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349 Old Stockbridge Road Lenox MA 01240

Lenox, MA349 Old Stockbridge Road

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 73567764

  • Residential
  • Bedrooms 31
  • Bathroom 29
  • Square Feet 38,415
  • High School Lenox Memorial

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style.The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate-historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

Listed by Selina Lamb of Birch Properties

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

100 The Paddock Circle Mashpee MA 02649

Mashpee, MA100 The Paddock Circle, New Seabury

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 73544612

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 3,904

This custom-built, 3-bedroom estate offers unparalleled luxury and resort-style living. The open-concept design features vaulted ceilings and hardwood floors. The main level primary suite provides a private sanctuary, with two additional ensuite bedrooms. Above the 3-car garage, discover a private, fully appointed guest suite. The exterior boasts a heated in-ground pool, hot tub, and a meticulously landscaped .7-acre lot with stone walls and mature plantings for privacy. A separate pool house includes a kitchenette, full bath, laundry, and AC. The lower level offers a professional 9-hole putt-putt course and a TV/ping pong playroom. Schedule a private tour today.

Listed by Mark Thompson of New Seabury Sotheby's International Realty

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Calvin Street Lexington MA 02420

Lexington, MA15 Calvin Street

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73522142

  • Residential
  • Next Open House: Sat 08/29 12:00 pm. to 1:30 pm.
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,279

**OPEN HOUSE SAT 12-1:30 ** Beautifully designed New Construction 5-bedroom, 4.5-bath home in historic Lexington, MA blends classic charm with modern amenities. The main floor features a gourmet kitchen with quartz countertops, breakfast bar, Thermador appliances, and walkthrough pantry to your formal dining and living spaces. . Family room has fireplace and slider with access to private fenced backyard with deck and patio. The second level offers 4 spacious bedrooms, laundry room, & 3 full baths including a luxurious primary suite with walk-in closet, spa bathroom, soaking tub, & double vanity. Relax in your third floor light-washed den, additional bedroom and full bath ideal for guests or a private retreat. Oak hardwood floors throughout, 2-car garage w/ epoxy (EV charger ready), & full unfinished basement is great for storage. Conveniently located near 95 & top-rated schools, this home offers space, elegance, & flexibility in one of Massachusetts' most historic & desired towns.

Listed by Northeast Venture Group and Nicholas Petmezis of Stuart St James,Inc.

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 Stanley Avenue Newburyport MA 01950

Newburyport, MA1 Stanley Avenue

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73526084

  • Residential
  • Next Open House: Fri 08/28 5:00 pm. to 6:30 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,657

Experience elevated coastal living in this exceptional new construction home by a premier local builder in one of Newburyport's most walkable neighborhoods. Just moments from downtown, the Rail Trail, parks, schools, and restaurants, this thoughtfully designed 3-bedroom, 4-bath home offers three finished levels of stylish living. The open-concept main level features a designer kitchen with semi-custom cabinetry, granite countertops, pantry, home office, mudroom with pocket doors, coffered ceilings, shiplap accents, and fireplace. White oak flooring and staircases, beautifully tiled baths, and high-end finishes throughout. The finished lower level includes a bedroom, full bath, family room, oversized laundry, and storage. Enjoy a professionally landscaped yard with a bluestone patio, outdoor lighting, and detached insulated garage with storage-offering low-maintenance living and exceptional access to all Newburyport has to offer.

Listed by Coastal Life Realty Team and Joshua Frappier of Real Broker MA,LLC

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

31 Kappius Path Newton MA 02459

Newton, MA31 Kappius Path

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73561475

  • Residential
  • Next Open House: Sun 08/30 12:00 pm. to 1:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,806

This spectacular 5 bedroom, 3.5 bath Newer build (2015) Colonial home on a flat lot with fully fenced in yard! The home offers dramatic living & entertaining spaces perfecting both form and function. 9ft ceilings, high-end finishes, custom layered crown moldings and wainscoting, open floor plan, and a gourmet eat-in-kitchen featuring state-of-the art appliances including a 5 burner Bertazzoni range. The kitchen leads into a nicely appointed great room which includes a gas fireplace with granite surround and access to patio; lovely level backyard perfect for playing or entertaining groups of friends & family. The master suite has an oversized walk-in-closet, separate double closet and cathedral ceiling, 3 more generous sized bedrooms on the 2nd floor, all with great closet space! Fully finished lower level with 1 more room and additional full bath make for a great play room/ or Au Pair Suite! Bonus walk-up unfinished attic! Located on quite residential cul-de-sac in Oak Hill Park , convenient to shopping & schools!

