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61 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$365,000
4 BD | 2 BA
Residential - Single Family

This well-loved home offers 4 bedrooms and 1.5 baths on a very large lot with beautiful open views. A classic enclosed front porch welcomes you inside, where old-world molding, window seats, hardwood floors, and handsome laminate flooring add warmth and character throughout.The spacious kitchen is fully applianced and features plenty of cabinetry, flowing into a separate breakfast/dining room with cathedral ceilings and a skylight that fills the space with natural light. The finished lower level provides bonus living space, while the walk-up unfinished attic offers excellent storage or potential for future expansion.


50 Photos
LAMACCHIA REALTY, INC
$374,900
6 BD | 3 BA
Multi-Family

Welcome to 91 Dalton Ave, a charming three-family home in the heart of Pittsfield, MA. This well-maintained property features three spacious apartments, each with two cozy bedrooms, perfect for families or professionals. Enjoy the convenience of a central location, with easy access to local shops, restaurants, and parks. Each unit offers comfortable living spaces, ample natural light, and individual utilities. The property is in close proximity to Berkshire Medical, General Dynamics and much more. Whether you're looking for an investment opportunity or a place to call home, 91 Dalton Ave is a must-see. Don't miss out on this fantastic opportunity in a vibrant community!


47 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$374,900
3 BD | 2 BA
Residential - Single Family

Inviting cape style home nestled between two of the Berkshires' most beautiful lakes- Pontoosuc and Onota set for outdoor water adventures and be surprised at home with an abundance of family spaces. Don't miss the oversized side yard a possible extra building lot (verification by buyer) for the accessory building, garage or second home. This home has three full levels of living offers opportunity, versatility and function for each and everyone in the clan. Be greeted by a beautiful etched glass front door, gleaming hardwood floors and spacious living room setting the stage to curl up in the evenings at the end of a busy day.


43 Photos
MOCKINGBIRD REAL ESTATE
$375,000
3 BD | 2 BA
Residential - Single Family

Charming Brick Cape with Classic Character & Comforts! Welcome to this 3-bedroom, 1.5-bath Cape offering 1,575 sp. ft. of comfortable living space. The living room features a cozy fireplace and wood floors. The eat-in kitchen offers ceramic tile flooring, all appliances and lovely cabinets for plenty of storage. Full bath and 2 bedrooms on the 1st floor, while second floor offers an additional 1/2 bath, 3rd bedroom & a spacious bonus room adding flexibility for an office or hobbies. The partially finished basement offers a family room, bar area, a convenient bonus shower, utility area and laundry/storage room. Outside, enjoy a partially fenced yard & outbuilding for extras. Gas heat & hot water provide efficiency and comfort. A warm, well-kept home with great space!


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WILLIAM PITT SOTHEBY'S - LENOX
$375,000
4 BD | 2 BA
Residential - Single Family

Spacious and adaptable, this Pittsfield home offers exceptional flexibility for today's lifestyle. The first floor features a sun-filled living room with hardwood floors and a bay window, a generous kitchen with an island and large dining area, and a mudroom with convenient first-floor laundry. A full bath and two bonus rooms on the main level provide versatile options for home offices, guest space, or additional bedrooms, allowing for the ease of one-level living if desired. Upstairs, a large landing creates the perfect spot for a home office or play area, while the primary bedroom boasts a walk-in closet and private exterior balcony. Three additional bedrooms and a full bath complete the second floor. Outside, enjoy a fenced-in backyard, one-car garage, solar panels, and


45 Photos
ASHMERE REALTY, INC.
$389,900
3 BD | 2 BA
Residential - Single Family

Step into this beautifully renovated home, where natural sunlight fills spacious, oversized rooms, creating a warm and inviting atmosphere. Every detail has been thoughtfully updated, showcasing a fresh, modern aesthetic with appliances. The expansive primary bedroom features two closets, with one large enough to serve as a nursery or home office, complete with two windows for abundant light. Perfectly positioned in a prime location--just minutes from Jiminy Peak Mountain Resort, tranquil lakes, and convenient shopping--this home seamlessly blends comfort, style, and accessibility.


