Chestnut Hill Homes under $2 million

Chestnut Hill Homes under $2 million

Welcome to Chestnut Hill, Massachusetts, a delightful blend of suburban charm and urban convenience. Nestled just a stone’s throw from Boston, this picturesque community is renowned for its tree-lined streets, historic architecture, and a vibrant local culture that captures the essence of New England living.

Chestnut Hill boasts a rich history and a diverse population, making it a wonderful place to call home. The area is characterized by its stunning homes, many of which reflect classic New England design, with expansive lawns and meticulously landscaped gardens. For those seeking the perfect residence, you'll be pleased to discover that there are beautiful homes available for under $2 million. This price range opens the door to a variety of options, from cozy single-family homes to spacious properties ideal for families or professionals looking for a serene retreat.

In addition to its charming residences, Chestnut Hill offers a plethora of amenities. Enjoy shopping at local boutiques, dining at exquisite restaurants, or taking a leisurely stroll through one of the many parks in the area. The nearby Chestnut Hill Reservoir provides a scenic backdrop for outdoor activities, including jogging, walking, and picnicking.

Families will appreciate the excellent schools in the region, which are known for their strong academic programs and community involvement. With easy access to public transportation and major highways, commuting to downtown Boston is a breeze, making Chestnut Hill an ideal location for those who want the best of both worlds.

Experience the warmth and welcoming spirit of Chestnut Hill, where your dream home awaits!

Newest Chestnut Hill Homes under $2 million

250 Hammond Pond Parkway Unit 310N, Newton
$550,000
1 Beds ⋅ 2 Baths ⋅ 73597326 MLS ⋅ ['Towers Of Chestnut Hill'] BLDG.
A rare opportunity to experience the very best of luxury living at The Towers of Chestnut Hill, Hammond Pond Parkway’s most distinguished condominium residence. A premier, five-star community, The Towers embodies the essence of sophisticated, maintenance-free Chestnut Hill living. On rare occasions, a one-bedroom residence with 1½ baths becomes available, making this third-floor offering particularly special. Spanning nearly 1,000 square feet, this gracious home showcases exceptional space, abundant natural light, and generously proportioned rooms that create an impressive sense of openness. Residents enjoy an extraordinary collection of amenities designed to complement an effortless lifestyle, including 24-hour concierge service, an indoor heated swimming pool, a newly installed fitness center, clubhouse, two resident lounges, library, pickleball and tennis courts, basketball court, landscaped gardens, gardening club, outdoor fire pit and grilling areas. Additional amenities include a children’s play area, game room featuring ping-pong and foosball, secure package room, bicycle storage, and two elevators. Ideally situated just steps from the Longwood Medical Area shuttle and minutes from Longwood Medical, premier shopping, dining, and everything Chestnut Hill has to offer. A truly rare offering in one of Chestnut Hill’s most iconic luxury condominium communities. 1 deeded garage space included in the sale. Solid investment.

250 Hammond Pond Parkway Unit 310N, Newton

Listing courtesy of Listing Agent: Richard C. Dore from Listing Office: Hammond Residential Real Estate.
622 Chestnut Hill Ave, Brookline
$1,379,000
3 Beds ⋅ 2 Baths ⋅ 73597241 MLS
Location, lifestyle & versatility await in Brookline's coveted Fisher Hill neighborhood! This charming 3-bed, 2-bath multi-level home offers the perfect blend of comfort, convenience & endless possibilities! Featuring a thoughtful layout, gleaming hardwood floors, an abundance of natural light & flexible living spaces, this home is designed to accommodate a variety of lifestyles. Recent updates include fresh interior & exterior paint, upgraded light fixtures, a brand-new induction range & more! Enjoy the privacy of a fenced-in backyard, perfect for outdoor entertaining, gardening or simply unwinding, plus the convenience of an attached one-car garage. Nestled in one of Greater Boston's most desirable communities, this home is just minutes from Boston College, The Shops at Chestnut Hill, Brookline Reservoir & the Green Line at Cleveland Circle, offering unparalleled access to shopping, dining, recreation & Boston. With Brookline's highly rated schools and an unbeatable location, this move-in-ready gem is ready for its next chapter. Bring your vision and make this special property your own!

622 Chestnut Hill Ave, Brookline

Listing courtesy of Listing Agent: The Dovetail Group from Listing Office: eXp Realty LLC - Corporate Office.
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
$1,799,000
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
$925,000
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.

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
$389,000
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.
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