Chestnut Hill Homes with Other (See Remarks) Style

Welcome to Chestnut Hill, Massachusetts—a picturesque community that perfectly blends suburban tranquility with urban convenience. Nestled just six miles west of downtown Boston, Chestnut Hill is renowned for its lush landscapes, charming streets, and vibrant cultural scene. This affluent neighborhood boasts a rich history, elegant architecture, and a strong sense of community, making it one of the most desirable places to live in the Greater Boston area.

As you explore Chestnut Hill, you’ll find a diverse array of homes, each reflecting a unique style and character. From stately colonial residences to modern masterpieces, the homes here cater to a variety of tastes. Notably, many properties feature the “Other” architectural style, showcasing creative designs that defy conventional classifications. These homes often blend elements of contemporary aesthetics with traditional charm, resulting in unique spaces that are as inviting as they are distinctive.

The community is also home to an array of amenities, including upscale shopping at The Chestnut Hill Mall, fine dining options, and access to beautiful parks and recreational areas. The nearby Boston College adds to the vibrant atmosphere, hosting cultural events and providing a youthful energy to the neighborhood.

In Chestnut Hill, you’re not just purchasing a home; you’re investing in a lifestyle. With its top-rated schools, friendly neighbors, and proximity to Boston’s rich cultural offerings, this enchanting community truly has it all. If you’re ready to discover your dream home in Chestnut Hill, let us guide you through the journey to find the perfect fit for your unique lifestyle.

Newest Chestnut Hill Homes with Other (See Remarks) Style

$8,999,000

6 Beds ⋅ 7 Baths ⋅ 73543132 MLS

Pre-Construction Opportunity – Limited 30-Day Offering. Situated on a 27,387 sq. ft. lot in one of Brookline's most coveted neighborhoods, this exceptional new construction estate will offer approximately 6746 sq. ft. of luxury living plus a Garage. Thoughtfully designed and crafted by a renowned luxury homebuilder with her decades of experience creating some of Greater Boston's most distinguished residences, the home features 6 en-suite bedrooms, including 5 on the second floor, soaring 11-foot ceilings on the main level and 10-foot ceilings upstairs, a private library, wine room, chef's kitchen with prep kitchen, and a luxurious primary suite with dual walk-in closets, a spa-inspired bath, and private roof deck. Additional highlights include heated 2+ car Garage, mudroom, and second-floor laundry. A rare opportunity to secure a premier Brookline residence and personalize select finishes during this limited 30-day pre-construction offering.

145 Woodland Road, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$3,390,000

5 Beds ⋅ 4 Baths ⋅ 73484859 MLS

Ideally situated on a private cul-de-sac in Chestnut Hill, this stunning architectural gem offers timeless elegance & modern luxury. Just minutes to the T, restaurants, coffee shops, & shopping, it boasts unobstructed park views from a Bluestone patio with a luxury outdoor kitchen and 8' gas fireplace perfect for entertaining. Inside, enjoy a sauna, home gym, wine cellar, billiards room, & a richly paneled library.First floor offers a radiant living room with fireplace and detailed moldings, a sunroom with three exposures, & a formal dining room with bay windows, original paneling, and wood-burning fireplace.The chef’s kitchen impresses with custom cabinetry and top-of-the-line appliances. Upstairs, the expansive primary suite features a gas fireplace, walk-in closet, and marble bath.Two additional large bedrooms, full bath, office, and laundry complete the second level.The third floor includes a media room, two bedrooms, and a playroom.Heated driveway & luxury systems throughout.

460 Heath Street, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$3,995,000

5 Beds ⋅ 6 Baths ⋅ 73484332 MLS

This elegant European-style country home is located in one of Old Chestnut Hill’s most desirable neighborhoods, ideal for modern family living and entertaining. The chef’s kitchen opens to a sun-filled family room and connects to both indoor and outdoor dining areas. The first floor also features a spacious living room and cozy library, both with fireplaces. Upstairs, the expansive primary suite includes dual walk-in closets and a luxurious bath with soaking tub and large shower. Four additional bedrooms and two baths complete the second floor. The third floor offers a bright new gym with skylights and a full bath with steam shower. The walk-out garden level includes a playroom, full bath, movie theater with Savant system, and dining area. Beautifully landscaped grounds feature two patios, a large play area, and a heated driveway. Steps to the T, the Chestnut Hill Reservoir, and the shops and restaurants at The Street.

85 Gate House Road, Newton

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$2,249,000

4 Beds ⋅ 5 Baths ⋅ 73482612 MLS

New construction townhouse-style condo with three levels & over 3,000 SqFt. Single-family space with condo convenience. Brookline schools. 8-inch white oak hardwood throughout. Natural light from every angle. Four bedrooms, each with a custom walk-in closet and en-suite full bath featuring built-in Bluetooth speakers. Quartz counters in kitchen & all bathrooms. Third floor includes dedicated laundry room with washer and dryer installed, plus bonus room ideal for home office, gym, or playroom. Open-concept main level with kitchen, living area, and half bath. Living room walks out to private deck and fenced garden perfect for upcoming spring & summer months. Common garage with automotive turntable and two assigned parking spots. Tiled mudroom entry with additional storage room. Steps from Chestnut Hill Square, The Street, and Chestnut Hill Mall. HOA covers snow removal, water, sewer, and master insurance. CO in hand, nothing left to do but move in.

811 Heath Street, Brookline

Listing courtesy of Listing Agent: Yasmeen Moukaddem from Listing Office: McCorry Real Estate, LLC.

$16,980,000

7 Beds ⋅ 11 Baths ⋅ 73445544 MLS

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

1014 Boylston Street, Brookline

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

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