Southern Berkshires: Find Your Perfect Community and Dream Home
February 24, 2023
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pending
132 Spencer Hill Road
Winchester, Connecticut 06098
$895,000
Very special land parcel. Western views overlooking Highland Lake. Pastures, fields, stone walls, brook & wooded areas showcase this wonderful building…
- TypeLand for Sale
- Lot82.0 Acres
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pending
37 Popple Swamp Road
Washington, Connecticut 06794
$3,350,000
Approximately 121 + or – Acres composed of open Lush pasture and a combination of assorted Woodlands. Road Frontage on Popple…
- TypeLand for Sale
- Lot121.5 Acres
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pending
118 West Morris Road
Washington, Connecticut 06794
$749,000
Spectacular Bantam Riverfront Property on quiet country road, within a short distance to Washington Depot and Bantam for great dining, shopping…
- TypeLand for Sale
- Lot25.79 Acres
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pending
400 5 1/2 Mile Road
Cornwall, Connecticut 06753
$14,995,000
This extraordinary estate with a beautiful Georgian Federal-style home was designed by the American architect Allan Greenberg for world-renowned tennis legend…
- TypeSingle Family
- Sq Ft18,000
- Year Built1992
- Lot445.615 Acres
- Bed10
- Bath15
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pending
173 Kennel Rd
Amenia, New York 12592
$3,995,000
Minutes from picturesque Millbrook Village, this stunning contemporary farmhouse reflects both the sophisticated genius of its world-renowned architect Pietro Cicognani and…
- TypeSingle Family
- Sq Ft4,551
- Year Built1996
- Lot172.71 Acres
- Bed4
- Bath5
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pending
2480 Green River Rd
Williamstown, Massachusetts 01267
$1,900,000
Amazing opportunity to own 244 acres of rolling hills, open fields and farmland surrounded by one of the most picturesque views…
- TypeSingle Family
- ParkingOther
- Sq Ft1,200
- Year Built1900
- Lot244.0 Acres
- Bed2
- Bath2
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pending
142 Christian Hill Rd
Washington, New York 12522
$745,000
Stunning mini-estate set on almost 6 park like acres tucked away near the end of one of the quietest dead-end country…
- TypeSingle Family
- Sq Ft3,165
- Year Built1962
- Lot5.9 Acres
- Bed2
- Bath2
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pending
110 Lower Church Hill Road
Washington, Connecticut 06794
$2,999,000
Stunning Stone Country House in premier Washington location. 4+ Bedrooms, 5 full & 3 half baths. Vaulted Living Room with wet…
- TypeSingle Family
- Sq Ft10,405
- Year Built2001
- Lot5.01 Acres
- Bed4
- Bath7
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pending
18 Homan Road
Stanford, New York 12581
$2,400,000
Perched atop a hill at the end of the long winding driveway sits this custom built 4 bedroom, 7 bathroom home…
- TypeSingle Family
- Sq Ft5,000
- Year Built1997
- Lot20.18 Acres
- Bed4
- Bath6
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pending
60 Good Hill Road
Roxbury, Connecticut 06783
$1,650,000
Sunny, spacious 4-bedroom contemporary colonial estate on 10 private acres with long driveway near the village of Roxbury. Bright airy rooms…
- TypeSingle Family
- Sq Ft4,928
- Year Built1996
- Lot10.11 Acres
- Bed4
- Bath3
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pending
115 Purple Mountain Pass
Williamstown, Massachusetts 01267
$2,950,000
With the ultimate in privacy, serenity and luxury, this mountainside sanctuary, high on a promontory overlooking a panorama extending from Vermont’s…
- TypeSingle Family
- ParkingUnder, Oversized, Auto Opener
- Sq Ft8,992
- Year Built2003
- Lot42.0 Acres
- Bed5
- Bath8
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pending
