Red-brick building with steep gables and tall chimneys, viewed from the tree-lined driveway.
Red-brick mansion with steep gables, tall chimneys, landscaped gardens, and a curved stone driveway.
Large red-brick building with steep gables and chimneys beside a broad lawn and playground.
Aerial view of a red-brick house with a pool, playground, and expansive lawn against wooded hills.
Red-brick property with an ornate stone entrance, decorative balcony, and steep gables.
Red-brick building with gabled roof and central steps, fronted by a curved path and green lawn.
Red-brick residence with multiple gables, a landscaped lawn, and a furnished terrace.
Red-brick home facade with pink-trimmed gables and an ornate stone balcony.
Stone retaining wall topped by a dark wooden fence with brick pillars.
Historic brick facade with dark-framed windows and an ornate carved stone panel.
Spacious vacant room with rich wood paneling, tall windows, and a raised carpeted platform.
Wood-paneled room with built-in shelves, tall windows, and an ornate stone fireplace.
Living room with a carved stone fireplace, dark wood paneling, built-in bookshelves, and a grand piano.
Wood-paneled interior with a raised platform, tall windows, glass entry doors, and an ornate white fireplace.
Ornately carved stone fireplace mantel with sculpted figures and fluted columns.
Vacant interior with ornate ceiling trim, wood floors, and a curved wall of tall windows.
Formal dining room with green paneled walls, ornate moldings, and tall windows.
Ornate interior wall trim with carved leaf motifs and fluted blocks.
Empty room with a curved wall of tall windows, polished hardwood floors, and ornate crown molding.
Ornate white exterior trim with symmetrical scrollwork, floral rosettes, and a central shell ornament.
Bright empty room with a blackboard wall, tall windows, dark wood floors, and a long wooden counter.
Empty carpeted room with gray walls and tall windows wrapping around two sides.
Empty carpeted room with built-in cabinets and a curved bay of tall windows.
Ornate carved capital atop an interior column beside a large multi-pane window.
Empty carpeted room with tall black-framed windows wrapping around two walls.
Virtually staged bedroom with a large upholstered bed, tufted bench, and tall curved windows.
Staircase with dark wood paneling, an ornate curved arch, and blue wainscoting.
Ornate carved wood paneling with a pointed arch and diamond-pattern metal mesh inset.
Dark wood staircase with turned balusters and paneled cabinetry beneath.
Ornate wooden doorway with paired carved pilasters and detailed scrollwork.
Aerial view of a red-brick property with a pool and playground on wooded grounds.
Long shingle-sided property beside a curved driveway, stone retaining walls, and a basketball hoop.
Furnished lounge with a round table, colorful chairs, and an open doorway to a room with a bed.
Bedroom with two single beds, a blue mini trampoline, and two wooden doors.
Recreation room with blue seating, a large exercise ball, and children’s artwork on the wall.
White Tudor-style property and matching outbuilding behind a broad lawn and large leafless tree.
Indoor basketball court with polished wood flooring, multiple hoops, and a high fabric-covered ceiling.
Angular brown wood-sided home with a brick chimney, surrounded by trees and spring landscaping.
Landscaped yard with a broad lawn, leafy trees, and part of a brown-sided house.
Living room with a vaulted wood ceiling, built-ins, hardwood floors, and a large brick fireplace.
Seating nook with a brick fireplace, brass doors, and an L-shaped built-in bench.
Living room with a vaulted wood ceiling, fireplace, and sliding glass doors overlooking a garden.
Dining room with a wood table, globe pendant lights, and vaulted wood-paneled ceiling.
Dining room with a wood-paneled ceiling, built-in cabinetry, and sliding doors overlooking a pool.
Dining area with a wood-paneled vaulted ceiling, globe pendants, and an open kitchen pass-through.
Kitchen with wood cabinetry, a vaulted wood ceiling, and a large stainless-steel gas range.
Entry area with a vaulted wood ceiling, wood floors, and multiple wood doors and closets.
Bedroom with a wood-paneled ceiling, broad windows, and a large bed.
Sunroom with green carpet and screened windows opening to an empty hardwood-floored room.
Sunroom with green carpet, built-in shelves, and expansive louvered windows overlooking the yard.
Empty room with hardwood floors and sliding glass doors opening onto a green yard.
Vacant room with hardwood floors, built-in shelving, and sliding glass doors opening to a leafy yard.
Landscaped yard with a wooden footbridge among spring trees and shrubs.
Brown wood-sided house with brick chimney and attached garage, surrounded by trees and spring landscaping.
Aerial view of a wooded property with multiple buildings, a pool, broad lawns, and a large parking area.
Aerial view of multiple buildings and wooded grounds, with broad lawns and landscaped garden beds.
Aerial view of a historic brick estate with outbuildings, a swimming pool, and playground.
Aerial parcel map outlining 16.76 acres along Old Stockbridge Road in blue.
Red-brick building with steep gables and multiple chimneys, framed by budding trees.
Three-floor floor plan with labeled rooms, offices, dining areas, and BerkshireMLS branding.
Four dormitory floor plans showing first- and second-floor layouts with bedrooms and shared common areas.
Miller dormitory first- and second-floor plans labeled with bedrooms, common areas, bathrooms, and exits.
Upper- and lower-level gymnasium floor plans, with a large gym court and surrounding classrooms and staff areas.
Floor plan of Overlee Estate office, with a large room labeled Supervisors Office.
Floor plan showing the first floor, studio, Florida room, and finished and unfinished basement.
SEE ALL PHOTOS
