South End

Neighborhood Description

The South End is a neighborhood of Boston which is bordered by the Back Bay, Chinatown, and Roxbury. It is distinguished from other neighborhoods by its Victorian Style houses. Made up of over 300 acres, the South End is the largest intact Victorian row house district in the country. Tremont Street, Columbus Avenue, Washington Street, and Harrison Street are lined with shops and restaurants and are home to some of Boston’s best restaurants, design stores and boutiques. SoWa (South of Washington) is where some of the city’s foremost contemporary art galleries are located.

Browse listings for sale in South End below. Contact Us with any questions or to schedule a tour for any listing below

Active Listings

Quintessential South End parlor level (entire 2nd floor) 1-bedroom condo on picturesque Pembroke Street. This sun-filled home's soaring 10-foot ceilings and tall windows bring the "WOW" factor you're looking for. Beautiful hardwood floors and preserved architectural details like "egg and dart" crown molding make for a warm yet distinctly sophisticated space. Newly painted, sparkling clean, and move-in-ready! In-unit laundry and ample storage including California Closet organizers. One side of the expansive bedroom easily accommodates a king-size bed; and the other side is an ideal work-from-home space with a built-in desk and bookcase/shelving. The association has recently replaced the roof and done some repointing. Pembroke Street's awesome location fits your lifestyle with dozens of both South End and Back Bay amenities close-by: world class restaurants, cafes, wine bars, galleries, and boutiques. Catch a show at one of the many nearby venues: Symphony Hall, Huntington Theatre, Boston Center for the Arts & more - or take an adult dance class at the Boston Ballet Studio. Close proximity to both Orange & Green Line T, #1 Bus to Cambridge & Harvard Sq. Very convenient to the Longwood Medical and Academic Area. Just a few blocks to Back Bay T Station, a true transportation hub with a shuttle to Boston Logan International Airport, multiple MBTA Commuter Rail lines, and frequent Amtrak trains to NYC and beyond.

$799,000 Active

130 Pembroke St 2 Boston, Massachusetts

1 Beds 1 Baths 765 SqFt

Rare South End opportunity at a price that almost never includes private outdoor space. 760 sq ft second floor one bedroom, one flight up, in a classic brownstone on Massachusetts Avenue. At roughly $724/sq ft in a neighborhood where the median runs near $1,090, the value here is real.Living room with original marble ornamental fireplace, tall windows w/deep sills and a generous closet. Private covered deck off the back overlooking trees & rooftops - a genuine rarity at this price in 02118. Kitchen w/stainless appliances, tile floor & peninsula seating, open to the living space. Full bath. In-unit washer/dryer.A second room off the living area can be used as a home office, guest room, nursery or den.Unit is dated and priced accordingly. Livable as is - renovate on your own schedule rather than all at once.Small 7-unit association, regularly maintained by the trustee. Rentals permitted with a 12-month minimum lease; no short-term rentals. Resident permit parking available through the City of Boston.Located on Massachusetts Avenue in the heart of the South End. Steps to the Mass Ave Orange Line station and multiple bus lines. Walking distance to Boston Medical Center, BU Medical & Dental campus, SoWa Open Market, Blackstone & Franklin Squares, and the restaurants, galleries & cafes of Tremont & Washington Streets. Convenient to Tufts Medical, Longwood Medical Area, Northeastern, Back Bay Station & the Financial District.An uncommon entry point into one of Boston's most established neighborhoods - well suited to a first-time buyer trading a rent payment for equity, or to an investor looking for a value-add hold in a market where one-bedrooms rent strongly.

$549,900 Active

664 Massachusetts Ave 4 Boston, Massachusetts

1 Beds 1 Baths 760 SqFt

Great for end-users or investors—an opportunity to get into the South End at a great price! This sunny, front-facing studio blends classic character with thoughtful updates, featuring an updated kitchen, walk-in closet, and rich hardwood floors throughout. The spacious layout comfortably accommodates both dedicated sleeping and living areas, while exposed brick detailing and a charming bay window bring warmth, character, and abundant natural light. Ideally situated in the heart of the South End, just moments from Back Bay, Southwest Corridor Park, and the restaurants, cafés, and neighborhood favorites along Columbus Avenue.

