Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move-in-ready appeal is what you'll find at this Heron Pond condo! Well-maintained, 1 br/1ba unit filled with natural light includes living room, separate dining room, updated bath and galley kitchen. Outside, relax on your own stone patio. Enjoy peaceful surroundings, the pond, and beautifully kept grounds. Perfect for full-time living, weekend retreat, or investment property. Low-maintenance living gives plenty of time to enjoy the benefit of being minutes from Stockbridge, Berkshire Theater Festival, Tanglewood and other area attractions. Quick access to hiking, nature trails, and recreation on Stockbridge Bowl. Whether you're looking for a cozy escape or turn-key purchase don't miss this one!

Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra acreage, an additional dwelling/guest house or to sell off in the future. Driveway to two sites. Excellent perc results and soil analyses from 2005 and engineered plans available. Great opportunity in Stockbridge.

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.

Bring your contractors and your imagination to this unique fixer-upper, an old carriage barn with an attached apartment. The spacious barn features original beams with large open areas. The lush grounds are complemented by charming rock walls and rustic outbuildings. With a convenient location close to all the Berkshire attractions, this property is ideal for transformation into a one-of-a-kind retreat!!

Log Cabin in Stockbridge! Tucked away at the end of a country road, this charming log home offers warmth, privacy, and convenience - and it's close to Tanglewood. Beautifully maintained inside and out, it sits on two wooded acres with a welcoming front porch. Inside you will find a cozy retreat - a living room with cathedral ceilings, pine floors, and a working fireplace. The updated kitchen features stainless Whirlpool appliances and generous cabinet space. Loft-style bedroom with wide pine floors, updated bath with tub and shower. Spiral staircase leads to a lower level with slate floors, office or hobby room, laundry with GE washer/dryer, and walkout to the backyard. Move right in and enjoy your own Berkshire hideaway

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The setting is exceptional, stroll just minutes to the Red Lion Inn, cafes, shops, and the library; at the end of the street, pick up beloved local trails toward Laura's Tower for quick nature escapes. A manageable 6,970 sq ft lot keeps weekends free for play, gardening, or launching out to the Berkshires' cultural highlights: Tanglewood, Norman Rockwell Museum, Naumkeag, and more.

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect you to the landscape. Your backyard is a protected nature preserve, guaranteeing permanent privacy. The property features a handsome 24x30 horse barn with 2+ acres of paddocks, plus a separate lower-level guest apartment--perfect for weekend visitors or a private home office. A complete package blending modern convenience with pastoral beauty and cultural access.

Welcome to this stunning one level living, 3 bedroom, 3 bathroom home on a serene 4 acre lot. Designed for comfort and style, it features a bright first floor living area with large picture windows and a charming fireplace. The spacious kitchen offers a skylight, breakfast nook, and access to a screened porch perfect for relaxing. Cherry Floors flow throughout (except the kitchen and baths), and the large dining room is ideal for entertaining. Enjoy a generous deck, two car garage, brand new Buderus Boiler, and new air conditioning system.This Berkshire escape could be yours to enjoy and is minutes from Tanglewood, Norman Rockwell, Chesterwood, Berkshire Theatre, and minutes to the charming towns of Stockbridge, Great Barrington, Lee, Lenox, West Stockbridge!

MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry closet. The second level features the primary bedroom with en suite full bath, walk in closet and bonus loft space; Guest bedroom and en suite full bath. Association beach rights to the Stockbridge Bowl, tennis courts, indoor pool, gym and hiking paths. All of this while being conveniently located near Tangelwood, Lenox Village and many cultural attractions here in the Berkshires.

Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area. Additionally there is an attached first floor In-law apartment with living room, kitchen, bedroom and full bath. Included with the house is a multi level barn with electricity. Lovely setting to relax on the back deck and take in the views or stroll into town to enjoy the cultural amenities This gem has great potential and is ready for the new owners vision

Location is everything with this light-filled contemporary ranch on Prospect Hill. Ready for quick occupancy! Five minutes from downtown Stockbridge or to Tanglewood and so close to the town beach on Stockbridge Bowl. This three bedroom, two bath home has been lovingly cared for. Living room and dining with hardwood floors, built-in shelving and built-in storage. Quality updates in the primary bath. Almost two acres of land with garden shed, many perennials and raised vegetable garden beds. Bonus features: spacious attached two car garage, back-up generator, first floor laundry for truly one-level living. The three-season sunroom and outdoor deck add to the charm of this Stockbridge home that's priced to sell!

Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated, blending original character with contemporary upgrades. Post and beam construction adds warmth and architectural texture, while a sleek gas fireplace anchors the open living and dining areas. The updated kitchen is ideal for gatherings both casual and festive. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two additional bedrooms and a full bath complete the

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. This sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

RARE BERKSHIRE OPPORTUNITY: READY-TO-BUILD MODERN RETREAT ON A PRIVATE POND + DEEDED STOCKBRIDGE BOWL BEACH RIGHTSDiscover a truly extraordinary offering in the heart of the Berkshires--9.1 pristine acres with direct frontage on Lily Pond, a private, non-motorized body of water celebrated for its serenity, protected natural setting, and sweeping views. Occupying the entire southern end of the pond, this estate parcel enjoys a commanding, unobstructed panorama over the water, creating an intimate, one-of-a-kind backdrop for your future home.A long, gently winding driveway follows a picturesque babbling brook and sets the stage for a memorable arrival. A **brand-new bridge--now fully completed--**leads to the exceptionally private, pond-front building site.

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal, boxwood garden, all of which have been meticulously maintained. There are two stone patios which look out over four acres of pasture to the west. This home is fueled by gas heat and is serviced by town water and sewer. Perhaps the famous Reverend, Johnathan Edwards and Chief Kondapot of the Stockbridge-Munsee Indians met in the front parlor a time or two.

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Garages for 5+ cars, perfect pool site, and privacy ensured by abutting protected land.

Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with a deftly designed addition that respects the home's proportions while opening new possibilities for contemporary living. Set along the Stockbridge-Lenox corridor on 13+/- acres (including 9 conserved), the property is ready for a thoughtful, design-forward restoration that brings its next chapter to life.Originally built in the 1830s, the residence showcases beautiful proportions, abundant natural light, and the kind of craftsmanship impossible to replicate today. The interiors unfold across more than 5,000 sq ft, with high ceilings, generous rooms, and an

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 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!

Set on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access to dining & shopping. Inside, bright & inviting spaces include living room w/ cathedral ceiling, fireplace, & is filled w/ natural light. Primary suite with vaulted ceiling & balcony w/ stunning mountain views. Renovated kitchen opens to a cozy den & breakfast nook connecting seamlessly to the pantry, laundry & mudroom. Lower level with flexible bonus space for family room, gym, office or