Chestnut Hill Real Estate

Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts, a picturesque suburban oasis that perfectly blends the charm of New England living with modern conveniences. Nestled just six miles west of downtown Boston, Chestnut Hill offers residents a serene retreat while maintaining easy access to the vibrant city life. Known for its beautiful tree-lined streets, historic architecture, and lush green spaces, this neighborhood is a haven for families, professionals, and retirees alike.

One of the highlights of Chestnut Hill is its stunning natural beauty. The area is home to the famous Chestnut Hill Reservoir, which provides a scenic backdrop for walking, jogging, and picnicking. The meticulously maintained parks and gardens, such as the nearby Larz Anderson Park, offer ample opportunities for outdoor recreation and relaxation. For golf enthusiasts, the prestigious Chestnut Hill Country Club provides a challenging course and a welcoming community.

Culturally rich and diverse, Chestnut Hill boasts an array of dining, shopping, and entertainment options. From quaint cafes to upscale restaurants, there’s something to satisfy every palate. The nearby Chestnut Hill Square features a mix of boutique shops and major retailers, ensuring that residents have everything they need just moments from home.

Education is a top priority in Chestnut Hill, with access to some of the best public and private schools in the state. The area is also home to renowned institutions like Boston College, fostering a vibrant academic atmosphere.

Whether you're drawn to its scenic beauty, community spirit, or proximity to Boston, Chestnut Hill is a delightful place to call home. Experience the perfect blend of suburban tranquility and urban excitement in this charming Massachusetts gem!

Newest Listings in Chestnut Hill

$3,999,999
6 Beds ⋅ 6 Baths ⋅ 73568425 MLS
Tucked at the end of a desirable cul-de-sac in Chestnut Hill, this classic shingle-style residence offers four beautifully finished levels of living with a timeless traditional design. Hardwood floors, gracious room proportions, and a warm, inviting floor plan create a home equally suited for everyday living and entertaining.Featuring 6 bedrooms and 6 full bathrooms, the residence offers exceptional flexibility for family, guests, home offices, and additional living spaces. The finished walk-out lower level adds another dimension of usable space with direct access outdoors, while the three-car garage provides both convenience and ample storage.Beautifully landscaped grounds enhance the home’s curb appeal and sense of privacy, with the property set on approximately 25,000 square feet of land. Combining substantial living space, classic New England architecture, and a sought-after Chestnut Hill cul-de-sac location, this is a special opportunity to enjoy comfort, scale, and timeless character.

31 Kesseler Way, Newton

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.
$579,000
1 Beds ⋅ 2 Baths ⋅ 73567312 MLS
Beautifully renovated 1-bedroom, 1.5 bath condo at 250 Hammond Pond Parkway. This spacious 899 sq. ft. residence features an inviting open floor plan with hardwood floors throughout the living and dining areas, a renovated kitchen with stainless steel appliances, and a spacious bedroom with its own remodeled en-suite full bathroom featuring a tiled shower. A convenient half bath with washer and dryer, is located off the foyer for guests. The dining area opens to a versatile enclosed balcony, can be used as an office, offering additional year-round living space and a comfortable retreat. The building also includes, tennis court, swimming pool, club house, concierge and one deeded parking space. Located on the 6th floor of a well-established high-rise community, this turnkey home offers comfortable living in a desirable Chestnut Hill location, close to Chestnut Hill mall and other shopping areas, restaurants, parks, public transportation, and major highways.

250 Hammond Pond Parkway Unit 609S, Newton

Listing courtesy of Listing Agent: Shahan Missaghian from Listing Office: William Raveis R.E. & Home Services.
$749,900
2 Beds ⋅ 1 Baths ⋅ 73565940 MLS ⋅ ['Lisa Condominium'] BLDG.
Welcome to 215 Crafts Road, a bright and inviting 2-bedroom condominium set on a tree-lined street in Brookline’s Chestnut Hill neighborhood. This well-maintained second-floor home offers approximately 930 square feet of living space with an open living and dining room layout, hardwood floors, and abundant natural light. The updated kitchen features stone countertops, stainless steel appliances, a gas range, and ample cabinet space. A rare bonus for the area, the home offers two private decks, providing valuable outdoor space for relaxing, dining, or enjoying the warmer months.Additional highlights include in-unit laundry, basement storage, one assigned off-street parking space, replacement double-pane windows installed in 2019, and a newer hot water tank. The home is part of a self-managed three-unit association with a lower-than-usual monthly condo fee.Conveniently located near both the Brookline Reservoir and Chestnut Hill Reservoir, with easy access to Washington Square, Cleveland Circle, the Green Line, and the shops, restaurants, and everyday conveniences along Route 9 in Chestnut Hill. A fantastic opportunity to enjoy a residential Brookline setting while remaining close to public transportation, outdoor recreation, dining, shopping, and area amenities.

