Vintage homes for sale & real estate in 01238, MA

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ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Just up the hill from downtown Lee, enjoy this well kept 3 bedroom home on almost a half acre. The fenced in backyard includes a new inground pool with retractable cover, hot tub, studio/pool house, and garden shed. The first floor bathroom has been recently remodeled.

$625,000

2 beds1 bath1,278 sq ft

Hot tub • Fenced in backyard • Inground pool

187 W Park St, Lee, MA 01238

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Welcome to 140 Orchard Street, an inviting three-bedroom, one-bathroom Lee home that effortlessly combines everyday convenience with a warm, relaxed atmosphere. Bathed in natural sunlight, the cozy interior features an easy-flowing floor plan anchored by a desirable first-floor bedroom and full bathroom, creating a comfortable and welcoming layout the moment you step through the front door and offering a wonderfully bright canvas ready for your personal touch. The home's exterior is an outdoor lover's delight, featuring an expansive, partially fenced yard that provides a serene setting for summer barbecues, lawn games, or simply relaxing in the fresh Berkshire air. An attached one-car garag

$350,000

3 beds1 bath1,224 sq ft

Attached garage • Full bathroom • First floor bedroom

140 Orchard St, Lee, MA 01238

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Tucked away on just under an acre of absolute privacy in beautiful Lee MA. , This modified Cape-style home is a masterclass in character. Ready for you to bring this home to its modern beauty! Step inside to find hardwood floors that guide you into a spectacular living room, where dramatic vaulted ceilings create an airy, sanctuary. Two cozy pellet stoves offer the ultimate in warmth and ambiance during crisp New England autumns. 4 spacious bedrooms and 2 full baths, the layout is as functional as it is inviting. Outside, your private yard oasis awaits--featuring an inground pool wrapped in serene privacy, a spacious two-car garage, and plenty of room to breathe.

$429,900

4 beds2 baths2,240 sq ft

Pellet stoves • Private yard oasis • Inground pool

15 Silver St, Lee, MA 01238

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Charming and full of character, this in town Lee home blends timeless original details with thoughtful modern updates. Beautiful hardwood floors, original woodwork, and classic architectural features create warmth throughout. The spacious layout offers comfortable living with abundant natural light and inviting spaces for everyday life or entertaining. A Tesla charger adds modern convenience, while the walkable location puts shops, restaurants, and local amenities just moments away. Located in Lee's Commercial Business Corridor (CBC) District, the property also offers added flexibility with a variety of permitted residential and commercial uses, subject to town zoning regulations. A unique

$350,000

4 beds2 baths1,624 sq ft

Tesla charger • Original woodwork • Hardwood floors

75 Housatonic St, Lee, MA 01238

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Welcome home to this sweet and petite one level easy living ranch style home. Sun filled bright spaces invite you to relax and enjoy the end of each day in this thoughtfully planned layout. Boasting a king size bedroom, two other bedrooms, and an updated full bath. The galley style kitchen is comfortable for baking and creating all the dinner gatherings you wish. Comfortable everyday dining is open to living and a lovely added sunroom for extra living space and enjoyment. French doors lead to a generously sized back yard with perrenial plantings and a shade tree for an outdoor cool evening escape and playtime. Central to all that is Berkshire and Lee with a quaint downtown, shopping, schoo

$249,900

3 beds1 bath875 sq ft

Shade tree • Updated full bath • Added sunroom

832 East St, Lee, MA 01238

Property at 485 Golden Hill Rd, Lee, MA 01238, 3 beds, 1 bath

$410,000

3 beds1 bath1,502 sq ft

485 Golden Hill Rd, Lee, MA 01238

Property at 19 Lakeside Dr, Tyringham, MA 01264, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths1,014 sq ft

19 Lakeside Dr, Tyringham, MA 01264

Property at 236 Main St, Lee, MA 01238, 10 beds, 6.5 baths

$975,000

10 beds6.5 baths9,024 sq ft

236 Main St, Lee, MA 01238

Property at 555 Marble St, Lee, MA 01238, 3 beds, 1 bath

$319,000

3 beds1 bath960 sq ft

555 Marble St, Lee, MA 01238

Property at 160 High St, Lee, MA 01238, 4 beds, 5 baths

$995,000

4 beds5 baths6,300 sq ft

160 High St, Lee, MA 01238

Property at 465 Chapel St, Lee, MA 01238, 10 beds, 9 baths

$995,000

10 beds9 baths5,690 sq ft

465 Chapel St, Lee, MA 01238

Property at 205 High St, Lee, MA 01238, 4 beds, 2 baths

$299,900

4 beds2 baths1,728 sq ft

205 High St, Lee, MA 01238

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ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet

$999,000

3 beds2.5 baths2,262 sq ft

Cozy gas fireplace • Updated windows • 0.99 acre lot

22 Post Rd, Lenox, MA 01240

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Historic 1815 compound — 3 independent income-producing units — $154K gross revenue in 2025. 1815 Greek Revival farmhouse duplex + converted barn — an investment rental property or family compound minutes from Main Street Stockbridge. Turnkey 5-star Airbnb, 6 years running, $154K/year. On historic registry as birthplace of a U. S. Supreme Court Justice. Compact, low-maintenance parcel — all the Berkshires, none of the yard work. Original wide-beam floors, log rafters, double-sided fireplace with brick vaulted bread oven, mature gardens with bistro tables. Three addresses — 1574, 1577 & 1579 Pleasant St. Each unit fully self-contained with own entrance, k

$1,260,000

5 beds4 baths3,334 sq ft

Mature gardens • Historic designation • Log rafters

1574-1579 Pleasant St, South Lee, MA 01260

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy office space, and a spacious, freshly updated kitchen with a breakfast nook and extra pantry space. Outside, the large open yard is anchored by a charming car barn--ideal for summer projects, kayaks, bicycles, and flexible loft space. Come make this home your Berkshire dream!

$485,000

4 beds2 baths1,720 sq ft

Front patio • Charming car barn • Large open yard

500 Walker St, Lenox, MA 01240

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Extraordinary opportunity to own a showcase of New England history and hospitality--17 Main Street, a masterfully restored Berkshire cottage in the vibrant heart of downtown Lenox. Originally built in 1883 and once owned by Gilded Age shipping magnate John Schermerhorn, this landmark property blends historic grandeur with modern comfort. Between 2021 and 2025, the residence underwent a comprehensive top-to-bottom renovation: a new 30-year roof, upgraded electrical and plumbing, 8.5 renovated bathrooms, custom millwork, and restored original hardwood floors. The gourmet kitchen features a Viking 8-burner oven, KitchenAid designer dishwasher, and commercial-grade refrigeration--perfect for bo

$3,925,000

8 beds8.5 baths6,000 sq ft

New 30-year roof • Renovated bathrooms • Gourmet kitchen

17 Main St, Lenox, MA 01240

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Unbeatable Lenox location! Near the top of Kemble Street, you'll find this charming 1950's-vintage ranch home that's a super short walk to the village. Timeless details merge with everyday comfort! Hardwood floors flow throughout. Living room features a wood-burning fireplace. Dining opens to expanded galley kitchen on one end and to a den/office flexible space on the other. Three bedrooms, two full baths. Home includes an attached two-car garage. Sunny open lot with private back yard. Location is everything here with shopping, dining, library and community life literally around the corner. Enjoy performances at Shakespeare right down the street and a short drive to Tanglewood!

