luxury houses for sale Jamaica Plain, United States

Four condo quality rental units and first level commercial space current use tavern/restaurant. Three story plus basement building originally built in 1930 with multi floor addition of residential units constructed in 2021. All residential units have large living rooms, hardwood floors, custom kitchens with white cabinets, quartz counters, GE stainless appliances, in unit laundry, each unit is self contained for heating/cooling/hot water, custom tile baths, generous size bedrooms and closet space. Delivered vacant. Liquor and entertainment licenses NOT included in the sale.

Welcome home to this beautifully crafted, newer-construction home in the heart of Jamaica Plain's coveted Sumner Hill Historic District - designed with distinctive eave brackets, high ceilings, and rich hardwood floors to respectfully echo the Italianate and Victorian character of its historic neighbors. This 4-bedroom, 3.5-bath home pairs period-inspired detail with a fully modern interior. The open floor plan flows effortlessly from a fireplaced living room into a well-appointed kitchen featuring Corian countertops and a handy office nook, perfect for remote work. Step directly from the kitchen onto the deck overlooking a lush perennial garden - a private retreat fully fenced for kids and pets. A first-floor laundry room and updated half bath add everyday ease. Upstairs are three bedrooms and two baths, including a generous primary suite with en-suite bath and walk-in closet. The finished ground floor includes a fourth bedroom and full bath - ideal as an au pair suite, home office, gym, or private guest space. Additional highlights include solar panels, abundant storage, and a rare 2.5-car garage. All this just a block from the Green Street Orange Line station and moments from JP's eclectic shops, restaurants, parks, and green space - an exceptional combination of historic charm, neighborhood living, and easy access to downtown Boston.

Come home to an exceptional Pondside custom-crafted Condominium by renowned local artisan Maple Hurst Builders. A private entrance opens to a gracious foyer and a residence that offers the comfort and ease of a single-family home. High ceilings, glistening wood floors, abundant windows, and an elegant flow of living and entertaining spaces create an inviting sense of light and scale. The main living level features a handsome library, living room with fireplace, chef's eat-in kitchen, formal dining room, study, and a powder room. Architectural details abound, from graceful columns and crown moldings to built-in bookcases and custom cabinetry throughout. The upper level is devoted to restful quarters, including a generous primary suite with fireplace, well-appointed 4-piece bath & a deep walk-in closet, an additional bedroom, a second full bath, and glass doors opening onto an elevated private deck. The top floor offers two expansive, versatile rooms & kitchenette with the possibility of a getaway bedroom suite, home office, exercise studio, or whatever your creative pursuits. Outside, established gardens and mature trees create a serene setting, with a charming trellised brick walkway leading to the garage parking and additional off-street spaces. All this in a coveted Jamaica Plain location, just one block from the neighborhood's vibrant mix of restaurants, shops, cultural destinations, and the natural beauty of Jamaica Pond along Olmsted's Emerald Necklace. A distinctive home in an extraordinary setting-look no further.

Built in 2017 with nearly 5,000 square feet across four floors, this Parkside residence lives more like a single-family home than a condo. Enter through a mudroom with cabinetry and tiled floors before arriving at the main level, featuring a chef's kitchen with a La Cornue range, Sub-Zero refrigerator, dining and living area, and powder room. The second floor offers three bedrooms, a full bath, sitting area, and access to the backyard oasis. The top floor hosts the primary suite, where exposed beams frame the space, with a marble bath featuring a soaking tub, glass shower, vanity, and open shelving. A balcony and bonus room complete the level. The lower level features heated floors, a bedroom or bonus space, separate shower room, and half bath. Garage and driveway parking complete the home. Moments from Franklin Park's 500 acres of trails, meadows, golf, and canopy paths, offering a setting that feels more Vermont than Boston while close to all that Jamaica Plain has to offer.