$480,000 Active

558 Columbus Ave 3F Boston, Massachusetts

1 Baths 403 SqFt 0.01 Acres

This one-bedroom home offers a sophisticated blend of historic character, modern updates, and convenient city living. Set in a beautiful building with two private entrances, the home features private outdoor space and one deeded parking space. The oversized, recently renovated chef’s galley kitchen showcases custom granite countertops, a new backsplash, and Viking appliances. The open living and dining area is ideal for relaxing or entertaining, with French doors leading to a private patio. Exposed brick and built-in bookshelves add warmth, character, and functional storage. The spacious bedroom accommodates a king-size bed and has two custom closets. The en-suite, spa-inspired bathroom features dual shower heads and marble finishes. Additional highlights include hardwood floors throughout, in-unit washer/dryer, central A/C, custom closets, off-street parking, and a private entrance. Ideally located near the restaurants and shops of the South End, the Prudential Center, and Back Bay’s Boylston and Newbury Streets, with convenient access to public transportation.

$849,000 Active

209 W Springfield St 1 Boston, Massachusetts

1 Beds 1 Baths 722 SqFt 0.02 Acres

Quinn 2-bedroom, 2-bathroom home with spectacular views of the Back Bay skyline. A desirable floor plan that feels more private, with bedroom suites on either end of the home. The open design of the main living area is ideal for entertaining and for taking in the expansive views through the floor-to-ceiling windows.The kitchen features white upper cabinets, light oak cabinets & integrated Thermador appliances, including a built-in wine cooler and quartz counters. Great closet space throughout, including two walk-ins, two linen closets, and three additional full-size closets. One garage space is included.Enjoy full-service living with a concierge staff, an 8,000-SF Equinox-designed gym, a SoulCycle bike room, a bouldering wall, a yoga studio, a basketball/squash court, a pool, and a sauna. Residents also have beautifully appointed lounges, both inside and outside. There's also a billiard room, video game room, library, and WFH spaces. Dine downstairs at Kaia. Across the street are Tatte and CVS. It's one block from Whole Foods and several fitness options. Highway and airport access is a breeze!

$1,925,000 Active

380 Harrison Ave 1011 Boston, Massachusetts

2 Beds 2 Baths 1,198 SqFt

Sunny one bedroom with private deck and garden views in the heart of the South End! Spacious bow front living room with ornamental marble mantel, separate dining alcove, modern kitchen with granite countertops and gas cooking. Large bedroom with ensuite bathroom. Glass doors lead to private deck. Central A/C, Washer/Dryer in unit. Pets OK.

$699,000 Active

599 Tremont St 6 Boston, Massachusetts

1 Beds 1 Baths 643 SqFt 0.01 Acres

Experience life in the South End on the edge of Back Bay, in this highly desirable, full service building at 75 Clarendon. This 6th floor, penthouse one bedroom features an extra space for an office or guest. You'll enjoy the open, galley kitchen, with tastefully chosen, top quality, stainless appliances, granite countertops and lots of cabinet storage. In the living room you'll find oversize windows facing southwest, that fill space with natural light, while you enjoy the charm of the fireplace and cherry hardwood floors. Or relax on the common roof deck and enjoy a beautiful city skyline view. Living at the corner of Clarendon and Columbus means easy access to Copley Square, Back Bay Station and I-93 and I-90, while a plethora of restaurants, cafe's and nightlife are just steps away. Central AC and Laundry in the condo. What more could you want?

$825,000 Active

75 Clarendon St 607 Boston, Massachusetts

1 Beds 1 Baths 640 SqFt 0.01 Acres

The Marais is an 8-unit boutique luxury building on a quiet tree-lined South End side street. Originally part of the historic St. James Hotel (1868), this sun-filled three exposure residence offers contemporary finishes in an elegant building with single-level living. A private elevator stop opens into the large foyer of this two bedroom, plus study, 2 and 1/2 bath home that has floor-to-ceiling windows and high ceilings throughout. The huge corner living room with an original marble gas fireplace opens to a large study/library with an adjacent powder room. The open plan kitchen/dining room has top of the line appliances with a vented gas Wolf range, a large island with seating for stools, and a pantry with a wine refrigerator. The spacious (29' 9"' x 8' 7") walk-out deck has great views and two gas grill hook-ups. The primary bedroom has another original fireplace mantle, built-in bookcases, and a walk-in closet while the primary bath has Carrara marble finishes, a double vanity, soaking tub and shower with a bench. The second bedroom has an en-suite bath with shower, and there is in-unit laundry and central A/C. The Marais is a professionally managed. building with bike storage, and a pet spa. Deeded parking space No. 2 (carport), a garage spot (No. 204) across the street at The Penmark and deeded storage are included.

