Homes with Pools for Sale in Chestnut Hill, MA

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ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, 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

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, 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 Chestnut Hill, MA:
Chestnut Hill, Brookline. Designed in 1905 by Chapman & Frazer, this Spanish Colonial estate unites house and garden across approx 1.3 acres. About 9,400 sq ft on four finished levels with 8 beds and 6.5 baths. Chef’s kitchen with oversized island, walk-in pantry, and pro appliances opens to dining and a stone terrace. Formal living and dining pair with a quiet library and a large family room. The serene primary suite offers a spa bath and custom dressing closets. Upper levels add flexible rooms for guests, work, and play. The finished lower level provides media, fitness, recreation, and storage. Courtyards, terraces, and defined garden rooms create a private setting. Historic 1

$8,750,000

8 beds6.5 baths9,400 sq ft

142 Crafts Rd, Chestnut Hill, MA 02467

Large family room • Quiet library • Stone terrace

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Ad

$19,000,000

7 beds9.5 baths13,343 sq ft

1014 Boylston St, Chestnut Hill, MA 02467

Grand entry hall • Sunken living room • Expansive great room

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
Renovate or build new, on one of Brookline’s most desirable and picturesque streets and sought after neighborhoods. Existing GLA of nearly 5k sqft (988 finished basement), or build 4396 sqft by right on upper floors. Survey and existing conditions plans are available. Demo hold expires October 2025

$2,295,000

4 beds4 baths4,855 sq ft

3 Glenoe Rd, Chestnut Hill, MA 02467

0.4 acre lot • 2 garage spots • Built 1939

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 130 Cabot St, Chestnut Hill, MA 02467, 6 beds, 8 baths

$6,995,000

6 beds8 baths9,755 sq ft

130 Cabot St, Chestnut Hill, MA 02467

Property at 321 Hammond Pond Pkwy #103, Chestnut Hill, MA 02467, 2 beds, 2 baths

$1,099,000

2 beds2 baths1,350 sq ft

321 Hammond Pond Pkwy #103, Chestnut Hill, MA 02467

Property at 321 Hammond Pond Pkwy Unit U301, Chestnut Hill, MA 02467, 2 beds, 2.5 baths

$1,225,000

2 beds2.5 baths1,527 sq ft

321 Hammond Pond Pkwy Unit U301, Chestnut Hill, MA 02467

Property at 0 Glenoe Rd, Chestnut Hill, MA 02467

$2,295,000

— beds— baths— sq ft

0 Glenoe Rd, Chestnut Hill, MA 02467

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ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
Experience the perfect blend of character and modern comfort in this sun-drenched Washington Square condo. This 1-bedroom garden-level residence features gleaming hardwood floors and a thoughtfully updated kitchen equipped with brand-new appliances. Residents enjoy the privacy of an individual entrance, along with the rare convenience of a deeded laundry room and a dedicated storage suite right next door. Situated steps from the Green Line, local dining, and Star Market, this home offers an effortless commute and exceptional value, with a condo fee that covers heat, hot water, and gas.

$429,000

1 bed1 bath557 sq ft

20 Claflin Rd Unit A, Brookline, MA 02445

Individual entrance • Updated kitchen • Deeded laundry room

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
1-Bed Garden-Level Condo | 502 Sq Ft | Cleveland Circle. PRICED FOR COMPLETE RENOVATION. Yes it needs everything: full kitchen, bathroom, flooring, heating radiators, windows, lighting, and paint. Prime Cleveland Circle location, Green Line, BC, restaurants, Street parking with rental spots often available across the street. Well-managed 130-unit complex with in-ground pool, on-site laundry, professional management. THE NUMBERS: Recent sale 2025 Unit-2 (537 sq ft, beautifully renovated) sold $374,000. Budget $40K-$50K+ for renovations. Assessed $333,000.Create your vision in a desirable location at a realistic price. This is an Estate Sale on behalf of an incapacitated person subject to obt

$295,000

1 bed1 bath502 sq ft

30 Kinross Rd #1, Brighton, MA 02135

In-ground pool • On-site laundry • $437 HOA

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
NEW CONSTRUCTION! 1BED+DEN/2BATH, 3.5% COBROKE THROUGH 2025! Ready for occupancy. Live the life of luxury on higher ground! Introducing 1515 Comm Ave, the top tier luxury condo community in the heart of vibrant Brighton. Designed & built to foster Feng Shui, our 102 meticulously crafted homes combine comfort & style with high-end fixtures, premium appliances & open layouts that enhance your every day living experience. With residences ranging from Studio-3Beds, we have over 15 layouts for you to choose from. Amenities include 24/7 concierge, co-working & private WFH spaces, fitness center equipped w/ on-demand fitness, expansive clubroom w/ catering kitchen, multi-sp

$849,000

1 bed2 baths903 sq ft

1515 Commonwealth Ave #509, Boston, MA 02135

New construction • Premium appliances • High-end fixtures

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
Welcome to this inviting 2-bedroom condo located in the sought-after Allston neighborhood. This home offers updated flooring throughout, a fully equipped kitchen, and a dedicated dining area perfect for entertaining. Both bedrooms are generously sized and complemented by a stylish, modern full bath. For added convenience, a common laundry room is located just down the hall. With close proximity to BU and BC and a quick, easy commute to downtown, this condo delivers comfort, convenience, and an unbeatable location.