125 Hillandale Road
Westport, Connecticut 06880
$5,250,000
Better price for this PRIME Greens Farms location and all the value this home offers. Stunning luxury house in the heart…
- TypeSingle Family
- Sq Ft10,350
- Year Built2015
- Lot1.0 Acres
- CommunityGreen's Farm
- Bed6
- Bath8
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pending
432 Frogtown Road
New Canaan, Connecticut 06840
$7,000,000
Introducing Tirranna – a stunning estate embodying Frank Lloyd Wright’s genius. Situated on 14 acres of protected land, this architectural marvel…
- TypeSingle Family
- Sq Ft7,861
- Year Built1956
- Lot13.94 Acres
- Bed7
- Bath9
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pending
20 Chestnut St
V. Rhinebeck, New York 12572
$1,530,000
This 1890’s Rhinebeck village Victorian home is uniquely located on one of the nicest streets and lot in the village. The…
- TypeSingle Family
- Sq Ft4,679
- Year Built1890
- Lot0.68 Acres
- Bed4
- Bath4
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pending
34 Macedonia Brook Road
Kent, Connecticut 06757
$3,300,000
Wow is the word for this fabulous Modern country home set on the most idyllic 17 acres of farm fields, light…
- TypeSingle Family
- Sq Ft6,251
- Year Built2004
- Lot16.63 Acres
- Bed4
- Bath5
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pending
112 North Farm Way
Stanford, New York 12581
$6,750,000
Private Renovated Retreat. This country estate is privately tucked down a mile-long winding driveway on 125-acres with a 6-acre lake. Countless…
- TypeSingle Family
- Sq Ft5,956
- Year Built2003
- Lot125.62 Acres
- Bed5
- Bath6
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pending
3853 Route 82
Washington, New York 12545
$619,000
Mid-Century in Millbrook! Professionally remodeled home, done right, with no shortcuts. This 4 bed, 2 Bath multi-level shows like a new…
- TypeSingle Family
- Sq Ft1,793
- Year Built1962
- Lot2.6 Acres
- Bed4
- Bath2
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pending
59 Shun Toll Rd
Egremont, Massachusetts 01252
$3,750,000
Orchard Farm is a bespoke estate that was reconstructed on the original house site. It’s as elegant as it is casual…
- TypeSingle Family
- ParkingMultiple, Detached
- Sq Ft5,145
- Year Built1989
- Lot32.6 Acres
- Bed4
- Bath3
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pending
51 Craryville Rd
Craryville, New York 12521
$1,495,000
THREE OAKS Step onto this 18-acre property situated on a quiet country road, and you’ll find yourself in a peaceful, park-like…
- TypeSingle Family
- ParkingDetached
- Sq Ft2,758
- Year Built1900
- Lot19.92 Acres
- Bed3
- Bath3
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pending
17 Birch Lane
New Milford, Connecticut 06776
$679,900
Quintessential Candlewood Lake House, located in the desirable Candlewood Lake Club. Enjoy the lifestyle and all this club offers. Amenities include…
- TypeSingle Family
- Sq Ft1,809
- Year Built1937
- Lot0.39 Acres
- Bed5
- Bath3
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pending
66 White House Crossing Rd
Millerton, New York 12546
$2,375,000
Big Sky! Set on 30 spectacular acres, this 4 bedroom, 3-1/2 bathroom modern French Country home features a soaring 25 foot…
- TypeSingle Family
- ParkingNone
- Sq Ft3,514
- Year Built2002
- Lot30.77 Acres
- Bed4
- Bath4
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pending
66 White House Crossing Rd
Millerton, New York 12546
$2,375,000
Big Sky! Set on 30 spectacular acres, this 4 bedroom, 3-1/2 bathroom modern French Country home features a soaring 25 foot…
- TypeSingle Family
- ParkingNone
- Sq Ft3,514
- Year Built2002
- Lot30.77 Acres
- Bed4
- Bath4
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pending
4318 Route 44
Washington, New York 12545
$1,950,000
