Maggie Barry

Maggie Barry

Real Estate Salesperson

Great Barrington

306 Main Street
Great Barrington, MA 01230

Lenox

34 Church Street
Lenox, MA 01240
  • Born In:
    Pittsfield
  • Live In:
    Lee
  • Passion:
    My Family
  • Interests:
    Playing Poker , Kayaking, Boating, Traveling, Skiing
  • Favorite Lyric:
    You may say I'm a dreamer, but I'm not the only one
  • Can’t Live Without:
    Coffee
  • Inspiration:
    The Ocean

Born and raised in the Berkshires, Maggie grew up in a family of local architects, engineers and contractors which shaped her love for design and renovations. She left the Berkshires to pursue a degree in Accounting at the Eisenberg School of Management at the University of Massachusetts. She minored in Spanish and studied in Granada, Spain and Florence, Italy. During her time overseas, she traveled through much of Europe developing an appreciation for different cultures.

After living briefly in Boston & Fort Lauderdale, Maggie returned home to the Berkshires and started her career in the hospitality industry. She soon became the manager of two successful local restaurants while working part time at a local public accounting firm.

Maggie became interested in real estate and purchased her first income property which she renovated and designed with the help of her family. After realizing how much she loved the design and renovation process, she took part in the purchase and renovations of the historical LakeHouse Inn, which she currently owns and manages.

Maggie’s local connections, attention to detail and diverse background in accounting, hospitality, & construction helps her clients throughout every stage of the buying and selling process. 

Born and raised in the Berkshires, Maggie grew up in a family of local architects, engineers and contractors which shaped her love for design and renovations. She left the Berkshires to pursue a degree in Accounting at the Eisenberg School of Management at the University of Massachusetts. She minored in Spanish and studied in Granada, Spain and Florence, Italy. During her time overseas, she traveled through much of Europe developing an appreciation for different cultures.

After living briefly in Boston & Fort Lauderdale, Maggie returned home to the Berkshires and started her career in the hospitality industry. She soon became the manager of two successful local restaurants while working part time at a local public accounting firm.

Maggie became interested in real estate and purchased her first income property which she renovated and designed with the help of her family. After realizing how much she loved the design and renovation process, she took part in the purchase and renovations of the historical LakeHouse Inn, which she currently owns and manages.

Maggie’s local connections, attention to detail and diverse background in accounting, hospitality, & construction helps her clients throughout every stage of the buying and selling process. 

Born and raised in the Berkshires, Maggie grew up in a family of local architects, engineers and contractors which shaped her love for design and renovations. She left the Berkshires to pursue a degree in Accounting at the Eisenberg School of Management at the University of Massachusetts. She minored in Spanish and studied in Granada, Spain and Florence, Italy. During her time overseas, she traveled through much of Europe developing an appreciation for different cultures.

After living briefly in Boston & Fort Lauderdale, Maggie returned home to the Berkshires and started her career in the hospitality industry. She soon became the manager of two successful local restaurants while working part time at a local public accounting firm.

Maggie became interested in real estate and purchased her first income property which she renovated and designed with the help of her family. After realizing how much she loved the design and renovation process, she took part in the purchase and renovations of the historical LakeHouse Inn, which she currently owns and manages.

Maggie’s local connections, attention to detail and diverse background in accounting, hospitality, & construction helps her clients throughout every stage of the buying and selling process. 

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My Listings

67 Rowe Rd $990,000 link

67 Rowe Rd

Egremont, MA 01230 | Berkshire County
$990,000
5 Beds 3/1 Baths 3,684 Sqft 24.9 Acres

This extraordinary home and horse barn is perfectly situated on just under 25 pastoral acres. With amazing westerly views over-looking Catamount Mountain and the Green River, you'll...

5
bed
3/1
bath
3,684
sqft
384 Pittsfield Rd $825,000 link

384 Pittsfield Rd

Lenox, MA 01240 | Berkshire County
$825,000
4 Beds 1/1 Baths 2,100 Sqft 3.16 Acres

Prime location on Route 7/20 in Lenox, this 3-acre parcel is allocated for commercial development. One residential building currently on the property has hardwoods throughout,...

4
bed
1/1
bath
2,100
sqft
90 Brodie Mountain Rd $540,000 link

90 Brodie Mountain Rd

Lanesborough, MA 01237 | Berkshire County
$540,000
3 Beds 2/1 Baths 3,817 Sqft 1.8 Acres

This exceptional, custom Deltec Design Home is privately tucked away on a wooded 1.8 acre lot just a short drive to Jiminy Peak. Deltec homes are best known for their quality,...

3
bed
2/1
bath
3,817
sqft

My Sales

86 Interlaken Rd $2,050,000 link

86 Interlaken Rd

Stockbridge, MA 01262 | Berkshire County
$2,050,000
8.63 Acres

A once-in-a-lifetime opportunity to renovate or potentially to build on an existing 6,328sf footprint, in a prime 8.63-acre spot with significant lake frontage on the west side...

