luxury real estate for sale Brookline, United States

19 Linden offers a unique opportunity for investors, developers, and owner-occupants looking to build or invest in their dream home in Brookline. Ideally located in Brookline Village—one of the town’s most sought-after neighborhoods—this property sits on a 17,689 square feet level lot on a quiet one-way street and is zoned M10. Buyers should perform their own due diligence to understand potential development or renovation options under local zoning codes. The property features a large 1840s Greek Revival home with stunning original period details, along with a small attached two-bedroom apartment. Its location is a commuter’s dream, offering convenient access to the Green Line T, Longwood Medical Area, downtown Boston, and all that Brookline has to offer. With vision and patience, this property can become a standout investment, condo conversion, or dream home. A must-see! Seller is open to offers with buyer concessions.

Coolidge Corner at your doorstep! Sun-splashed two bed at The Warwick, a well-located elevator building offering a stunning common roof deck and seamless access to everything. Enter to a dramatic wall of windows, wide-open layout and exceptional natural light that defines the living space. Renovated and freshly painted, this home delivers true move-in ease. The eat-in kitchen is built for real use with stainless steel appliances, stone counters and abundant custom cabinetry. Gleaming wood floors, two well-proportioned bedrooms and flexible live/work space create a layout that lives larger than expected. Enjoy sweeping skyline views from the shared roof deck, perfect for sunset evenings or morning coffee above it all. Bike storage. Close to top-tier, fit-for-foodie restaurants, Coolidge Corner Theatre, Longwood Medical Area, Washington Square, Green Line (C), Whole Foods, Trader Joe’s and key commuter routes. Professionally managed and pet friendly.

Coolidge Corner! Tucked on a leafy, tree-lined street that feels worlds away, yet just a couple blocks from the pulse of one of Brookline’s most dynamic commercial hubs & minutes to Boston/Cambridge—this is city living with breathing room. A handsome 3-story 1910 Colonial greets you w/ a 3 season enclosed glass front porch that spills into a gracious foyer & a statement staircase. The vibe is classic with just the right edge: a cozy den lit by striking stained glass, a formal LR that flows seamlessly into an elegant DR w/ a fireplace.The butler’s pantry adds a touch of old-school charm, while the fully equipped kitchen keeps things current, complete w/ a window framing a stunning cherry tree & backyard. Upstairs, the 2nd floor offers 3 BR's, 2 BA's, & the kind of convenience that matters—laundry right where you need it. The 3rd floor flexes with 2 more BR's, an office & a full bath. Timeless, warm and well maintained-this home doesn't just check boxes, it sets the tone.

Timeless Victorian architecture elevated by a masterfully executed, full historical renovation delivering a reimagined home with all the modern amenities imaginable and blending the best of urban and suburban living in desirable Brookline. On coveted Osborne Road, this four bed, four bath residence lives with the scale and presence of a single family across ~4,100 square feet of refined interiors blending period detail and modern design. Chef-caliber kitchen anchors with top-of-the-line Thermador appliances, dramatic waterfall quartz island, matching backsplash, bespoke cabinetry and exceptional storage, flowing seamlessly into sunlit living/dining spaces designed for both intimate gatherings and large-scale entertaining. Main-level living room with full bath allows future ensuite. Primary retreat delivers generous proportions, den and spa-inspired bath. Upper-level bedrooms provide privacy and architectural charm. Finished lower level, radiant bath floors. A rare offering where historic character and modern luxury exist in perfect balance!

Nestled in the heart of Coolidge Corner on one of Brookline’s most coveted tree-lined streets, this rare, fully updated home offers 5,000+ square feet, five bedrooms, and six full baths, including a primary suite worthy of a five-star hotel. The main level features a welcoming foyer, formal living room with a marble-mantled fireplace, dining room, wet bar, full bath, soaring nine plus ft ceilings, and a chef’s kitchen with top-of-the-line appliances and an oversized island. A large deck just off the kitchen is perfect for outdoor dining or relaxing after work. The second floor offers four spacious bedrooms and a laundry closet, while the third floor includes a 5th bedroom and full bath. The finished lower level features a home office, full bath, and laundry room. Completing the home is a detached two-car garage with EV charging, making 18 Naples truly exceptional.

Grand Queen Anne Victorian Home, formerly of the Weber Estate, nestled in a meticulously appointed British Garden with nearby urban and natural amenities. Through an expansive entertainment hall with comfortable living and dining rooms, stained glass windows of intriguing colors and shapes guide you through the home, creating a jeweled ribbon up the main staircase to the family rooms. The amount of original detailing maintained over the generations offers clear personalization of timeless designs, while allowing for the introduction of modern amenities. A prominent exposure floods the house with light and delight all day. The outdoor grounds reflect a curated effort to do justice to such a period estate, featuring spring flowering beds and sitting patios that usher in a summer of full, mature trees accompanying dahlias, delphiniums and hollyhocks, as well as vegetable patches that make room for perennials to create a wonderful private park.

