Chestnut Hill Real Estate

Welcome to Chestnut Hill, Massachusetts—a picturesque suburb that beautifully blends the charm of small-town living with the vibrancy of urban amenities. Nestled just six miles from downtown Boston, this enchanting community is renowned for its lush landscapes, historic architecture, and a strong sense of community.

One of Chestnut Hill’s most appealing features is its stunning natural beauty. The area is adorned with tree-lined streets, manicured gardens, and expansive parks, providing residents with ample opportunities for outdoor recreation. The Chestnut Hill Reservoir offers a serene setting for walking, jogging, or simply enjoying a peaceful afternoon by the water.

Chestnut Hill is also home to a diverse array of cultural and educational institutions. It boasts prestigious schools, including Boston College and the renowned Chestnut Hill Academy, making it an ideal choice for families seeking quality education. The vibrant shopping scene at The Chestnut Hill Mall and local boutiques offers a delightful mix of high-end retail and unique finds, while the culinary landscape features an array of dining options, from cozy cafés to upscale restaurants.

Community spirit thrives in Chestnut Hill, with numerous events and gatherings throughout the year, fostering connections among residents. With its prime location, rich history, and a welcoming atmosphere, Chestnut Hill is more than just a place to live; it’s a place to call home. Whether you’re exploring the local parks, savoring a meal at a neighborhood eatery, or attending a community event, Chestnut Hill invites you to experience the best of suburban living with easy access to the vibrant culture of Boston.

Newest Listings in Chestnut Hill

$2,199,000

4 Beds ⋅ 5 Baths

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 : Marjorie Gold ---- Hammond Residential Real Estate

$2,850,000

6 Beds ⋅ 4 Baths

Discover timeless elegance and exceptional versatility in this beautifully updated 1938 Cape, thoughtfully designed for today's discerning family. Offering 6 bedrooms and 3.5 baths, the home features two primary bedrooms with private ensuite baths, including a sought-after first-floor retreat ideal for multigenerational living, guests, or an au pair. The chef's kitchen is appointed with stainless steel appliances, a gas range, wall oven, stone countertops, and a center island with seating for three. A welcoming den, formal dining room, and sun-filled breakfast area provide inviting settings for both everyday life and elegant entertaining. The finished lower level offers a versatile recreation room with a dedicated laundry area. Completing the home are an attached two-car garage and two additional off-street parking spaces, blending classic New England charm with modern comfort and convenience. Close to Roland Hayes School & Brookline High School, Route 9, Chestnut Hill Reservoir, Golf Courses, Green Line (MBTA) and The Mall at Chestnut Hill. Quick drives to Newton Centre or Brookline hubs for everyday groceries and dining.

44 Valley Rd, Brookline

Listing Courtesy of : The Kelleher Spalding Team ---- Gibson Sotheby's International Realty

$534,900

2 Beds ⋅ 1 Baths

Lovely, sunny one-bedroom condo currently configured as a two-bedroom, with the flexible second room also ideal for a home office or den.. The fully renovated interior features an open-concept floor plan, abundant natural light, new flooring, fresh paint, generous closet space, large bedrooms and individually controlled heat and air conditioning. The updated kitchen includes stainless steel appliances, white cabinetry, stone countertops, and a breakfast bar that opens to the living area. The renovated bathroom and flexible layout add comfort and versatility. Additional features include covered carport parking space #67 and additional deeded storage space. The professionally managed elevator building offers an on-site management office, renovated common areas, common laundry, two seasonal outdoor in-ground pools, landscaped grounds, a shared cookout area with grills and polenty of visitor parking. No smoking and no pets. Located near The Street Chestnut Hill and Wegmans, approximately 0.3 mi away, with shopping, dining, and fitness options nearby. The Shops at Chestnut Hill and Bloomingdale’s are approximately 0.9 mi away, Hammond Pond Reservation is approximately 0.8 mi away, and the Chestnut Hill Green Line D station is approximately 0.8 mi away. MBTA Route 60 bus service along the nearby Route 9 corridor provides access toward Kenmore Square and the Longwood Medical Area. Convenient access to Route 9 and I-95. Area schools include Bowen Elementary School, Oak Hill Middle School, and Newton South High School; buyers should verify current school assignments.

