Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts, a picturesque community that beautifully blends suburban charm with urban convenience. Nestled just six miles west of downtown Boston, Chestnut Hill is renowned for its stunning landscapes, historic architecture, and vibrant local culture. With tree-lined streets, lush parks, and a rich history, this idyllic neighborhood offers an inviting atmosphere for families, young professionals, and retirees alike.

Chestnut Hill is home to several prestigious educational institutions, including Boston College and Pine Manor College, adding a youthful energy to the area. Residents enjoy easy access to a variety of shopping and dining options, from quaint boutiques to upscale restaurants. The Chestnut Hill Shopping Center and The Mall at Chestnut Hill provide an array of retail experiences, ensuring that everything you need is just a stone's throw away.

Nature enthusiasts will appreciate the proximity to the scenic Chestnut Hill Reservoir, perfect for jogging, walking, or simply enjoying a leisurely afternoon. The area is also rich in history, with beautiful homes dating back to the early 20th century, showcasing a mix of architectural styles from Colonial Revival to Tudor.

With excellent public transportation options and a strong sense of community, Chestnut Hill offers a harmonious blend of tranquility and accessibility. Whether you're looking for a cozy place to call home or an active lifestyle filled with cultural experiences, Chestnut Hill is a gem waiting to be discovered. Come and explore the unique charm and vibrant life that this exceptional neighborhood has to offer!

Newest Listings in Chestnut Hill

$685,000

1 Beds ⋅ 2 Baths ⋅ 73575960 MLS

2.625% assumable mortgage — $154K, 15 yrs left. - Fully gut-renovated 1BR/1.5BA at prestigious Imperial Towers, Chestnut Hill. Every finish custom, no expense spared. Oval tray ceiling with ambient & recessed lighting, smooth ceilings throughout (popcorn removed), engineered hardwood floors, thermally insulated replaced windows and balcony door. Custom Wolfers Lighting throughout every room.Lacquered handcrafted Norwegian kitchen: paneled refrigerator, dishwasher, trash & recycle bin, Miele wine cooler, Thermador gas cooktop, Miele oven, brand-new never-used Thermador oven, waterfall stone island, reverse osmosis filtration, recessed lighting.Spa full bath: heated floors, glass-enclosed Grohe shower, floating double vanity, floor-to-ceiling ceramic tile, recessed lighting. Half bath: floating vanity, floor-to-ceiling ceramic tile. Norwegian custom walk-in closet: ceiling-height cabinetry, built-in drawers, full-height cabinet tower. Remote-controlled blackout shades, California custom sconces.Private balcony, prime covered carport. 24hr concierge, gym, outdoor pool, EV charging. 100% owner occupied. HOA includes heat, gas, water, sewer, AC, insurance & more. Steps to Capital Grille, Seasons 52, Bloomingdale's, Wegmans, Life Time Fitness, medical centers, movie theater. Bus #60 at front door. Well-managed association with robust reserves — no special assessments.

280 Boylston St Unit 308, Newton

$1,575,000

4 Beds ⋅ 3 Baths ⋅ 73574921 MLS

This move-in-ready Chestnut Hill ranch offers privacy, convenience, and easy single-level living on a quiet Newton street. The sun-filled main level features four bedrooms and two full bathrooms, including a private primary suite, a beautifully renovated kitchen (2022), and two updated bathrooms (2023), plus scenic treetop views. The partially finished lower level adds a recreation room, third bathroom, laundry, and generous storage. Major upgrades include a tankless water heater (2022), new roof and two high-efficiency Mitsubishi heat pumps (2023), plus new gutters, paver patio, premium Marvin windows, and sliding glass door (2024). Ideally located near Ward Elementary School, Boston College, Newton Commonwealth Golf Course, and the MBTA Green Line B and C branches, with convenient access to downtown Boston.

18 Travis Dr, Newton

$2,250,000

3 Beds ⋅ 4 Baths ⋅ 73574038 MLS

Rarely available fully renovated end-unit 3 bed+office / 3.5 bath townhouse at The Residences at Chestnut Hill offers an enviable combination of privacy, space and convenience. Set back from Boylston Street and abutting a tranquil conservation area, this beautifully appointed residence has been thoughtfully renovated offering an abundance of natural light and features generous proportions, including a magnificently renovated kitchen and beautifully updated bathrooms. The main living level boasts 9’ ceilings, a convenient powder room and a chef’s dream kitchen with a center island, custom cabinetry and a charming bay-windowed eat-in area. The kitchen flows seamlessly into a spacious living room anchored by a gas fireplace and custom built-ins, a dining area and a sliding door opening to a private deck overlooking the landscaped side yard. The second floor is comprised of a spacious primary suite with two walk-in closets, in-unit washer/dryer and a luxurious en-suite bath featuring a double vanity, walk-in shower and separate soaking tub with skylight overhead. An oversized guest bedroom with an adjacent full bathroom completes the second floor. The finished lower level offers flexibility with an additional bedroom, full bathroom and a separate office/den area. Additional highlights include a 2-car attached garage, mudroom area, 20’ grand foyer entry, central air, recessed lighting throughout and access to the association's fitness center. Ideally located near an abundance of shopping/restaurants at Chestnut Hill Square/Wegmans, The Shops at Chestnut Hill, The Street and just steps from Lifetime Fitness and the trails of Lost Pond Reservation, this exceptional residence offers effortless suburban living just minutes from Boston.

