Browse All Brookline MA Properties with Pool for Sale

7 Beds ⋅ 16 Baths ⋅ ACTIVE Status ⋅ 73590483 MLS ⋅ 19,138 SqFt.

There are exceptional homes, and then there are properties conceived on an entirely different scale. 55 Singletree is the latter. Perched atop a secluded hill on more than two private acres in Brookline, adjacent to the reservoir, this extraordinary estate offers a rare sense of privacy and tranquility just minutes from Boston. Its elevated position and naturally sheltered setting create remarkable seclusion, with no neighboring homes overlooking the pool or private outdoor spaces. Years of vision, craftsmanship, and investment have been brought to life through an extensive two-phase construction project by Thoughtforms, one of New England’s most respected custom home builders. The result is not simply a residence, but a world unto itself—an estate with the scale and experience of a private resort. The property's commanding elevation captures views toward the Boston skyline, culminating at a rooftop terrace overlooking the city. Across the grounds, architecture and landscape have been conceived as one experience. Water features introduce movement and serenity, expansive outdoor spaces invite both gathering and escape, and a private tennis and sports court creates a level of recreation rarely found so close to the city. Inside, monumental scale meets intimate refinement, with exceptional materials, custom craftsmanship, and thoughtfully designed spaces equally suited for grand entertaining and everyday family life. An estate of this scale, caliber, and extraordinary privacy would be exceptionally difficult to replicate today. 55 Singletree represents a singular opportunity: a secluded residential sanctuary offering remarkable sophistication, recreation, and proximity to Boston.

55 Singletree Rd, Brookline

$1,175,000

2 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579776 MLS ⋅ 1,240 SqFt.

Tucked away at the end of a long private drive, this detached residence at Sargent Estates offers the privacy and feel of a single-family home with the ease of condominium living. The thoughtfully designed, single-level floor plan features beautifully refinished hardwood floors and an open kitchen with white cabinetry, quartz countertops, stainless steel appliances and a center island. The kitchen flows seamlessly into the dining and living areas, creating an inviting setting for everyday living and entertaining. French doors from the living area open to an oversized patio bordered by lawn and mature landscaping. Two spacious bedrooms include a primary suite with a full bath. Additional highlights include generous storage, a cedar closet and an attached two-car garage. Association amenities include an in-ground pool, landscaping and snow removal. Convenient to public transportation, the Longwood Medical Area and downtown Boston.

18 Chestnut Pl, Brookline

$23,000,000

6 Beds ⋅ 12 Baths ⋅ ACTIVE Status ⋅ 73576839 MLS ⋅ 16,856 SqFt.

An extraordinary opportunity to own one of Brookline's most prestigious estates, set on nearly 1.75 acres in the most coveted location. This majestic brick Georgian Colonial has been masterfully renovated with museum-quality craftsmanship and timeless architectural detail. Offering over 16,000 sq. ft. of elegant living space, the home features a grand two-story foyer, 6 bedrooms, 9 full and 3 half baths, a gourmet kitchen, oversized fireplaced living room, formal dining room, Parisian-inspired bar, tea room, mahogany library, and a dramatic two-story family room with a spiral staircase leading to a private office. The exceptional primary suite offers dual spa-like baths, two walk-in closets, and a private office.The lower level features a media room,50's billard and bar area, wine cellar ,en suite bedroom with sitting area ,fitness room and indoor pool. Resort-style grounds include professionally landscaped park-like gardens, a 4-car garage, 2 swimming pools, a full pool cabana with kitchen, living room and full bathroom and a lighted tennis court. A truly iconic estate offering unparalleled luxury and timeless elegance.

381 Warren Street, Brookline

$2,595,000

5 Beds ⋅ 5 Baths ⋅ CONTINGENT Status ⋅ 73573502 MLS ⋅ 3,913 SqFt.

ABSOLUTELY INCREDIBLE OPPORTUNITY AT THIS PRICE!!!!!! A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.

284 Woodland Road, Brookline

$11,750,000

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73570794 MLS ⋅ 7,502 SqFt.

One of Brookline’s most exceptional offerings in over a decade, this remarkable 1929 Colonial Revival estate is set on two beautifully landscaped acres in the town’s prestigious estate area. The 14-room residence offers 7,500 square feet of living space and showcases timeless architecture and exceptional craftsmanship. Set atop a private drive marked by stately stone pillars, the home is surrounded by sweeping lawns, specimen trees, perennial gardens, and a tranquil man-made freshwater creek. An inviting in-ground pool enhances the serene outdoor setting. Inside are six spacious bedrooms, four full baths, and two half baths, including a luxurious primary suite with a spa-like bath. Elegant formal rooms flow seamlessly into comfortable living areas, ideal for both grand entertaining and everyday living.Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay.

71 Sears Road, Brookline

$2,395,000

4 Beds ⋅ 5 Baths ⋅ CONTINGENT Status ⋅ 73569446 MLS ⋅ 4,067 SqFt.

Set along one of Chestnut Hill’s picturesque tree-lined streets, this handsome brick Tudor offers a thoughtful blend of classic architecture, generous proportions & comfortable everyday living. A welcoming foyer introduces elegant living & dining rooms with hardwood floors & distinctive period details, while the spacious eat-in kitchen, with abundant cabinetry, updated appliances & wet bar, opens naturally to a relaxed family room with direct access to the backyard. Upstairs, four well-proportioned bedrooms include a generous primary suite overlooking the backyard, complete with a sizable walk-in closet & ensuite bath. A second ensuite bedroom, along with two additional bedrooms, provides flexibility for family, guests or a home office. The lower level offers versatile space for recreation, hobbies, storage or future expansion, with convenient access to the garage. Outdoors, a tiered backyard creates a private setting with a pool, deck & lawn, offering multiple spaces for entertaining, relaxing & enjoying the warmer months. Fresh paint, new and refreshed flooring & an updated back deck enhance the home’s appeal while preserving its distinctive character. Ideally situated in the Baker School District, with easy access to Route 9, shopping, dining & the amenities of Chestnut Hill, this is a home with both an inviting sense of place & room to make it your own.