$2,895,000 Active

19 Father Francis Gilday Street 201 Boston, Massachusetts

2 Beds 3 Baths 1,962 SqFt

Set on the parlor and garden levels of an unusually wide South End/Back Bay building, this 2019 gut-renovated three-bedroom plus office duplex lives like a single family. The generous parlor has a bay of oversized windows that flood the main living space with light all day long. The huge chef's kitchen has a rare adjacent pantry which houses a floor to ceiling Sub-Zero wine fridge, extra beverage drawers and suburban like storage for dry goods. The living room boasts a warm gas fireplace and is an entertainer's dream with enough space for all of your friends and neighbors. The kitchen anchors it all: Sub-Zero and Wolf gas appliances, stone counters, custom cabinetry and a convenient island for morning coffee - the kind of setup that makes hosting effortless, whether it's a dinner party for twelve or a quiet Sunday morning. Hardwood floors run throughout, tying the whole home together. The bedroom level has three true bedrooms, a dedicated office/gym space, a full laundry room and extra storage. Location-wise, you get the best of both worlds. You're close enough to the Pru, Newbury Street, and Copley Square to walk to the Back Bay, but step outside and you're immediately in South End — brownstone-lined streets, a slower pace, neighbors who actually know each other. The restaurants, galleries, and sidewalk energy that make the South End special are just steps from your door. A short hop to Titus Sparrow park for green space, playgrounds and outdoor bands in the summer make this the ideal local spot to enjoy all that the South End has to offer.

$2,250,000 Active

131 St Botolph St 1 Boston, Massachusetts

3 Beds 3 Baths 1,991 SqFt

This sun-filled upper floor residence on a quiet tree-lined side street has one bedroom and two full baths in a gorgeously renovated townhouse. The bow-front living room has an original Italian Carrara mantlepiece, hardwood floors, original crown moldings and high (10' 3") ceilings. The crisply renovated kitchen includes a dishwasher and microwave, with white counters, cabinetry and subway tile backsplash. The spacious bedroom has hardwood floors, a sunny private primary bath, and large walk-in closet area with a washer/dryer hookup. The furnished common roof deck has amazing skyline views and includes a hard-piped Weber gas barbecue for easy outdoor grilling! Claremont Park is just minutes from the Prudential Center and the Orange and Green lines, as well as the shops and restaurants of the South End.

$849,000 Active

4 Claremont Park 2 Boston, Massachusetts

1 Beds 2 Baths 734 SqFt 0.05 Acres

Experience sophisticated South End living at 100 Shawmut Avenue. This beautifully appointed one bedroom, one bathroom residence offers a thoughtfully designed open layout with 9-foot ceilings, white oak flooring, and contemporary finishes throughout. The sleek chef’s kitchen features a generous island and integrated Thermador appliances, Silestone countertops, gas cooking, and pendant lighting—creating an inviting space for both everyday living and entertaining. In-unit laundry, central air, and excellent closet space add everyday convenience. Residents of 100 Shawmut enjoy an exceptional collection of amenities, including 24/7 concierge service, an elegant lobby lounge and great room, library, private dining and entertaining spaces, fitness and wellness center, billiards and activity lounges, children’s playroom, pet spa, and a beautifully landscaped third-floor courtyard. The rooftop Sky Lounge and 100 Club offer gas grills, fire tables, and impressive views toward Back Bay. Ideally situated in Boston’s vibrant South End, Unit 414 places some of the best dining, shopping, parks, hospitals, cultural destinations, and transportation within easy reach. A refined city residence combining modern design, full-service amenities, and an outstanding Boston location. Join us for champagne and French macarons at the open houses on Saturday 9/19 and Sunday 9/20 from 11:30-1:30.