This isn’t a fairy tale, it’s for real. This pretty and playful, energy-forward 1893 Victorian offers five bedrooms and two and a half baths over three levels, with a fireplace, owned solar panels, fenced backyard with treehouse, and two-car parking. Set on a tree-lined street in Egleston Square, four blocks from Stony Brook T. New renovations and energy-efficiency upgrades make it even more compelling. Past the front porch swing, a long foyer with stained glass, a graceful staircase and vintage floors welcome you. Under 9.5 ft ceilings, the elegant 230 sq ft bow-front living room opens through pocket doors to an airy central dining room with ornate fireplace (newly lined, ready for a wood, electric or gas insert). Linger for breakfast in the skylit kitchen with center island, tall cabinetry and sunroom dining nook, bright from southwest-facing windows and graced by a vintage built-in pantry hutch. The redesigned layout lets light and movement circle through the level, just right for entertaining, lounging and games of tag. Daydream at the large corner windows while steeping tea at the induction stove and farmhouse sink. A half bath completes the floor. The second level with 9 ft ceilings offers two oversizes, nearly 200 sq ft bedrooms that each fit a king bed. One adjoins by pocket doors a 90 sq ft sitting room for an office, nursery or dressing room. The gut-renovated bathroom features a deep teal shower, marble floor and double vanity with polished cement counter. A laundry closet sits next door. The top level offers a full bath with tub, a sizable fourth bedroom, and a fifth with a magical sitting or sleeping alcove. All-new full-house mini splits provide 5-zone heating and cooling. With the solar panels, let the grid reward you with free air conditioning. (A gas furnace in the full basement with bulkhead remains as winter back-up.) Outside, the urban dreamscape continues. When last have you encountered a custom-built treehouse? The fenced yard suits running and hiding, gardening and patio dining, with a 50-year-old Concord grape vine, fruit trees and berry bushes. The driveway fits two cars tandem. Enjoy the Painted Lady stylings and scalloped shingles as you swing on the front porch. On the Jamaica Plain/Roxbury border, near Stony Brook T, the Southwest Corridor Park bike path, and the Mendell and Rafael Hernández schools. Blocks to Chilacates; Ula Cafe, The Haven and Mike’s Fitness at the Sam Adams Brewery complex; Drawdown Brewing; and Franklin Park trails.

Set on nearly an acre within Brooklines coveted Estate Section, this extraordinary 2015-built residence offers a rare blend of privacy, scale, & exceptional construction rarely found in todays market. Spanning nearly 8,000 sq ft including a finished lower level, the home features solid mahogany floors,marble baths, custom granite stonework, 7 bedrooms, 9 bathrooms, a steam room, and multiple fireplaces including a striking outdoor granite fireplace on the covered rear deck for year-round entertaining. A fully restored original Carriage House provides two additional floors ideal for a gym, studio, or guest quarters, while a separate private office or nanny suite offers its own entrance. Built to an impressive standard with geothermal heating and cooling across six zones, radiant floor heating, Andersen Architectural Series windows, 600-amp electrical service, EV charging, and extensive CAT5 wiring. Minutes to The Country Club, Dexter Southfield, Larz Anderson Park, and downtown Boston https://maps.app.goo.gl/tJD9RCiqeG5rjJ7z6

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

Gracious and timeless historic single family attached home in Brookline's prestigious Fisher Hill Estates. This 5 bedroom/4.5 bath home offers more than 7,000 sqft of elegant living space with spectacular views of the Brookline Reservoir! This majestic home features period architectural details, a grand staircase, high ceilings, original built-ins and gleaming hardwood floors. Sundrenched by floor to ceiling windows, the main level offers a gracious living room/dining room with fireplace, a stunning mahogany library with fireplace, a beautiful family room, breakfast area and a chef's kitchen with direct access to a lovely garden area. The second floor primary suite features a spa like bath, walk-in closet, fireplace and a picturesque private deck with outstanding views. Completing this level is an additional en suite bedroom. The third floor offers two additional bedrooms and a full bath. The finished lower level features a direct entry guest suite with a living area, full bath and kitchen - perfect for an au pair. Completing this home is a two car detached garage and multiple outdoor private garden areas. Community amenities include pool and tennis court. Close to shopping, restaurants, schools, Downtown Boston and so much more! This home is definitely a must see!!

Exquisite in every detail, this magnificent brick Georgian boasts modern style design, suitable for grand scale entertaining & comfortable family living. A large, elegant foyer w/sweeping staircase & venetian plaster walls, opens to an elegant living room w/fireplace. A sunroom, just off the foyer, offers spectacular views of the level, acre+ lot w/ frontage on Cramond Street. There is a majestic dining room w/acoustic padded walls & a handsome family room w/custom cabinetry. The fully renovated chef's kitchen features a center island, butler's pantry & dining nook-truly exceptional w/top-grade appliances. The 2nd level has a luxurious primary suite w/fireplace & spa-like bath. There are 3 additional bedrooms, 3 full baths, an office & a laundry room on this level. The 3rd floor offers 2 additional bedrooms & a full bath. The lower level has a large media room, gym room, full bath, 2nd laundry room, mudroom & access to the 2-car garage. Easy access to highways, schools & airport.

Prime Roslindale Village location! This turn-key Victorian-era multi-family home blends timeless period craftsmanship with modern comfort, just steps from local restaurants, shops, and the Commuter Rail to downtown Boston. Complete with efficient natural gas heating and separate utilities for both units, each residence showcases soaring high ceilings, extensive custom picture-frame wall moldings, rich hardwood floors, and large windows that fill the rooms with natural light.Unit 1 offers effortless single-level living featuring a generous living room framed by elegant millwork, an eat-in kitchen with a pantry and laundry hookups, two spacious bedrooms, and a full bath. Unit 2 spans the second and third floors as an expansive multi-level retreat. It features an eat-in kitchen with in-unit laundry, two full baths, three bright bedrooms, and a grand living room with direct access to a private, sunlit entertainment deck. The finished third-floor attic level adds versatile bonus living, perfect for a dedicated home office, guest suite, or creative studio alongside extensive unfinished attic storage. Outdoor spaces include a welcoming covered front porch, the private upper deck, and a fenced yard. A rare detached two-car garage provides sought-after off-street parking. Perfect for owner-occupants seeking rental income, multi-generational living, or savvy investors looking for an architectural gem in one of Boston's premier walkable neighborhoods.

Boston built very few late Victorian era Craftsman houses, and fewer still kept their interiors intact. This one did!! Behind an enclosed porch on Doctor's Row, a second door opens to a paneled Arts and Crafts hall with original casement windows, a window seat, and hand-blocked Sanderson Morris paper. It's something to behold. Beyond it, gumwood beams run the length of the living and dining rooms over high wood paneling. A plate rail on carved brackets carries the full wall, with the mantel set just below it and a firebox in patterned brick tile. Dividing the two rooms is a colonnade screen: one broad arched opening flanked by a pair of smaller blind arches on heavy posts. These details are unforgettable. Two glass-front china cabinets are built into the dining room. The woodwork was never painted over. Oak runs underfoot through the main rooms and gives way to mahogany flooring in the kitchen, where a large marble slab counter once served a working chef. Soft and warm red fir runs through the second floor. Afternoon light fills the living room, and an enclosed sun porch off the dining room stays bright through the day, a personal favorite of the current owners. The first floor loops: hall to living to dining to kitchen and back again, with a front office (originally a dentist office) and a half bath off the run. Upstairs, four bedrooms include a primary suite with walk-in closet and renovated bath in herringbone and marble, plus a bedroom now used as a den with a bow window and window seat. The finished walk-up third floor adds dormers, AC, a skylight, and room to spread out. Recent work covers the 2026 rear deck, exterior paint, repointed chimney, and cleaned flue, with a high-efficiency gas boiler from 2020. Fenced yard, garage/storage bay under the house, generous on-street pkg, and a corner lot that takes light on three sides. Roslindale Village, Fallon Field, the Arboretum, Roches Brothers/Centre Street, and the Bellevue commuter rail stop are all close by. This home represents a rare find for the buyer who appreciates a vintage home like this. First come, first serve!