Listed by Yoni Haiminis of Compass

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

349 Old Stockbridge Road Lenox MA 01240

Lenox, MA349 Old Stockbridge Road

Price$2,295,000The price has recently decreased

MLS Number 73567766

  • CommercialSale
  • Acreage 11.9
  • Zoning R1A

A rare opportunity to acquire an established 11.90± acre campus in Lenox, Massachusetts, with substantial institutional infrastructure and educational use permitted by right within the property's R1A residential zoning district.At its center is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The historic mansion has served as the academic and administrative center of Hillcrest Educational Center, with classrooms, offices, and gathering spaces throughout. Original details remain, including handsome woodwork, fireplaces, and a striking ballroom; the house also historically included bedrooms on its upper floors.The campus includes two dormitory buildings with approximately 24 bedrooms and shared common spaces, plus a separate multi-level academic/support building with commercial kitchen and dining facilities, classrooms, offices, library, conference, and medical/infirmary spaces. A substantial gymnasium offers potential for athletics, fitness, indoor tennis, pickleball, squash, wellness programming, or other recreational uses. Additional support buildings, parking, internal circulation, public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, and commercial sprinklering in select buildings support continued campus operation.The property is zoned R1A residential, with educational use permitted by right. Any alternative use, subdivision, or redevelopment is subject to Town of Lenox zoning and applicable approvals.Hillcrest currently operates on the property under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518283.Offered at $2,295,000.

Listed by Selina Lamb of Birch Properties

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

116 Thorndike Street Brookline MA 02446

Brookline, MA116 Thorndike Street, Unit 1A

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73524730

  • Condo
  • Next Open House: Sun 08/30 12:00 pm. to 1:30 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,663

A breathtaking, gut-renovated luxury condominium in the coveted heart of Coolidge Corner. This stunning, sun-drenched residence showcases an expansive open-concept layout, soaring ceilings, and exceptional architectural detail throughout. The sleek, state-of-the-art chef's kitchen features top-of-the-line appliances, custom cabinetry, and premium finishes-perfect for both everyday living and elegant entertaining. Four generously sized bedrooms and three and a half beautifully designed baths complete this sophisticated urban retreat, offering the ultimate blend of modern luxury, style, and comfort. There is a large patio off the kitchen for private entertaining. Also included are laundry hook ups in the unit and two outside spaces. Very close to public transportation and shopping.

Listed by The Kennedy Lynch Team, Karen Kennedy, Sandra Lynch and Jessica Shahda of Hammond Residential Real Estate

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

69 Horace Road Belmont MA 02478

Belmont, MA69 Horace Road

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73547136

  • Residential
  • Next Open House: Sun 08/30 12:30 pm. to 2:00 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,008

Get ready to fall in love with 69 Horace Road. The finishing details are complete on this spectacular full gut renovation and thoughtful expansion. This spectacular Colonial has been transformed into a modern masterpiece. Every aspect of the home is being reimagined with high-end finishes, state-of-the-art mechanicals and insulation, and a layout designed for today's lifestyle. The main level provides an open concept with a stunning kitchen featuring high-end appliances and ample counter space leading to the dining and living rooms designed for optimal entertainment areas. The second floor primary suite complete with balcony is breathtaking. The finished third floor with bedrooms and lower level playroom add flexible options. Professional landscaping includes a paver patio, sod and irrigation. From the expanded footprint that offers generous new living spaces to the top-tier craftsmanship evident in every detail, this isn't just a remodel-it's a total rebirth.

