Homes with Pools for Sale in Brookline, MA

111 homes

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OPEN SAT, 12PM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in Brookline, MA:
Attention developers, investors and end-users alike! Unlock the rare opportunity of this brick two-family that sits on a large lot in a convenient Chestnut Hill location. Both units feature two good sized bedrooms and one bathroom. Beautiful hardwood floors throughout and a fireplace in each unit’s living and dining areas. The kitchens lead to screened-in balconies which overlook the backyard. The lower-level boosts laundry, plenty of storage and two garage parking spaces. Easy access to The Street, the MBTA Green D line, Brookline Reservoir, Longwood Medical Area, and everything Brookline has to offer. Recently rented as furnished units, the property to be delivered without tenants.

$1,999,999

4 beds2 baths1,920 sq ft

675 Chestnut Hill Ave, Brookline, MA 02445

Brick two-family • Large lot • Backyard

OPEN WED, 10AM TO 11AM

ABOUT THIS HOME
Home with a Pool for sale in Brookline, MA:
A sweet house with loads of potentail. Needs everything. Large lot!

$1,100,000

2 beds2 baths1,230 sq ft

18 Cushing Rd, Brookline, MA 02445

9,839 sq ft lot • Garage • Community pool

ABOUT THIS HOME
Home with a Pool for sale in Brookline, MA:
Discover this charming home tucked behind a private gate in one of the area’s most sought-after estate locations. The home has been lovingly maintained and thoughtfully updated with finishes that elevate both style and functionality. A two-story foyer with a sweeping curved staircase sets an elegant tone upon entry. At the heart of the home, a new modern gourmet kitchen offers a large center island and sunlit breakfast area that flows seamlessly to the family room, and opens to an expansive patio and lush yard. A bedroom, den and office complete the first floor. Upstairs, the primary suite is complemented by four additional bedrooms, each with its own en-suite bathroom for exceptional

$6,649,000

6 beds6.5 baths7,450 sq ft

88 Cutler Ln, Chestnut Hill, MA 02467

Large center island • Lush yard • Expansive patio

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Brookline, MA:
Step into this sun-drenched and expansive 2 bedroom, 2 bath that lives large thanks to an open-concept design and generous windows allowing light to pour in throughout the day. The living and dining areas flow seamlessly to a balcony offering serene park views, creating the perfect setting for entertaining or relaxed everyday living. Key features include a modern, well-proportioned kitchen visible from the main living area, a primary suite with a private bath and ample walk-in closet space, a second bedroom or office, and hardwood floors throughout, with a neutral palette ready for any decor. The private balcony offers outdoor seating and greenery-filled views, overlooking the magically pea

$999,999

2 beds2 baths1,598 sq ft

80 Park St #23, Brookline, MA 02446

Open-concept design • Private balcony • Park views

ABOUT THIS HOME
Home with a Pool for sale in Brookline, MA:
Welcome to 80onVernon, a boutique collection of 8 new luxury condominiums in Brookline’s Coolidge Corner. Each home offers 3 bedrooms, modern finishes, garage parking, and private outdoor spaces. This unit features two garage parking spaces, two balconies, a den, and a direct access elevator. The building’s sleek exterior, oversized windows, and glass balconies maximize light and park views. Residents enjoy a stylish lobby with secure mail and package areas. Interiors feature 9-foot ceilings, floor-to-ceiling Drutex windows, open living spaces with fireplaces, and kitchens with waterfall-edge stone countertops, Dell Anno cabinetry, and Thermador appliances. Wood accents and desi

$3,695,000

3 beds2.5 baths2,125 sq ft

80 Vernon Unit 2B, Brookline, MA 02446

Open living spaces • Glass balconies • Oversized windows

Property at 757 Washington St Unit 2 - PH, Brookline, MA 02446, 5 beds, 4.5 baths