8.63
acre
64 Worth Ln $1,820,000

64 Worth Ln

Monterey, MA 01245 | Berkshire County
$1,820,000
3 Beds 4/1 Baths 2,728 Sqft 0.49 Acres

First time to the market we welcome this beautiful contemporary home just yards from the banks of much sought after Lake Garfield in Monterey, MA, considered the best recreational...

3
bed
4/1
bath
2,728
sqft
236 Bulkley St $1,446,000 link

236 Bulkley St

Williamstown, MA 01267 | Berkshire County
$1,446,000
3 Beds 4 Baths 4,990 Sqft 42.5 Acres

Designed by legendary Bauhaus architect Marcel Breuer, this Mid-Century Modern masterpiece is a rare, iconic work of art. Exemplifying the luxury of great modern design are Breuer's...

3
bed
4
bath
4,990
sqft
429 Stratton Rd $1,015,000 link

429 Stratton Rd

Williamstown, MA 01267 | Berkshire County
$1,015,000
5 Beds 4/2 Baths 3,929 Sqft 6.51 Acres

Stunning light-filled Contemporary, set on six acres with beautiful westerly mountain views, in a prime Williamstown location. Sparkling modern design, spacious rooms, cathedral...

5
bed
4/2
bath
3,929
sqft
1560 Pleasant St $1,000,000 link

1560 Pleasant St

Lee, MA 01238 | Berkshire County
$1,000,000
10 Beds 10/1 Baths 6,052 Sqft 2.5 Acres

Seeking a terrific business and lifestyle opportunity? Look no further than the Federal House Inn, an elegant 1824 mansion, convenient to year-round cultural, recreational, and...

10
bed
10/1
bath
6,052
sqft
15 Maple View Dr $862,500 link

15 Maple View Dr

West Stockbridge, MA 01266 | Berkshire County
$862,500
4 Beds 4 Baths 2,941 Sqft 5.9 Acres

Enjoy country living at its best. This extraordinary property offers privacy, gorgeous views, comfortable accommodations for family and guests, and 5.9 acres to delight you in...

4
bed
4
bath
2,941
sqft
15 Berkshire Heights Rd $860,000 link

15 Berkshire Heights Rd

Great Barrington, MA 01230 | Berkshire County
$860,000
4 Beds 2/1 Baths 3,700 Sqft 2.02 Acres

This exceptional, custom-designed Contemporary home is privately sited on the crest of The Hill, within walking distance of shops, restaurants, the Mahaiwe Performing Arts Center,...

4
bed
2/1
bath
3,700
sqft
36 Bentrup Ct $800,000 link

36 Bentrup Ct

Lenox, MA 01240 | Berkshire County
$800,000
6 Beds 4/1 Baths 3,856 Sqft 0.69 Acres

Move right in and enjoy all the Berkshires have to offer in this fabulous home, in a centrally located Lenox neighborhood close to cultural & outdoor activities. At the end...

6
bed
4/1
bath
3,856
sqft
8 Oak St $675,000 link

8 Oak St

Great Barrington, MA 01230 | Berkshire County
$675,000
4 Beds 2/1 Baths 3,384 Sqft 0.28 Acres

Spacious, light-filled, beautifully maintained American Foursquare on The Hill. This well located Great Barrington classic features expansive double parlors, a dining room with...

4
bed
2/1
bath
3,384
sqft
120 Blythewood Dr $669,000 link

120 Blythewood Dr

Pittsfield, MA 01201 | Berkshire County
$669,000
5 Beds 2 Baths 2,426 Sqft 1.7 Acres

Relaxation awaits you in this meticulously maintained lake house in one of the most popular private communities on Onota Lake. This 5 Bedroom, 2 Bath cottage sits on 1.7 private...

5
bed
2
bath
2,426
sqft
176 Old Stockbridge Rd #Chadsey 1 $633,000 link

176 Old Stockbridge Rd #Chadsey 1

Stockbridge, MA 01262 | Berkshire County
$633,000
3 Beds 3/1 Baths 2,900 Sqft

This beautifully appointed home at Winden Hill combines wonderful indoor and outdoor living spaces. A great room with fireplace and den alcove opens to a balcony with incredible...

3
bed
3/1
bath
2,900
sqft
100 Shore Dr $620,000 link

100 Shore Dr

Hinsdale, MA 01235 | Berkshire County
$620,000
4 Beds 2/1 Baths 2,200 Sqft 0.99 Acres

Enjoy sunset views over one of the most beautiful lakes in the Berkshires from this spacious, well-built, impeccably maintained lake-front retreat. You'll love the single-level...

4
bed
2/1
bath
2,200
sqft