Listed by The Joyce Team, Bryan Joyce and Matthew Joyce of Compass

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 Cottage Street Provincetown MA 02657

Provincetown, MA24 Cottage Street

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73553223

  • Residential
  • Next Open House: Sat 08/29 10:30 am. to 12:00 pm.
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,422

Nestled on a quiet street in Provincetown's coveted West End, this single-family home blends classic Cape Cod charm with modern comfort. Offering approximately 1,422 square feet of thoughtfully designed living space, the home features two private ensuite bedrooms, each on its own level, plus a convenient half bath. The open-concept living, dining, and kitchen open seamlessly to a mahogany three-season screened porch overlooking the beautifully landscaped yard, creating an inviting space for relaxing or entertaining. Interior finishes include hardwood floors, custom millwork and built-ins, a fireplace, and quality stone and tile baths. Abundant closets and integrated storage enhance functionality. A fieldstone foundation, red cedar shingle roof, gardening shed, and custom built outdoor shower complete this turnkey West End home.

Listed by Brett Holmes of Berkshire Hathaway HomeServices Robert Paul Properties

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

38 Upwey Road Wellesley MA 02481

Wellesley, MA38 Upwey Road

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73546333

  • Residential
  • Next Open House: Sun 08/30 1:00 pm. to 2:30 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,776

Welcome to 38 Upwey Road, offering generous living space, a flexible floor plan and an unbeatable Wellesley location. Built in 1993, this 4-bedroom, 3.5 bath home offers three finished levels, an oversized 2-car garage and a bright, open-concept floor plan. Newly refreshed, the kitchen features brand-new countertops and appliances, while recent roof and system updates offer added peace of mind. A dedicated home office provides the perfect work-from-home space. The walk-out lower level adds tremendous versatility with a spacious recreation area, full bath and wine storage room. Enjoy a private backyard while being just moments from Linden Square, Wellesley's commuter rail, schools and major commuting routes. A wonderful opportunity to enjoy space, convenience and a prime Wellesley location.

Listed by Erica Lockberg of Berkshire Hathaway HomeServices Town and Country Real Estate

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

292 Cross Street Norwell MA 02061

Norwell, MA292 Cross Street, Unit D

Price$2,295,000The price has recently decreased

Est. Mortgage: $/month

Open House

MLS Number 73536349

  • Residential
  • Next Open House: Fri 08/28 10:00 am. to 1:00 pm.
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,186

Welcome to this stunning 5,186-square-foot board-and-batten modern farmhouse, thoughtfully designed to balance luxury, comfort, and functionality. Every detail has been carefully curated, blending timeless style with elevated finishes throughout. At the heart of the home is a beautifully designed chef's kitchen with a walk-in pantry-perfect for both everyday living and effortless entertaining-complemented by a custom-crafted wet bar. A private first-floor office offers an ideal work-from-home retreat, while generously sized bedrooms provide comfort and privacy. The finished lower level adds versatile space for guests, recreation, or extended living. With abundant storage and well-designed living areas throughout, this home offers the perfect blend of sophistication and practicality. This home is “to be built” with an expected delivery date of spring/summer 2027. For GPS purposes use 292 Cross St

Listed by Melissa McNamara Group of William Raveis R.E. & Home Services

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

70 Hedge Road Plymouth MA 02360

Plymouth, MA70 Hedge Road

Price$2,290,000The price has recently decreased

Est. Mortgage: $/month

Under Agreement

MLS Number 73298535

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,106

1.6 ACRES-340 FEET of direct waterfront in N. Plymouth, overlooking Bug Light, Duxbury Bay, and endless sunrises. Privately owned & custom-built sea wall, with private beach. Here is that diamond waiting to be restored or renovated to your own private waterfront dream house. In the same family for generations, this sprawling ranch has seen many years of family parties, including full size tent weddings on the expansive lawn. There are 3 bedrooms & 2.5 baths in the home, plus a large living room, sitting room and screened-in porch. Plenty of room for everyone! With central AC and a generator. A huge unfinished walk-up attic awaits your imagination to become a stunning primary suite or more living space with panoramic views. Modern foundation and full basement with full bathroom and garage provides a home for all the beach gear. Also on the property is a separate accessory studio which has a newer propane heater and would make an ideal guest house or rental. Once in a lifetime property!

Listed by Lauren Mello and Shepard Long of Advocate Realty Associates,Inc.

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.65% last updated on 2026-08-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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