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Hilltowns Real Estate

Below, you'll find all real estate listings in the Hilltowns of Massachusetts. Contact Delap Real Estate at 413-586-9111 or online for more information.

138 Main Road Westhampton MA 01027

MLS Number 72996135

  • CommercialSale
  • Acreage 10
  • Zoning AR

Iconic Westhampton Landmark and Farm. For over 100 years Outlook Farm has offered apples, fruits, vegetables, sweet apple cider, farm fresh pork and homemade baked goods while being a centerpiece of Westhampton society. Today the new post and beam barn with farm store, restaurant, deli and gift shop continues that legacy and has endless possibilities for the future owners. Approximately 20 +/- acres of apple orchards and farm land with multiple out buildings. Could be a conference center or wonderful wedding venue or a destination farm to table restaurant. Sold with 136 Main Rd., a historic 5 bedroom Farmhouse- MLS# 72996138

Listed by Trailside Team and Kristin Vevon, The Murphys REALTORS®,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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136 Main Road Westhampton MA 01027

Westhampton, MA136 Main Road

Price$2,900,000

Est. Mortgage: $/month

MLS Number 72996138

  • Residential
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 3,344

Historic Westhampton Treasure! In 1781 Eliza Norton built the Norton Tavern at the top of the hill in Westhampton. The front upstairs of the house was an open air dance hall and the original fiddler's step still remains! In 1860 Warner Bartlett bought the Tavern. He ran the farm until 1920 when Will Fiske bought the homestead and renamed it Outlook Farm and started peddling his farm products, produce and Outlook Farm sausage throughout the valley. Since its earliest time this 5 bedroom, 2 bath Colonial has been an important part of Westhampton's society. It's been a tavern, stage coach stop, Inn and recently a B & B - but its greatest role was that of beloved homestead and gathering place for generations of families and friends. Historic features include wide board floors, wood beams, and built-ins. Tavern room with fireplace & pool table is still the place to have fun! Large barns have endless possibilities. A little updating will go along way. Sold with Outlook Farm MLS # 7299613

Listed by Trailside Team and Kristin Vevon, The Murphys REALTORS®,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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184 Cudworth Road Worthington MA 01098

Worthington, MA184 Cudworth Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 73048610

  • Residential
  • Bedrooms 7
  • Bathroom 9
  • Square Feet 14,241

Looking for a weekend Berkshire escape, an exquisite family estate? This home is sure to check all the boxes. You will fall in love with the bedroom wing, its warm tones, thoughtful lighting and beautifully appointed bathrooms. Enjoy a spa like experience in the fitness room or salt water indoor pool. The heart of the home is designed for entertaining. The kitchen, equipped with all Viking appliances and poured concrete counters, looks out over aged maples, stone walls and a pond. Extended family will be comfortable in the in-law suite. The car enthusiast will love the 11 heated garage spaces and the equestrian will enjoy breathing new life into the 2 stall horse barn and pastures. The barn, also has a studio which can be used for visitors, farm help or bring back the recording studio. The radiant heat and whole house generator will keep you comfortable no matter what the weather brings. Looking for more? Think artisan or yoga retreat, BnB, catering or music venue. Just imagine!

Listed by Grace Golden and Paige Murray, Equine Homes Real Estate,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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34 Sumner Mountain Road Shutesbury MA 01072

Shutesbury, MA34 Sumner Mountain Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 73030057

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,542
  • High School Amherst High

Country Contemporary, breathtaking views and 20+ acres bordering Amherst! Sunsets over the Pioneer Valley and stretching to the Berkshires. Enjoy an end of the road, extremely private setting complimented with gardens, rock outcroppings and wildlife abound. Incredible attention to detail and no expense spared from the custom built-ins and exquisite materials throughout. What a great opportunity with the high-speed fiber optic Internet/TV already in place, work from home in the multi-room commercial office space or utilize it as the guest quarters or in-law suite. All of this neighboring the Town of Amherst watershed & substantial conservation land further expanding your private setting. Just minutes to Amherst College/UMASS/downtown Amherst; 3 hours to NYC, 2 hours to Boston and less than 90 minutes to the Berkshires. Additional building lot included.

Listed by Jeffrey Loholdt and George Cain, William Pitt Sotheby's International Realty

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%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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141 Buckland Road Ashfield MA 01330

MLS Number 72999770

  • CommercialSale
  • Acreage 0.56
  • Zoning Mixed

The Ashfield Lake House is more than a restaurant, it's a magical destination. A welcoming place for locals or tourists to gather year round with friends. Owners Dre and Chris revitalized the historical community hub as a successful farm to table eatery and special event venue including new dining pavilions on the private beach, extensive terraced stonework, and a spacious deck overlooking the beautiful lake . Located in the lovely town of Ashfield, at the foothills of the Berkshires, western Massachusetts, this is a gem of a property and a unique opportunity : Turn-key restaurant with revenue streams from the restaurant / private events / and 4 additional rental properties. This property is being sold with 143A-143C Buckland Rd. See MLS #72999773

Listed by Jeffrey Loholdt, William Pitt Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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86 Southampton Road Westhampton MA 01027

Westhampton, MA86 Southampton Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 73028956

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,734

IMAGINE PURCHASING THIS 54.33 ACRE PIECE OF PARADISE WITH YOUR VERY OWN AIRFIELD AND HANGAR!! WELL HERE IT IS!!! For pilots, flying is not just a quick means of transportation but it's a way of life. Here is your opportunity to purchase your own retreat and live the life you have always dreamed of. This property affords the lucky buyer tremendous freedom to either relax around the house or embark on an airborne adventure or do both in the same day!! This incredible buying opportunity also includes a Lovely Ranch Home offering 7 room, 3 bedroom, 2.5 bath home and an inviting side to side 3 season room overlooking the field and grounds. This LOVED home is just waiting for the next buyer's finishing touches. Escape the hustle and bustle of everyday life and take to the skies and live the quality of life you deserve. Schedule your private showing today!!!

Listed by Paul Zingarelli, Berkshire Hathaway HomeServices Realty Professionals

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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190 Brier Hill Road Ashfield MA 01330
Open House

MLS Number 73049046

  • Residential
  • Next Open House: Sat 12/3 12:30 pm. to 2:00 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,627

Antique home w/ modern updates & spectacular views on 14 gorgeous acres. Tiled entry w/ half bath, beautifully renovated kitchen w/ cherry floors & custom cabinets, built-in desk, granite countertops, all new appliances incl. 6-burner stove, open to a breakfast area w/ stone fireplace, cherry shelves, & tall windows. Butler’s pantry is around the corner, along w/ laundry room. Generous DR flows into the equally generous LR w/ stone fireplace. Off the LR is a glorious 4-season sunroom. Upstairs, flexible layout w/ 2 staircases offers many options, w/ 2.5 baths & a nice sunny sitting room. One bedroom & en suite bath open to a gorgeous newer deck, amazing mountain views. Behind the house, relax on the Goshen stone patio, or walk up to the gazebo. The land across the quiet road features gentle hills, a pond, a barn w/ concrete floor & two stalls, an additional storage building, & generous two-car garage. Close to Chapel Brook & Bear Swamp conservation areas. Hilltown life at its finest!

Listed by Rachel Simpson, Maple and Main Realty,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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 Buffington Hill Road Worthington MA 01098

MLS Number 72992355

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 4,146

Impeccably restored high-style Georgian-Federal equidistant to the Berkshires and Northampton.The Jonathan Woodbridge House, 1806, exhibits the classic hallmarks of Georgian design: elegant proportions, symmetry and magnificent carved Palladian details. The eleven gracious rooms retain original Georgian details and moldings and include four bedrooms, two parlors, a library/office, two grand halls, two baths and six fireplaces. Few structures in the Berkshires possess this degree of both architectural and historical significance. The house has undergone a complete restoration with modern amenities including custom kitchen/great room, new mechanicals and restored chimneys. The property includes nearly three acres of gardens and woods. Located in the highlands of western Massachusetts it is equidistant to the cultural amenities of the Berkshires and Northampton, MA. Welcome home.

