The Greater Point, MA homes for sale & real estate

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22 Chestnut Pl #111, Brookline, MA 02445
22 Chestnut Pl #111, Brookline, MA 02445
22 Chestnut Pl #111, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Enjoy the best of urban living in this beautifully landscaped property near Longwood Medical Area, Brookline Village, Coolidge Corner, Brookline Hills T stop, shops, restaurants, Jamaica Pond, and the Emerald Necklace. This oversized 900 sq ft one-bedroom, 1.5 bath home in desirable Sargent Estates features a renovated kitchen that opens to a spacious living/dining area—ideal for entertaining. Large windows fill the home with natural light, enhanced by wood flooring and ample closet space. The updated baths include stylish tile, modern fixtures, and contemporary lighting. Professionally managed building with full amenities: concierge service, seasonal outdoor pool with lifeguard, saun

$579,000

1 bed1.5 baths901 sq ft

22 Chestnut Pl #111, Brookline, MA 02445

$467 HOA • Community pool • Very walkable

22 Chestnut Pl Unit G1, Brookline, MA 02445
22 Chestnut Pl Unit G1, Brookline, MA 02445
22 Chestnut Pl Unit G1, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Condo Fee: $387/mo. Experience elevated 1st floor corner unit living at Sargent Estates. This renovated 1-bedroom, 1-bath residence blends modern elegance with comfort in a pet-friendly building offering concierge service, a pool, and sauna. Ideally located near Longwood Medical Center, Brookline Village, and the MBTA Green D Line, it offers both serenity and urban accessibility. A neutral palette, abundant natural light, and open-concept layout create a welcoming, airy ambiance. The kitchen features Quartz counters, stainless steel appliances, and a breakfast bar flowing seamlessly into the living space—perfect for refined entertaining. Upscale comfort and convenience. Enjoy the best

$554,999

1 bed1 bath935 sq ft

22 Chestnut Pl Unit G1, Brookline, MA 02445

$387 HOA • Garage • Community pool

23 Cushing Rd, Brookline, MA 02445
23 Cushing Rd, Brookline, MA 02445
23 Cushing Rd, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Exceptional modern residence in Brookline, built in 2012 with cutting-edge green architecture. Crafted for efficiency and style, it features super-insulated, airtight construction, triple-pane windows, and rooftop solar. The striking façade and corner-wrapping windows flood the home with natural light. A sleek foyer leads to open living spaces, a showstopping acrylic staircase, and a first-floor primary suite with spa-like bath and adjacent office. The kitchen offers floating base cabinets, premium appliances, and south-facing glass walls. Upstairs includes a flexible family room, additional bedrooms, and access to a private rooftop deck with green roof. The lower level adds a rec ro

$3,245,000

3 beds4 baths4,047 sq ft

23 Cushing Rd, Brookline, MA 02445

8,509 sq ft lot • Very walkable

371 Walnut St, Brookline, MA 02445
371 Walnut St, Brookline, MA 02445
371 Walnut St, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
This 7BD, 5.5BA c1880 Greek Revival reflects historic character while embracing a meticulous, modern renovation. Set on a landscaped . 96AC lot, this stately 6,100+SF residence has been thoughtfully expanded & updated to enhance today’s modern living. Soaring ceilings, bespoke millwork & 5 FP highlight the architecture, while clean, timeless finishes offer understated elegance. Gracious entry connects 1st floor. LR w/ FP, built-ins, & french doors lead to porch. Cozy den w/ FP. DR w/ FP & french doors open to patio. Kitchen w/ custom cabinetry, eat-in, walk-in pantry, & butler’s pantry. Sun-filled FR w/ FP. Office, laundry, 1.5 BA complete level. 2nd

$5,250,000

7 beds5.5 baths6,193 sq ft

371 Walnut St, Brookline, MA 02445

0.96 acre lot • 4 garage spots • Very walkable

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77 Pond Ave #312, Brookline, MA 02445
77 Pond Ave #312, Brookline, MA 02445
77 Pond Ave #312, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Urban living at its finest in Brookline! Spacious one-bedroom unit with hardwood floors and central air conditioning. Enjoy the convenience of heated garage parking. The Brook House offers exceptional amenities, including onsite management, 24/7 security, a heated outdoor pool, a state-of-the-art fitness center (with steam room, sauna, weight room, and yoga studio), a resident lounge, tennis and basketball courts, and BBQ areas. Ideally located near the T (D/E lines), Brookline Village, Coolidge Corner, the Longwood Medical Area, Fenway, shopping, dining, and adjacent to Leverett Pond. Ideal for both homeowners and investors. Take advantage of unparalleled amenities and a prime location&mda

