Pittsfield, MA Homes for Sale with Pool

OPEN HOUSE CANCELLED! Experience the perfect blend of professional utility and luxurious comfort at 1 Almon Ave., a beautifully constructed and impeccably maintained retreat located in a BG-zoned area. This home offers an exceptional opportunity for those looking to operate a business or maintain a home-office setup without sacrificing lifestyle quality. The main residence provides four spacious

Stacy Chojnowski WILLIAM PITT SOTHEBY'S - LENOX

Move-in ready and filled with upgrades, this southeast Pittsfield colonial home offers five bedrooms and flexible living space. The first floor includes a bedroom and full bath, while the second floor features a primary ensuite plus three additional spacious bedrooms. Enjoy a beautifully landscaped, very private backyard with an above-ground pool and convenient access from the kitchen

Susan Calkins STONE HOUSE PROPERTIES, LLC

Brand new construction at Berkshire Country Meadows! Must see this 2000 square foot single-family condo is now ready for immediate occupancy. With the ease of one-level living, you'll enter into a great room with hardwood flooring, gas fireplace and bathed in natural light. Fully applianced kitchen with large work island. This unit features 3 bedrooms, 2 baths, central a/c, natural gas heat.

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

162 Woodlawn Ave is comprised of two (2) 2-Bedroom/1-Bathroom units, eleven (11) 1-Bedroom/1-Bathroom units, and five (5) Studio units with 8,653 square feet of gross living area in 11,653 square feet of gross area. The Property is situated upon a 0.47-acre parcel and offers twenty (20) off-street parking spaces. The Property is well-positioned within Pittsfield’s established Morningside

Michael Bradley Horvath & Tremblay

Gracefully situated on a gentle sloping hillside street this distinctively designed multi-level home offers distant and seasonal Berkshire mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home and grounds, you can embrace the vast privacy, open land and natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

Set along the shores of beautiful Pontoosuc Lake, this extraordinary private estate captures the very best of Berkshire waterfront living. Enjoy sweeping lake and mountain views, a private dock, heated pool, outdoor kitchen and fire pits designed for unforgettable entertaining. Inside, open-concept living showcases the views, while a chef's kitchen with Wolf and Sub-Zero appliances anchors the

Katie Soules WILLIAM RAVEIS - BERKSHIRE

Welcome to this charming, updated ranch tucked into a quiet neighborhood and conveniently located near shopping and restaurants. Enjoy the ease of single-level living with thoughtful updates throughout. Recent improvements include an updated bathroom, new driveway (2026), siding and Trex deck (2025), and furnace (2018), with the roof replaced in 2011. Move right in and enjoy a comfortable home

Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

This 3-bedroom, 2-bath ranch sits on a quiet street in one of Pittsfield's most desirable areas. The home has been meticulously maintained with an efficient layout and no wasted space. The kitchen was fully updated with quartz countertops. The basement has also been updated, adding real living space, not just storage. Both bedrooms have California Closet built-ins. Outside, a 32x16 inground pool

Seth Alden ALTON & WESTALL REAL ESTATE AGENCY, LLC

Welcome to this bright and inviting 3-bedroom, 1-bath ranch, ideally located just moments from beautiful Pontoosuc Lake on a spacious double lot. This home features a generous living room with oak hardwood floors, a formal dining room, and an updated kitchen with newer countertops. Additional highlights include a spacious basement with abundant storage, an oversized one-car garage, and an

Jose Larios Lamacchia Realty, Inc.

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready home offers the perfect combination of comfort, thoughtful updates, and low-maintenance living in a truly special lakefront setting.The open and airy living room features soaring vaulted ceilings, expansive windows that capture stunning lake views,

Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

Side-by-side two-family home renovated in the last few years! Improvements include roof, windows, flooring, painting, and more! The home offers an enclosed front porch to access both units, and a side porch for each apartment independently. Each unit features living room, dining room, kitchen, 2 bedrooms and 1 bath. The apartments have large enclosed back porches upstairs overlooking the yard.

Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

Move right into this stunning single-family home at highly desirable Berkshire Country Meadows. Nearly new and impeccably maintained, this spacious home offers the ease of condominium living with the feel of a private residence. The open-concept design features a beautiful kitchen, dining area, and living room with a cozy gas fireplace, perfect for entertaining or everyday living, and a separate

Victoria Standring Lamacchia Realty, Inc. - Dalton

A Landmark Berkshire Estate of Extraordinary Provenance. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The

Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

Cape-style 3-bedroom, 1-bath home in a coveted Southeast Pittsfield location directly across from Deming Park and close to coffee shops, restaurants, a pharmacy, convenience stores, and other Elm Street amenities. Features include newer windows, a newer roof, new carpeting upstairs, and a recently renovated bath. The interior offers an opportunity for additional cosmetic updates and

Marc Bellora Lamacchia Realty, Inc. - Dalton

Live, Love, & Play in Blythewood Estates priced favorable $250,000 less than assessed value for a quick sale to allow you enjoyment this beautiful Berkshire season. A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX