Chestnut Hill Homes under $2 million

Welcome to Chestnut Hill, Massachusetts – a charming suburban oasis that perfectly blends the tranquility of nature with the vibrancy of city life. Nestled just a stone's throw away from downtown Boston, Chestnut Hill boasts an enviable location that offers residents easy access to the cultural and professional opportunities of the city while providing a serene retreat at home.

Known for its picturesque streets lined with stately trees and elegant homes, Chestnut Hill is a community that prides itself on its rich history and architectural diversity. From classic Colonial-style houses to contemporary designs, the real estate market here offers a delightful variety of options, including stunning homes priced under $2 million. This makes it an ideal choice for families, young professionals, and anyone looking to invest in a beautiful property without breaking the bank.

In addition to its stunning homes, Chestnut Hill is home to top-rated schools, lush parks, and vibrant shopping districts, including the popular Chestnut Hill Square and The Mall at Chestnut Hill. Residents can enjoy a leisurely afternoon at the picturesque Hammond Pond Reservation or explore the local dining scene, which features everything from cozy cafes to upscale restaurants.

Whether you’re seeking a peaceful retreat or a lively community atmosphere, Chestnut Hill offers the best of both worlds. With its affordable yet luxurious homes and an abundance of amenities, this enchanting neighborhood is truly a hidden gem waiting to be discovered. Come and experience the charm of Chestnut Hill – your dream home awaits!

Newest Chestnut Hill Homes under $2 million

$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.

$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..

$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!

280 Boylston Street Unit 908, Newton

Listing courtesy of Listing Agent: Cary Berger from Listing Office: Coldwell Banker Realty - 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.

$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.

$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.

$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.

$1,749,000

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

Listing courtesy of Listing Agent: Mary Lochner from Listing Office: Coldwell Banker Realty - 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. Laundry room in unit. Plentiful storage includes coat & linen closets, bedroom walk-in closet. 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 of beautiful grounds, snow removal, on-site property management. Prime location across from Chestnut Hill Reservoir’s scenic trail & sunset views. Within a half mile of Cleveland Circle shopping & dining, Boston College, Cassidy Park tennis courts, several subway & bus lines.

2430 Beacon Street Unit 104, Boston

Listing courtesy of Listing Agent: Jonathan Minerick from Listing Office: homecoin.com.

250 Hammond Pond Parkway Unit 1105S, Newton

$700,000

2 Beds ⋅ 2 Baths ⋅ 73569956 MLS ⋅ ['Towers Of Chestnut Hill'] BLDG.

Distinguished luxury living at the prestigious Towers of Chestnut Hill in Chestnut Hill, Massachusetts. This impressive 11th-floor residence offers 2 bedrooms, 2 bathrooms, and breathtaking panoramic views of the Boston skyline. As the most prominent landmark on Hammond Pond Parkway, the Towers is renowned for its exceptional lifestyle and premier amenities.Enjoy picturesque scenery, spectacular sunrises, and full-service living with a 24-hour concierge, doorman, on-site superintendent, and gated security. Residents have access to an indoor swimming pool, tennis and pickleball courts, basketball court, two private resident lounges, and a dedicated Longwood Medical Area shuttle. Ideally located just moments from Longwood Medical, The Street at Chestnut Hill, The Shops at Chestnut Hill, fine dining, and everyday conveniences, this is luxury condominium living at its finest.

250 Hammond Pond Parkway Unit 1105S, Newton

Listing courtesy of Listing Agent: Richard C. Dore from Listing Office: Hammond Residential Real Estate.

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