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Explore Similar Apartments Within 10 Miles of Monterey, MA

  • /8

    $465,000

    • 3 Beds
    • 3 Baths
    • 2,480 Sq Ft

    Unlisted Address

    Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained.

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    Unlisted Address
  • /34

    $1,260,000

    • 6 Beds
    • 4 Baths
    • 3,334 Sq Ft

    1574 Pleasant St, Lee, MA 01260

    Steeped in history and elegance, the Henry Billings Brown House (c.1815) offered at $1,260,000, is a rare Berkshire estate. This three-unit residence on the historic registry is a masterful blend of preserved history and refined updates for modern living. Anchoring its timeliness character are wide-plank floors, stately brick hearths, and marble sourced from the same quarries as the U.S. Capitol.

    Ashley Rose Compass

    1574 Pleasant St, Lee, MA 01260
  • /29

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,538 Sq Ft

    208 Main St, Lee, MA 01238

    Prime Downtown Lee Investment Opportunity Located on a highly visible corner lot in the heart of downtown Lee, this versatile three-unit building offers a blend of residential and commercial income potential. The property includes two residential units--currently operated as successful short-term rentals--and one commercial space currently leased to a massage therapist. The first-floor efficiency

    Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    208 Main St, Lee, MA 01238
  • /8

    $535,000

    • 8 Beds
    • 8 Baths
    • 2,657 Sq Ft

    180 Center St, Lee, MA 01238

    Discover an exceptional investment opportunity to own two duplex homes on a single parcel, perfect for investors looking for a practical investment in the town of Lee. Four units total, these properties are ideal for generating consistent rental income. Close to downtown, shopping, major employers as well as banking and all popular Berkshire attractions. Tenants enjoy attached, private garaged

    Tim Gallagher STONE HOUSE PROPERTIES, LLC

    180 Center St, Lee, MA 01238
  • /54

    $649,000

    • 5 Beds
    • 2.5 Baths
    • 2,750 Sq Ft

    168 Main St, Sheffield, MA 01257

    Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

    Tony Segalla LANCE VERMEULEN RE, INC

    168 Main St, Sheffield, MA 01257
  • /44

    $1,200,000

    • 9 Beds
    • 4.5 Baths
    • 8,406 Sq Ft

    2049 S Undermountain Rd, Sheffield, MA 01257

    An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a

    Tony Segalla LANCE VERMEULEN RE, INC

    2049 S Undermountain Rd, Sheffield, MA 01257
  • /37

    $600,000

    • 6 Beds
    • 5 Baths
    • 3,502 Sq Ft

    53 Mahaiwe St, Great Barrington, MA 01230

    A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to

    Tony Segalla LANCE VERMEULEN RE, INC

    53 Mahaiwe St, Great Barrington, MA 01230
  • /30

    $695,000

    • 3 Beds
    • 6 Baths
    • 4,044 Sq Ft

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

    Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

    Tony Segalla LANCE VERMEULEN RE, INC

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
  • /19

    $775,000

    • 8 Beds
    • 4 Baths
    • 3,192 Sq Ft

    35 Main St, West Stockbridge, MA 01266

    Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

    Matt Carlino MACCARO REAL ESTATE

    35 Main St, West Stockbridge, MA 01266
  • /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
  • /20

    $999,999

    • 5 Baths
    • 5,180 Sq Ft

    406 Main St, Great Barrington, MA 01230

    FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for

    Jason Saphire www.HomeZu.com

    406 Main St, Great Barrington, MA 01230
  • /53

    $1,275,000

    • 7 Beds
    • 7 Baths
    • 3,896 Sq Ft

    91 & 95 Miller Rd, Canaan, NY 12029

    Last Chance to own a Storybook Historic Estate on 10+ Bucolic Acres in Canaan, NY Offered for the first time in over 40 years, this timeless 10.7-acre estate is the ultimate countryside escape—just 2.5 hours from NYC and 2 hours from Boston. Nestled between the Berkshires and Hudson Valley, the property features two fully restored historic homes that blend 18th- and 19th-century charm

    Jessie Bennett William Pitt Sothebys Intn'l

    91 & 95 Miller Rd, Canaan, NY 12029
  • /46

    $649,900

    • 9 Beds
    • 4 Baths
    • 4,152 Sq Ft

    1057 Main St, Great Barrington, MA 01236

    Great investment opportunity! A very rare property offered for the first time outside the family in over 90 years! This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior and updated units are just a few of the benefits of this investment. In the bustling village of

    Ryan Lane GILCREST PROPERTIES

    1057 Main St, Great Barrington, MA 01236
  • /53

    $849,000

    • 8 Beds
    • 4 Baths
    • 3,044 Sq Ft

    328 Park St, Great Barrington, MA 01230

    Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

    Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    328 Park St, Great Barrington, MA 01230
  • /70

