Chestnut Hill Homes with Contemporary Style

Welcome to Chestnut Hill, Massachusetts—a picturesque community that seamlessly blends suburban charm with urban convenience. Nestled just six miles from downtown Boston, Chestnut Hill offers an idyllic retreat where lush landscapes meet vibrant city life. Known for its historic architecture and tree-lined streets, this charming neighborhood is a haven for families, young professionals, and retirees alike.

One of the standout features of Chestnut Hill is its rich diversity of homes, particularly those boasting contemporary style. These modern residences are designed with sleek lines, open floor plans, and abundant natural light, catering to today's discerning buyers. Contemporary homes in Chestnut Hill often feature cutting-edge amenities, eco-friendly designs, and innovative layouts that promote a seamless indoor-outdoor living experience. Imagine hosting gatherings in spacious living areas that flow effortlessly into beautifully landscaped backyards—perfect for entertaining or simply enjoying a quiet evening under the stars.

Beyond the stunning homes, Chestnut Hill is also home to a variety of upscale shopping, dining, and recreational options. The nearby Chestnut Hill Mall and The Street offer an array of boutique shops and gourmet restaurants, ensuring you’ll never run out of exciting places to explore. Additionally, the area boasts excellent schools and parks, making it an ideal location for families seeking a nurturing environment.

Whether you’re drawn to the contemporary architecture or the vibrant community spirit, Chestnut Hill is a place where you can truly feel at home. Discover your dream contemporary residence in this charming neighborhood and embrace the lifestyle you’ve always envisioned!

Newest Chestnut Hill Homes with Contemporary Style

$2,399,000

4 Beds ⋅ 3 Baths ⋅ 73547641 MLS

Prepare to be impressed by this beautifully renovated 4 Bed 3 Bath mid-century modern ranch in Chestnut Hill Brookline on the edge of the golf course! Set on over a half acre of beautiful landscaping surrounding the flat back yard lead to the golf course. Breathtaking renovations highlight modern living with soaring exposed beam ceilings, a dramatic living room with a wood-burning fireplace, and a wall of windows overlooking the screened porch, deck, and tranquil Japanese rock garden. The renovated kitchen features sleek cabinetry, updated countertops, appliances, a peninsula, pantry, and eat-in area. The main level offers three spacious bedrooms, including a large primary suite, while the finished walkout lower level includes a great room with kitchenette, fourth bedroom, full bath, studio, bonus room, patio access, and abundant storage. Perfect location with quick access to 9 & I-93 and a quick hop to local restaurants, shopping, Wegman's, and much more!

365 Newton St, Brookline

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

$3,299,999

4 Beds ⋅ 4 Baths ⋅ 73543931 MLS

An architectural masterpiece, this stunning custom-built contemporary home showcases modern design at its finest. Featuring soaring ceilings, an open-concept layout, and gallery-style lighting, the home is filled with natural light from expansive walls of windows offering breathtaking views. The gourmet kitchen is equipped with Miele appliances, perfect for both everyday living and entertaining. A fireplaced library on the main level provides a warm and inviting retreat. Enjoy spectacular sunsets from the sunroom or the private second-story balcony off the luxurious primary suite. The finished walk-out lower level offers exceptional additional space, featuring a dedicated gym area, a spacious game room, multiple bonus rooms that can be used as guest rooms, or office spaces, and abundant storage throughout. Step outside to a beautifully landscaped outdoor retreat with exterior stairs leading to a serene, courtyard garden, creating a peaceful setting for relaxation or entertaining.

28 Kesseler Way, Newton

Listing courtesy of Listing Agent: Xianbin Yin from Listing Office: Harmony Hill Realty LLC.

$2,749,999

5 Beds ⋅ 6 Baths ⋅ 73523918 MLS

Luxury Living in Chestnut Hill, Brookline. Spacious 5-bedroom home designed for extended families, aging parents, or long-term guests. Four bedrooms feature private en suite bathrooms, offering comfort and privacy throughout. Two bedrooms are conveniently located on the main level, while two upstairs bedrooms feature skylights filled with natural light. An additional lower-level bedroom creates flexible living options. Enjoy a warm family room with a fireplace, plus a finished lower level complete with a second fireplace, a kitchenette, and flexible space perfect for a family room, theater room, game room, or private guest retreat. Step outside to your private inground pool and enjoy peaceful surroundings near the renowned Brookline Golf Course. Complete with a 2-car garage and close proximity to Boston, medical centers, shopping, dining, and major routes, this home blends luxury, flexibility, convenience, and multigenerational living in the heart of Chestnut Hill.

171 Shaw Rd, Brookline

Listing courtesy of Listing Agent: Melvin A. Vieira Jr. from Listing Office: RE/MAX Real Estate Center.

$4,998,500

4 Beds ⋅ 5 Baths ⋅ 73520842 MLS

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb

9 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.

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