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.

Classic brick-front, center-entrance Colonial in a well-established neighborhood. This 4 bed, 3.5 bath home is ready for a full renovation or potential gut, an ideal canvas to create your dream home. A gracious entry leads to a front-to-back living room with fireplace, formal dining room, and a family room with picture window overlooking a level backyard. Upstairs offers three spacious bedrooms and a primary suite with full bath, plus two additional full baths. Features include two staircases, a two-car garage (one bay currently used as a laundry room), and a partially finished basement. Many system updates already in place. Sold as is, endless upside in a prime location.

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

292 Clinton Road is a timeless Victorian residence, built in 1892 and prominently situated in Brookline's Fisher Hill neighborhood. Rich in architectural detail, this meticulous home has been thoughtfully updated while preserving elegance and craftsmanship. A welcoming front porch leads to a gracious foyer with soaring ceilings, abundant natural light and original woodwork. Designed for grand entertaining and comfortable everyday living, the first floor features a fireplaced living room, dining room, family room with a bay window, a renovated Chef's kitchen, pantry, mudroom and half bath. A stunning staircase leads to the second level, with a charming sun-drenched landing and a wall of glass. The primary suite offers a custom walk-in closet, and renovated en-suite bath, accompanied by two additional good-sized bedrooms with en-suite baths and a second-floor laundry room. The third floor offers flexibility with three additional bedrooms, a full bath, and a spacious room ideal for a home office.

Introducing 12 Williams Street, a thoughtfully designed new development in the heart of Brookline's highly sought-after Coolidge Corner. This intimate community features two beautifully appointed townhomes, each with private parking, along with a separate studio residence-offering a rare combination of new construction, thoughtful design, and exceptional convenience.This spacious four-level townhome offers 3 bedrooms and 3.5 bathrooms, with a private elevator providing effortless access throughout all four levels. The home also features a private balcony and two covered parking spaces, combining the comfort and scale of a single-family home with the convenience of new construction.Just steps from everything Coolidge Corner has to offer, 12 Williams places you within easy reach of independent bookstores, the iconic Coolidge Corner Theatre, Trader Joe's, Stop & Shop, acclaimed restaurants, cafs, and everyday conveniences. The nearby MBTA Green Line provides direct service into Boston, making commuting and exploring the city effortless.With its exceptional location, private elevator, generous four-level layout, outdoor space, and two covered parking spaces, 12 Williams Street offers a distinctive opportunity to enjoy modern living in one of Brookline's most vibrant neighborhoods.

Welcome to 732 West Roxbury Parkway, a timeless 1933 Tudor-style Colonial where classic architectural charm meets complete, high-end modern living in coveted Roslindale! Situated on an enviable corner lot, this captivating 4-bedroom, 3.5-bathroom sanctuary boasts over 2,700 square feet of brilliantly designed living space crafted for both effortless everyday comfort and sophisticated entertaining. From the moment you step inside, rich hardwood floors and elegant period details frame light-filled, airy rooms. The main floor features an open layout, seamlessly connecting a spacious living room to a beautifully updated gourmet kitchen—thoughtfully remodeled with sleek cabinetry, premium finishes, and top-tier appliances. Off the living area, a dedicated home office provides the perfect, tranquil work-from-home setup. The second floor features three generous bedrooms with gracious closets, including a luxurious primary suite retreat. The finished third floor houses the fourth bedroom with a full bath, making a perfect private getaway for guests. The fully finished basement adds versatile bonus space—perfect for a playroom, media lounge, or home gym. No detail has been overlooked in its 2018 complete gut renovation including new HVAC, plumbing, Electrical, and finishes, ensuring absolute peace of mind and modern energy efficiency. Step outside to enjoy a private, low-maintenance exterior, featuring a paver patio, professional irrigated landscapes, and a fully fenced in rear yard, along with the rare convenience of a newly built (2018) two car detached garage and paved off-street parking. Located just moments from Roslindale Village’s vibrant shops, renowned farmers' market, commuter rail, and scenic green spaces like Bellevue Hill and the Arnold Arboretum, this turn-key residence offers the ultimate suburban feel with seamless urban access. Don't miss the opportunity to make this exquisite Roslindale gem your forever home!

