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Luxury Homes of the Southern Berkshires

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56 Crooked Hill Road Alford MA 01230

Alford, MA56 Crooked Hill Road

Price$3,295,000

Est. Mortgage: $/month

MLS Number 245476

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,238
  • Acreage 19.3

Alford stunner! Exceptionally designed turnkey home with mountain views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the perfect assemblage of textures and materials.Antique douglas fir floors and mushroom wood ceilings frame the living room's locally quarried stone fireplace and large southwest-facing windows with mountain views. The living room opens to a light-filled, elegant dining room, which then connects to a marvelous chef's kitchen.

Listed by Elle Villetto and Jared Kelly of WILLIAM PITT SOTHEBY'S - LENOX

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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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349 Old Stockbridge Road Lenox MA 01240

Lenox, MA349 Old Stockbridge Road

Price$3,100,000

Est. Mortgage: $/month

Pending

MLS Number 245369

  • Residential
  • Bathroom 30
  • Bedrooms 32
  • Square Feet 38,415
  • Acreage 11.9

A rare, once in a lifetime opportunity to own an original berkshire cottage! This spectacular property is situated on a 12-acre campus in lenox, overleigh was built in 1903 by samuel frothingham. Its history is detailed in the popular coffee table book ''the berkshire cottages-a vanishing era'', by carole owens. This property is located just 1.8 mi. From downtown lenox and within minutes to the most popular berkshire attractions. Designed by adams and warren out of nyc and built by joseph clifford's sons, a firm responsible for several cottage era constructions and renovations in berkshire county. A rare find, this property has deep roots in being used as an academic setting for several diverse private residential schools and has been well maintained throughout the years.

Listed by Timothy Gallagher of STONE HOUSE PROPERTIES,LLC

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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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813 East Street Lenox MA 01240

Lenox, MA813 East Street

Price$2,995,000

Est. Mortgage: $/month

MLS Number 245332

  • Residential
  • Bathroom 9
  • Bedrooms 7
  • Square Feet 6,578
  • Acreage 4.92

Listed by Mary Jo Piretti-Miller of PIRETTI REAL ESTATE

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$
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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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1 Lahey Cross Road Stockbridge MA 01262

Stockbridge, MA1 Lahey Cross Road

Price$2,595,000

Est. Mortgage: $/month

Pending

MLS Number 237363

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,847
  • Acreage 22.63

Custom built estate on a 22+ acre picturesque lot. Thoughtfully designed with exceptional detail and quality. Enjoy a winding tree-lined driveway, seasonally blooming landscape, renowned goshen stonework, in-ground pool, & guest house w/ private deck. In the main house, a 2-story foyer leads you to a grand living room w/ superb views, & a library perfect for book lovers. Farmhouse kitchen, dining room w/ fireplace, & sweeping windows lead you to a screened porch. A 2nd-floor primary suite includes walk-in closets, european style bath & dual pedestal sinks. Perfect for entertaining w/ 5 total bedrooms, butlers pantry, wine cellar, & plenty of outdoor space overlooking the manicured landscape. Nearby attractions: norman rockwell museum, berkshire botanical garden, tanglewood, & chesterwood.

Listed by Joshua Stephens of NON-MEMBER / RECIPROCAL

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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1373 Boardman Street Sheffield MA 01257

Sheffield, MA1373 Boardman Street

Price$2,500,000

Est. Mortgage: $/month

MLS Number 245292

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,100
  • Acreage 5.13

The ultimate live-work-play retreatstep onto a property as striking as the berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''the factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked by 3,000-sq ft of stunning living spaces that seamlessly blend design, sophistication, comfort. From the glass walls that open to sweeping views, to its bespoke kitchen or design forward guest suite, every inch has been crafted to inspire. Host gatherings on the spacious screened deck, unwind by the 360 glass fireplace, find solitude in the ''tower'' - and redefine living, creating, & thriving.

Listed by Chapin Fish of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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84 B Undermountain Road Egremont MA 01258

Egremont, MA84 B Undermountain Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 239959

  • Residential
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,254
  • Acreage 34.08

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Listed by Antonio M Segalla and Lance Vermeulen of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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978 Clayton Mill River Road New Marlborough MA 01259

MLS Number 244124

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5,000
  • Acreage 51.12

The ephraim chapin house, a.K.A the ''landlord abel house'' was built in chicopee c. 1725. In 1979 this handsome home & tavern was dismantled and relocated to southfield. There it was re-erected upon a new foundation atop a hill, where it now resides on a 51-acre estate straddling the banks of konkapot river. Once the beloved retreat of an artist and a serious collector of early american art and antiques this 3-story 4-bedroom home has been painstakingly rebuilt and restored.Original wainscoting in the ''keeping room'' is a rare example of interior decorative painting by the scroll painter, a documented but unnamed american decorative artist active the 1790's. Other details include original floorboards & exposed chestnut beams, center chimney with 6 brick fireplaces... (see ''more''.)

Listed by Vashti Poor of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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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14 Pinecrest Cross Road Egremont MA 01258

Egremont, MA14 Pinecrest Cross Road

Price$2,295,000

Est. Mortgage: $/month

MLS Number 245678

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 4,060
  • Acreage 5.01

As seen in the ny times: extraordinary and unique home, nestled on a country lane in a quaint berkshire town. Contemporary living spaces enhanced by a repurposed 1540 post & beam structure imported from england ! Open plan livingroom w 30' ceilings & fireplace. Gourmet kitchen w/sunny dining area. Warm paneled den w/fireplace. 5 bedrooms total, with 2 primary suites (including one on the main level). Pool, pond and 4 car garage. The best of everything. Minutes to skiing, shopping, dining, tanglewood and everything berkshires.

Listed by Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* 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

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