Chestnut Hill, Brookline. 1905 Chapman & Frazer Spanish Colonial on approximately 1.3 acres with over 9,400 square feet across four finished levels. Town-recognized for its Arts and Crafts house-and-garden composition, the estate features courtyards, terraces, and defined garden rooms, plus a historic 1906 Chapman & Frazer auto house. Main level includes a chef’s kitchen with oversized island, professional appliances, and walk-in pantry that opens to casual dining and a stone terrace, along with formal living and dining rooms, a quiet library, and a generous family room. The primary suite offers a marble spa bath and custom dressing closets. Upper floors provide flexible secondary bedrooms and work or play space. Finished lower level adds media, fitness, recreation, and storage. Architect-led updates documented in 1911 and 1929. Within the Chestnut Hill North Local Historic District and contributing to the Chestnut Hill National Register District. By all indications, among the largest single-family homes in the district and appears to be the district’s largest single-family lot. First time available in more than 30 years. Near Boston College, The Street, Chestnut Hill Mall, Wegmans, the Green Line, Longwood Medical, and the cultural amenities of Brookline and Newton.

This spacious three-bedroom, two-bath condominium offers 1,732 square feet of living space and presents a compelling opportunity for investors, contractors, renovators, or end users with vision. The unit is in need of significant repairs and updating, but its generous room sizes, well-proportioned layout, and garage parking provide an excellent foundation for renovation. Whether the goal is resale, long-term investment, or creating a customized personal residence, this property offers substantial upside in a well-established and highly desirable location. Property to be sold as is.

Timeless Victorian architecture elevated by a masterfully executed, full historical renovation delivering a reimagined home with all the modern amenities imaginable and blending the best of urban and suburban living in desirable Brookline. On coveted Osborne Road, this four bed, four bath residence lives with the scale and presence of a single family across ~4,100 square feet of refined interiors blending period detail and modern design. Chef-caliber kitchen anchors with top-of-the-line Thermador appliances, dramatic waterfall quartz island, matching backsplash, bespoke cabinetry and exceptional storage, flowing seamlessly into sunlit living/dining spaces designed for both intimate gatherings and large-scale entertaining. Main-level living room with full bath allows future ensuite. Primary retreat delivers generous proportions, den and spa-inspired bath. Upper-level bedrooms provide privacy and architectural charm. Finished lower level, radiant bath floors. A rare offering where historic character and modern luxury exist in perfect balance!

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 2 garage parking spaces, 2 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 designer lighting add warmth and sophistication. Located steps from Saint Mark's Park, the Coolidge Corner Theatre, Trader Joe's, and acclaimed restaurants, plus the MBTA Green Line for direct Boston access, 80onVernon blends modern design, everyday convenience, and community charm. Expected delivery late summer 2026.

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 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

One of Brookline's most distinctive residences, this rare 1880 Carriage House near Coolidge Corner seamlessly blends historic architecture with thoughtfully integrated modern updates. A 2022 landscape by Curbs Studio, inspired by Japanese zen gardens, features terraced granite, custom stonework, Ipê decking, integrated lighting, mature plantings, an outdoor kitchen, and fire-pit lounge. Inside, 10.5' ceilings, exposed beams, a wood-burning stove, and tall French doors create dramatic, light-filled living spaces. Four vaulted-ceiling bedrooms and 2.5 baths include two beautifully renovated bathrooms by Feinmann Inc. (2021). Recent improvements include HVAC (2024), windows, retaining wall, paint, and EV charging. A remarkable alternative to new construction, and condos, offering timeless craftsmanship and modern comfort moments from Longwood Medical Area, Fenway Park, restaurants, parks, the MBTA, the Museum of Fine Arts, Boston, the Isabella Stewart Gardner Museum, and all of Boston!

Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and serene 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.

Set on nearly an acre of landscaped grounds in one of Brookline's most prestigious neighborhoods, this stately 1929 residence by Philip Stearns Avery offers over 7,300 square feet and 7 bedrooms. Mature landscaping provides privacy and tranquility, enhancing the home's timeless elegance and scale. A gracious foyer opens to a three-season porch and terrace with sweeping views of the grounds. The living room features a grand fireplace, the dining room is ideal for entertaining, and the richly paneled library offers an intimate retreat. The kitchen includes two pantries and views of the property. Upstairs, the corner primary suite has a fireplace and walk-in closet, along with five additional bedrooms and three baths, including an optional guest suite. The 3rd floor adds wonderful space with a bedroom, family room, kitchen, and full bath, while the lower level includes a family room, gym, and two-car garage. Rich in architectural character and heritage, this is a rare Brookline offering.

