Montgomery Real Estate

Welcome to Montgomery, Massachusetts – a hidden gem nestled in the heart of Hampden County! This charming town offers a unique blend of rural tranquility and community spirit, making it an ideal place for those seeking a serene lifestyle without sacrificing convenience.

Montgomery is characterized by its picturesque landscapes, featuring rolling hills, pristine forests, and sparkling streams that create a peaceful backdrop for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking leisurely strolls, the natural beauty of this area provides endless opportunities for exploration and relaxation.

The town’s rich history adds a unique charm to its character. Founded in the early 19th century, Montgomery has retained its small-town feel while embracing modern amenities. Residents here take pride in their community, and local events often bring neighbors together, fostering a strong sense of belonging.

Montgomery is conveniently located, offering easy access to major highways, making commutes to nearby cities like Springfield and Westfield a breeze. Local schools are highly regarded, and families will appreciate the safe, nurturing environment that Montgomery provides for children to grow and thrive.

With its blend of natural beauty, community warmth, and convenient location, Montgomery, MA, is more than just a place to live; it’s a place to call home. Whether you’re looking to settle down or invest in a piece of this charming town, Montgomery welcomes you with open arms and endless possibilities. Come discover the quiet charm of Montgomery – your perfect slice of New England awaits!

Newest Listings in Montgomery

$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.

$329,900

73456293 MLS

Discover the perfect setting for your future home on this 8.26-acre single-family–zoned lot just 10 minutes from downtown Huntington and 20 minutes from Tekoa Country Club. This sloping, wooded parcel offers privacy, and natural beauty. Located on a public, paved street with electric nearby, the property combines convenience with a peaceful, rural feel. Ideal for those seeking space, nature, and quick access to area amenities. Perc results on file at the Montgomery Health Department (done in 2002). Don’t miss this opportunity to create your own retreat in a prime location!

Lot 9 Jourdan Road, Montgomery

Listing courtesy of Listing Agent: Nikolay Yusenko from Listing Office: Class Realty, Inc..

$319,900

73456292 MLS

Discover the perfect setting for your future home on this 5.14-acre single-family–zoned lot just 10 minutes from downtown Huntington and 20 minutes from Tekoa Country Club. This sloping, wooded parcel offers privacy, and natural beauty. Located on a public, paved street with electric nearby, the property combines convenience with a peaceful, rural feel. Ideal for those seeking space, nature, and quick access to area amenities. Perc results on file at the Montgomery Health Department (done in 2002). Don’t miss this opportunity to create your own retreat in a prime location!

Lot 2 Jourdan Road, Montgomery

Listing courtesy of Listing Agent: Nikolay Yusenko from Listing Office: Class Realty, Inc..

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Montgomery Real Estate

Newest Listings in Montgomery

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