$725,000 Active

100 Shawmut 414 Boston, Massachusetts

1 Beds 1 Baths 631 SqFt

Tucked away in the heart of the South End, this stylish one-bedroom condo delivers the perfect urban retreat. Enter through your own private entrance into a bright, open-concept living and dining area designed for easy, everyday living. The kitchen has been thoughtfully gut renovated in 2013 with quartz countertops, white shaker cabinetry, and stainless steel appliances, equal parts functional and refined.The fully renovated bathroom features a sleek tiled shower, while the private back patio offers a quiet outdoor escape ideal for grilling or gathering. Storage is anything but an afterthought, a generous bedroom closet and a walk-in closet off the living room keep everything in its place. Laundry and dedicated storage right outside your door, this one's a no-brainer for first-time buyers and investors alike.

$445,000 Active

15 Saint George St A Boston, Massachusetts

1 Beds 1 Baths 465 SqFt 0.01 Acres

In the heart of the South End’s coveted Eight Streets neighborhood, this beautifully appointed one-bedroom home pairs a thoughtful layout with an exceptional private outdoor space. Overlooking the greenery of Ringgold Park, the open living and dining area enjoys a peaceful backdrop and an inviting connection to the outdoors. The updated kitchen features quartzite countertops, stainless steel appliances and direct access to an oversized private patio—an impressive extension of the living space with room to dine, entertain and unwind. Inside, the spacious bedroom offers a large walk-in closet, while a dedicated home office provides a distinct and valuable work-from-home space. Custom storage, wood floors and in-unit laundry complete the 710-square-foot residence. Pet-friendly and just moments from neighborhood cafés, restaurants, boutiques and the dog park, 75 Waltham Street offers the combination that makes the Eight Streets so desirable: a quintessential South End setting, smartly designed interiors and truly usable private outdoor space.

$885,000 Active

75 Waltham St 1 Boston, Massachusetts

1 Beds 1 Baths 710 SqFt 0.02 Acres

South End living at its finest. This two-bedroom condo gives you the location you want with a layout that just works. The open living and dining room is anchored by a fireplace, creating a warm, inviting space for everyday living or entertaining. The galley kitchen has a separate breakfast area—perfect for morning coffee or a casual meal. Two good-sized bedrooms offer plenty of flexibility, with built-in dressers for smart storage without taking up extra space. And then there are the things that make city living so much easier: laundry right in the unit and, yes, one-car deeded parking. No circling the block looking for a spot! Comfortable, convenient and right in the heart of the South End with all of the great restaurants. This is the one you’ve been waiting for.

$899,000 Active

29 Worcester Sq 5 Boston, Massachusetts

2 Beds 1 Baths 880 SqFt

NEW CONSTRUCTION. A sophisticated 3-bedroom plus study, 3.5-bath home offers a remarkable connection between beautifully designed interiors and extraordinary private outdoor spaces. The main living level is designed for everyday living and entertaining, with a marble-surround gas fireplace and a beautifully appointed kitchen featuring an AGA range, custom cabinetry, SubZero refrigeration + beverage center. A wall of windows extend the kitchen and living space directly onto a private deck, creating a seamless transition outdoors that overlooks the tiered garden with brick and stone hardscape, and a generous lawn area. Outdoor spaces are plumbed for natural gas grilling. The serene primary suite includes a Juliette balcony overlooking the garden, a walk-in closet, and a luxe bathroom w dual vanities, Ann Sacks tile and Arabescato marble. Two additional bedrooms and a separate study provide exceptional flexibility, along with a wet bar in the family room. Three and a half luxurious Waterworks-appointed baths showcase sophisticated materials and detailing throughout. Ideally situated in the coveted Eight Streets neighborhood, moments from the restaurants and shops of Tremont Street, Ringgold Park and Peter’s Park. A rare opportunity to enjoy the scale and character of a South End townhouse, the refinement of new construction, and an extraordinary indoor/outdoor lifestyle in the heart of the city. Brought to you by Highstreet Development and design by Embarc.

