Homes for Sale near St. Mary's School

/5
$998,000
- Land
- 9 Acres
- $109,670 per Acre
19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

Selina Lamb

BIRCH PROPERTIES

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
/40
$1,795,000
- 4 Beds
- 3 Baths
- 5,469 Sq Ft
17 East St, Lenox, MA 01240

Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

Selina Lamb

BIRCH PROPERTIES

(413) 300-6860

17 East St, Lenox, MA 01240
/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/30
$2,450,000
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
165 Kemble St Unit 17, Lenox, MA 01240

Nestled within the serene, world-renowned Canyon Ranch Lenox campus, this bespoke two-bedroom, two-and-a-half-bath home is among the most private and luxuriously appointed in the Berkshires. A rare opportunity to own a residence where every detail--from architecture to finishes--echoes sophisticated European elegance while embracing the wellness-centered ethos of Canyon Ranch living.Inside,

Selina Lamb

BIRCH PROPERTIES

(413) 547-4966

165 Kemble St Unit 17, Lenox, MA 01240
/53
$2,649,000
- 6 Beds
- 6.5 Baths
- 4,289 Sq Ft
250 West St, Lenox, MA 01240

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

Selina Lamb

BIRCH PROPERTIES

(413) 423-1264

250 West St, Lenox, MA 01240
/82
$2,550,000
- 6 Beds
- 6.5 Baths
- 7,143 Sq Ft
13 Taconic Ave, Lenox, MA 01240

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

13 Taconic Ave, Lenox, MA 01240
/54
$979,000
- 5 Beds
- 4.5 Baths
- 2,800 Sq Ft
850 Summer St, Lee, MA 01238

Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

Katie Williams STONE HOUSE PROPERTIES, LLC

850 Summer St, Lee, MA 01238
/56
$979,000
- 5 Beds
- 4.5 Baths
- 2,800 Sq Ft
850 Summer St Unit M14, Lee, MA 01238

Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

Katie Williams STONE HOUSE PROPERTIES, LLC

850 Summer St Unit M14, Lee, MA 01238
/45
$1,499,000
- 4 Beds
- 4.5 Baths
- 3,190 Sq Ft
121 E Dugway Rd, Lenox, MA 01240

Stunning Georgian Colonial style home on a lovely 4A private lot is ready for its new owners! In pristine condition, this 4 BR, 4.5 baths home offers hardwood floors throughout, first floor Primary Suite, open great room concept with cherry cabinetry in kitchen and granite counters, gas fireplace in the great room, formal dining or music room and first floor study with full bath. The second

Mary Jo Piretti PIRETTI REAL ESTATE

121 E Dugway Rd, Lenox, MA 01240
/114
$929,900
- 4 Beds
- 2.5 Baths
- 3,608 Sq Ft
67 Dunmore Ct, Lenox, MA 01240

This gorgeous 4-bedroom, 3-bathroom home sits on a spacious corner lot surrounded by beautiful native landscaping, offering both privacy and curb appeal. Step inside to find a bright and inviting layout with ample space for entertaining and everyday living. The kitchen features newly redone floors (2025), and the large back deck provides the perfect space for outdoor gatherings or quiet

Sara Bresett NOCHER REALTY

67 Dunmore Ct, Lenox, MA 01240
/62
$1,750,000
- 4 Beds
- 4.5 Baths
- 4,349 Sq Ft
11 Blossom Hill, Lenox, MA 01240

Nestled within the beautifully landscaped grounds of Miraval Lenox, formerly the famed Cranwell Resort Spa and Golf Club, this spacious and light-filled residence offers a coveted Berkshire lifestyle with exclusive access to resort amenities.Enjoy a reduced-rate membership to Wyndhurst Club & Manor, featuring tennis courts, indoor and outdoor pools, a full fitness center, spa services, dining,

Paula McLean PAULA MCLEAN REALTORS INC.

11 Blossom Hill, Lenox, MA 01240
/16
$939,000
- 11 Beds
- 10.5 Baths
- 2,016 Sq Ft
3949 Jacobs Ladder Rd, Becket, MA 01223

A unique lakefront cedar home with 8 room motel. many possibilities.Approximately 2.7 acres with over 500 ' lake frontage on Beautiful Greenwater Pond . Close to Appalachian trail and many Berkshire cultural and recreational venues.