41 Photos
MOCKINGBIRD REAL ESTATE
$392,000
3 BD | 2 BA
Residential - Single Family

JUST REDUCED.....Step into this bright and sunny newly renovated 3 bedroom 1 1/2 bath home. From the moment you walk in, you will notice the new kitchen, bathroom and fresh paint. There is a large finished basement ideal for family room, workout room, or playroom. Add 2 other rooms in the lower level complete with laundry and 1/2 bath. Walk onto the deck from the dining area and enjoy the privacy with a fenced in backyard.There is a large 2 car attached garage. All situated close to shopping, parks, walking trails and more


27 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$398,500
4 BD | 3 BA
Residential - Condo/Townhouse

Move-in ready and thoughtfully designed, this spacious 4-bedroom, 3-bath condo offers comfort, flexibility, and the ease of minimal-maintenance living. The inviting living room features a gas-burning fireplace, creating a warm and welcoming space to relax or entertain. The updated kitchen is equipped with granite countertops and ample cabinetry, opening seamlessly to the main living area. A first-floor bedroom with a full bathroom offers excellent versatility and can easily serve as a home office or den. The primary suite includes a walk-in closet and a private en-suite bath. Two additional generously sized bedrooms and a full bathroom complete the second floor. An attached garage and driveway provide ample parking in this quiet 12-unit cul-de-sac neighborhood.


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$399,999
4 BD | 2 BA
Residential - Single Family

Welcome to this beautifully maintained ranch offering the perfect blend of comfort, style and functionality. This move in ready home features 4 bedrooms , 2 full baths and a finished basement. Step inside to find wood floors, a warm and inviting layout with plenty of natural lightening. The kitchen opens to the dinning area. Outside enjoy a lovely front porch for morning coffee, in the backyard enjoy a private oasis with a deck and built in pool ideal for relaxing and hosting summer gatherings. The attached garage provides convince and extra storage, completing this picture perfect property. If you're looking for a well cared for home with great outdoor living this one checks all the boxes.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$425,000
2 BD | 2 BA
Residential - Condo/Townhouse

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail--from the textured walls to the light pouring in at all hours--creates a sense of romance and possibility.The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest.


72 Photos
NOCHER REALTY
$449,900
4 BD | 3 BA
Residential - Single Family

From the moment you turn the corner into this highly sought-after neighborhood, you'll feel a sense of belonging. The quiet streets lead you to a home that stands with a classic split-level silhouette--a design built for both privacy and togetherness. A bright welcome as you step through the front door, the first thing you'll notice is the radiance. The generous living room lives up to its name, acting as a sun-trap where massive windows invite the outdoors in. The freshly painted walls catch the morning light, creating a crisp, airy canvas that makes the entire home.... want more of the story ? Schedule a showing today!


45 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$450,000
4 BD | 3 BA
Residential - Single Family

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard. Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room. Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint (2025).


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COMPASS MASSACHUSETTS , LLC GB
$455,000
3 BD | 2 BA
Residential - Single Family

Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system brings energy efficiency and electricity credits. Front porch, back deck and two car garage with second story and an EV charger complete this in-town gem!


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WILLIAM PITT SOTHEBY'S - LENOX
$480,000
4 BD | 4 BA
Residential - Single Family

Mid-Century Classic with Timeless Appeal: Split-Level RanchStep back in time to the golden era of design with this beautifully preserved 1963 Split-Level Ranch. A true mid-century classic with a lot of character. It's ready for modern-day love and personal touches. This home perfectly blends the clean lines of the Ranch style with the functional, multi-level living of a split-level, offering distinct spaces for every activity. This 4-bedroom home has had multiple updates in the last 4-7years. Windows, roof, driveway & the kitchen with beautiful cabinets, counter tops & stainless appliances. Situated in a great, secluded neighborhood while remaining incredibly convenient--you're just minutes from town centers and all necessary shopping.