344 Boylston Street Unit A, Newton

$2,250,000

3 Beds ⋅ 4 Baths ⋅ 73574004 MLS ⋅ ['The Residences At Chestnut Hill'] BLDG.

344 Boylston Street Unit A, Newton

$799,000

2 Beds ⋅ 2 Baths ⋅ 73573602 MLS ⋅ ['Imperial Towers'] BLDG.

Welcome to luxury full-service living at Newton’s highly desirable Imperial Towers. Tucked quietly on the fourth floor as a sought-after back-corner unit, this sun-filled residence offers an ideal blend of peaceful privacy, scenic views, and exceptional potential to customize. A bright, expansive open floor plan invites you inside, set off by beautifully updated hardwood floors that run continuously throughout the living spaces.The generous main living and dining area provides a seamless layout for everyday comfort and effortless entertaining. Large glass doors open directly onto your private balcony—a tranquil outdoor oasis perfect for sipping morning coffee or taking in the evening breeze. The eat-in kitchen features crisp white cabinetry, stainless steel appliances, and abundant counter space and cabinetry storage, offering a functional workspace.The primary bedroom suite serves as a spacious retreat, featuring a well-proportioned layout, ample storage, and an en-suite bathroom. The second bedroom offers ideal flexibility as a guest bedroom, nursery, or dedicated work-from-home office, serviced by a second full bathroom. Crisp, neutral paint throughout makes the home bright, fresh, and move-in ready from day one. Residents at Imperial Towers enjoy an unparalleled resort-style lifestyle with top-tier amenities, including 24-hour concierge service, professional management, an on-site superintendent, and a sophisticated, newly renovated lobby. Community perks feature a sparkling outdoor swimming pool, elegant clubroom, fitness and yoga studio, peaceful library, private extra storage space, elevator access, and dedicated laundry facilities located conveniently on every floor. This residence comes complete with deeded parking space #57, along with ample guest parking for your visitors. Situated in a prime Chestnut Hill location along Route 9, you are minutes from world-class shopping at Bloomingdale's, premier restaurants, Wegmans, public transit, major commuter highways, top-rated local schools, and renowned medical facilities. Unmatched convenience, full-service comfort, and privacy await.

280 Boylston Street Unit 411, Newton

$3,995,000

4 Beds ⋅ 5 Baths ⋅ 73573585 MLS

Welcome to this stunning center-entrance Colonial in Brookline's Chestnut Hill estate area, set on a level half-acre lot. This expansive home features 4+ bedrooms, 4 full and 1 half baths & offers over 4,895 square feet across three finished levels. The foyer opens to a fireplaced living room and a formal dining room that seats 12. The Chef’s kitchen features a Wolf range, Sub-Zero refrigerator, double wall ovens including steam, Cove dishwashers, two sinks, custom cabinetry & granite counters. A library with built-ins cabinetry sits off the dining room & kithcen. The family room, with gas fireplace opens through French doors to a bluestone patio and a broad, fenced, level yard. Upstairs, the primary suite includes a private balcony, Carrara marble bath, dressing area, and two walk-in closets. Three additional bedrooms and two full baths & laundry complete the floor. The lower level consists of a media/playroom, gym, wet bar, beautiful full bath with glass enclosed shower + another set of laundry. Central air & Sonos throughout, EV charging & 2-car garage. Close proximity to the D Line at Chestnut Hill, shops and restaurants at The Street at Chestnut Hill, Soule Playground, and Dane Park.

17 Glenoe Rd, Brookline

$3,100,000

5 Beds ⋅ 5 Baths ⋅ 73573502 MLS

A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.

284 Woodland Road, Brookline

$2,950,000

3 Beds ⋅ 4 Baths ⋅ 73573464 MLS ⋅ ['Longyear At Fisher Hill'] BLDG.

Located at Longyear at Fisher Hill, this 3,445 SF single-level residence offers 3 bedrooms, 3.5 baths, and the ease of a gated community and its full suite of amenities. Thoughtfully designed for comfortable living and effortless entertaining, the home features formal living and dining rooms flow seamlessly into the spacious kitchen, family room, breakfast nook, and office. The primary suite offers abundant closet space and a spa-like bath with a dual-sink vanity, soaking tub, and separate shower. Two additional bedrooms each feature en-suite baths. Private outdoor space, two garage parking spaces, additional storage, and elevator access within the building complete the home. Residents enjoy the privacy of a gated community with exceptional amenities, including a fitness center, outdoor swimming pool, beautifully landscaped grounds, and professional management, all moments from the shops, restaurants, and conveniences of Chestnut Hill.