$3,150,000

5 beds4.5 baths3,838 sq ft

757 Washington St Unit 2 - PH, Brookline, MA 02446

Property at 1731 Beacon St #1502, Brookline, MA 02445, 2 beds, 2 baths

$1,150,000

2 beds2 baths1,263 sq ft

1731 Beacon St #1502, Brookline, MA 02445

Property at 90 Addington #1, Brookline, MA 02445, 5 beds, 4 baths

$2,995,000

5 beds4 baths3,450 sq ft

90 Addington #1, Brookline, MA 02445

Property at 37 Englewood Ave #3, Brookline, MA 02445, 3 beds, 3 baths

$1,275,000

3 beds3 baths1,814 sq ft

37 Englewood Ave #3, Brookline, MA 02445

Property at 1778 Beacon St #302, Brookline, MA 02445, 2 beds, 1 bath

$1,157,000

2 beds1 bath1,157 sq ft

1778 Beacon St #302, Brookline, MA 02445

Property at 1880 Beacon St #6, Brookline, MA 02445, 1 bed, 1 bath

$489,000

1 bed1 bath474 sq ft

1880 Beacon St #6, Brookline, MA 02445

Property at 255 Tappan St, Brookline, MA 02445, 7 beds, 5 baths

$2,999,999

7 beds5 baths4,171 sq ft

255 Tappan St, Brookline, MA 02445

Property at 142 Crafts Rd, Chestnut Hill, MA 02467, 8 beds, 6.5 baths

$8,750,000

8 beds6.5 baths9,400 sq ft

142 Crafts Rd, Chestnut Hill, MA 02467

Property at 1763 Beacon St Unit A, Brookline, MA 02445, 1 bed, 1 bath

$499,900

1 bed1 bath585 sq ft

1763 Beacon St Unit A, Brookline, MA 02445

Property at 3 Englewood Ave #9, Brookline, MA 02445, 1 bed, 1 bath

$559,000

1 bed1 bath680 sq ft

3 Englewood Ave #9, Brookline, MA 02445

Property at 19 Westbourne #2, Brookline, MA 02446, 1 bed, 1 bath

$489,000

1 bed1 bath670 sq ft

19 Westbourne #2, Brookline, MA 02446

Property at 125 Pleasant St #201, Brookline, MA 02446, 1 bed, 1 bath

$715,000

1 bed1 bath798 sq ft

125 Pleasant St #201, Brookline, MA 02446

Property at 55 Reservoir Rd #2, Chestnut Hill, MA 02467, 3 beds, 1.5 baths

$799,000

3 beds1.5 baths1,087 sq ft

55 Reservoir Rd #2, Chestnut Hill, MA 02467

Property at 60 Longwood Ave #307, Brookline, MA 02446, 1 bed, 1.5 baths

$675,000

1 bed1.5 baths955 sq ft

60 Longwood Ave #307, Brookline, MA 02446

Property at 72 Cypress St #1, Brookline, MA 02445, 2 beds, 1 bath

$998,000

2 beds1 bath1,115 sq ft

72 Cypress St #1, Brookline, MA 02445

Property at 771 Heath St #771, Chestnut Hill, MA 02467, 2 beds, 3.5 baths

$1,750,000

2 beds3.5 baths3,070 sq ft

771 Heath St #771, Chestnut Hill, MA 02467

Property at 45 Bartlett Cres #305, Brookline, MA 02446, 2 beds, 2 baths

$1,233,850

2 beds2 baths946 sq ft

45 Bartlett Cres #305, Brookline, MA 02446

Property at 80 Vernon Unit 3B, Brookline, MA 02446, 3 beds, 2.5 baths

$3,649,000

3 beds2.5 baths2,125 sq ft

80 Vernon Unit 3B, Brookline, MA 02446

Property at 16 South St, Chestnut Hill, MA 02467, 6 beds, 5 baths

$3,800,000

6 beds5 baths5,667 sq ft

16 South St, Chestnut Hill, MA 02467

Property at 14 Green St Ph 1, Brookline, MA 02446, 3 beds, 3.5 baths

$3,325,000

3 beds3.5 baths2,056 sq ft

14 Green St Ph 1, Brookline, MA 02446

Property at 24 Auburn Unit U2, Brookline, MA 02446, 4 beds, 3 baths

$2,550,000

4 beds3 baths1,855 sq ft

24 Auburn Unit U2, Brookline, MA 02446

Property at 487 Boylston St #3, Brookline, MA 02445, 4 beds, 2 baths

$1,440,000

4 beds2 baths2,276 sq ft

487 Boylston St #3, Brookline, MA 02445

Property at 1125 W Roxbury Pkwy, Chestnut Hill, MA 02467, 4 beds, 3 baths

$2,799,000

4 beds3 baths3,859 sq ft

1125 W Roxbury Pkwy, Chestnut Hill, MA 02467

Property at 184 Rawson Rd, Brookline, MA 02445, 5 beds, 3.5 baths

$2,000,000

5 beds3.5 baths2,460 sq ft

184 Rawson Rd, Brookline, MA 02445