En Route is a chic Hudson Valley gem that combines impeccable design with comfort and livability. Original details blend seamlessly with…
- TypeSingle Family
- Sq Ft3,598
- Year Built1930
- Lot6.01 Acres
- Bed3
- Bath4
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pending
100 Gavitt Road
Barkhamsted, Connecticut 06063
$629,000
NEW CONSTRUCTION! GORGEOUS, TRADITIONAL FARM HOUSE COLONIAL TO BE BUILT on private 2+ acre lot in Barkhamsted. +/- 2675 SF, 4…
- TypeSingle Family
- Sq Ft2,675
- Year Built2023
- Lot2.36 Acres
- Bed4
- Bath3
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pending
63 Flat Rock Road
Kent, Connecticut 06785
$599,000
Rare opportunity in estate area of South Kent previously owned by well known antique dealers. Private wooded lot with stone walls…
- TypeSingle Family
- Sq Ft2,714
- Year Built1972
- Lot4.9 Acres
- Bed2
- Bath2
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pending
3440 Route 44
Millbrook, New York 12545
$995,000
1750’s farmhouse combined with an 1890 Greek Revival home located in Millbrook, Dutchess County, NY. The home has been featured in…
- TypeSingle Family
- Sq Ft3,540
- Lot3.6 Acres
- Bed5
- Bath5
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pending
123 Littlefield Road
New Milford, Connecticut 06776
$574,900
Come and see this tastefully restored 18th Century antique charmer, set on a quiet corner lot in New Milford’s historic north…
- TypeMulti Family
- Sq Ft2,952
- Lot1.39 Acres
- Bed6
- Bath3
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pending
39 Main St
Stockbridge, Massachusetts 01262
$1,399,000
RARE GEM! Impeccably preserved, unique and elegant Italianate residence looking for its new custodian. Perfect for refined in-town living and seamless…
- TypeSingle Family
- ParkingAuto Opener
- Sq Ft5,333
- Year Built1850
- Lot0.56 Acres
- Bed6
- Bath6
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pending
215 West Wakefield Boulevard
Winchester, Connecticut 06098
$1,195,000
LAKEFRONT stunning Queen Anne 1880 Victorian with sweeping lake views and 200′ direct waterfront with decks and docks! Gracious entry between…
- TypeSingle Family
- Sq Ft2,873
- Year Built1880
- Lot3.0 Acres
- Bed8
- Bath3
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pending
61 Bramble Ln
Lenox, Massachusetts 01240
$1,125,000
Lake life at its best Stunning mid century home on Laurel Lake. Wake up to coffee on your deck or oversized…
- TypeSingle Family
- ParkingAuto Opener
- Sq Ft2,596
- Year Built1955
- Lot0.37 Acres
- Bed3
- Bath3
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pending
45 Fox Ridge Drive
New Milford, Connecticut 06776
$799,900
Joyful Living! Big beautiful spaces with superior enhancements and windows, windows, windows highlight this super-sized, super-livable home in gorgeous Fox Ridge…
- TypeSingle Family
- Sq Ft6,492
- Year Built2003
- Lot1.38 Acres
- Bed4
- Bath5
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pending
55 Falls Mountain Road
Salisbury, Connecticut 06068
$3,995,000
Luxury Estate Showcases The Best Of Salisbury Living – Experience the best of the Salisbury lifestyle in this exciting new custom…
- TypeSingle Family
- Sq Ft5,652
- Year Built2021
- Lot56.03 Acres
- Bed5
- Bath5
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pending
255 South Street
Litchfield, Connecticut 06759
$699,000
Impeccably maintained historic district home is close to town and all its amenities including a renowned library, restaurants and shops. Bordered…
- TypeSingle Family
- Sq Ft2,537
- Year Built1886
- Lot1.16 Acres
- Bed4
- Bath2
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pending
94 Nearwater Lane
Darien, Connecticut 06820
$5,495,000
94 Nearwater Lane – Sean Shay’s latest entry into Darien’s luxury real estate market – offers the rare opportunity to own…
- TypeSingle Family