Ideally situated near The Country Club, this exceptional 10-room, 4-bedroom, 3.5-bath residence offers the warmth and character of a private Vermont retreat in one of Brookline's most coveted neighborhoods. Set back from the road behind a circular driveway, the home is surrounded by mature landscaping, creating exceptional privacy and a true sense of escape. A welcoming slate foyer leads to gracious living spaces highlighted by two impressive wood-burning fireplaces. The renovated kitchen opens to a spacious family room, while the elegant front-to-back living room features a fireplace and built-in bar, ideal for entertaining. The thoughtfully converted two-car garage serves as a dedicated wellness retreat, perfect for a gym, studio, or private sanctuary, with a versatile great room above. Outdoor amenities include a pool, sport court, patio, and fire pit, offering year-round enjoyment. Conveniently located near Allandale Farm, Dexter Southfield, The Park School, and The British School

Ideally situated on a private cul-de-sac in Chestnut Hill, this stunning architectural gem offers timeless elegance & modern luxury. Just minutes to the T, restaurants, coffee shops, & shopping, it boasts unobstructed park views from a Bluestone patio with a luxury outdoor kitchen and 8' gas fireplace perfect for entertaining. Inside, enjoy a sauna, home gym, wine cellar, billiards room, & a richly paneled library.First floor offers a radiant living room with fireplace and detailed moldings, a sunroom with three exposures, & a formal dining room with bay windows, original paneling, and wood-burning fireplace.The chefs kitchen impresses with custom cabinetry and top-of-the-line appliances. Upstairs, the expansive primary suite features a gas fireplace, walk-in closet, and marble bath.Two additional large bedrooms, full bath, office, and laundry complete the second level.The third floor includes a media room, two bedrooms, and a playroom.Heated driveway & luxury systems throughout. Coming down Heath take a right into a cul de sac, home is the second house on the right hand side.

Bright and inviting, this move-in ready home sits at the end of a quiet cul-de-sac, offering privacy, and a peaceful setting. Minutes to bus lines and the Green Line for easy access to Longwood, Harvard Square, and downtown Boston.This 4-bed, 3.5-bath home features an open layout with a spacious living room with fireplace, dining area, and updated kitchen with stone countertops and stainless steel appliances. A sunroom overlooking the backyard adds a bright retreat.The main level includes a primary suite, two bedrooms, and a full bath. The walk-out lower level is above grade and offers a family room with fireplace, access to a screened porch and backyard, plus a guest suite, powder room, and laundry.Set on a rarely available, private and level 10,000+ sq ft lot, with central air and a two-car garage. Near Hayes School, Chestnut Hill Reservoir, parks, and shops.

Magnificent estate on one of Brooklines most beautiful residential streets, blending timeless architecture with modern luxury. Expansive first floor features elegant period details, grand entertaining rooms, an impressive foyer, custom chefs kitchen, and spacious family room, with a covered porch and large deck extending the living space outdoors. The home offers a palatial primary suite with fireplace, multiple closets, & a spa-like bath, along with additional en-suite bedrooms and a third-floor recreation space.The fully finished lower level includes a kitchen, gym, theater, recreation room, additional bedrooms, and full bath. Additional highlights include radiant heated floors, smart home technology, and an oversized double-depth garage accommodating up to six cars. Set on nearly one acre of beautifully landscaped grounds w/ a swimming pool, clay tennis court, and heated driveway and walkways for snowmelt. An exceptional residence offering luxury, privacy, extraordinary amenities. https://goo.gl/maps/d4sKFyfzjCHDAAzh7

Welcome to 84 Winthrop Rdan extraordinary two-family residence in the heart of Brookline, offering nearly 8,000 sq. ft. of luxurious living. With 10 bedrooms and 8 and half bathrooms across two expansive homes, this property is designed for both elegance and functionality. Inside, discover chef-inspired kitchens appointed with premium Miele and Viking appliances, custom cabinetry, and sophisticated finishes that set a new standard for multi-family living. Each residence showcases grand open layouts, spa-like baths, and abundant natural light, blending timeless style with modern comfort. Perfect as a trophy investment or multigenerational living, this rare opportunity combines scale, design, and prestige in one of Brooklines most coveted locations. Use GPS

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.

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.

Location, Location, Location! Exceptional two-unit mixed-use building in the heart of Brookline, featuring a NNN-leased commercial space occupied by a premier national restaurant operator with a recent $2M+ buildout. The property includes a rare Brookline 1:00 AM full liquor license, elevator access for commercial deliveries, and expansive outdoor patio seating. The second floor offers a refined 3-bedroom, 1.5-bath residence with open living, dining area, in-unit laundry, and an extraordinary private roof terrace exceeding 1,000 SF. Unmatched setting just steps to the Green Line, Coolidge Corner, BU, Longwood Medical, H-Mart next door, and Boston's most vibrant destinations.

Sophisticated contemporary home totally transformed in 2022 by a prestigious luxury developer. Meticulously crafted for modern living with 5500+ sq ft including two additional suites with kitchenettes & private entrances designed as In-Law/Au-Pair apartment + home office. Spectacular living room with 6' linear gas fireplace complimented by a 8' wide granite wall. Extraordinary chef's kitchen with quartz countertops & massive 10 foot center island. Wolf/Subzero/Thermador appliances, 2 dishwashers, 2 sinks, professional hood, micro lift, dual wine fridge & breakfast sitting area. Dramatic primary bedroom suite with marble fireplace, walk-in closet, balcony & spa-like bath with glass enclosed shower & soaking tub. Top floor offers yoga/studio/office. Sprawling roof deck with breathtaking views of downtown Boston & Prudential. Exterior bluestone patio, gas fireplace perfect for entertaining. 6 parking (2 garage), smart home technology & surround sound complete this exceptional residence!