Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts – a picturesque enclave that beautifully marries suburban charm with urban accessibility. Nestled just six miles west of downtown Boston, Chestnut Hill is renowned for its stunning landscapes, historic architecture, and a vibrant community spirit that makes it one of the most sought-after neighborhoods in the Greater Boston area.

As you stroll through the tree-lined streets, you’ll be captivated by the elegant homes that reflect a rich tapestry of architectural styles, from colonial revivals to modern masterpieces. The area is known for its spacious properties, many of which boast lush gardens and breathtaking views, creating a serene retreat from the hustle and bustle of city life.

Chestnut Hill is not just about beautiful homes; it’s also a hub of culture and recreation. Residents enjoy access to the sprawling grounds of the Chestnut Hill Reservoir, perfect for jogging, walking, or simply soaking in the natural beauty. Golf enthusiasts can indulge in a round at the prestigious Brae Burn Country Club, while families appreciate the top-rated public and private schools that serve the area, ensuring an excellent education for children.

Shopping and dining options abound, with the Chestnut Hill Shopping Center offering a delightful mix of boutiques, cafes, and gourmet eateries. Whether you’re savoring a meal at a local bistro or enjoying a leisurely afternoon at one of the nearby parks, Chestnut Hill’s vibrant community ensures that there’s always something to do.

With its perfect blend of suburban tranquility and urban convenience, Chestnut Hill is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the charm of Chestnut Hill, where your dream home awaits!

Newest Listings in Chestnut Hill

$719,900

1 Beds ⋅ 1 Baths ⋅ 73553728 MLS ⋅ ['Covenant Residences On Commonwealth'] BLDG.

Don't miss out on this prime 1+ bedroom (lives like 2) unit across the street from Boston College and the green line (B). Lovely cherry cabinets with breakfast bar and stainless steel appliances in kitchen that opens to large bright living room. Wonderful master bedroom with walk in closet. Bathroom has access from primary bedroom and hallway. The den has french doors and a closet and could serve as an at home office or perfect guest room. Interior freshly painted. Condominium has an exercise room, deck and exterior outdoor space. These units do not come on very often!

35 Commonwealth Ave Unit 110, Newton

Listing courtesy of Listing Agent: Dina Browne from Listing Office: Neponset Valley Real Estate.

$1,999,000

4 Beds ⋅ 3 Baths ⋅ 73552349 MLS

Chestnut Hill - Baker School neighborhood. This 9-room brick Tudor pairs classic architectural charm with 3,123 square feet of updated living space, offering 4 bedrooms, 2.5 bathrooms on three levels. A beautifully updated eat-in kitchen, gracious living room with ornate fireplace and dining room set the stage for elegant entertaining. A first floor great room with vaulted ceiling opens to a 31'x19' patio and private backyard. Handsome masonry work throughout the beautifully landscaped outdoor spaces. The finished lower level features a family room with fireplace and stone surround. Direct access garage parking. A prime location near Chestnut Hill shopping and dining. Easy access to Cambridge, Boston, area hospitals and universities.

142 Beverly Rd., Brookline

Listing courtesy of Listing Agent: Friedler / Marchant Living Group from Listing Office: Hammond Residential Real Estate.

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 73549795 MLS

Fantastic move-in-ready 4 bedroom, 2.5 bathroom in Chestnut Hill. Set on a 15,000+ level private lot, close to schools, shops, restaurants, public transportation, golf & Skyline Park with its trails, playgrounds, fields and other amenities. Filled with natural light, the main level has beautiful hardwood floors throughout, a fireplaced living room, lovely dining room, stainless and granite eat-in kitchen, family room, home office and guest bathroom. Upstairs are 4 very generous bedrooms. and a full hallway bathroom.The primary bedroom has vaulted ceilings, sky lights and, in addition to the large ensuite bathroom, a second separate dressing room with its own sink and vanity. The home's lower level has high ceilings and unlimited potential to be used as a gym, movie theatre or what ever your needs maybe. There is central a/c.The backyard is level and private, with an expansive deck off the kitchen and family room for entertaining. A 2 car garage and large driveway complete this offering

75 Hammond Pond Parkway, Brookline

Listing courtesy of Listing Agent: Amy Sassoon from Listing Office: Coldwell Banker Realty - Brookline.