215 Crafts Rd Unit 2, Brookline

Listing courtesy of Listing Agent: Western Atlantic Group from Listing Office: Compass.
$675,000
2 Beds ⋅ 2 Baths ⋅ 73565254 MLS ⋅ ['Hammond Park Condominiums'] BLDG.
Top-Floor Corner Residence in the Heart of Chestnut Hill. Experience exceptional light, space, and privacy in this breathtaking top-floor corner residence at Hammond Park. This beautifully redesigned 2-bedroom, 2-bath condominium offers nearly 1,300 square feet of thoughtfully designed living space and feels even larger thanks to its open-concept layout and oversized walls of windows. The completely redesigned kitchen is bright and sophisticated, featuring custom finishes and windows that bring in ample natural light. The spacious open living and dining areas create an ideal setting for both everyday living and entertaining. Set within a solid, well-maintained condominium building with a beautiful front-entry lobby and elegant hallways, this home offers both comfort and convenience. Ideally located just steps from the Longwood Medical shuttle and minutes from Longwood Medical, the MBTA, and the vibrant shopping and dining of Chestnut Hill. A rare combination of top-floor privacy, corner exposure, exceptional natural light, generous proportions, and an unbeatable Chestnut Hill location.

10 Hammond Pond Parkway Unit 607, Newton

Listing courtesy of Listing Agent: Richard C. Dore from Listing Office: Hammond Residential Real Estate.
$569,000
1 Beds ⋅ 1 Baths ⋅ 73564944 MLS ⋅ ['Imperial Towers'] BLDG.
Fabulous Imperial Towers in Chestnut Hill totally renovated and updated One bedroom unit. Worry free lifestyle with the ease of full-service condominium living.Featuring high ceilings with decorative moldings and custom built in cabinetry, abundant natural light & very generous closets, Renovated bathroom and oversize kitchen with breakfast bar. Enjoy the many amenities—heated seasonal pool, a new fitness center, a clubroom, library, EV Charging Station, bicycle storage & extra storage. 2 car deeded parking (#36, #126). including 1 carport space. The 24 Hour concierge, on-site management and live-in superintendent ensure effortless living, 100% owner occupied. Prime location near Chestnut Hill Square,The Street, The Shops at Chestnut Hill , Wegman's & many wonderful restaurants. Easy access to Boston & Longwood Medical area. A very well maintained building with many updates. Unit 213 at the Imperial Towers is Chestnut Hill living at its finest!

280 Boylston Unit 213, Newton

Listing courtesy of Listing Agent: Cary Berger from Listing Office: Coldwell Banker Realty - Newton.
$449,000
1 Beds ⋅ 1 Baths ⋅ 73564774 MLS ⋅ ['Broadlawn Park Condominiums'] BLDG.
Penthouse living at its best! This spacious 1-bedroom, 1-bathroom condo features high vaulted ceilings, central A/C, and a beautifully updated interior. Numerous updates enhance this inviting home, including new kitchen flooring and backsplash, freshly painted interiors, updated light fixtures, and custom built-in shelving in both the living room and bedroom. The beautifully refreshed bathroom features new flooring, a stylish vanity and mirror, plus a built-in linen closet for added storage. A private balcony provides the perfect spot to relax and enjoy some fresh air. The unit includes one deeded parking space, plus ample visitor parking. Laundry facilities are conveniently located within the building. Residents can also enjoy an in-ground pool and clubhouse. Ideally located near the Chestnut Hill Mall, VFW Parkway, the Green Line, parks, shopping, dining, and so much more! A wonderful opportunity to enjoy comfortable, low-maintenance living in an unbeatable location! Don’t miss your chance to see this incredible unit—schedule a showing today!

55 Broadlawn Park Unit 16B, Boston

Listing courtesy of Listing Agent: Patricia Candela from Listing Office: Centre Realty Group.
$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.
$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.
$1,995,000
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, LEAD FREE, perfect for INVESTOR or END USER, 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 hardwoods, a fireplaced living room, lovely dining room, 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.
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