Montgomery Homes for Sale

Welcome to Montgomery, Massachusetts, a hidden gem nestled in the heart of Hampden County. This picturesque town boasts a rich history, charming landscapes, and a close-knit community, making it an ideal place for anyone looking to settle down. With its serene rural atmosphere, Montgomery offers a peaceful retreat from the hustle and bustle of city life, yet is conveniently located just a short drive from larger urban centers.

Montgomery is characterized by its rolling hills, lush forests, and scenic views that change beautifully with the seasons. Outdoor enthusiasts will appreciate the abundance of recreational opportunities, from hiking and biking trails to fishing and camping spots. The town’s commitment to preserving its natural beauty is evident in its well-maintained parks and open spaces, perfect for family outings or quiet contemplation.

For those considering a move to this enchanting town, there are a variety of homes for sale that cater to diverse tastes and lifestyles. Whether you’re seeking a charming historic home, a modern family abode, or a cozy cottage, Montgomery has something to offer. The real estate market here features spacious lots, providing ample room for gardens and outdoor activities, while many properties showcase stunning views of the surrounding countryside.

Living in Montgomery means embracing a lifestyle rich in community spirit, with local events and gatherings that foster connections among residents. With excellent schools, friendly neighbors, and a welcoming atmosphere, it’s no wonder that so many are drawn to call Montgomery home. Explore our listings today and discover the perfect place to create lasting memories in this idyllic town!

Newest Montgomery Homes for Sale

$999,900

3 Beds ⋅ 4 Baths ⋅ 73586045 MLS

Looking for resort-style living without leaving home? This is not your average Cape Cod! Set on +- 2.5 acres, this exceptional home offers +- 3,171 sq. ft. of living space, a 3-car garage, & an incredible heated inground pool creating a private backyard retreat. The main level features a beautifully updated kitchen with granite countertops, center island, & new stainless-steel appliances, plus a convenient laundry/pantry & half bath. The inviting living room showcases hardwood floors and a beautiful stone propane fireplace, while the sun-filled family room with lots of windows offers tray ceilings and recessed lighting. A dedicated office & 3 bedrooms, including a spacious primary suite with walk-in closet & private bath featuring a jetted tub, provide plenty of room for comfortable living. A tiled sunroom with electric fireplace overlooks the spectacular pool area & offers the perfect space to relax and entertain. The third floor offers tremendous potential for additional living space and already includes a half bath and bar. Whole house generator (APO) & on demand hot water are just a few extras here. Exceptional indoor and outdoor space, expansive grounds, and fabulous amenities rarely found in one property, make this home exceed expectations. Make your appointment today and expect to be impressed!

1527 Southampton Road, Montgomery

Listing courtesy of Listing Agent: The Ayre-DeFilipi Team from Listing Office: Ayre Real Estate Co, Inc..

$1,100,000

5 Beds ⋅ 5 Baths ⋅ 73572102 MLS

Where privacy meets breathtaking mountain views, this custom-built residence delivers dramatic architecture, expansive living spaces and an exceptional connection to its surroundings. Soaring ceilings, exposed wood beams, walls of windows and rich hardwood floors set the tone, while a floor-to-ceiling stone fireplace creates a commanding focal point in the great room. The kitchen makes a statement with extensive wood cabinetry, granite countertops, an expansive peninsula with generous seating and structural beams adding depth and distinction. Just beyond, a custom built-in beverage center features additional cabinetry, display shelving, granite counters, dual refrigerators and a tiled backsplash. The open design flows into the dining area, framed by natural light and scenic views. The first-floor primary suite features a private bath with a vaulted ceiling, Jacuzzi tub and separate glass-enclosed shower. A dedicated office and laundry room complete the main level. Upstairs, an airy loft provides a striking vantage point overlooking the soaring great room, stone fireplace and dramatic wall of windows below. Three additional bedrooms and a full bath complete this level. The finished lower level is designed for elevated entertaining, featuring a spacious game and lounge area, custom bar with stone detailing, beverage refrigeration and distinctive barn doors opening to a dedicated movie theater. An additional bedroom and full bath create an impressive destination for overnight guests and relaxed evenings at home. An attached in-law suite offers its own kitchen, living room, bedroom, bath and office, providing beautifully defined accommodations with direct access to the main residence. A newer roof, wraparound deck, exterior hot tub and outdoor spaces complement the setting, with amazing views and endless hiking trails nearby. With natural stone, dramatic architecture, beautifully proportioned interiors and extraordinary scenery, this mountain residence offers an exceptional combination of privacy, sophistication and connection to its surroundings.

89 Pomeroy Road, Montgomery

Listing courtesy of Listing Agent: Marisol Franco from Listing Office: Coldwell Banker Realty - Western MA.

$499,000

4 Beds ⋅ 3 Baths ⋅ 73526878 MLS

Private wooded setting. Flexible living space. Nature at your doorstep. This distinctive custom-built contemporary offers a rare opportunity to enjoy the peace and privacy of a wooded retreat while remaining conveniently close to shopping, medical care, and major highways.Set on a private lot surrounded by trees and abutting hundreds of acres of trails and protected wildlife area, this spacious home invites you to slow down and enjoy its natural surroundings. Inside, soaring vaulted ceilings, exposed beams, and hardwood floors create an open, welcoming atmosphere, while the dramatic fieldstone fireplace brings warmth and character to the main living area.The first-floor primary suite features a walk-in closet and full bath, while two additional bedrooms share a second full bath. First-floor laundry and a convenient two-car garage make everyday living easy.Upstairs, the light-filled great room—with skylights, vaulted ceilings, and its own full bath—offers endless possibilities. Use it as a fourth bedroom, home office, studio, or keep it as the ultimate game and gathering space, complete with the slate pool table currently in place.And when it’s time to get outside, adventure is close by. Kayak on Littleville Lake, cool off in the river at Gardner State Park in Huntington, or explore Hampden Ponds State Park. Whether you’re looking for a peaceful escape, a home with room to spread out, or a property that offers both privacy and convenience, this one-of-a-kind contemporary is ready to welcome you home.

79 Pine Ridge Rd, Montgomery

Listing courtesy of Listing Agent: Paige Laliberte from Listing Office: StartPoint Realty.

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Montgomery Homes for Sale

Newest Montgomery Homes for Sale

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