A rare opportunity to own an architecturally significant Arts and Crafts residence in one of Brookline’s most sought-after neighborhoods. Set on three-quarters of an acre within the Chestnut Hill North Historic District, 91 Spooner Road is a distinctive five-bedroom, four-and-a-half-bath residence designed by the renowned architectural firm Putnam & Cox–built as William Putnam’s personal residence. The home was designed around a distinctive interior courtyard and was featured in American Country Houses of Today 1912, underscoring its architectural significance. Dramatically sited atop a high ledge, the property overlooks a wooded landscape to the east, with a rustic path descending toward the street to the north. Cherished by the same family for 60 years, the home showcases thoughtful design, generous proportions, abundant architectural detail, and three fireplaces. The interior courtyard, with screen doors and columns on three sides, brings natural light to the residence. Notable features include a gracious front-to-back entry gallery with brick floors and a sitting alcove; a formal living room with tall ceilings and a striking fireplace with a tiled surround; and a concealed, full-height built-in safe. Additional architectural highlights include a fireplace office or studio with loft, a tree-top sleeping porch with wraparound windows, expansive attic spaces, and separate guest quarters with a full bath. Two pantries, meandering walkways, copper gutters and downspouts, a private terrace, and a whole-house generator further distinguish this exceptional property. Offering an extraordinary opportunity for comprehensive renovation, this property combines architectural provenance, substantial grounds, privacy, and a remarkable natural setting. For those who appreciate historic architecture and envision restoring a residence of enduring character, the possibilities are exceptional. Conveniently located near the Green Line, Route 9, the shops and restaurants at The Street at Chestnut Hill, Roland Hayes Elementary, Brimmer and May, and the Chestnut Hill Schools.

Rarely does a Gilded Age landmark arrive so thoroughly reborn. Designed in 1905 by architect Alfred L. Darrow, 46 Powell Street commands a coveted corner lot in the Cottage Farm Historic District, guarded by carved stone griffins and a scrolled wrought-iron gate. Stone, stucco, half-timbered gables, carved-bracket eaves and a terra cotta roof frame approx. 7,028 SF of Arts & Crafts and Tudor Revival grandeur, delivered with every modern comfort. A 2022 renovation rewired the entire home (400-amp service, integrated alarm, smoke and CO detection, ADT security with outdoor cameras), added central air, a new gas boiler, radiant-heated floors, and a sensor-driven snow-melt driveway and rear walkway, all without sacrificing a single carved detail. Some original doors were repurposed as pocket doors. Step into a two-story marble and mosaic foyer beneath a barrel-vaulted, rosette-coffered ceiling. A hand-carved bridal staircase rises to a soaring atrium lit by leaded-stained glass restored by Jim Anderson of “This Old House”. Five fireplaces, a library with gilt-carved bookcases and medieval English plaster ceiling, and a Jacobean dining room with butler’s pantry set the formal stage. The chef’s kitchen, featured in New England Home magazine, pairs mahogany, burlwood, brass and marble with Visual Comfort lighting, a Sub-Zero refrigerator, Thermador six-burner range, coffee bar with refrigerated drawers, and an antique bell box. It opens to a breakfast nook, a rear deck and a sunlit solarium with domed plaster ceiling. Upstairs, the primary suite offers a fireplace with Roman-tile surround, two leaded-glass bay windows, dressing area, walk-in closet and dual-sink bath with radiant-heated floors. The second suite adds a marble fireplace, walk-in closet and Paris-Metro tiled bath beneath a Tiffany-style transom. Six bedrooms and 4.5 renovated baths. The third floor delivers a kitchenette, walk-in laundry, cedar closet with sauna potential and a cathedral-loft billiard room with king-post beams and Franklin stove, ideal for media or games. The 2,534 SF lower level offers open space and a wine cellar. Private parking for three in the heated driveway plus a detached 1919 Spanish Colonial two-car garage. Specimen plantings and old-growth trees surround the grounds, and commercial-grade internet serves modern households. Just 100 yards to Beacon Street and the C Line, under one mile to Kenmore Square and 2.5 miles to the Public Garden. A fully renewed architectural icon.

Welcome to this stunning center-entrance Colonial in Brookline's Chestnut Hill estate area, set on a level half-acre lot. This expansive home features 4+ bedrooms, 4 full and 1 half baths & offers over 4,895 square feet across three finished levels. The foyer opens to a fireplaced living room and a formal dining room that seats 12. The Chef's kitchen features a Wolf range, Sub-Zero refrigerator, double wall ovens including steam, Cove dishwashers, two sinks, custom cabinetry & granite counters. A library with built-ins cabinetry sits off the dining room & kithcen. The family room, with gas fireplace opens through French doors to a bluestone patio and a broad, fenced, level yard. Upstairs, the primary suite includes a private balcony, Carrara marble bath, dressing area, and two walk-in closets. Three additional bedrooms and two full baths & laundry complete the floor. The lower level consists of a media/playroom, gym, wet bar, beautiful full bath with glass enclosed shower + another set of laundry. Central air & Sonos throughout, EV charging & 2-car garage. Close proximity to the D Line at Chestnut Hill, shops and restaurants at The Street at Chestnut Hill, Soule Playground, and Dane Park.

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!

Romantic, beautiful, and done. This designer-owned 1905 Gambrel Shingle-Style home on historic Meeting House Hill is a rare piece of Boston architectural history - meticulously restored by an award-winning design firm, with every detail already resolved, so you can simply move in and live. A picturesque wraparound porch with white columns and ceiling fans welcomes you home, setting the tone before you even reach the door. Inside, a grand foyer leads to formal living and dining rooms anchored by a wood-burning fireplace with original Chelsea tile - original character, fully brought back to life. Six bedrooms, two and a half baths and private parking are wrapped in finishes rarely found in a typical renovation, including a custom kitchen that earned Architectural Digest recognition: Thermador appliances, tiled walls, quartzite counters and a walk-in butler's pantry ready for effortless hosting from day one.The layout is finished top to bottom for how you actually live: four bedrooms and a spa-like bath on the second floor, and a third-floor retreat with peek-a-boo city views, two more bedrooms (one currently a studio), and a skylit bath. Central air conditioning and a tankless water heater keep the comfort as modern as the finishes throughout. Perched high on the hill, the home is fully set up to enjoy its elevation, with skyline views rarely found in a single-family Dorchester home. Outside, a manageable sunny backyard, garage-top patio and that wraparound porch are ready-made for slow mornings and al fresco dinners - no projects, no punch list just enjoy it.This is Dorchester living at its best - a tree-lined street once known as Doctor's Row, moments from Ronan Park, neighborhood playgrounds, local shops and Comfort Kitchen, in one of Boston's most vibrant, fast-evolving communities. Two Red Line T stops keep you connected to everywhere else. A home this rare, this restored and this connected doesn't come along twice - schedule your private showing today.

A truly special opportunity to own a piece of Dorchester history. Built in 1910, 25–27 Kenwood Street is a side-by-side two-family situated on a quiet street with convenient access to schools, the T, parks, shopping, and major highways. Offering an exceptional combination of location, scale, and potential, this expansive 4,410-square-foot property features 10 bedrooms and 3 bathrooms across two spacious residences. Rich in original character, highlights include hardwood floors, built-ins, bay windows, porches, and four off-street parking spaces. Unit 1 offers 6 bedrooms and 2 bathrooms, while Unit 2 features 4 bedrooms and 1 bathroom. Each unit benefits from separate utilities and its own gas-fired hot water boiler. With its substantial footprint, historic charm, and versatile layout, this property presents an exciting opportunity to preserve its original character, renovate and reimagine the existing spaces, or explore future possibilities.

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.