litchfield Center for great dining and shopping. The large open floor plan with Great room opens on to the Kitchen and creates great flow for entertaining. Kitchen opens on to a bluestone patio which overlooks the pool. The Level yard, Fenced pool area and Mature plantings and professionally landscaped grounds round out the feeling of a mini estate.. There are 4 generous sized bedrooms with 2.5 baths, hardwood floors and a Lower Level game room.

Listed by Kathryn Clair of William Pitt Sotheby's Int'l

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

56 Sandy Beach, Goshen, CT 06756

Price$799,000

Est. Mortgage: $/month

Open House

MLS Number 170083546

  • Single Family
  • Next Open House: Sun 27th 11:00 am - 1:00 pm
  • Square Feet 3,035
  • Bedrooms 3
  • Bathroom 3

Pristinely maintained builder's own waterfront cape cod style home with 90 feet of water frontage on 185 acre tyler lake offers the perfect location for year-round or seasonal living. The gently sloping yard leads to long dock perfect for mooring watercraft. A wrap-around porch as well as a screened porch are perfect for entertaining while enjoying breath-taking lake and distant views of the countryside. There is also a 4 bay barn/garage with the possibility of an apartment above. This lovely home is conveniently located to multiple cultural events such as the yale school of music, nutmeg ballet, the thomaston opera house, tanglewood, and jacob's pillow. Shopping, fine restaurants, hiking and skiing trails, private schools, and a fine library are all within a short drive.

Listed by Constance Breakell of Murphy E J Realty

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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Lakeville Lakefront

37 Canterbury, Salisbury, CT 06039

Price$799,000

Est. Mortgage: $/month

MLS Number 170000869

  • Single Family
  • Square Feet 4,704
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1971

This home is just a four minute walk to the association's 120 feet of private beach on Lakeville's Lake Wononsopomuc. Beach area has a dock, a float and room to store your kayak and canoes. Located on a quiet cul de sac with only eight residences, this brick home with lake views, has three recently remodeled bathrooms with quality finishes, fresh coat of paint and new carpeting throughout. A series of new sliding doors in the living room and kitchen face the lake and keep the house light filled and the large deck offers plenty of entertainment space. The spacious living room features a lovely stone fireplace. Home is fully air conditioned and move in ready. Full basement offers potential.

Listed by Mary Taylor of Best & Cavallaro

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Pond Ridge, Goshen, CT 06756

Price$799,000

Est. Mortgage: $/month

MLS Number 170085213

  • Single Family
  • Square Feet 3,000
  • Bedrooms 5
  • Bathroom 4
  • Year Built 2018

Waterfront!! To Be Built Home by one of Goshen's best builders! Meticulous attention to detail with coffered ceilings, stunning bathrooms, hardwood flooring, finished lower level. Main level master suite, great Dog Pond lakefront lot, 400 feet of private lakefront. One of a kind! Taxes are currently assessed on lot only,not house and lot. Lot also available for sale without a to be built house.

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

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

104 Hart, Litchfield, CT 06759

Price$798,500

Est. Mortgage: $/month

MLS Number L10137819

  • Single Family
  • Square Feet 4,116
  • Bedrooms 3
  • Bathroom 4
  • Year Built 1989

Spring is coming and everything will start blooming around this private sanctuary with INDOOR 16x32 POOL (not leaves, no bugs)! The fully heated 31x72 (2232 sq.ft.)pool/rec. room is ADD'L sq.ft. to this home which incl. exercise rm (poss. BR), add'l kitchen w/breakfast bar, entertaining space, skylights & multiple sliders to wrapped deck & courtyard. Enjoy a morning or midnight swim direct from your master suite. If you appreciate privacy... this single level California Style home was TOTALLY TRANSFORMED & EXPANDED in 1989 and is surrounded by stunning gardens on 7 Acres! A wonderful covered deck area leads to both a beautiful gardened courtyard with built-in infrared grill, 4 car att. garage & wrapped deck. ALSO featured is a 864 sq.ft. ACCESSORY APT. off garage which incl. 1 Bedroom, full kit., LR, W/D setup, walk-in closet and slider to yard. Great for in-law, caretaker, guest quarters or au pair. The main house offers an expansive living area with features such as a 3 sided gas fireplace, vaulted/cath. ceiling, open concept Kitchen dining area, office, 2 En Suites and an awesome Pub Room w/wet bar, fireplace and radiant heat. Central Vac, zoned CA, whole house generator are just some of the extra features. This home is truly an Oasis for the person that needs to get away from the hub bub of the busy world, needs easy access to highway & shops but doesn't want to pay the crazy price. If you're an entertainer or a naturalist, this home will certainly fit your needs.

Listed by John Sniffen and Ellen Waterhouse of William Pitt Sotheby's Int'l

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

Winchester, CT 06098

Price$798,000

Est. Mortgage: $/month

MLS Number 170013381

  • Land
  • Acreage 160
  • Waterfront
  • Zoning RU-2
  • Subdividable Unknown

Step away from the pressure of city life and enjoy your own enchanted retreat. Just minutes from schools and entertainment, in Winsted, CT, and less than 2.5 hours to either NYC or Boston, this 5 bedroom home on 160 lush acres, could be your perfect private getaway. This vintage charmer is conveniently located to Route 44 and Route 8; is backed by state land and a breathtaking pond; and also offers a separate dwelling, currently used as a workshop and art studio, along with other smaller out-buildings. Approximately 20 acres of beautiful, gently sloping fields, provide opportunity to keep horses, if you wish; or just enjoy nature all around you, easily accessed by the old logging trails through the woods ..... Almost the entire parcel is in PA 490, which results in the incredibly low assessment and taxes ..... Bring your imagination, and come see this stunning property! Reference Residential listing MLS#170012830

Listed by Elaine Tobiasz and Integrity Team of Integrity Real Estate

{$agent->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

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.