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MOCKINGBIRD REAL ESTATE
$525,900
6 BD | 3 BA
Residential - Single Family

Beautiful, spacious 6 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated kitchens with granite counters and stainless steel appliances. Ample room for the kids and pets to play in the fully fenced in backyard with playset. Enjoy relaxing in the hot tub on the lower level while have shelter from the upper deck! This gorgeous home has all you could need! Surveillance cameras are active outside in the front & back of home.


62 Photos
PAULA MCLEAN REALTORS INC.
$549,000
4 BD | 4 BA
Residential - Single Family

Welcome to 100 Northumberland Road - Storybook Berkshire Retreat where timeless charm meets exceptional space and possibility. Located in south east Pittsfield this home sits on .44 acres offering an inviting blend of elegance, comfort & room to grow. Inside, generous living spaces, sun filled rooms, rich architectural details and thoughtful updates create an environment perfect for both everyday living and unforgettable gatherings. 4 bedrooms, 4 bathrooms, expansive common area's featuring a grand living room with fireplace, formal dining room and quiet den this home offers endless flexibility. Host holidays with ease, celebrate milestones, or simply enjoy peaceful evenings. Each room feels like a backdrop for future traditions to be cherished.


45 Photos
PAULA MCLEAN REALTORS INC.
$575,000
3 BD | 2 BA
Residential - Condo/Townhouse

Welcome to South Pond Farm Condominiums, a serene waterfront community nestled on the shores of Richmond Pond. This beautifully maintained residence offers effortless living with the perfect blend of privacy, comfort, and natural beauty.Enjoy woodland views, an inviting interior, and access to exclusive community amenities -- including a private beach, tennis, pool, and walking trails. Whether you're seeking a peaceful year-round home or a Berkshire getaway, South Pond Farm is your invitation to relax, unwind, and live surrounded by nature's finest.Experience lakeside living at its best -- just minutes from Tanglewood, Lenox, and the cultural heart of the Berkshires.


56 Photos
STONE HOUSE PROPERTIES, LLC
$590,000
4 BD | 3 BA
Residential - Single Family

Set on 3 private, beautifully landscaped acres in the heart of Richmond, Massachusetts, 1772 Swamp Road offers a wonderful blend of space, comfort, and opportunity. This 4-bedroom, 2.5-bath home features a flexible floor plan, solid construction, and recent improvements including newly exposed hardwood floors and a thoughtful interior refresh that enhances the home's warmth and character.Additional updates in all the right places include a newer furnace, metal roof, and whole-house generator, providing peace of mind while allowing room to personalize. Inside, the bright and spacious layout offers multiple living areas ideal for everyday living, entertaining, or working from home. The large living room features a propane insert, while a second wood-burning fireplace in the


90 Photos
STONE HOUSE PROPERTIES, LLC
$670,000
4 BD | 4 BA
Residential - Single Family

Sprawling and estate-like, this expansive home is set on 2.4 private acres with a full acre of manicured grounds. Designed to appear as a ranch from the road, the home offers highly desirable one-level living with a renovated second floor for added flexibility.The dramatic living room features a striking Goshen stone fireplace wall and opens to a sunken conversation pit--an architectural showpiece ideal for entertaining. Two additional fireplaces warm the dining room and finished lower level, while a bright three season sunroom connects seamlessly to nature.Two generously sized first-floor primary bedrooms are connected by a spacious spa-like bath with radiant heated floors, large walk-in shower, and jet tub. This flexible layout


53 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$670,000
4 BD | 3 BA
Residential - Single Family

Beautifully updated 4-bedroom, 2.5-bath colonial located on a quiet dead-end street with easy access to both Lenox and Pittsfield. This home offers a perfect blend of classic design and modern comfort. The kitchen features an expansive island with granite counter tops and stainless-steel appliances which flows seamlessly into the informal dining room, family room, and sunroom--ideal for everyday living and entertaining alike. Formal living and dining spaces are filled with natural light from oversized windows. Upstairs, the spacious primary suite is highlighted by a stunning designer bath with radiant heat and a walk-in shower. Three additional generously sized bedrooms share a beautifully finished full bath.

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