20 Hammond Pond Pkwy Unit 506, Newton

Listing Courtesy of : John Hollis ---- Amo Realty - Boston City Properties

$719,900

1 Beds ⋅ 1 Baths

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 : Dina Browne ---- Neponset Valley Real Estate

$1,995,000

4 Beds ⋅ 3 Baths

Fantastic move-in-ready 4 bedroom, 2.5 bathroom in Chestnut Hill. Set on a 15,000+ level private lot, 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 hardwood floors throughout, a fireplaced living room, lovely dining room, stainless and granite 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 : Amy Sassoon ---- Coldwell Banker Realty - Brookline

$1,299,000

3 Beds ⋅ 3 Baths

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 : Jessica Nagle ---- Maloney Properties LLC

$702,000

1 Beds ⋅ 2 Baths

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 : Patrick Reardon ---- Jason Mitchell Group

$2,399,000

4 Beds ⋅ 3 Baths

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 : Rose Hall ---- Blue Ocean Realty, LLC

$2,999,900

4 Beds ⋅ 4 Baths

An architectural masterpiece, this stunning custom-built contemporary home showcases modern design at its finest. Featuring soaring ceilings, an open-concept layout, and gallery-style lighting, the home is filled with natural light from expansive walls of windows offering breathtaking views. The gourmet kitchen is equipped with Miele appliances, perfect for both everyday living and entertaining. A fireplaced library on the main level provides a warm and inviting retreat. Enjoy spectacular sunsets from the sunroom or the private second-story balcony off the luxurious primary suite. The finished walk-out lower level offers exceptional additional space, featuring a dedicated gym area, a spacious game room, multiple bonus rooms that can be used as guest rooms, or office spaces, and abundant storage throughout. Step outside to a beautifully landscaped outdoor retreat with exterior stairs leading to a serene, courtyard garden, creating a peaceful setting for relaxation or entertaining.

28 Kesseler Way, Newton

Listing Courtesy of : Xianbin Yin ---- Harmony Hill Realty LLC

$2,895,000

2 Beds ⋅ 3 Baths

Price Reduction!Residence E201 occupies a privileged position as one of only five homes in the Mansion at Longyear, where history and modern luxury coexist in perfect harmony. Bathed in natural light, the home unfolds across nearly 2,300 square feet of elegant single-level living. The thoughtfully designed floor plan features two spacious bedroom suites with walk in closets, a private terrace, home office or comfortable space for an overnight guest, formal dining room, gourmet kitchen, and generous living areas that balance sophistication with comfort. For your guests convenience, a powder room is located off the living room. Two deeded garage parking spaces, private storage, elevator access, and a dedicated 24/7 staffed gatehouse complete a lifestyle defined by convenience and peace of mind. Only a handful of owners will ever call the Longyear Mansion home. Opportunities to acquire one of these residences are exceptionally rare. The home has been upgraded with new lighting, brand new carpeting, paint and new flat screen TVs. The unit includes a side by side washer and dryers. A well equipped gym is located within the Mansion. The historic grounds are well manicured and feature a seasonal pool with oversized umbrellas and seating.

120 Seaver St Unit E201, Brookline

Listing Courtesy of : Hope Krakoff ---- Coldwell Banker Realty - Boston

$749,900

2 Beds ⋅ 2 Baths

Rarely available first-floor residence at Chestnut Hill Towers, one of Chestnut Hill's premier full-service luxury communities. This spacious 2-bedroom, 2-bath home offers approximately 1,300 sq. ft. of comfortable living space with hardwood floors, an updated kitchen with stainless steel appliances, a generous primary suite with walk-in closet and renovated bath with walk-in shower, new bedroom flooring, in-unit laundry, and two deeded parking spaces conveniently located near the unit. A standout feature is the private fenced patio, creating an exceptional outdoor living space rarely found in condominium living. Residents enjoy outstanding amenities including a heated indoor pool, fitness center, tennis and pickleball courts, library, game room, walking trails, 24-hour concierge, on-site management, and beautifully maintained grounds. Conveniently located near The Street, Chestnut Hill Square, Wegmans, Longwood Medical Area, MBTA, and downtown Boston.

250 Hammond Pond Parkway Unit 102N, Newton

Listing Courtesy of : The Presti Group ---- Barrett Sotheby's International Realty

$549,900

1 Beds ⋅ 1 Baths

Chestnut Hill - Unique first floor 1 bedroom with family room, full dining room, eat in kitchen and 1 bath.Air conditioned, updated kitchen with white cabinetry, vinyl flooring, and corian counters Excellent closet space with additional storage in the basement. Elevator,1 assigned parking space, as well as available guest parking. Ideal south//west exposure and open concept floor plan allows natural all day bright light or sunlight year round. Professionally managed with an on sight office. Access to 2 outdoor, inground pools as well as a cookout area complete with grill. Great location, Newton Schools, walk to Wegmans, Equinox Fitness, C.H.Mall, Bloomingdales, The Street and more. Easy commute to Longwood Medical, #60 bus to Kenmore Square, close to C.H, Green Line T-Stop, Needs some TLC / decorating

20 Hammond Unit 102, Newton

Listing Courtesy of : Louis Wolfson ---- Louis Wolfson

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