Chestnut Hill Homes with Contemporary Style

Welcome to Chestnut Hill, Massachusetts, a picturesque community that beautifully blends suburban charm with urban convenience. Nestled just a stone's throw from downtown Boston, Chestnut Hill offers residents a serene environment while keeping them connected to the vibrant cultural and social life of the city. Known for its lush landscapes, tree-lined streets, and a strong sense of community, this area is perfect for families, professionals, and anyone seeking a tranquil refuge.

Chestnut Hill is particularly renowned for its stunning homes, many of which showcase contemporary architectural styles. These modern residences are designed with an eye for sophistication and functionality, featuring open floor plans, large windows that flood interiors with natural light, and sleek finishes that appeal to today’s discerning buyers. Whether you’re drawn to a chic single-family home or a stylish condominium, the contemporary properties in Chestnut Hill offer a perfect blend of luxury and comfort.

Living in Chestnut Hill means enjoying a wealth of amenities, including upscale shopping at The Street, fine dining options, and access to top-rated schools. The area is also home to several parks and recreational spaces, perfect for outdoor enthusiasts. With its unique mix of modern living and classic New England charm, Chestnut Hill stands out as a desirable destination for those seeking a vibrant yet peaceful lifestyle. Explore the contemporary homes available in this enchanting region, and discover the perfect place to call your own!

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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