120 Seaver Street Unit C102, Brookline

$795,000

2 Beds ⋅ 2 Baths ⋅ 73572897 MLS ⋅ ['Hammond Park Condominiums'] BLDG.

Enjoy effortless living in the heart of Chestnut Hill from this beautifully updated 5th floor corner residence. This meticulously maintained, spacious 2 bed 2 bath unit features an open-concept layout with oversized living and dining, designed for comfortable living and entertaining. A beautifully renovated chef’s kitchen features granite countertops, a large island with seating, SS appliances and pantry. The primary suite offers exceptional storage with 3 closets, including 2 walk-ins, along with an updated en-suite bath. The second bedroom, also includes a substantial closet and easy access to the second updated full bath. Expansive walls of windows throughout, offer lovely views overlooking the pool. Residents enjoy a host of amenities, including two heated outdoor swimming pools, BBQ, updated common areas, and covered carport parking. Ideally situated near shopping, dining and entertainment, with convenient access to Wegmans, The Street, Green Line MBTA and bus service. Just move in and enjoy! Also listed for Rent - MLS ID 73573578

20 Hammond Pond Pkwy Unit 504, Newton

$2,765,000

5 Beds ⋅ 4 Baths ⋅ 73572599 MLS

Come fall in love with this storybook 5-bed, 3.5-bath Colonial Revival set on 0.3AC in Brookline’s Chestnut Hill. Built in 1926, this charming 4,028SF residence offers a layout tailored for modern living. Streaming southern sunshine, timeless architecture, 3 fireplaces, and oversized windows define the home. Welcoming entry connects the main living spaces. Gracious living room w/ fireplace and built-ins flows into bright conversatory. Opposite is a family room with fireplace, which opens to a bright dining room. Classic butler’s pantry connects to the kitchen. With ample counter space and a cozy eat-in area, the kitchen serves as the heart of the home with direct access to deck and yard. Mudroom and half bath complete floor. Upstairs has bright en-suite primary, 4 additional bedrooms, office, and 2 full baths. Walkout lower level with playroom and laundry. Attached garage. Landscaped grounds create a true sense of privacy. Close to “The Street”, top schools, and Green D line train.

401 Heath Street, Brookline

$1,790,000

4 Beds ⋅ 3 Baths ⋅ 73572511 MLS

Captivating colonial tastefully designed for elegant entertaining and comfort in mind. Privacy + nature abound in this 4 bedrooms, 3 bathrooms + 2450 square feet of refined living space in a premier Chestnut Hill location. Near Baker Elementary school (grades K-8) + close proximity to Putterham Shops, tennis, golf, wildlife sanctuary, Longwood Medical Area, Arnold Arboretum + Jamaica Pond. First floor has living room with wood burning fireplace, family room, bedroom with full bath + access to expansive outdoor deck. In the heart of the residence is a beautifully renovated kitchen with custom white shaker cabinets, sleek black granite countertops, stainless steel appliances + generous center island. Upper level has a sprawling primary bedroom suite complimented by majestic sunset views + an abundance of attributes such as walk-in closet, separate sitting area + spa-like bath with dual sink vanity, glass enclosed shower + soaking tub/jacuzzi. Additional finished lower level provides versatile space for a fitness gym, home theatre or home office to meet today's evolving lifestyle needs. One car garage, one carport + plenty of additional driveway parking make this an ideal residence to call home.

133 Wolcott Road, Brookline

$698,000

1 Beds ⋅ 1 Baths ⋅ 73572280 MLS ⋅ ['The Waterworks At Chestnut Hill'] BLDG.

Updated condo in stunning carriage house conversion, surrounded by green space with city convenience & culture. Inviting layout flows from foyer to open-concept living/dining area to chef’s kitchen with high-end stainless steel appliances (SubZero, Wolf, Miele, GE Profile) & granite countertops. Spa-like marble tiled bathroom. Plentiful storage includes coat closet & bedroom walk-in closet. Laundry room. New hardwood floors throughout. Spacious feel with soaring high ceilings. Custom Hunter Douglas window shades. Upgraded energy-efficient heat, central air conditioning, smart thermostat. Deeded parking space. Amenities include fitness center, common room, visitor parking, EV chargers, landscaping, snow removal, on-site property management. Beautiful grounds with striking architecture. Prime location across from Chestnut Hill Reservoir’s scenic trail & sunset views. Short distance to Cleveland Circle shopping & dining, Boston College, Cassidy Park tennis courts, several subway & bus lines.

2430 Beacon Street Unit 104, Boston

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