Red-brick building with steep gables and tall chimneys, viewed from the tree-lined driveway.
Red-brick mansion with steep gables, tall chimneys, landscaped gardens, and a curved stone driveway.
Large red-brick building with steep gables and chimneys beside a broad lawn and playground.
Aerial view of a red-brick house with a pool, playground, and expansive lawn against wooded hills.
Red-brick property with an ornate stone entrance, decorative balcony, and steep gables.
Red-brick building with gabled roof and central steps, fronted by a curved path and green lawn.
Red-brick residence with multiple gables, a landscaped lawn, and a furnished terrace.
Red-brick home facade with pink-trimmed gables and an ornate stone balcony.
Stone retaining wall topped by a dark wooden fence with brick pillars.
Historic brick facade with dark-framed windows and an ornate carved stone panel.
Spacious vacant room with rich wood paneling, tall windows, and a raised carpeted platform.
Wood-paneled room with built-in shelves, tall windows, and an ornate stone fireplace.
Living room with a carved stone fireplace, dark wood paneling, built-in bookshelves, and a grand piano.
Wood-paneled interior with a raised platform, tall windows, glass entry doors, and an ornate white fireplace.
Ornately carved stone fireplace mantel with sculpted figures and fluted columns.
Vacant interior with ornate ceiling trim, wood floors, and a curved wall of tall windows.
Formal dining room with green paneled walls, ornate moldings, and tall windows.
Ornate interior wall trim with carved leaf motifs and fluted blocks.
Empty room with a curved wall of tall windows, polished hardwood floors, and ornate crown molding.
Ornate white exterior trim with symmetrical scrollwork, floral rosettes, and a central shell ornament.
Bright empty room with a blackboard wall, tall windows, dark wood floors, and a long wooden counter.
Empty carpeted room with gray walls and tall windows wrapping around two sides.
Empty carpeted room with built-in cabinets and a curved bay of tall windows.
Ornate carved capital atop an interior column beside a large multi-pane window.
Empty carpeted room with tall black-framed windows wrapping around two walls.
Virtually staged bedroom with a large upholstered bed, tufted bench, and tall curved windows.
Staircase with dark wood paneling, an ornate curved arch, and blue wainscoting.
Ornate carved wood paneling with a pointed arch and diamond-pattern metal mesh inset.
Dark wood staircase with turned balusters and paneled cabinetry beneath.
Ornate wooden doorway with paired carved pilasters and detailed scrollwork.
Aerial view of a red-brick property with a pool and playground on wooded grounds.
Long shingle-sided property beside a curved driveway, stone retaining walls, and a basketball hoop.
Furnished lounge with a round table, colorful chairs, and an open doorway to a room with a bed.
Bedroom with two single beds, a blue mini trampoline, and two wooden doors.
Recreation room with blue seating, a large exercise ball, and children’s artwork on the wall.
White Tudor-style property and matching outbuilding behind a broad lawn and large leafless tree.
Indoor basketball court with polished wood flooring, multiple hoops, and a high fabric-covered ceiling.
Angular brown wood-sided home with a brick chimney, surrounded by trees and spring landscaping.
Landscaped yard with a broad lawn, leafy trees, and part of a brown-sided house.
Living room with a vaulted wood ceiling, built-ins, hardwood floors, and a large brick fireplace.
Seating nook with a brick fireplace, brass doors, and an L-shaped built-in bench.
Living room with a vaulted wood ceiling, fireplace, and sliding glass doors overlooking a garden.
Dining room with a wood table, globe pendant lights, and vaulted wood-paneled ceiling.
Dining room with a wood-paneled ceiling, built-in cabinetry, and sliding doors overlooking a pool.
Dining area with a wood-paneled vaulted ceiling, globe pendants, and an open kitchen pass-through.
Kitchen with wood cabinetry, a vaulted wood ceiling, and a large stainless-steel gas range.
Entry area with a vaulted wood ceiling, wood floors, and multiple wood doors and closets.
Bedroom with a wood-paneled ceiling, broad windows, and a large bed.
Sunroom with green carpet and screened windows opening to an empty hardwood-floored room.
Sunroom with green carpet, built-in shelves, and expansive louvered windows overlooking the yard.
Empty room with hardwood floors and sliding glass doors opening onto a green yard.
Vacant room with hardwood floors, built-in shelving, and sliding glass doors opening to a leafy yard.
Landscaped yard with a wooden footbridge among spring trees and shrubs.
Brown wood-sided house with brick chimney and attached garage, surrounded by trees and spring landscaping.
Aerial view of a wooded property with multiple buildings, a pool, broad lawns, and a large parking area.
Aerial view of multiple buildings and wooded grounds, with broad lawns and landscaped garden beds.
Aerial view of a historic brick estate with outbuildings, a swimming pool, and playground.
Aerial parcel map outlining 16.76 acres along Old Stockbridge Road in blue.
Red-brick building with steep gables and multiple chimneys, framed by budding trees.
Three-floor floor plan with labeled rooms, offices, dining areas, and BerkshireMLS branding.
Four dormitory floor plans showing first- and second-floor layouts with bedrooms and shared common areas.
Miller dormitory first- and second-floor plans labeled with bedrooms, common areas, bathrooms, and exits.
Upper- and lower-level gymnasium floor plans, with a large gym court and surrounding classrooms and staff areas.
Floor plan of Overlee Estate office, with a large room labeled Supervisors Office.
Floor plan showing the first floor, studio, Florida room, and finished and unfinished basement.
Courtesy of BIRCH PROPERTIES, Selina Lamb Listing Contact: 413-331-7483 
For Sale

