177 properties for sale in Risingdale

Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, containing that classic period charm. Step inside to discover a welcoming floor plan with ample natural light, hardwood floors, and period details. The kitchen and living areas are perfect for entertaining or relaxing with family. Upstairs, the bedrooms offer privacy and comfort, with plenty of storage throughout. Warm and efficient forced hot water heating. The back apartment has potential to turn the attic into living space: think office, den, TV room, or mediation space. Your ideas await! Enjoy the peaceful backyard, ideal for gardening, BBQ, play, or quiet evenings under the stars. Whether you're looking to settle into the vibrant Great Barrington community or invest in a high-demand rental market, 41 Pearl Street is a r

Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property, also zoned commercially, has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a nice flat side yard, and views of the Housatonic river winding below. Clean and classic, all you have to do is move in and start making it your own!

Truly, a one of a kind, stunning property both inside and out with scenic views of the sprawling land down to Long Pond. This thoughtfully crafted and designed home was curated to incorporate the natural serene outdoors into gracious open common spaces allowing warm natural light and comfortable flow. The first floor boasts the great room with wood burning fireplace open to the chefs kitchen with a large pantry and dining with built ins, unique sunroom with walls of glass and screened porch that extends the indoor outdoor living space while overlooking the pergola, play house and down to the water. The first floor primary en suite and office/den sitting area offer privacy in its own separate wing. The second level has ample guest space with three bedrooms, two en suite full baths and guest laundry. Completing the home on the lower level walkout is the guest suite with family room, private kitchen, two more additional bedrooms, office, full bath and patio. All of this set way back from

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence and generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette and massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard and patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours and has received a Garden Club of America award for its ethos and thoughtful use of b

THIS HOME HAS BEEN UNDER CONSTRICTION SINCE 2018. PRICE DOES NOT REFLECT CURRENT MARKET CONDITIONS. PRICES ARE NOT AT THIS PRICE POINT ANY LONGER. Open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. HOA covers all lawn maintenance, plowing, shoveling up to the front door. Quality New Construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000

MOTIVATED SELLER*Nestled in the heart of Great Barrington, this spacious 4 bedroom, 4 bathroom residence offers the perfect blend of family-friendly comfort and private sophistication. The home greets you with gleaming wood floors and a stunning fieldstone fireplace that anchors the living spaces in warmth and character. Cook like a chef in the large open kitchen, where generous countertops, a welcoming island, and ample natural light inspire everyday gatherings. The first-floor primary suite provides convenience without sacrificing privacy, ideal for busy households seeking single-level living when desired. Step outside to your expansive outdoors: a grand deck that overlooks lush acreage, plus a screened-in porch and an oversized porch ideal for morning coffees, evening entertaining, and quiet moments surrounded by nature. This property delivers both space for growing families and the seclusion you crave, all within the desirable Great Barrington lifestyle-top schools, outdoor adventu

Beautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bright, sunny, and truly move-in ready, this inviting home offers a combination of classic charm and comfortable modern living. The first floor features a welcoming mudroom, updated kitchen, heated sunroom, dining room, living room, family room, laundry, and full bath, providing plenty of space for both everyday living and entertaining. Upstairs are three comfortable bedrooms and a second full bath. Outside, enjoy a lovely yard and charming covered porch-perfect for relaxing and enjoying the neighborhood. Ideally located with easy access to Great Barrington's vibrant town center, library, restaurants, shops, and churches. A warm and beautifully cared-for home in a wonderful convenient location

This meticulously maintained 1900 farmhouse seamlessly blends timeless historic character with refined modern updates, creating a move-in ready retreat just minutes from the vibrant energy of downtown Great Barrington. Every corner of this classic three-bedroom, two-bathroom home reflects thoughtful care and craftsmanship, offering an ideal balance of warmth, functionality, and quintessential Berkshire charm. At the heart of the residence is a stunning cook's kitchen, thoughtfully renovated and fully outfitted with updated appliances, expansive counter space, and storage. Sunlit living spaces flow naturally throughout the main floor, showcased by rich, beautifully preserved wood floors that anchor the home in timeless elegance. Architectural charm continues outdoors with a classic front porch and a private back porch that adds seamless transitional space between the interior and the grounds. Outside, the property transforms into a true personal oasis, featuring thoughtfully designed pa

Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless indoor-outdoor experience. The first-floor primary suite features a luxurious bath and tranquil views. An exceptional cinema room includes theater-style reclining seats and a half bath. Generous guest accommodations throughout. A private office suite with full bath. Outdoors, enjoy an infinity pool, bluestone patios, lush gardens, a charming pool house - all just three miles from downtown Great Barrington

'Located in Great Barrington's coveted residential neighborhood surrounded by million-dollar-plus estates, this home offers an unbeatable entry point into luxury Berkshire living. Designed with distinct living zones, the two-level layout provides the ultimate setup for weekend guests, remote working, family room or great potential for multi-generational living. The main living level features bright, flowing living space framed by natural views, perfect for effortless entertaining after a day in town or on the trails. Enjoy beautiful mature landscaping, outdoor living spaces and prime proximity to downtown Great Barrington at an accessible price point