    $895,000

    • 9 Beds
    • 7 Baths
    • 5,267 Sq Ft

    567 S Main St, Sheffield, MA 01257

    Investment opportunity in Sheffield. Versatile investment opportunity set on 11 private acres. This multi-building property, held by the same family for four decades, offers strong income potential with flexible configurations across three separate structures. Main House with (4) 1BR and (1) 2BR apartment, a second 3 BR home, and a three-bay garage. Just 15 minutes from GB and 10 minutes to

    Claire Pollart LANCE VERMEULEN RE, INC

    567 S Main St, Sheffield, MA 01257
  • /30

    $655,000

    • 5 Beds
    • 3 Baths
    • 3,035 Sq Ft

    133 Front St, Great Barrington, MA 01236

    Unique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal

    Judi Panzano HOUSATONIC REAL ESTATE

    133 Front St, Great Barrington, MA 01236
  • /41

    $1,499,900

    • 12 Beds
    • 7 Baths
    • 7,956 Sq Ft

    45 Forest St, Lee, MA 01238

    This stunning 6-family home sits on 1.5 acres, just a couple minutes away from the Lee Outlets, a convenient location with easy access to the Mass Pike. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and primary bedroom on the the 1st floor, and 3 bedrooms

    Maria Liccardi Lamacchia Realty, Inc.

    45 Forest St, Lee, MA 01238
  • /52

    $1,675,000

    • 12 Beds
    • 7 Baths
    • 8,881 Sq Ft

    29 Main St, West Stockbridge, MA 01266

    Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

    Suzann Ward HOUSATONIC REAL ESTATE

    29 Main St, West Stockbridge, MA 01266
  • /16

    $299,000

    • 2,950 Sq Ft

    16 Depot St, Great Barrington, MA 01230

    Prime Commercial / Residential / Multi-Family Space in Downtown Housatonic! A chance to create a central hub for commerce and discover the endless possibilities with a versatile commercial space. Spanning 2,950 square feet, this property offers a unique opportunity to breathe new life into the area and create a thriving business hub. Ready to be transformed into a cozy coffee shop, a vibrant meat

    John Segalla HOUSATONIC REAL ESTATE

    16 Depot St, Great Barrington, MA 01230
  • /4

    $549,000

    • 5 Beds
    • 3 Baths
    • 2,899 Sq Ft

    5, 15, 17 Fuller St, Lee, MA 01238

    Prime Commercial / Residential / Mixed-Use Development Parcel on Route 20. Corner Parcel. Almost a full Acre. Comprised of 2 Lots. High traffic count,. Zoning allows for several uses. **Includes 2 Residential Buildings that can be delivered tenanted, vacant or can be raised by Seller for an additional fee.(note: Property delineation lines on photographs are approximations only.)

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    5, 15, 17 Fuller St, Lee, MA 01238
  • /11

    $799,000

    • 6 Beds
    • 5 Baths
    • 4,016 Sq Ft

    129 W Shore Rd, Otis, MA 01253

    Otis Reservoir Deeded Access is steps away from this versatile property. Four units primarily used, on a casual basis, as vacation rentals with nightly rates ranging from $140 to $171. Current retiring owner has set the stage for the next owner to grow a highly profitable venture. Most furniture, fixtures and supplies convey so the new owner can hit the ground running. Portions of the

    Karen Chenausky Cetto Real Estate

    129 W Shore Rd, Otis, MA 01253
  • /34

    $589,000

    • 4 Beds
    • 4 Baths
    • 5,044 Sq Ft

    163 Front St, Great Barrington, MA 01230

    Suzann Ward HOUSATONIC REAL ESTATE

    163 Front St, Great Barrington, MA 01230

Why Live in Monterey

Monterey, MA, nestled in the southern Berkshires, is a mountain town known for its natural beauty and strong community ties. The area boasts numerous hiking trails and fishing lakes, including the popular Lake Garfield, which offers year-round activities such as swimming, kayaking, fishing, and ice skating. Beartown State Forest provides 12,000 acres for hiking, camping, mountain biking, and winter sports. Monterey's housing market features early 20th-century cottages and lakefront properties, with many being converted into larger year-round homes. The Southern Berkshire Regional School District, which includes Mount Everett Regional School, is noted for its smaller class sizes and individual attention. Residents often travel to nearby towns like Lee and Great Barrington for shopping and dining, with Great Barrington offering a variety of bakeries, cheese shops, and international cuisine. Cultural attractions are abundant, with the Boston Symphony Orchestra's summer home at Tanglewood in Lenox, just 15 miles north, and local art exhibitions at the Monterey Library. Despite its rural charm, Monterey is car-dependent, with main roads like Route 23 and Route 57 connecting to larger highways. The town is about 50 miles west of Springfield and 20 miles south of Pittsfield.

Home Trends in Monterey, MA

Housing Trends

Median Sale Price
$967,500
Median Single Family Sale Price
$885,000
Median 1 Bedroom Sale Price
$385,000
Average Price Per Sq Ft
$442
Number of Homes for Sale
12
Last 12 months Home Sales
10
Months of Supply
14.40
Median List Price
$922,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
102%
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