$1,299,000

3 Beds ⋅ 3 Baths ⋅ 73549224 MLS ⋅ ['The Fairways'] BLDG.

Welcome to The Fairways, a sought-after community in the heart of Chestnut Hill, adjacent to Newton Commonwealth Golf Course. This beautifully maintained residence offers 2,230 square feet of thoughtfully designed living space across two levels. Sun-filled interiors feature high tray ceilings, decorative moldings, and a wood-burning fireplace. Recent capital improvements include a brand-new HVAC system (2025), newer windows and sliders, and a completed building envelope renovation, offering lasting value and exceptional peace of mind. The spacious primary suite features a spa-inspired bath with heated floors. Enjoy multiple private outdoor spaces, including an elevated deck with treetop views, a fenced yard, and front patio, plus access to the in-ground pool. Complete with a detached garage and an additional parking space, this home offers sophisticated, low-maintenance living. Welcome home!

85 Algonquin Road Unit 85, Newton

Listing courtesy of Listing Agent: Jessica Nagle from Listing Office: Maloney Properties LLC.

$702,000

1 Beds ⋅ 2 Baths ⋅ 73549146 MLS ⋅ ['Towers Of Chestnut Hill'] BLDG.

Completely and wonderfully renovated 12th floor unit boasts generously sized rooms, beautiful natural light and a stunning Boston skyline view. The Towers offers amenities, service, privacy and luxurious living. The fully equipped building includes a heated indoor pool and a newly upgraded fitness center. Enjoy premium amenities including a 24/7 doorman for added convenience. Situated mere minutes from Longwood, Back Bay, Beacon Hill, South End, and Coolidge Corner, this property also comes with a dedicated garage parking space.

250 Hammond Pond Parkway Unit 1207S, Newton

Listing courtesy of Listing Agent: Patrick Reardon from Listing Office: Jason Mitchell Group.

$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.

$2,895,000

2 Beds ⋅ 3 Baths ⋅ 73543781 MLS ⋅ ['Longyear At Fisher Hill'] BLDG.

Price Reduction!Residence E201 occupies a privileged position as one of only five homes in the Mansion at Longyear, where history and modern luxury coexist in perfect harmony. Bathed in natural light, the home unfolds across nearly 2,300 square feet of elegant single-level living. The thoughtfully designed floor plan features two spacious bedroom suites with walk in closets, a private terrace, home office or comfortable space for an overnight guest, formal dining room, gourmet kitchen, and generous living areas that balance sophistication with comfort. For your guests convenience, a powder room is located off the living room. Two deeded garage parking spaces, private storage, elevator access, and a dedicated 24/7 staffed gatehouse complete a lifestyle defined by convenience and peace of mind. Only a handful of owners will ever call the Longyear Mansion home. Opportunities to acquire one of these residences are exceptionally rare. The home has been upgraded with new lighting, brand new carpeting, paint and new flat screen TVs. The unit includes a side by side washer and dryers. A well equipped gym is located within the Mansion. The historic grounds are well manicured and feature a seasonal pool with oversized umbrellas and seating.

120 Seaver St Unit E201, Brookline

Listing courtesy of Listing Agent: Hope Krakoff from Listing Office: Coldwell Banker Realty - Boston.

$749,900

2 Beds ⋅ 2 Baths ⋅ 73540055 MLS ⋅ ['Chestnut Hill Towers'] BLDG.

Rarely available first-floor residence at Chestnut Hill Towers, one of Chestnut Hill's premier full-service luxury communities. This spacious 2-bedroom, 2-bath home offers approximately 1,300 sq. ft. of comfortable living space with hardwood floors, an updated kitchen with stainless steel appliances, a generous primary suite with walk-in closet and renovated bath with walk-in shower, new bedroom flooring, in-unit laundry, and two deeded parking spaces conveniently located near the unit. A standout feature is the private fenced patio, creating an exceptional outdoor living space rarely found in condominium living. Residents enjoy outstanding amenities including a heated indoor pool, fitness center, tennis and pickleball courts, library, game room, walking trails, 24-hour concierge, on-site management, and beautifully maintained grounds. Conveniently located near The Street, Chestnut Hill Square, Wegmans, Longwood Medical Area, MBTA, and downtown Boston.

250 Hammond Pond Parkway Unit 102N, Newton

Listing courtesy of Listing Agent: The Presti Group from Listing Office: Barrett Sotheby's International Realty.

$549,900

1 Beds ⋅ 1 Baths ⋅ 73538790 MLS ⋅ ['Hammond Park Condominiums'] BLDG.

Chestnut Hill - Unique first floor 1 bedroom with family room, full dining room, eat in kitchen and 1 bath.Air conditioned, updated kitchen with white cabinetry, vinyl flooring, and corian counters Excellent closet space with additional storage in the basement. Elevator,1 assigned parking space, as well as available guest parking. Ideal south//west exposure and open concept floor plan allows natural all day bright light or sunlight year round. Professionally managed with an on sight office. Access to 2 outdoor, inground pools as well as a cookout area complete with grill. Great location, Newton Schools, walk to Wegmans, Equinox Fitness, C.H.Mall, Bloomingdales, The Street and more. Easy commute to Longwood Medical, #60 bus to Kenmore Square, close to C.H, Green Line T-Stop, Needs some TLC / decorating

20 Hammond Unit 102, Newton

Listing courtesy of Listing Agent: Louis Wolfson from Listing Office: Louis Wolfson.

$350,000

1 Beds ⋅ 1 Baths ⋅ 73538049 MLS

MOVE IN READY! Sunny and spacious top-floor condo in desirable Chestnut Village offering an ideal combo of comfort, convenience, and value. Oversized windows fill the spacious living room with natural light, creating an inviting setting for everyday living and entertaining. The updated eat-in kitchen provides ample cabinetry and workspace, while the renovated bath features clean, timeless finishes. A generously sized bedroom, excellent closet space, and an efficient floor plan maximize every square foot. Professionally managed, the association fee includes heat and hot water for added convenience. Ideally located near The Street at Chestnut Hill, Wegmans, restaurants, shops, parks, and public transportation, this move-in-ready home offers easy access to everything Chestnut Hill and West Roxbury have to offer.

68 Bryon Rd. Unit 5, Boston

Listing courtesy of Listing Agent: Nicole Blanchard from Listing Office: Compass.

$4,898,000

6 Beds ⋅ 7 Baths ⋅ 73532609 MLS

Set on a picturesque, tree-lined street, this exceptional 2016 brick Colonial offers an unparalleled combination of luxury and privacy in desirable Chestnut Hill. Built with uncompromising attention to detail and thoughtfully designed for both grand-scale entertaining and sophisticated everyday living. A gracious floor plan features soaring 10-ft ceilings, exquisite millwork, and beautifully proportioned rooms filled with natural light. The chef's kitchen with premium appliances and custom cabinetry flows seamlessly into a spectacular family room overlooking an expansive patio and professionally landscaped grounds. The residence offers 6 bedrooms, 6.5 baths, including a luxurious primary suite with a spa-inspired bath and custom walk-in closet. The lower level elevates the lifestyle experience with a home theater, fitness studio, private office, and full bath. Just moments from premier schools, fine dining, upscale shopping, and convenient to downtown Boston. Heated 3-car garage.

129 Rangeley Rd, Brookline

Listing courtesy of Listing Agent: Ingvild Brown from Listing Office: Keller Williams Realty.

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