PUBLIC OPEN HOUSE: Saturday October 10 from 10-1. See you there! Enjoy the relaxing Berkshire lifestyle on a friendly cul-de-sac within walking distance of town and Lake Mansfield. As the first house built on the street, the property has matured beautifully - seasonal flowering trees and pollinator-friendly gardens bring color and life to the yard from spring through fall. Cedar columns frame a distinctive front door that opens into 3,800 square feet of tastefully designed living space, where soaring ceilings, a linear gas fireplace, and built-in bookcases set the tone. The living room flows out to a screened-in porch with a treehouse-like view of the wooded backyard - the perfect spot for morning coffee or summer evenings. area and living room for easy entertaining. Also on the main floor: a primary suite with walk-in closet and spacious bath, two additional bedrooms (one with floor-to-ceiling built-in bookshelves), a full bath, a half bath, and dedicated mud and laundry rooms. Though

STILL HOUSE brings a new level of contemporary design to the Berkshires-quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me and General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home.Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living level opens into a dramatic kitchen, dining and living space with cathedral ceilings, two stories of glass and views into the surrounding landscape. The custom Porcelanosa kitchen features richly veined stone, a substantial island, induction cooking, double ovens, integrated refrigeration, microwave drawer, dedica

Built in 2021, this custom contemporary offers about 5,670 sq ft of finished living space on 2+ acres, just 5 minutes to Great Barrington center, with mountain views and sunsets to the west. The open first floor features vaulted ceilings, a propane fireplace and a chef's kitchen with a large island, coffee bar and generous storage, opening to the dining and living areas. A large screened porch extends the living space three seasons a year. A mudroom with laundry off the oversized 3-car garage, two offices and a powder room complete the main level. Upstairs, two guest rooms with en suite baths and a primary suite with fireplace and a large bath. The finished lower level adds about 1,900 sq ft: game room, gym, media room, guest bedroom and full bath. Central air, high-speed fiber available, and truly turnkey, with sunset views over the neighboring private airport

$100,000 PRICE IMPROVEMENT! Set on nearly 3 private acres in sought-after ALFORD, this 4-bedroom home blends privacy, comfort and Berkshire charm. Built by Howard Chezar with passive-solar design, the home features open living spaces, beautiful wood details and a flexible finished third-floor bonus room. Enjoy the spacious deck, in-ground pool and peaceful setting. An 8-year-young roof, low Alford taxes and a location just minutes from Great Barrington, hiking, skiing, dining and Berkshire attractions complete the package!

Nestled within a mixed use residential/commercial block this renovated space is ready for the next creative commercial endeavor. Rent the house and use the studio for art, office, store or Live and work all within walking distance to town center. Thoughtfully brought from a commercial office space to a 2 bedroom, 1.5 bath, bright open and airy living space with 5 parking spots and a nice size yard

Move right into this beautifully renovated mid-century Cape, where modern updates blend seamlessly with timeless charm. Designed for easy single-floor living, this bright and airy home features an open-concept kitchen, dining, and living area that creates an inviting space for both everyday living and entertaining. The living room is highlighted by a soaring cathedral ceiling and abundant natural light, enhancing the home's spacious feel.The thoughtfully designed layout includes a private primary suite with an en suite bath,offering comfort and convenience. French doors open from the living room to a rear deck overlooking a fire pit area, creating the perfect setting for outdoor gatherings, relaxing evenings, and enjoying the surrounding landscape.Ideally located just minutes from downtown Great Barrington, Ski Butternut, and the public boat launch at Lake Buel, this move-in-ready home provides easy access to the best of the Berkshires, from outdoor recreation to dining, shopping, and

Living history awaits your vision! Own a piece of history dating back to the 1700's -one of the oldest homes in Lee. A captivating antique home that began its story over two centuries ago, with a significant brick addition in the 1800's. The results are layers of character rarely found today. Living and dining rooms with fireplaces, Four bedrooms and two baths offer solid bones for a savvy renovator, and the bonus walk-in attic is a hidden gem - vaulted ceiling, back staircase ready to add creative space. This is a true marathon investment for someone who sees beyond the to-do list to the incredible potential underneath. Storied charm, endless possibility, bring your vision and make history your own. Two car garage, set on almost an acre of open sunny land on a quiet country road

Experience upscale, maintenance-free living in desirable Devon Meadows, where the beauty and tranquility of the Berkshires meet exceptional comfort and convenience. Ideally located near Lenox and Stockbridge and just 5 minutes from Tanglewood, this impressive luxury condominium places you close to the heart of the region's renowned cultural, dining, shopping, and outdoor attractions while offering the peaceful surroundings of a country setting. Designed with both everyday living and entertaining in mind, the home features a spacious, open floor plan with an easy flow between living areas. The first floor provides the convenience of one-level living with a generous primary bedroom suite and first-floor laundry. A versatile fifth bedroom on this level offers flexibility and could easily serve as a private home office, den, library, or comfortable guest room. The second floor provides additional space for family and guests with three generously sized bedrooms and two full baths. A spaciou

Immaculate and well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded acres. Designed for easy living and low maintenance, this home offers an open floor plan with high ceilings, wood floors, and a beautiful fieldstone fireplace anchoring the main living space. The kitchen opens to another living area creating a comfortable flow for everyday living and entertaining. Enjoy the lovely screened porch and outdoor deck overlooking the natural setting. Three bedrooms and 3.5 baths, including guest quarters or apartment space for added flexibility. Large two-car garage. It is in a very private setting, but is also a short distance (walking distance) to the elementary and secondary schools. Easy transition for a first floor primary bedroom

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. MORE The main level of the home includes a generous living room, a formal dining room featuring a custom four-wall mural by noted (formerly local) artist Laurel Tewes, a cozy library or den, a well-appointed kitchen with three refrigeration units including a side-by-si

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths. A large screen porch and patio takes in the lovely landscape. A three-car garage completes this magnificent property located in centrally located Stockbridge. Central to all Berkshire County and cultural venues!

Special opportunity to take over the 5BR owners' unit as part of this 4-unit compound and let the other 3 pay your mortgage. Relaxing property in the center of Housatonic village with two charming, recently renovated duplex homes - each with historic details left intact. The front house has a flex 4/5BR 2200 sq. foot owners' unit which feels like its own house. Split on 2 floors, it has 2 full baths, privacy, its own screened-in porch and outdoor BBQ area. Currently operating as a high-end furnished rental. Use it as your FT residence, weekend home or mid-term rental (i.e. traveling nurses), turn-key and ready to go. The remaining 3 x 2BR units are filled with wonderful tenants; each home has their own W/D, outdoor space and there is an expansive shared yard- -in back with fruit trees and a community garden. Property includes plenty of parking for all and entrepreneurs take note: it is zoned mixed-use so the street-facing rooms, currently separate and used as storage, can be turned int

Mixed-use property in vibrant Housatonic village center. Three flexible units: two residential apartments above commercial space. Prime location within walking distance to local shops, art galleries, restaurants, town library, and neighborhood park with playground. Stunning views of the iconic Housatonic water tower and historic mill town industrial architecture. Property features mature gardens, private walled patio area, three dedicated parking spaces, plus rear garage requiring renovation work. Perfect investment opportunity for entrepreneurs seeking rental income or business owners wanting live-work space. The building offers excellent potential in this growing creative community hub with strong local character and charm. A must see!

Some Berkshire homes are simply places to live. Others become part of the way you want to live. The Oronoque Villas are among those rare places. Built in the mid-1990s on the historic grounds of Oronoque-one of Stockbridge's great Berkshire cottages-just eight freestanding villas were thoughtfully sited within the estate landscape, complementing the original mansion, now home to distinctive condominium residences. Surrounded by mature trees, sweeping lawns, and established gardens, this villa offers the warmth and privacy of a house, the simplicity of one-level living, and the freedom to lock the door and leave whenever adventure calls. Whether as a year-round home or a favorite Berkshire retreat, life here has a wonderful way of slowing you down. Originally selected as the model residence for the Oronoque Villas, this three-bedroom, two-bath home offers 1,773 square feet of thoughtfully planned, beautifully proportioned living space. A gracious covered porch welcomes you inside, where

Some Berkshire homes are simply places to live. Others become part of the way you want to live. The Oronoque Villas are among those rare places. Built in the mid-1990s on the historic grounds of Oronoque-one of Stockbridge's great Berkshire cottages-just eight freestanding villas were thoughtfully sited within the estate landscape, complementing the original mansion, now home to distinctive condominium residences. Surrounded by mature trees, sweeping lawns, and established gardens, this villa offers the warmth and privacy of a house, the simplicity of one-level living, and the freedom to lock the door and leave whenever adventure calls. Whether as a year-round home or a favorite Berkshire retreat, life here has a wonderful way of slowing you down. Originally selected as the model residence for the Oronoque Villas, this three-bedroom, two-bath home offers 1,773 square feet of thoughtfully planned, beautifully proportioned living space. A gracious covered porch welcomes you inside, where

Discover a unique condo in a converted mill building where historic factory character meets modern style in the heart of Housatonic. Soaring ceilings and beautiful wood floors throughout complement two generously sized bedrooms, one full bathroom, a large living room with views of Flag rock and a spacious dining room. An enclosed porch offers a cozy spot to unwind while a community deck provides space to relax and gather. Enjoy local restaurants and numerous hiking trails just moments away. Come see what makes this distinctive condo such a special place to call home

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

Moments from Lake Mansfield and Main Street, this turnkey contemporary offers clean lines, natural light, and effortless Berkshire living. The main level features an open-concept floor plan anchored by a show-stopping Duvemala tiled stove, serving as a striking centerpiece for gatherings and cozy evenings by the fire. Enjoy the convenience of a first-floor bedroom alongside one of the home's three well-appointed full baths. Upstairs, an expansive primary suite impresses with vast cathedral ceilings. The finished lower level adds a versatile bonus room, providing extra square footage for a home gym or game room. Outside, relax and entertain on the sun-soaked deck overlooking the oversized grounds of this rare double-sized parcel

Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful sub-dividable acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck-perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington