Lenox Dale, MA Homes for Sale

/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
/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

(413) 308-6698

135 East St, Lee, MA 01238
/36
$299,000
- 3 Beds
- 2 Baths
- 1,494 Sq Ft
20 Summer St, Lee, MA 01238

Antique Greek Revival style home overlooking downtown Lee! Beautiful view with splendid sunrises over October Mountain. Wise investment, located within the up-and-coming downtown redevelopment district in historic Lee, Ma. ''Gateway to the Berkshires'', voted one of the top ten small towns, known for the scenery, the arts and activities. This lovely home offers wood flooring throughout, light &

Lisa Kelley

MACCARO REAL ESTATE

(413) 779-8698

20 Summer St, Lee, MA 01238
/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
/10
$199,000
- Land
- 1.31 Acres
- $151,907 per Acre
245 Spring St, Lee, MA 01238

One of two beautiful building lots available on Spring Street, Lee. Lee has been voted one of the top 10 northeastern small towns in New England. Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table

Lisa Kelley

MACCARO REAL ESTATE

(413) 722-5964

245 Spring St, Lee, MA 01238
/8
$199,000
- Land
- 1.31 Acres
- $152,025 per Acre
235 Spring St, Lee, MA 01238

Beautiful building lot available on Spring Street, Lee. Voted one of the top 10 small northeastern towns in New England! Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table food and world class

Lisa Kelley

MACCARO REAL ESTATE

(413) 610-4308

235 Spring St, Lee, MA 01238
/26
$429,000
- 2 Beds
- 2 Baths
- 1,521 Sq Ft
43 Chapman Rd, Pittsfield, MA 01201

Designer style one level living garden bungalow with beautiful Berkshire bucolic pastoral and mountain views! Easy living and low maintenance with 2 bedrooms and 2 full bathrooms, conveniently located on the Lenox/Pittsfield line. Beautifully renovated with open floor plan, spacious living room, beautiful kitchen and dining room w/amazing views. Option to purchase furnished with Paul Rich & Sons

Lisa Kelley

MACCARO REAL ESTATE

(413) 500-0374

43 Chapman Rd, Pittsfield, MA 01201
/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
/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
/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
/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
/70
$1,290,000
- 3 Beds
- 2.5 Baths
- 2,844 Sq Ft
257 W Mountain Rd, Lenox, MA 01240

Nestled in the heart of the Berkshires, 257 W Mountain Road offers a rare blend of luxury and tranquility. This exquisite property is set on a serene, tree-lined road just minutes from downtown Lenox and Tanglewood. With refined finishes, spacious living areas, and walls of windows framing the lush landscape, every detail reflects elegance and comfort. The landscaped grounds feature stone

Nicole Moore KELLER WILLIAMS REALTY

257 W Mountain 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
/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
/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
/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
/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
/62
$629,000 Open Sat 10:30AM - 12PM
- 4 Beds
- 2 Baths
- 1,716 Sq Ft
90 Via Franco, Lee, MA 01238

OPEN HOUSE SAT 7/26/25 10:30am-12:00pm. Don't miss this exceptional opportunity to own a spacious and beautifully updated home nestled on 1.34 acres in the heart of the Berkshires. Tucked away in a private setting yet just minutes from shopping, cultural attractions, and I-90, this home offers the perfect balance of peace and convenience. Enjoy the ease of one-level living with an updated kitchen

Cindy Carrigan LAMACCHIA REALTY, INC

90 Via Franco, Lee, MA 01238
/44
$396,500
- 3 Beds
- 2.5 Baths
- 1,951 Sq Ft
7 Cynthia Ln, Pittsfield, MA 01201

A great opportunity to own in Southview. With only 24 units, turnover is unusual in this Khoury-built established condo community! Tri-level townhouse unit offers great space for year-round or vacation living. First floor boasts a spacious great room/living w hardwood flooring, fireplace, dining and entrance to large and private rear deck. Kitchen with eat-in area. Upper level includes

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

7 Cynthia Ln, Pittsfield, MA 01201
/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
/14
$240,000
- 1 Bed
- 1 Bath
- 800 Sq Ft
260 Pittsfield Rd Unit B-5, Lenox, MA 01240

Freshly updated 1 BR/1 BA condo at Lenox Heights. This light‑filled, 800 sq ft condo boasts a thoughtfully renovated kitchen with new cabinetry and stainless‑steel appliances, plus plush wall‑to‑wall carpeting for a fresh, clean aesthetic. Step outside onto your private balcony to enjoy your morning coffee. On‑site amenities include an outdoor

Samantha Homeyer BIRCH PROPERTIES

260 Pittsfield Rd Unit B-5, Lenox, MA 01240
/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
/40
$309,000
- 2 Beds
- 1 Bath
- 912 Sq Ft
100 Cummings Ave, Pittsfield, MA 01201

Don't miss this well-maintained ranch in a nice quiet neighborhood! Offers a bright and open living room with plenty of light, a functional kitchen, and two bedrooms on the first floor. The full finished basement provides extra living space or plenty of storage. Outside, enjoy a fenced yard, full-width deck, screened-in patio, and off-street parking with a private driveway. Don't miss this

Martha Pope BISHOP WEST REAL ESTATE

100 Cummings Ave, Pittsfield, MA 01201
/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
/13
$313,000
- 2 Beds
- 3 Baths
- 1,770 Sq Ft
2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

If you are looking for location, Rolling Hills is the place to be. Just minutes from Tanglewood, Shakespeare & Company, skiing, arts, and all of the Culture the Berkshires has to offer. This unit is right across from the Clubhouse/Pool/fitness room. This unit has 2 bedrooms, 3 baths, and additional family room on the lower level. Enjoy the Tennis/pickle ball courts or take swim in the pool or

Toni Marie Gage SIGNATURE ASSOCIATES

2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
/58
$4,995,000
- 7 Beds
- 8 Baths
- 13,261 Sq Ft
319 Under Mountain Rd, Lenox, MA 01240

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

319 Under Mountain Rd, Lenox, MA 01240
/38
$710,000
- 3 Beds
- 2 Baths
- 2,081 Sq Ft
51 New Lenox Rd, Lenox, MA 01240

Meticulous craftsmanship and timber frame construction define this charming Colonial Dutch gambrel residence, combining comfort and practicality for everyday living. High-grade timber framing and solid construction give this home character and a warm, inviting atmosphere with its wood accents.Gather around the stone fireplace in the inviting living room, or whip up meals in the kitchen equipped

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

51 New Lenox Rd, Lenox, MA 01240
/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
/57
$635,000
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
4 Evergreen Trail, Lenox, MA 01240

Heirloom peonies and fragrant David Austin rose varieties adorn the walkway of this Berkshire hidden gem inviting you into tranquillity, peace and calm. Once indoors, you'll find easy living. The first level has an open kitchen and living area with a gas fireplace, large primary bedroom with a full bath and walk-in closet along with a screened in patio which overlooks a well established low

Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

4 Evergreen Trail, 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
/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
/25
$374,900
- 3 Beds
- 1 Bath
- 1,986 Sq Ft
349 New Lenox Rd, Lenox, MA 01240

Spacious 3 Bed/1 Bath Colonial located in a quiet Lenox neighborhood. This charming home offers: gleaming hardwood floors, an oversized family room which could be used as a 1st floor primary, a new Refrigerator & Stove, Washer & Dryer hook ups on the 1st floor, attached garage, steam heat and plenty of light throughout! Savor the beautiful Berkshires, while you lounge in your expansive flat

Timothy Johnson NOCHER REALTY

349 New Lenox Rd, 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

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