72 Beverly Rd, Brookline

$11,750,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73536353 MLS ⋅ 10,000 SqFt.

A rare opportunity to reimagine and create a $20+M compound in Brookline, set on two private acres in the coveted estate area. Conceived by an award-winning architect, the proposed design masterfully blends timeless elegance and exceptional craftsmanship with the features most desired for modern living soaring ceilings, abundant natural light, clean architectural lines, and a thoughtfully designed floor plan ideal for both grand entertaining and everyday comfort. The proposed plans showcase an expansive open-concept kitchen and family room with a dramatic cathedral ceiling, elegant formal living and dining rooms, spacious library, a screened porch, a gracious 1st floor bedroom, and an exceptional 2nd floor primary suite. Additional customization options include an elevator servicing all levels, a golf simulator, and a swimming pool. Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay

Sears Road, Brookline

$8,200,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73526856 MLS ⋅ 9,301 SqFt.

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

$4,795,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73520842 MLS ⋅ 6,790 SqFt.

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level with separate entrance offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb Chestnut Hill location with easy access to Boston, shopping, dining and Medical Centers.

9 Singletree Rd, Brookline

$3,495,000

5 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73517349 MLS ⋅ 5,234 SqFt.

Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and seasonal water views on nearly a half-acre with bluestone patio and pool. The gracious entry opens into a grand foyer flanked by sun-drenched rooms. Bay windows in the living room, dining room, family room, and primary suite frame reservoir and garden views. Four fireplaces, high ceilings, crown molding, and custom woodwork throughout. Well-equipped kitchen for serious cooks with breakfast area and counter seating. Private first-floor study. Enchanting screened porch access the dining and living rooms for al fresco dining. Second floor: three bedrooms, two baths, and a primary suite with large dressing room, ensuite bath, and private deck. Third floor: two additional bedrooms and full bath. Lower level: exercise room, sauna, wine cellar and lav. Two-car garage. Minutes from Chestnut Hill shopping, Longwood Medical Area, and universities.

68 Dudley Street, Brookline

$7,500,000

6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 73487838 MLS ⋅ 7,780 SqFt.

A rare find in Brookline, this property offers privacy and tranquility on a secluded lot adjacent to Sargent Estates. Spanning three finished levels plus a lower level, the home features 6 bedrooms and 6 full and 2 half baths, with meticulous craftsmanship and striking architectural details throughout. A grand rotunda entry leads to a chef’s kitchen, expansive living and dining rooms, family room, and mudroom. The second floor includes three bedroom suites, each with its own bath, plus two office spaces. The third floor offers two additional bedroom suites, while the lower level includes a sixth suite, gym, large family room, and laundry. Surrounded by mature landscaping and set well back from the street, the property boasts a pool, hot tub, sauna, outdoor fireplace, pizza oven, and full outdoor kitchen—an exceptional setting for both relaxation and entertaining. Not to be missed!

1 Chestnut Place, Brookline

$16,000,000

6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 73480812 MLS ⋅ 9,411 SqFt.

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

63 Goddard Avenue, Brookline

$5,995,000

7 Beds ⋅ 11 Baths ⋅ UNDER AGREEMENT Status ⋅ 73474446 MLS ⋅ 8,921 SqFt.

55 Leicester presents a RARE offering in one of Brookline’s premier, private locations, now offered at a price point rarely matched for a home of this caliber. Behind its grand facade, this extraordinary estate awaits its next chapter. Repositioned BELOW SIX MILLION — a significant adjustment representing compelling value for the size and location — it stands among the most attractive listings currently available in Brookline. The home showcases soaring ceilings, walls of windows overlooking landscaped grounds, and an open, light-filled floor plan. The scale and layout exists for a visionary buyer to reimagine and restore its full potential. Signature luxurious features such as the heated driveway, limestone floors, an elevator to all levels, 5-car garage, in-ground pool, roof deck, and wine cellar further elevate the appeal. For developers, investors, or end-users, 55 Leicester is an unmatched canvas to create a world-class residence in an A+ Brookline location.

55 Leicester St, Brookline

$627,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73050996 MLS ⋅ 2,937 SqFt.

Welcome Home to Flint Meadow Drive in charming Brookline! This home is a gem year round with Springs full of cherry blossoms and flower beds, Summers by the in-ground pool, colorful Autumn leaves, and Winters in the cozy fireplaced family room. 3 Large Bedrooms, 2.5 baths and over 2900 sqft. Beautiful hardwood floors throughout the first floor. Sunken living room, Formal dining room with built-in’s, Eat-in kitchen w/pantry, Family room with Wood Burning Fireplace and wet bar, dedicated office or possible 4th bedroom complete the 1st floor. Upstairs your master suite awaits, with tiled bath, custom vanity, and walk in closet. Two more generously sized bedrooms and spacious hall bath. The finished basement adds plenty of additional space for a rec room, home gym or play-room, also a large separate laundry room with added storage. 2 car attached garage, central A/C, and high efficiency windows throughout. Great commuter location in the award winning Hollis-Brookline School District.

6 Flint Meadow Dr, Brookline

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Brookline Homes with Pool

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Browse All Brookline MA Properties with Pool for Sale

Brookline Homes with Pool

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