Chestnut Hill Homes under $2 million

Chestnut Hill Homes under $2 million

Welcome to Chestnut Hill, Massachusetts—a picturesque suburb that beautifully marries the charm of New England with modern conveniences. Nestled just six miles from downtown Boston, this vibrant community is known for its lush landscapes, historic architecture, and a welcoming atmosphere that makes it a sought-after destination for families and professionals alike.

Chestnut Hill boasts a rich history, with tree-lined streets and stunning homes that reflect a variety of architectural styles, from classic colonial to contemporary designs. The area is renowned for its top-rated schools, making it an ideal place for families looking to settle down. With a strong sense of community, residents enjoy easy access to local parks, upscale shopping, and a plethora of dining options that cater to every palate.

For those seeking their dream home in this idyllic suburb, Chestnut Hill offers a range of properties under $2 million. Whether you're in the market for a cozy single-family home or a spacious property with ample outdoor space, you'll find options that cater to diverse tastes and needs. Many homes feature beautiful gardens, modern amenities, and easy access to public transportation, ensuring a seamless commute to Boston while enjoying the tranquility of suburban life.

As you explore Chestnut Hill, you'll discover a vibrant community that values both tradition and innovation. With its stunning homes, excellent schools, and a variety of recreational opportunities, Chestnut Hill is not just a place to live—it's a place to thrive. Come and experience the charm of this enchanting neighborhood for yourself!

Newest Chestnut Hill Homes under $2 million

77 Payson Rd, Brookline
$849,900
3 Beds ⋅ 1 Baths ⋅ 73594577 MLS
Entering Brookline! Welcome home! Lovely entryway with closet welcomes you into fire placed, sunlit living room with mellow hardwood floors that opens to ample dining room perfect for holiday entertaining. Three season sunroom and fully applianced kitchen round out the first floor. Direct entry garage is a bonus! Second level offers 2 generous bedrooms and a smaller nursery or office and full bath. Basement is partially finished for bonus space! Situated on a lovely fenced lot. Bring your ideas and pack your bags. There is so much potential with this property. Excellent location, Baker school district. Best value in Chestnut Hill! Don't miss! Offers, if any, due Tuesday at noon!

77 Payson Rd, Brookline

Listing courtesy of Listing Agent: Patsy Brennan from Listing Office: Vogt Realty Group, LLC.
99 Florence St Unit 10-5B, Newton
$1,900,000
2 Beds ⋅ 3 Baths ⋅ 73591946 MLS ⋅ ['The Farm'] BLDG.
Sunlight fills this distinctive penthouse crowning The Farm, with sweeping views of the pond, waterfall, and beautifully landscaped grounds. The spacious living room features a fireplace, built-in bookshelves, and a concealed wet bar, with access to a private balcony overlooking the tranquil setting. The sunny eat-in kitchen is a welcoming space for everyday meals and easy entertaining. Two thoughtfully separated bedrooms provide privacy, and the generous primary suite is a true retreat, with skylights, a dressing area, a full bath, and a separate office. With three full baths in all, the home is comfortable for residents and guests alike. Parking is a luxury in itself: two deeded spaces in the building, plus a separate garage for a third car with room for additional storage. A rare opportunity for carefree living at one of Chestnut Hill’s most sought-after addresses.

99 Florence St Unit 10-5B, Newton

Listing courtesy of Listing Agent: Suburban Boston Team from Listing Office: Compass.
250 Hammond Pond Parkway Unit 812 N, Newton
$529,000
1 Beds ⋅ 2 Baths ⋅ 73591578 MLS ⋅ ['The Towers Of Chestnut Hill'] BLDG.
Eighth Floor Beauty! Rarely available one bedroom, one- and one-half bath, light and bright unit in the North Building of The Towers of Chestnut Hill. with 24-hour concierge, a deeded parking spot just outside the door, heated swimming pool, recently renovated workout room and more! Set on over 17 lush acres with walking trails galore and just minutes to shopping (Wegman’s, The Street, Chestnut Hill Mall) and medical offices (Longwood, NE Baptist). Move right in or bring your decorating ideas. Thoughtful renovations include granite countertops, generous cabinet space in the kitchen and marble countertop in the half bath. Newer SS refrigerator and in-unit washer/dryer. Amenities include gated entrance, library, game room, pickleball and tennis courts, garden area and two beautiful residence lounges. The ultimate in luxury and convenience, make the Towers of Chestnut Hill your new home!