- Sq Ft6,500
- Year Built2023
- Lot1.1 Acres
- CommunityNorton
- Bed5
- Bath8
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pending
475 Oblong Rd
Williamstown, Massachusetts 01267
$1,250,000
Welcome home to this meticulously cared for custom contemporary on the highly sought-after scenic Oblong Road.This exceptional property offers the convenience…
- TypeSingle Family
- ParkingAuto Opener
- Sq Ft3,715
- Year Built1991
- Lot3.21 Acres
- Bed3
- Bath3
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pending
26 Oak Hill Rd
Amenia, New York 12501
$795,000
Dream House – Nearly 15 acres, with distant views, and the house is sheer unadulterated romance! A very large Great Room…
- TypeSingle Family
- Sq Ft1,025
- Year Built2013
- Lot14.62 Acres
- Bed1
- Bath1
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pending
46 Crosstrees Hill Road
Essex, Connecticut 06426
$5,440,000
Perfection! Every room. Every single space. A sense of calm and understated coastal elegance is felt throughout at this unparalleled Essex…
- TypeSingle Family
- Sq Ft5,451
- Year Built2021
- Lot0.49 Acres
- Bed3
- Bath5
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pending
46 Crosstrees Hill Road
Essex, Connecticut 06426
$5,440,000
Perfection! Every room. Every single space. A sense of calm and understated coastal elegance is felt throughout at this unparalleled Essex…
- TypeSingle Family
- Sq Ft5,451
- Year Built2021
- Lot0.49 Acres
- Bed3
- Bath5
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pending
43 Contentment Island Road
Darien, Connecticut 06820
$5,250,000
Nestled on Contentment Island in Tokeneke, this meticulously renovated Nantucket-style colonial sits on 1.24 acres of manicured grounds with seasonal water…
- TypeSingle Family
- Sq Ft6,454
- Year Built1962
- Lot1.24 Acres
- CommunityTokeneke
- Bed4
- Bath6
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pending
62 Branch Court
Watertown, Connecticut 06795
$639,900
Welcome to this impeccably cared for 1995 Eric Strachan custom built colonial home. Nothing to do but move into this 3032…
- TypeSingle Family
- Sq Ft3,032
- Year Built1995
- Lot2.92 Acres
- Bed3
- Bath3
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pending
23 Maplewood Drive
New Milford, Connecticut 06776
$525,000
You will love this classic 4 BR 2.5 bath colonial in one of New Milford’s more desirable subdivisions on the southern…
- TypeSingle Family
- Sq Ft2,186
- Year Built1986
- Lot1.55 Acres
- Bed4
- Bath3
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pending
65 Lambert Road
Sharon, Connecticut 06069
$850,000
Nestled amidst the serene beauty of Litchfield County lies a hidden gem. Surrounded by over 33 acres, this custom-built log home…
- TypeSingle Family
- Sq Ft1,470
- Year Built2004
- Lot33.15 Acres
- Bed3
- Bath2
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pending
25 Coventry Lane
Harwinton, Connecticut 06791
$569,000
Welcome to 25 Coventry Lane! This lovely home is a nature lovers dream. A custom built 1800’s reproduction, from the salvaged…
- TypeSingle Family
- Sq Ft2,387
- Year Built1974
- Lot2.45 Acres
- Bed3
- Bath4
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pending
7892 Valley Stream Farm R
Clinton, New York 12572
$1,995,000
Follow the stream into the woods at the end of a Private lane, to the site of a former horse and…
- TypeSingle Family
- Sq Ft2,377
- Year Built1900
- Lot38.9 Acres
- Bed3
- Bath3
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pending
78 Valley Stream Farm R
Clinton, New York 12572
$1,495,000
Follow the stream into the woods and at the end of a Private lane to find this updated c1900 country farmhouse…
- TypeSingle Family
- Sq Ft2,377
- Year Built1900
- Lot13.93 Acres
- Bed3
- Bath3
-
pending
11 East West Hill Road
Barkhamsted, Connecticut 06063
$655,000