$490,000

2 beds1 bath746 sq ft

10 Scottfield Rd #2, Allston, MA 02134

Updated flooring • Common laundry room • $408 HOA

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
Welcome to The Jordan, Brighton’s newest boutique condominium ideally located on the Brookline town line. This well-designed complex features 34 modern units, just steps from Whole Foods and public transportation, offering unparalleled convenience for urban living. Residents enjoy premium amenities, including a landscaped private courtyard with grill, a spacious rooftop terrace with 360° views, a fitness center, resident lounge and secure underground assigned parking. Each unit showcases open-concept layouts and high-end finishes, with a gourmet kitchen featuring Fisher & Paykel appliances and sleek quartz countertops. With over a dozen unique floor plans, The Jordan offers

$1,299,000

2 beds2 baths1,134 sq ft

249 Corey Rd #203, Boston, MA 02135

Rooftop terrace • Fitness center • Gourmet kitchen

ABOUT THIS HOME
Home with a Pool for sale in Chestnut Hill, MA:
Experience refined living at The Jordan, ideally located near the Brookline town line in vibrant Brighton. This two-bedroom plus den corner residence boasts expansive triple-pane windows, open-concept living, dining, and kitchen areas with natural light and sweeping views. The modern kitchen features sleek quartz countertops and premium Fisher & Paykel stainless steel appliances, perfect for both everyday living and entertaining. The primary suite includes a private en-suite bath, offering comfort and privacy. One garage parking space is included. With over a dozen distinctive floor plans available, The Jordan offers exceptional options to match your lifestyle.

$1,149,000

2 beds2 baths1,166 sq ft

249 Corey Rd #207, Boston, MA 02135

Quartz countertops • Triple-pane windows • Corner residence

Property at 1666 Commonwealth Ave #24, Brighton, MA 02135, 1 bed, 1 bath

$449,900

1 bed1 bath573 sq ft

1666 Commonwealth Ave #24, Brighton, MA 02135

Property at 1620 Beacon St, Brookline, MA 02446, 3 beds, 5 baths

$4,600,000

3 beds5 baths99,999 sq ft

1620 Beacon St, Brookline, MA 02446

Property at 1607 Commonwealth Ave #14, Brighton, MA 02135, 1 bath

$324,000

0 beds1 bath425 sq ft

1607 Commonwealth Ave #14, Brighton, MA 02135

Property at 1650 Commonwealth Ave Unit 304A, Brighton, MA 02135, 2 beds, 2 baths

$879,000

2 beds2 baths954 sq ft

1650 Commonwealth Ave Unit 304A, Brighton, MA 02135

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 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 686 Centre St, Newton, MA 02458, 6 beds, 5 baths

$2,890,000

6 beds5 baths6,420 sq ft

686 Centre St, Newton, MA 02458

Property at 20 Hamlet St #1, Newton, MA 02459, 3 beds, 4 baths

$1,899,000

3 beds4 baths3,669 sq ft

20 Hamlet St #1, Newton, MA 02459

Property at 249 Corey Rd #408, Boston, MA 02135, 1 bed, 1 bath

$684,000

1 bed1 bath786 sq ft

249 Corey Rd #408, Boston, MA 02135

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 147 Kelton #305, Allston, MA 02134, 2 beds, 2 baths

$649,999

2 beds2 baths974 sq ft

147 Kelton #305, Allston, MA 02134

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

$529,000

1 bed1 bath680 sq ft

3 Englewood Ave #9, Brookline, MA 02445

Property at 36 Colborne Rd, Brighton, MA 02135, 27 beds, 19 baths

$8,500,000

27 beds19 baths10,455 sq ft

36 Colborne Rd, Brighton, MA 02135

Homes with Pools for Sale in Chestnut Hill

There are currently 10 homes with pools for sale in Chestnut Hill at a median listing price of $3M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestnut Hill stay on the market for 73 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 Chestnut Hill every 15 minutes.

In the past month, 4 homes have been sold in Chestnut Hill. In addition to houses in Chestnut Hill, there were also 9 condos, 1 townhouse, and 1 multi-family unit for sale in Chestnut Hill last month. Chestnut Hill is a moderately walkable neighborhood in Middlesex County with a Walk Score of 52. Chestnut Hill is home to approximately 9,146 people. Find your dream home in Chestnut Hill 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 Chestnut Hill are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestnut Hill. If you're looking to sell your home in the Chestnut Hill area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestnut Hill with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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