Anthony Caropreso MACCARO REAL ESTATE

3949 Jacobs Ladder Rd, Becket, MA 01223
/68
$1,400,000
- 4 Beds
- 5 Baths
- 6,500 Sq Ft
160 High St, Lee, MA 01238

Once the First Methodist Episcopal Church, built in 1898, this incredible 6,500 sq ft property has been thoughtfully reimagined as a two-family residence and offers unparalleled potential for an artist's dream live/work space. Located just a short walk from downtown on a 3/4 lot abutting an 18 acre nature reserve, this building is ideally positioned to offer both the tranquility of the Berkshires

Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

160 High St, Lee, MA 01238
/70
$1,299,000
- 5 Beds
- 4 Baths
- 3,289 Sq Ft
49 Main St, Stockbridge, MA 01262

Improved stunning Stockbridge Village property that boasts an updated main house and includes a separate three apartment carriage house. The main property offers great natural light and ample common spaces that are gracious in size, updated lovely kitchen, five bedrooms, four baths, screened porch and inviting outdoor spaces. It has been thoughtfully updated while keeping the charm and character

Cortney Dupont COHEN & WHITE ASSOCIATES

49 Main St, Stockbridge, MA 01262
/78
$1,475,000
- 3 Beds
- 2.5 Baths
- 3,443 Sq Ft
28 Main Rd, Lee, MA 01238

THEY DON'T BUILD HOUSES LIKE THIS ANYMORE.They don't build love at first sight anymore, either. But Sky Hill Farm - a genuine 1798 Federal colonial in Tyringham Valley - has been creating that exact feeling for over two centuries.In 1912, Adele LeBourgeois Chapin wrote about first arriving here at dusk, walking through high grass to the old front door with its worn stone steps and feeling the

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

28 Main Rd, Lee, MA 01238
/29
$912,000
- 4 Beds
- 4 Baths
- 2,280 Sq Ft
21 East St, Stockbridge, MA 01262

**Price Improvement** Nestled in the heart of the Berkshires, this spacious Colonial sits on over 14 acres, offering privacy, potential, and long-term value. Currently operating as a doggy day care, but you wouldn't know it when you walk inside! Well-maintained & cared for. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while still leaving room for

Brianna Boffoli Cameron Prestige, LLC

21 East St, Stockbridge, MA 01262
/38
$895,000
- 5 Beds
- 3.5 Baths
- 3,194 Sq Ft
33 Interlaken Rd, Stockbridge, MA 01262

Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

Lori Rose STONE HOUSE PROPERTIES, LLC

33 Interlaken Rd, Stockbridge, MA 01262
/59
$895,000
- 4 Beds
- 3 Baths
- 2,732 Sq Ft
135 East St, Lee, MA 01238

Rustic Style Expansive Cape. Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French

Lisa Kelley MACCARO REAL ESTATE

135 East St, Lee, MA 01238
/4
$950,000
- 3 Beds
- 2 Baths
- 1,909 Sq Ft
0 Goose Pond Rd, Tyringham, MA 01264

This is a '' To Be Built'' home. All one level living. Wonderful flow to the design with a primary bedroom suite in a separate area of the house. Turn key home price includes all interior finishes. Final price will vary depending on buyer's selections and/or upgrades. Price does not include excavation, septic, or well.

Tanya Shepardson LAMACCHIA REALTY, INC

0 Goose Pond Rd, Tyringham, MA 01264
/63
$1,100,000
- 4 Beds
- 3.5 Baths
- 2,861 Sq Ft
1 Train Hill Rd, Stockbridge, MA 01262

This Stockbridge Colonial has it all....location, separate guest suite and plenty of country chic design. This historic home boasts all the charm of yesteryear with fabulous wide pine floors, state of the art country kitchen that retains it's charm, formal dining room with fireplace, gracious banister to the second floor of guest bedrooms with renovated bath all while seamlessly blending with the

Cortney Dupont COHEN & WHITE ASSOCIATES

1 Train Hill Rd, Stockbridge, MA 01262
/43
$725,000
- 4 Beds
- 3 Baths
- 2,610 Sq Ft
770 Summer St Unit 15A, Lee, MA 01238

Enjoy unobstructed views of Laurel Lake from this first-floor unit at Lakeside at Foxhollow. This spacious 4-bedroom, 3-bath condo features two fully finished levels, two outdoor decks (including one waterfront), and two primary suites--one on each floor--plus resort-style amenities. The perfect opportunity to create your ideal lakeside retreat.The professionally managed community offers an

Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

770 Summer St Unit 15A, Lee, MA 01238
/20
$3,995,000
- 15 Beds
- 15 Baths
- 11,945 Sq Ft
615 Laurel St, Lee, MA 01238

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

Pamela J Long EAST COAST INN BROKERS

615 Laurel St, Lee, MA 01238
/42
$485,000 Open Sat 10AM - 12PM
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
42 East St, Stockbridge, MA 01262

Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

Conor Meehan STONE HOUSE PROPERTIES, LLC

42 East St, Stockbridge, MA 01262
/13
$290,000
- 1 Bed
- 1 Bath
- 709 Sq Ft
3 Morgan Manor Unit 3 - 8, Lenox, MA 01240

Welcome to 3‑8 Morgan Manor, a charming one-bedroom condo nestled in the heart of Lenox Village. This move-in-ready unit offers a sunlit layout with cozy carpeting, and efficient space. The condo fee includes heat, hot water, gas, water, and sewer, making for truly hassle-free living. Located in a well-maintained building just steps from downtown Lenox, you'll enjoy easy access to

Katie Soules WILLIAM RAVEIS REAL ESTATE

3 Morgan Manor Unit 3 - 8, Lenox, MA 01240
/47
$579,000
- 4 Beds
- 2.5 Baths
- 2,040 Sq Ft
65 Pease Terrace, Lee, MA 01238

This lovely home boasts 4 generously sized bedrooms with hardwood floors, primary has ensuite bath. It also has a 2nd full and 1 half bath. Large family room with vaulted ceiling, substantial deck on one side & screened porch on opposite side. Hardwood floors in formal dining room & beautiful living room with fireplace. French doors from living room to screened-in porch. A Buderus Boiler for

Mary Blair SIGNATURE ASSOCIATES

65 Pease Terrace, Lee, MA 01238
/26
$425,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
153 E Dugway Rd, Lenox, MA 01240

**Opportunity Awaits!**Great Lenox location. Three bedroom, one bath Ranch style home is nestled on 1.14 acres of land on a picturesque street, this gem offers 1344 sq ft on the main floor, with a full walkout lower level to a beautiful large yard. Minutes to downtown, Tanglewood and the best of the Berkshires.

Matt Carlino MACCARO REAL ESTATE

153 E Dugway Rd, Lenox, MA 01240
/19
$949,000
- 11 Beds
- 6 Baths
- 4,863 Sq Ft
Unlisted Address

Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

Matt Carlino MACCARO REAL ESTATE

Unlisted Address
/50
$1,950,000
- 5 Beds
- 4.5 Baths
- 4,301 Sq Ft
20 E Dugway Rd, Lenox, MA 01240

Lenox Estate on 36 Acres - Two HomesJust one mile from the center of Lenox, this unique estate offers exceptional space and versatility with two separate residences. The main home boasts 4,100 square feet with five bedrooms and three and a half bathrooms--perfect for spacious living or entertaining. The second home is a charming 1,200-square-foot residence with two bedrooms and two full baths,

Tanya Shepardson LAMACCHIA REALTY, INC

20 E Dugway Rd, Lenox, MA 01240
/20
$299,900
- 1 Bed
- 1 Bath
- 658 Sq Ft
2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

Heron Pond Condominiums in Stockbridge (at intersection of 2 Wallace Rd. also known as 26 East St.) is adjacent to the village and the Red Lion Inn. Famous for having been the former Shaggy Dog Recording Studio, that was a location for prominent musicians of the 60's and 70's. Come experience the beauty of the four seasons in the center of the Berkshires. Enjoy 1-level living, 1-bed, 1-bath

Susan Calkins STONE HOUSE PROPERTIES, LLC

2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
/38
$385,000
- 3 Beds
- 2 Baths
- 1,405 Sq Ft
880 East St Unit 1A, Lee, MA 01238

Desirable end unit at October Mountain Village in Lee, MA, offering a serene and picturesque setting. This unit is a short stroll to the tennis courts and community pool. The open-concept living and dining areas feature laminate flooring and a charming two-sided wood-burning fireplace, shared with the vaulted family room. Two skylights and a ceiling fan bring abundant natural light and airflow.

Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

880 East St Unit 1A, Lee, MA 01238
/48
$640,000
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
770 Summer St Unit 5D, Lee, MA 01238

Welcome to 5D Lakeside at Foxhollow - a beautifully updated 3-bedroom, 3-full-bath condo offering the perfect blend of modern comfort and classic Berkshire charm.Enjoy seasonal views of sparkling Laurel Lake from your enclosed summer porch, the ideal spot for morning coffee or evening gatherings. Inside, you'll find a thoughtfully updated kitchen and baths, a cozy wood-burning fireplace, and

Paula McLean PAULA MCLEAN REALTORS INC.

770 Summer St Unit 5D, Lee, MA 01238
/45
$599,900
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
31 Saint Ann's Ave, Lenox, MA 01240

OWN - Instead of Renting - this Tanglewood Season! A unique opportunity with past rental income up to $16,000 for the summer months--ideal for music lovers and art-minded Berkshires visitors. This 1915 gem--the Claude and Louise Delahaye House--is tucked away on peaceful St. Ann's Ave, just steps from the iconic St. Ann's Church. Enjoy an easy stroll to downtown Lenox's shops, dining, and

Audrey Matys BERKSHIRE LISTINGS

31 Saint Ann's Ave, Lenox, MA 01240
/45
$369,000
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
205 High St, Lee, MA 01238

Enjoy downtown living in this 4 Bedroom 2 Bath New England farmhouse. Built in the early20th century, this home has a diverse use of residential, commercial or mixed use on a residential street. The kitchen has been updated with plenty of cabinet space. A cozy living room fireplace and a enclosed porch with numerous windows that welcome fresh summertime breezes and a patio for summer leisure

Anthony Caropreso MACCARO REAL ESTATE

205 High St, Lee, MA 01238
/50
$2,250,000
- 4 Beds
- 4 Baths
- 2,738 Sq Ft
8 Yale Hill Rd, Stockbridge, MA 01262

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

8 Yale Hill Rd, Stockbridge, MA 01262
/27
$1,969,000
- Land
- 56 Acres
- $35,161 per Acre
26 A Stonebridge Way, Tyringham, MA 01264

Own the entire mountain top! If privacy and views are your top priority then this is for you. You'll own 56 acres that includes a 4 bed/3 bath house, workshop, 2 chicken coups, and a barn. Stunning views over Goose Pond and sunrises you'll never tired of. The land stretches down into Tyringham valley where you can enjoy riding on your own trails. Minutes to Goose Pond boat launch, less than

Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

26 A Stonebridge Way, Tyringham, MA 01264
/29
$649,000
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
170 Stockbridge Rd, Lee, MA 01238

Charming 1930s Retreat with Water Views and Historic Charm - 170 Stockbridge Road, Lee MANestled just five minutes from both Stockbridge and the village of Lee, this beautifully restored 1930s gem offers the best of Berkshire living. Located near world-class cultural destinations--including Tanglewood, The Norman Rockwell Museum, and Jacob's Pillow--this home sits on a desirable lot overlooking

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

170 Stockbridge Rd, Lee, MA 01238
/24
$349,900
- 3 Beds
- 1.5 Baths
- 1,140 Sq Ft
90 Maple St, Lee, MA 01238

Come and see this quaint, cape style home situated close to downtown Lee. This home has been completely renovated. A spacious kitchen includes new cabinets, stone countertops and appliances. The living room and dining room are flooded with natural light and are the perfect space for entertaining. Also located on the first floor are a bedroom and a half bath. The primary bedroom and full

Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

90 Maple St, Lee, MA 01238
/13
$185,000
- Land
- 11 Acres
- $17,209 per Acre
83 Goose Pond Rd, Tyringham, MA 01264

Build your dream home with deeded rights to Goose Pond with boat docking availability. Lot is mostly cleared. A rough drive is in place. 10.75 Acres. Minimal HOA includes Tennis Court and Deeded right to private beach on the pond. Goose Pond is considered a pristine lake in the foothills of the Berkshires. Close to all the Berkshires has to offer. Minutes to the MA Pike, Lee, Lenox Tanglewood,

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

83 Goose Pond Rd, Tyringham, MA 01264
/17
$499,000
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
lot 1 N Beckett, Lee, MA 01238

Single Family modular home on 3 Acres of land, in a serene and beautiful setting. There are two Modular homes to pick from, the New Haven and the Rolling Brook. Nestled in a peaceful, wooded landscape, this lot offers a perfect blend of privacy and natural beauty while being conveniently located. Minutes to walking trails, Basin Pond, and Finery Pond are at your back yard. Lenox and Stockbridge's

The Mary Scimemi Team Leading Edge Real Estate

lot 1 N Beckett, Lee, MA 01238

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