250 Hammond Pond Parkway Unit 812 N, Newton

Listing courtesy of Listing Agent: Maureen Murphy Olsen from Listing Office: Louise Condon Realty.
30 Hackensack Road, Brookline
$995,000
3 Beds ⋅ 2 Baths ⋅ 73590431 MLS
Charming Colonial in a Coveted Brookline Location! Situated in an excellent neighborhood just a stone’s throw from Allandale Farm, Larz Anderson Park and Brookline's top-rated schools, this 3-bedroom, 1.5-bath Garrison Colonial presents a wonderful opportunity to create your dream home. The property features hardwood floors throughout, garage parking with direct access to the home and a generous lot of over 7,500 square feet. In need of updating, this home offers tremendous potential for renovation, personalization and long-term value in a highly desirable location. A rare opportunity to bring your vision to life in one of Brookline’s sought-after neighborhoods, close to parks, local amenities, hospitals and excellent educational opportunities. Offers, if any, to be reviewed on Monday, 10/19 by 2pm.

30 Hackensack Road, Brookline

Listing courtesy of Listing Agent: DelRose McShane Team from Listing Office: Coldwell Banker Realty - Belmont.
57 Broadlawn Park Unit 3A, Boston
$398,000
1 Beds ⋅ 1 Baths ⋅ 73582234 MLS ⋅ ['Broadlawn Park Condominium'] BLDG.
Discover the easy living lifestyle at Broadlawn Park Condominiums in Chestnut Hill. This one-bedroom 2nd floor unit offers a comfortable place to relax, work, and entertain, with the convenience of a Chestnut Hill address, with wonderful shopping and dining amenities at The Street in Chestnut Hill, which is across the street from Wegman's for groceries. There is excellent closet space within the unit, as well as an oversized, locked private storage bin in the lower level for spillover belongings. Whether you’re looking for your first home, a place to downsize, or a Boston-area retreat, this well maintained condominium is an inviting opportunity to make the space your own. Spacious open living/dining great room with sliders to your private balcony for morning coffee and end of day sunsets. The building features landscaped grounds, professional management, clean laundry room, elevator, storage and a terrific, clean & modern clubhouse and outdoor pool for resident use! The clubhouse has excellent amenities like kitchen facilities, ping pong table, a library of books, and is almost an extension of your unit for a quiet place to sit and read, work from home, compose your next novel or entertain friends and family in a huge room with walk out access to the pool and large patio areas. Your parking space is just beyond your balcony, and there are typically rental spaces available for a 2nd car. There is a lot of appeal in this established condominium setting. Priced to sell and easy to show.

57 Broadlawn Park Unit 3A, Boston

Listing courtesy of Listing Agent: Ed Lyon from Listing Office: Preservation Properties.
250 Hammond Pond Parkway Unit 1611N, Newton
$1,349,000
3 Beds ⋅ 2 Baths ⋅ 73581961 MLS ⋅ ['The Towers Of Chestnut Hill'] BLDG.
Rare opportunity to own this distinctive three-bedroom luxury residence in one of Chestnut Hill’s most prominent buildings, ideally located on Hammond Pond Parkway and just minutes from Longwood, Back Bay, Beacon Hill, the South End and Coolidge Corner. Framed with over-sized windows throughout, this 16th-floor residence in the North Tower offers breathtaking southwest-facing views, spectacular sunsets and nearly 1,700 square feet of spacious, comfortable living with a thoughtfully designed open floor plan is ideal for both everyday living and entertaining. The modern kitchen features custom cabinetry, quartz countertops and stainless steel appliances, while the adjacent dining area provides a perfect setting for casual meals or hosting guests. The spacious primary suite offers an en-suite bath with an expansive closet and a dedicated dressing area. Two additional generously sized bedrooms another full bath, in-unit laundry, generous closet space and numerous thoughtful details create an exceptional sense of comfort and scale. The residence includes two deeded parking spaces: one garage space (#337) and one outdoor space (#1). Residents enjoy full-service living with professional on-site management, maintenance staff and a 24-hour doorman, along with an impressive array of amenities. These include an indoor heated swimming pool, recently upgraded fitness center, brand-new pickleball court, tennis courts, outdoor playground and indoor children's playroom--all set on 17 professionally landscaped acres. The Towers is ideally situated in a prime Chestnut Hill location, close to Chestnut Hill Mall, The Street, Wegman's, Movie Theatre, the MBTA and Longwood Medical Center shuttle services. With convenient access to public transportation, shopping, dining, and nature, this exceptional residence offers a combination of space, luxury, convenience, and resort-style living.