349 Old Stockbridge Rd

349 Old Stockbridge Rd, Lenox, MA 01240

$3,195,000
349 Old Stockbridge Road and 40 Frothingham Crossing together represent a rare 16.76+- acre contiguous institutional campus and redevelopment opportunity in the heart of Lenox--one of the Berkshires' most established and sought-after destination markets.

At the center of the offering is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan / Jacobean Revival style. Over time, the estate evolved into a fully integrated campus, thoughtfully organized around the original mansion and supported by a collection of dormitory residences, academic and administrative buildings, dining infrastructure, and recreational facilities. Today, the property offers scale and infrastructure that are increasingly difficult to replicate in the Berkshires: 32 dormitory-style bedrooms across multiple buildings, shared common and staff housing spaces, a multi-level academic and dining center, and a substantial gymnasium well-suited for athletics, wellness programming, or event use. Existing systems include public water, commercial sprinklering, mixed heating systems, and electrical capacity up to 600 amps in select buildings.

The offering also includes 40 Frothingham Crossing, a 1,826 SF mid-century residence set on 4.74+- acres across three contiguous parcels, offering flexibility for owner occupancy, guest accommodations, staff housing, or future subdivision and development planning.

While currently operated as an educational campus, the property's scale, layout, and existing infrastructure create compelling long-term potential for a range of future uses.

The combined acreage and campus framework lend themselves to a variety of possibilities, including educational or nonprofit continuation, retreat or wellness campus, medical or therapeutic use, hospitality or inn redevelopment, residential or senior living concepts, or a mixed-use institutional setting.

Importantly, the property is not listed on the National Historic Registry nor designated as a Lenox "Great Estate," which may allow for greater flexibility in future planning.

All buyers are encouraged to conduct their own due diligence regarding potential uses and approvals with the Town of Lenox.

Hillcrest Educational Center currently occupies the property under a tenancy expected to conclude in February 2027, providing near-term continuity while allowing time for planning, permitting, and phased repositioning.

Offered at $3,750,000 (combined offering).

15
baths

40,241 Sq.Ft. LIVING AREA

16.67 Acres lot

Selina Lamb

Selina Lamb

Features & Amenities

Interior

  • Total bathrooms15
  • full bathrooms15
  • APPLIANCES Washer, Refrigerator, Range Hood, Range, Microwave, Freezer, Dishwasher, Counter Grill, Built-In Electric Oven
  • other interior Features Air Cond, Alarm System, Emp Break Room, Emp Kitchen, Sprink Sys-Wet

Area & Lot

  • Status For Sale
  • Living Area40,241 Sq.Ft.
  • Total Area40,241 Sq.Ft.
  • Lot Area16.67 Acres
  • MLS® ID249507
  • TypeCommercial
  • YEAR BUILT1903
  • NeighborhoodLENOX

Exterior

  • water SourcePublic
  • roofMembrane, Metal, Asphalt
  • parkingOff Street
  • HEAT TYPENat Gas, Oil, Boiler, Pellet Stove, Forced Air, Hot Water
  • sewerPublic Sewer
  • other exterior FeaturesInground Pool

Financial

  • Sales Price$3,195,000
  • Real Estate Tax $99,187/yr
Red-brick mansion with steep gables, tall chimneys, landscaped gardens, and a curved stone driveway.

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.
Thank you for your interest in 349 Old Stockbridge Rd, Lenox, MA 01240. We are reviewing your request and will be in touch shortly!
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Contact Details

Birch Properties

Phone

(413) 613-4363

Email

[email protected]

Address

48 Main STREET Lenox, MA 01240

Selina Lamb |  License #9529248

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