$689,000

3 beds2 baths1,532 sq ft

Private back yard • 0.46 acre lot • 2 garage spots

19 Kemble St, Lenox, MA 01240

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 01238, MA:
Set on a desirable tree-lined dead-end street in the heart of Lenox, this beautifully restored 1937 Cape blends timeless character with exceptional craftsmanship. Featured in Berkshire Magazine, the 3,740 sq. ft. home offers original heart pine floors, a wood-burning fireplace, and extensive updates including new plumbing, electrical, Pella windows, roof, and central AC. The three-level layout features 3 bedrooms, 4 full baths, two upper-level suites, and a finished lower level with a guest suite, office, and workshop. French doors open to a wraparound veranda overlooking Goshen stone terraces, fruit trees, and a fire pit. Enjoy sidewalk access to downtown, and Tanglewood is just minutes aw

$1,400,000

3 beds4 baths3,740 sq ft

New plumbing • New electrical • Pella windows

41 Tucker St, Lenox, MA 01240

Property at 528 Walker St, Lenox Dale, MA 01242, 3 beds, 2 baths

$279,900

3 beds2 baths1,710 sq ft

528 Walker St, Lenox Dale, MA 01242

Property at 11 Hawthorne, Stockbridge, MA 01262, 19 beds, 23 baths

$14,500,000

19 beds23 baths19,364 sq ft

11 Hawthorne, Stockbridge, MA 01262

Property at 137 Housatonic St, Lenox, MA 01240, 3 beds, 2 baths

$350,000

3 beds2 baths1,708 sq ft

137 Housatonic St, Lenox, MA 01240

Property at 11 Hawthorne Rd, West Stockbridge, MA 01266, 19 beds, 23 baths

$14,500,000

19 beds23 baths19,364 sq ft

11 Hawthorne Rd, West Stockbridge, MA 01266

Property at 53 Main St, Stockbridge, MA 01262, 5 beds, 5 baths

$1,900,000

5 beds5 baths4,670 sq ft

53 Main St, Stockbridge, MA 01262

Property at 10 Prospect Hill Rd, Stockbridge, MA 01262, 4 beds, 2 baths

$895,000

4 beds2 baths2,515 sq ft

10 Prospect Hill Rd, Stockbridge, MA 01262

Property at 19 Cliffwood St, Lenox, MA 01240, 5 beds, 3.5 baths

$2,100,000

5 beds3.5 baths3,387 sq ft

19 Cliffwood St, Lenox, MA 01240

Property at 850 Summer St Unit m14, Lee, MA 01238, 5 beds, 4.5 baths

$949,000

5 beds4.5 baths2,800 sq ft

850 Summer St Unit m14, Lee, MA 01238

Property at 3664 Jacobs Ladder Rd, Becket, MA 01223, 3 beds, 1 bath

$225,000

3 beds1 bath1,222 sq ft

3664 Jacobs Ladder Rd, Becket, MA 01223

Property at 349 Old Stockbridge Rd, Lenox, MA 01240, 34 beds, 23.5 baths

$3,750,000

34 beds23.5 baths40,241 sq ft

349 Old Stockbridge Rd, Lenox, MA 01240

Property at 20 E Dugway Rd, Lenox, MA 01240, 7 beds, 6.5 baths

$1,650,000

7 beds6.5 baths5,693 sq ft

20 E Dugway Rd, Lenox, MA 01240

Property at Undisclosed address, Stockbridge, MA 01262, 11 beds, 6 baths

$865,000

11 beds6 baths4,863 sq ft

Undisclosed address, Stockbridge, MA 01262

Property at 2 Kemble, Lenox, MA 01240, 13 beds, 13.5 baths

$4,850,000

13 beds13.5 baths9,510 sq ft

2 Kemble, Lenox, MA 01240

Property at 8 Yale Hill Rd, Stockbridge, MA 01262, 4 beds, 4 baths

$1,995,000

4 beds4 baths2,738 sq ft

8 Yale Hill Rd, Stockbridge, MA 01262

Vintage Homes for Sale in 01238

There are currently 12 vintage homes for sale in 01238 at a median listing price of $500K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 01238 stay on the market for 43 days. This map is refreshed with the newest listings in 01238 every 15 minutes.

In the past month, 6 homes have been sold in 01238. In addition to houses in 01238, there were also 2 condos, 0 townhouses, and 3 multi-family units for sale in 01238 last month. Find your dream home in 01238 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 01238 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 01238. If you're looking to sell your home in the 01238 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 01238 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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