$509,000

1 bed1 bath710 sq ft

77 Pond Ave #312, Brookline, MA 02445

$1,130 HOA • Garage • Community pool

111 Perkins St #072, Boston, MA 02130
111 Perkins St #072, Boston, MA 02130
111 Perkins St #072, Boston, MA 02130
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Sparkling two bedroom home on the 7th floor. This corner unit will welcome you home with a charming foyer with two closets leading to the expansive dining and living room. Your eye will be drawn to the picture window with treetop views and private balcony. Updated kitchen with designer cabinetry, stone countertops and stainless appliances. The primary bedroom has a walk in closet and great west facing views with sensational sunsets. The second bedroom works perfectly as a guest room, den, nursery or office. The bath has been renovated with new tile and vanity. Jamaicaway Tower is a full service building with amenities rarely found. There are 24/7 doormen, onsite management and maintenance

$479,000

2 beds1 bath1,130 sq ft

111 Perkins St #072, Boston, MA 02130

$1,452 HOA • Garage • Community pool

14 Irving St, Brookline, MA 02445
14 Irving St, Brookline, MA 02445
14 Irving St, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Truly stunning with historic charm, this Brookline Georgian Revival is ready for its next chapter. Ideally located in the Pill Hill District, this home is a rarity given most of the original detailing & features remain intact from the Palladian windows to the tracery in the sidelights & fanlight at the sunlit front entrance. Gracious formal dining & living room with Delft tile fireplace surround and more original detailing. Eat in kitchen w/ adjacent to an over-sized Butler's pantry. Rear mudroom entry and powder room complete the first level. Second level is graced by a second Palladian window and lovely, open landing. Three nicely proportioned bedrooms sit at each corner

$2,500,000

5 beds3.5 baths3,873 sq ft

14 Irving St, Brookline, MA 02445

7,670 sq ft lot • 2 garage spots • Community pool

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99 Pond Ave #608, Brookline, MA 02445
99 Pond Ave #608, Brookline, MA 02445
99 Pond Ave #608, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Discover your urban oasis in Brookline! Newly updated, a spacious 1-bedroom unit offers breathtaking courtyard views, a beautifully modern kitchen & bath, gleaming hardwood floors, and central AC. Heated garage parking adds convenience. The Brook House redefines luxury living with onsite management, 24/7 security, a heated outdoor pool, extensive gym (steam/sauna, weight room, yoga studio), resident lounge, tennis/basketball courts, and BBQ areas. Enjoy an A+ location near the T (D/E lines), Brookline Village/Coolidge Corner, Longwood Medical Area, Fenway, shops, and restaurants, adjacent to Leverett Pond & the Emerald Necklace. Perfect for homeowners & investors. Experien

$579,000

1 bed1 bath765 sq ft

99 Pond Ave #608, Brookline, MA 02445

$787 HOA • Garage • Community pool

33 Pond Ave Ph 1208, Brookline, MA 02445
33 Pond Ave Ph 1208, Brookline, MA 02445
33 Pond Ave Ph 1208, Brookline, MA 02445
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
Experience elevated living in this fully renovated two bedroom, two level penthouse spanning 1,840 sq. ft. Thoughtfully redesigned for modern luxury, this home features a sleek chef’s kitchen, expansive open-concept living/dining area with soaring ceilings, recessed lighting, red oak floors, and sweeping views from oversized windows. Dual-level access adds convenience, while a private rooftop terrace offers your own urban oasis. Both bedroom suites boast elegant ensuite baths, generous closets, and custom window treatments. Enjoy resort-style amenities including a heated Olympic-style pool, fitness center, tennis courts, BBQ patio, resident lounge, 24-hour security, and two-car garage