A beautifully unique, executive ranch home currently being built on 5+ acres in quiet, rural Barkhampsted, CT. The home sits on…
- TypeSingle Family
- Sq Ft2,655
- Year Built2023
- Lot5.2 Acres
- Bed3
- Bath3
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pending
200 Sharon Mountain Road
Sharon, Connecticut 06069
$850,000
Wonderful Newer Farmhouse Set Along Gorgeous Secondary Town Rd. 4 Bedrooms, 3.5 Baths Including Main Level Primary Bedroom/Bath. Very Livable Floor-Plan…
- TypeSingle Family
- Sq Ft3,105
- Year Built2002
- Lot7.01 Acres
- Bed4
- Bath4
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pending
112 Lower Church Hill Road
Washington, Connecticut 06794
$3,595,000
Totally Private & Newly Updated Shingle Style with Modern Edge. Prominent Washington CT Location, Merely 5 Min to Village. 4 Bedrooms,…
- TypeSingle Family
- Sq Ft4,495
- Year Built1997
- Lot10.36 Acres
- Bed4
- Bath5
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pending
15 Otis Drive
Watertown, Connecticut 06795
$699,000
Well maintained English Tudor situated on a 1.62 acre, corner lot located on a beautiful, private cul-de-sac! A spacious foyer welcomes…
- TypeSingle Family
- Sq Ft3,990
- Year Built1977
- Lot1.64 Acres
- Bed5
- Bath4
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pending
36 Fox Lane
Clermont, New York 12583
$1,995,000
Nestled in the tranquil embrace of Columbia County’s rolling hills rests 36 Fox Ln, a remarkable single-story abode that transcends contemporary…
- TypeSingle Family
- Sq Ft3,775
- Year Built2023
- Lot5.2 Acres
- Bed4
- Bath4
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pending
60 Midwood Road
Greenwich, Connecticut 06830
$7,250,000
Extraordinary opportunity in Deer Park! First time on the market in over 40 years. This classic white brick Colonial with slate…
- TypeSingle Family
- Sq Ft4,582
- Year Built1929
- Lot1.71 Acres
- Bed5
- Bath5
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pending
90 Millerbrook Lane
Copake, New York 12516
$1,895,000
Escape to the country in this idyllic 4 bedroom, 5 bathroom Copake Craftsman nestled on a private road in upstate New…
- TypeSingle Family
- Sq Ft2,654
- Year Built2007
- Lot11.33 Acres
- Bed4
- Bath5
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pending
51 Maple
Germantown, New York 12526
$1,995,000
Stylishly renovated 1800’s Greek Revival. Located in Germantown within easy reach of the historic hamlet, this classic home has been thoughtfully…
- TypeSingle Family
- Sq Ft3,067
- Year Built1850
- Lot1.1 Acres
- Bed4
- Bath4
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pending
829 Tower Hill Road
Washington, New York 12545
$2,200,000
Stunning sweeping Catskill Mountain views from this stately brick colonial. Boasting 6,694 finished square feet, the home provides a spacious canvas…
- TypeSingle Family
- Sq Ft6,694
- Year Built1966
- Lot30.0 Acres
- Bed5
- Bath7
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pending
21 Finkle Road
Ancram, New York 12503
$1,785,000
The Horse Institute. This pristine equestrian estate is located on 26.27 acres in the bucolic hamlet of Ancramdale and surrounded by…
- TypeSingle Family
- Sq Ft3,997
- Year Built1989
- Lot26.3 Acres
- Bed3
- Bath3
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pending
26 Fox Lane
Clermont, New York 12583
$1,795,000
Nestled amidst the picturesque rolling hills of enchanting Columbia County, 26 Fox Lane is a testament to modern aesthetics in the…
- TypeSingle Family
- Sq Ft2,150
- Year Built2023
- Lot5.0 Acres
- Bed3
- Bath3
-
pending
26 Fox Lane
Clermont, New York 12583
$1,795,000
Nestled amidst the picturesque rolling hills of enchanting Columbia County, 26 Fox Lane is a testament to modern aesthetics in the…
- TypeSingle Family
- Sq Ft2,150
- Year Built2023
- Lot5.0 Acres
- Bed3
- Bath3