Listed by Jeffrey Loholdt and George Cain, William Pitt Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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80 Easthampton Road Westhampton MA 01027

Westhampton, MA80 Easthampton Road

Price$895,000

Est. Mortgage: $/month

MLS Number 72588713

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,707
  • High School Hrhs

Massive 20,000 sf, 2 story Post & Beam constructed barn with 22 horse box stalls with mahogany wood and iron doors. Second floor hay loft to drop hay conveniently into each horse stall. Picturesque 10 acres of property with fenced pasture land and views of surrounding property all within a few miles of downtown Easthampton and Northampton. Additional foundation poured for purpose of indoor riding arena. House is bright and cheery renovated 1771 Antique Cape. Explore the possibilities!

Listed by Robert A Canon, Canon Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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482 Newhall Road Conway MA 01341

Conway, MA482 Newhall Road

Price$875,000

Est. Mortgage: $/month

MLS Number 73055253

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,996
  • High School Frontier Hs

Peace and privacy protect this Quintessential New England home known as Open View Farm. A well preserved Antique house with breathtaking views at the dead end of a country road. The 3 story renovated barn has an equipped woodshop and office space.The open fenced land could return to an active farm for animals. The rooms are generous sizes for entertaining as well as more intimate spaces. The first floor has a huge eat in kitchen with wood stove. There is a grand living room with f.p. and deck leading to a gazebo with hot tub. Formal dining room, laundry, full bath and family room with copious built-ins.There's an attached 4 room apt with deck.The second floor has 4 gracious bedrooms and full bath. The third floor master suite is a recent and creative addition. There are long range views to the south looking over expansive fields. Beautiful details and wood flooring throughout. 15 minutes to 91 and Shelburne Falls. This property is one of a kind and must be seen to be appreciated.

Listed by Joanie Schwartz, Joanie Schwartz Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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68 Van Nuys Road Colrain MA 01340

Colrain, MA68 Van Nuys Road

Price$829,000

Est. Mortgage: $/month

MLS Number 73045902

  • Residential
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 6,356

Live in a home that will inspire you! The Roundhouse not only feels homey but brings friends, family, & guests together in this wonderful entertainment home. This unique home featured on ABC and PBS has incredible views and lots of space and privacy. The first floor is open and ideal for large gatherings. The grand hall has a cathedral dome ceiling and an open central spire that reaches four stories above the hardwood floor. A large kitchen complete with a pantry would envy any chef. There are five bedrooms and 2 ½ baths with many built-in private cubbies to relax and reflect. Several decks and patio areas allow you to enjoy the views. Amenities include a sauna, outdoor oven, and two outdoor showers. The barn mirrors the home's unique architectural design. A third building on the property could provide separate living quarters and large garage bays. All living quarters can be heated with wood or oil, and solar helps reduce utility costs.

Listed by Herbert Butzke, William Pitt Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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37 Fisher Place Conway MA 01341

Conway, MA37 Fisher Place

Price$750,000

Est. Mortgage: $/month

MLS Number 73057918

  • Residential
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 1,100
  • High School Frontier Hs

This magical property with stunning views in 3 directions is off the grid. The light-filled contemporary home is designed to maximize an indoor/outdoor feel, with open concept living that is highly efficient in every way: sited due south, with 13 inch walls, double-pane windows and an earthen roof. A second smaller cottage is in mid-construction. The current owner plans to finish, adding an expanded solar array to serve both buildings. The 8+ acres include 3500 sf annual/perennial garden, an orchard with a variety of fruit trees, an experimental rice bed, a nut grove, a small, terraced permaculture forest garden and plantings throughout that offer 3-seasons of food for pollinators and wildlife habitat. There is also a vine-covered arbor with seating, a small greenhouse, a barn used as a classroom, and a root cellar. For more info refer to Wildside Gardens website. Be part of a thriving Community of Conway. Walk to the library and town pond. 10 minutes to 91.

Listed by Joanie Schwartz, Joanie Schwartz Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.