Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts, a charming suburban enclave that perfectly marries the tranquility of residential living with the vibrancy of urban amenities. Nestled just six miles west of downtown Boston, Chestnut Hill boasts a rich history and a picturesque landscape, making it a highly sought-after destination for families, professionals, and retirees alike.

One of the standout features of Chestnut Hill is its stunning architecture, which ranges from classic colonial homes to modern masterpieces. Tree-lined streets and beautifully manicured gardens create a serene atmosphere that invites leisurely strolls and outdoor gatherings. The community is known for its strong sense of belonging, where neighbors become friends and local events foster connections.

Chestnut Hill is also home to an array of top-tier educational institutions, including Boston College and the prestigious Chestnut Hill Academy, making it an ideal location for families prioritizing education. The area’s parks and recreational facilities, such as the Chestnut Hill Reservoir and the nearby Hammond Pond Reservation, provide ample opportunities for outdoor activities, from jogging and biking to picnicking and birdwatching.

In addition to its natural beauty, Chestnut Hill offers a variety of shopping and dining experiences. The Chestnut Hill Shopping Center and The Mall at Chestnut Hill feature a mix of boutique shops, renowned retailers, and delightful eateries that cater to diverse tastes.

Whether you’re looking for a peaceful retreat or an engaging community, Chestnut Hill, MA, is a place where you can truly feel at home. Discover the allure of this exquisite neighborhood and let it captivate your heart!

Newest Listings in Chestnut Hill

$2,199,000

4 Beds ⋅ 5 Baths ⋅ 73560438 MLS

This exceptional contemporary townhome offers 3,193 square feet of sophisticated living space in the heart of Chestnut Hill. Located in the highly desirable Brookline school district, this four-bedroom, four-and-a-half-bath residence combines refined contemporary design, premium finishes, and the comfort of single-family living with the convenience of condominium ownership.Bathed in natural light from oversized black-framed windows, the open-concept main level features 8-inch white oak hardwood flooring, soaring ceilings, and a beautifully appointed chef's kitchen with custom cabinetry, quartz countertops, premium stainless steel appliances, a six-burner Bosch gas range, and an oversized center island overlooking the dining and living areas. Sliding glass doors open to a private patio and fenced yard, creating seamless indoor-outdoor living, while a stylish tiled powder room completes the main level.The second level features two spacious en-suite bedrooms, including a luxurious primary suite with a custom walk-in closet and spa-inspired bath featuring elegant tilework and a frameless glass shower. The top level offers two additional en-suite bedrooms, a striking glass-enclosed office, and a dedicated laundry room.Additional highlights include designer lighting, a tiled mudroom with custom built-ins, abundant storage, and two assigned heated garage parking spaces.Moments from The Street Chestnut Hill, Chestnut Hill Square, Hammond Pond Reservation, Skyline Park, Route 9, Longwood Medical Area, and downtown Boston. Never occupied, this extraordinary residence offers a rare opportunity to own a turnkey luxury home in one of Brookline's most sought-after neighborhoods.

811 Heath St Unit Rear, Brookline

Listing courtesy of Listing Agent: Marjorie Gold from Listing Office: Hammond Residential Real Estate.

$2,850,000

6 Beds ⋅ 4 Baths ⋅ 73558881 MLS

Discover timeless elegance and exceptional versatility in this beautifully updated 1938 Cape, thoughtfully designed for today's discerning family. Offering 6 bedrooms and 3.5 baths, the home features two primary bedrooms with private ensuite baths, including a sought-after first-floor retreat ideal for multigenerational living, guests, or an au pair. The chef's kitchen is appointed with stainless steel appliances, a gas range, wall oven, stone countertops, and a center island with seating for three. A welcoming den, formal dining room, and sun-filled breakfast area provide inviting settings for both everyday life and elegant entertaining. The finished lower level offers a versatile recreation room with a dedicated laundry area. Completing the home are an attached two-car garage and two additional off-street parking spaces, blending classic New England charm with modern comfort and convenience. Close to Roland Hayes School & Brookline High School, Route 9, Chestnut Hill Reservoir, Golf Courses, Green Line (MBTA) and The Mall at Chestnut Hill. Quick drives to Newton Centre or Brookline hubs for everyday groceries and dining.

44 Valley Rd, Brookline

Listing courtesy of Listing Agent: The Kelleher Spalding Team from Listing Office: Gibson Sotheby's International Realty.

$534,900

2 Beds ⋅ 1 Baths ⋅ 73558824 MLS ⋅ ['Hammond Park Condominiums'] BLDG.

Lovely, sunny one-bedroom condo currently configured as a two-bedroom, with the flexible second room also ideal for a home office or den.. The fully renovated interior features an open-concept floor plan, abundant natural light, new flooring, fresh paint, generous closet space, large bedrooms and individually controlled heat and air conditioning. The updated kitchen includes stainless steel appliances, white cabinetry, stone countertops, and a breakfast bar that opens to the living area. The renovated bathroom and flexible layout add comfort and versatility. Additional features include covered carport parking space #67 and additional deeded storage space. The professionally managed elevator building offers an on-site management office, renovated common areas, common laundry, two seasonal outdoor in-ground pools, landscaped grounds, a shared cookout area with grills and polenty of visitor parking. No smoking and no pets. Located near The Street Chestnut Hill and Wegmans, approximately 0.3 mi away, with shopping, dining, and fitness options nearby. The Shops at Chestnut Hill and Bloomingdale’s are approximately 0.9 mi away, Hammond Pond Reservation is approximately 0.8 mi away, and the Chestnut Hill Green Line D station is approximately 0.8 mi away. MBTA Route 60 bus service along the nearby Route 9 corridor provides access toward Kenmore Square and the Longwood Medical Area. Convenient access to Route 9 and I-95. Area schools include Bowen Elementary School, Oak Hill Middle School, and Newton South High School; buyers should verify current school assignments.

20 Hammond Pond Pkwy Unit 506, Newton

Listing courtesy of Listing Agent: John Hollis from Listing Office: Amo Realty - Boston City Properties.

$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! Easy to show - on lockbox.

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.

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