$999,000

2 beds2.5 baths1,840 sq ft

33 Pond Ave Ph 1208, Brookline, MA 02445

22.96 acre lot • $1,901 HOA • 2 garage spots

111 Perkins St #108, Boston, MA 02130
111 Perkins St #108, Boston, MA 02130
111 Perkins St #108, Boston, MA 02130
ABOUT THIS HOME
The Greater Point, MA Homes for Sale
NEW TO MARKET!!! Beautiful 10th floor one bedroom with great views and private balcony. Freshly painted. Plenty of closet space. Jamaicaway Tower and Townhouses is a full-service building in the heart of Jamaica Plain on the Emerald Necklace and Jamaica Pond. A carefree lifestyle with professional doormen, on-site management and maintenance and great recreational facilities including a heated seasonal pool, tennis/pickleball court and gym facilities. This is a Coop, which means that monthly fees include everything except garage parking, cable and electric. A short commute to downtown Boston and Longwood Medical area.

$329,000

1 bed1 bath845 sq ft

111 Perkins St #108, Boston, MA 02130

$1,562 HOA • Garage • Community pool

Property at 32 Juniper St #91, Brookline, MA 02445, 2 beds, 1 bath

$639,000

2 beds1 bath822 sq ft

32 Juniper St #91, Brookline, MA 02445

Property at 99 Pond Ave #326, Brookline, MA 02445, 1 bed, 1 bath

$569,000

1 bed1 bath870 sq ft

99 Pond Ave #326, Brookline, MA 02445

Property at 60 Glen Rd #107, Brookline, MA 02445, 1 bed, 1 bath

$499,900

1 bed1 bath582 sq ft

60 Glen Rd #107, Brookline, MA 02445

Property at 77 Pond Ave Spot 478, Brookline, MA 02445

$200,000

— beds— baths— sq ft

77 Pond Ave Spot 478, Brookline, MA 02445

Property at 111 Perkins St #42, Boston, MA 02130, 2 beds, 1 bath

$459,900

2 beds1 bath1,134 sq ft

111 Perkins St #42, Boston, MA 02130

Property at 33 Pond Ave Ph 1207, Brookline, MA 02445, 2 beds, 2.5 baths

$966,000

2 beds2.5 baths1,800 sq ft

33 Pond Ave Ph 1207, Brookline, MA 02445

Property at 65 Glen Rd Unit H4, Brookline, MA 02445, 2 beds, 1.5 baths

$849,000

2 beds1.5 baths1,213 sq ft

65 Glen Rd Unit H4, Brookline, MA 02445

Property at 21 Sargent Crossway, Brookline, MA 02445, 5 beds, 6.5 baths

$8,000,000

5 beds6.5 baths5,772 sq ft

21 Sargent Crossway, Brookline, MA 02445

Property at 36 Allerton St, Brookline, MA 02445, 5 beds, 4.5 baths

$4,350,000

5 beds4.5 baths5,122 sq ft

36 Allerton St, Brookline, MA 02445

Property at 30 Cumberland Unit W-4, Brookline, MA 02445, 2 beds, 2 baths

$945,000

2 beds2 baths1,246 sq ft

30 Cumberland Unit W-4, Brookline, MA 02445

Property at 99 Pond Ave #706, Brookline, MA 02445, 2 beds, 2 baths

$695,000

2 beds2 baths975 sq ft

99 Pond Ave #706, Brookline, MA 02445

Property at 33 Pond Ave #419, Brookline, MA 02445, 2 beds, 2 baths

$825,000

2 beds2 baths1,270 sq ft

33 Pond Ave #419, Brookline, MA 02445

Property at 111 Perkins St #174, Boston, MA 02130, 1 bed, 1 bath

$415,000

1 bed1 bath805 sq ft

111 Perkins St #174, Boston, MA 02130

Property at 99 Pond Ave #802, Brookline, MA 02445, 2 beds, 2 baths

$999,999

2 beds2 baths1,855 sq ft

99 Pond Ave #802, Brookline, MA 02445

Average home prices near The Greater Point, MA

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The Greater Point, MA real estate trends

All Home Types trends in The Greater Point, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$880,000

+15.7% YoY | May 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

May 2025

Growth

% YoY

The Greater Point, MA

$880,000

+15.7%

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