250 Hammond Pond Parkway Unit 1611N, Newton

Listing courtesy of Listing Agent: Ilene Solomon from Listing Office: Coldwell Banker Realty - Newton.
250 Hammond Pond Pkwy Unit 1006N, Newton
$849,000
2 Beds ⋅ 2 Baths ⋅ 73578905 MLS ⋅ ['Chestnut Hill Condominium'] BLDG.
Experience luxury high-rise living at the sought-after Chestnut Hill Condominium! Positioned on the 10th floor, this expansive single-level residence offers 2 spacious bedrooms and 2 full bathrooms. The light-filled layout features rich hardwood floors, an inviting open living room, a distinct dining area, with central air. The fully equipped kitchen. The spacious primary suite highlights plush wall-to-wall carpeting, a large walk-in closet, and a private en-suite bathroom. A second bright bedroom with hardwood floors is paired with a second full bathroom. This unit includes 2 assigned parking spaces, including 1 garage space under the building. Set on 17+ landscaped acres directly behind The Shops at Chestnut Hill, enjoys 24-hour concierge service, security gate access, an indoor heated pool, fitness center, tennis courts, and clubroom. Live close to luxury shopping at The Street, fine dining, Hammond Pond Reservation, and direct Boston transit via Route 9 and the MBTA Green Line. A true turn-key retreat!

250 Hammond Pond Pkwy Unit 1006N, Newton

Listing courtesy of Listing Agent: Delince P. Louis from Listing Office: Redfin Corp..
280 Boylston Street Unit 908, Newton
$549,000
1 Beds ⋅ 2 Baths ⋅ 73578825 MLS ⋅ ['Imperial Towers'] BLDG.
Fabulous Imperial Towers Chestnut Hill, totally updated One bedroom unit. Worry free lifestyle with the ease of full-service condominium living. Featuring an abundance of natural light, open floor plan, sweeping skyline city and tree top views, generous closets/storage space, Renovated bathrooms and kitchen. Enjoy the many amenities—heated seasonal pool, a new fitness center, a clubroom, library, EV Charging Station, bicycle storage & extra storage.1 car deeded carport space #53. The 24 Hour concierge, on-site management and live-in superintendent ensure effortless living, 100% owner occupied, move in/out fee $400. 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 908 at the Imperial Towers is Chestnut Hill living at its finest! OPEN HOUSE SHOWINGS BY APPOINTMENT ONLY, CONTACT LISTING AGENT.

280 Boylston Street Unit 908, Newton

Listing courtesy of Listing Agent: Cary Berger from Listing Office: Coldwell Banker Realty - Newton.
51 Florence St Unit 51, Newton
$1,585,000
3 Beds ⋅ 3 Baths ⋅ 73568608 MLS
Stylish 3-bed, 2.5-bath townhouse that lives like a single-family home, with a large side and backyard, private front entrance, and peaceful pine tree views. The main level features a spacious primary suite with walk-in closet and newly designed bath with double vanity. The updated kitchen offers a new oven and microwave, granite counters, and bar seating, opening to the living and dining areas with a wood-burning fireplace and beautiful hardwood floors. Sliding doors lead to a private deck, and a half bath completes the main level. Upstairs are two additional bedrooms, a fully renovated bath, and separate laundry room. The finished lower level provides extra living space ideal for a family room or home theater. Additional features include gas heat and cooking, central A/C, a 2-car garage, and two outdoor parking spaces. Convenient to Route 9, Route 128, and the Mass Pike, with Wegmans, Life Time, The Shops at Chestnut Hill, The Street Chestnut Hill, and more nearby.

51 Florence St Unit 51, Newton

Listing courtesy of Listing Agent: Alexander Averbuch from Listing Office: Averbuch Realty.
280 Boylston St Unit 308, Newton
$685,000
1 Beds ⋅ 2 Baths ⋅ 73575960 MLS
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. 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. Seller concessions are available towards buyers closing costs.

280 Boylston St Unit 308, Newton

Listing courtesy of Listing Agent: Dave White from Listing Office: OwnerEntry.com.
280 Boylston Street Unit 411, 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

Listing courtesy of Listing Agent: Gloria Conviser from Listing Office: Keller Williams Realty.
20 Hammond Pond Pkwy Unit 504, Newton
$749,000
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

Listing courtesy of Listing Agent: Alice Miles from Listing Office: Coldwell Banker Realty - Brookline.
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