Property at 45 Bartlett #206, Brookline, MA 02446, 2 beds, 2 baths

$1,315,000

2 beds2 baths1,013 sq ft

45 Bartlett #206, Brookline, MA 02446

Property at 1014 Boylston St, Chestnut Hill, MA 02467, 7 beds, 9.5 baths

$19,000,000

7 beds9.5 baths13,343 sq ft

1014 Boylston St, Chestnut Hill, MA 02467

Property at 65 Francis, Brookline, MA 02446, 4 beds, 4.5 baths

$2,845,000

4 beds4.5 baths2,900 sq ft

65 Francis, Brookline, MA 02446

Property at 540 Chestnut Hill Ave, Brookline, MA 02445, 5 beds, 4.5 baths

$5,000,000

5 beds4.5 baths6,419 sq ft

540 Chestnut Hill Ave, Brookline, MA 02445

Property at 125 Crowninshield Rd #125, Brookline, MA 02446, 3 beds, 2.5 baths

$1,995,000

3 beds2.5 baths2,163 sq ft

125 Crowninshield Rd #125, Brookline, MA 02446

Property at 77 Pond Ave #1103, Chestnut Hill, MA 02467, 1 bed, 1 bath

$572,000

1 bed1 bath860 sq ft

77 Pond Ave #1103, Chestnut Hill, MA 02467

Property at 71 Greenough St Unit 71-1, Brookline, MA 02445, 3 beds, 3.5 baths

$2,999,999

3 beds3.5 baths2,552 sq ft

71 Greenough St Unit 71-1, Brookline, MA 02445

Property at 15 Glenland, Chestnut Hill, MA 02467, 5 beds, 4.5 baths

$3,749,000

5 beds4.5 baths4,711 sq ft

15 Glenland, Chestnut Hill, MA 02467

Property at 77 Pond Ave #1103, Brookline, MA 02445, 1 bed, 1 bath

$572,000

1 bed1 bath860 sq ft

77 Pond Ave #1103, Brookline, MA 02445

Property at 3 Glenoe Rd, Chestnut Hill, MA 02467, 4 beds, 4 baths

$2,295,000

4 beds4 baths4,855 sq ft

3 Glenoe Rd, Chestnut Hill, MA 02467

Property at 80 Vernon St Unit 1-A, Brookline, MA 02446, 3 beds, 2.5 baths

$2,759,000

3 beds2.5 baths1,662 sq ft

80 Vernon St Unit 1-A, Brookline, MA 02446

Property at 58 Kent Unit U404, Brookline, MA 02445, 2 beds, 2 baths

$1,999,000

2 beds2 baths1,189 sq ft

58 Kent Unit U404, Brookline, MA 02445

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The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Redfin are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated Wed Dec 03 2025. Neither the listing broker nor Redfin shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. All properties are subject to prior sale, changes, or withdrawal. © 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Homes with Pools for Sale in Brookline

There are currently 111 homes with pools for sale in Brookline at a median listing price of $1.62M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Brookline stay on the market for 49 days and receive 1 offers. Popular neighborhoods include Jamaica Plain, Roslindale, Brighton, Allston, and West Roxbury. This map is refreshed with the newest listings in Brookline every 15 minutes.

In the past month, 44 homes have been sold in Brookline. In addition to houses in Brookline, there were also 153 condos, 18 townhouses, and 10 multi-family units for sale in Brookline last month. Brookline is a fairly walkable city in Norfolk County with a Walk Score of 81. Brookline is home to approximately 59,627 people. Find your dream home in Brookline using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Brookline are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Brookline. Our Brookline real estate stats and trends will give you more information about home buying and selling trends in Brookline. If you're looking to sell your home in the Brookline area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Brookline with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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