$3,200,000 Active

32 Hanson 1 Boston, Massachusetts

3 Beds 4 Baths 2,004 SqFt

Set on the third floor of a classic South End brownstone, this sun-filled residence pairs historic charm with thoughtfully updated interiors. The front-facing living room is bright and inviting, while the renovated kitchen features stainless steel appliances, modern finishes, and a functional layout. The spacious primary bedroom is distinguished by an original fireplace and mantel, adding the architectural character that makes South End homes so special. A second bedroom offers flexibility for guests, a home office, or additional living space, and the updated bathroom features a sleek stone shower, with in-unit laundry. All of this is just moments from the neighborhood’s acclaimed restaurants, galleries, shops, and public transportation. First open house Sunday, September 20th from 11am - 1pm.

$625,000 Active

88 W Springfield St 3 Boston, Massachusetts

1 Beds 1 Baths 642 SqFt 0.01 Acres

Beautifully appointed 2 bedroom, 2 bathroom corner home with garage parking and sweeping City views at The Quinn - the South End's premier full-service residences. Enter to a spacious open concept living/dining area with floor to ceiling windows streaming natural light. Designer chef's kitchen features Bosch and Thermador appliances, wine cooler, abundant cabinetry & sleek countertops with island seating for 3. King size primary suite offers 3 closets & en-suite marble bath with double vanities. Second queen-size bedroom offers 2 closets & is adjacent to second full bath with shower stall. High ceilings, gleaming hardwood floors, central AC and in-unit laundry complete this spectacular offering. Amenities include state-of-the-art concierge services, indoor pool & sauna, 8,000 SF gym, squash court, billiards room, lounges & an expansive roof terrace w/ BBQ grills and lounge seating. Ideally situated within South End's vibrant Ink Block and SoWa district, moments from acclaimed restaurants, shops, Whole Foods, galleries, public transit, highway access & more.

$1,925,000 Active

380 Harrison Ave 1013 Boston, Massachusetts

2 Beds 2 Baths 1,235 SqFt

An opportunity of this magnitude, within Boston's historic South End does not typically exist at such an affordable price. Priced to sell, this ~1,000 above grade sf, first floor unit is situated next to tranquil Franklin Square, and walking distance to Boston Medical Center and Boston University School of Medicine. Minutes to the Seaport, the Back Bay, South Boston, major highways, public transportation, & world-renowned restaurants and shopping. The unit is in terrific condition and was finished in 2016. Features include a large living room, hardwood floors, updated kitchen and stainless-steel appliances, in-unit laundry, walk-in master closet, southeastern sun exposure, and more. Building is professionally managed

$848,000 Active

19 Father Francis Gilday St 102 Boston, Massachusetts

2 Beds 1 Baths 961 SqFt

511 Chester Square in the historic South End is 2018 new construction by noted builder Kennedy Design Build. An open-concept layout, high ceilings and dramatic and sunny west-facing floor-to-ceiling windows fill the home with natural light throughout the afternoon. Designer kitchen featuring sleek custom cabinetry, a refined monochromatic palette, brass accents, premium Wolf/Miele appliances and counter seating feeds to a generous private deck perfect for al fresco dining and grilling. Modern gas fireplace creates a lovely focal point for the living area. King-sized primary suite occupies the tall double windowed bow front of the home and features a custom walk-in closet as well as spa-inspired en-suite bath with double sink vanity & step-in shower. Bright 2nd bedroom also enjoys Back Bay views while a beautifully appointed guest bath offers a tub w/shower and clean contemporary finishes. Only one flight up once in the building, additional highlights include central AC & in-unit laundry. Just out the front door are boutiques, cafes & acclaimed restaurants including Mida & Toro. Garage parking space for rent only 500FT away!

$1,225,000 Active

511 Massachusetts Avenue 3 Boston, Massachusetts

2 Beds 2 Baths 1,063 SqFt

Set within one of the South End’s coveted brownstone streets, this penthouse at 7 Upton Street offers a rare combination of space, scale, and effortless single-level living. This two bedroom plus a separate office condo is just one flight from the building entrance, creating an easy and private transition from street to home. You enter in to a welcoming drop station before ascending one flight to a thoughtfully designed floor plan where the living spaces and all bedrooms are conveniently located on one level, a truly unique feature in a historic South End brownstone. The expansive living room flows seamlessly into the dining area and spacious kitchen. The generous proportions throughout the home give it an exceptional sense of openness and flexibility. Both bedrooms are generously sized, offering comfortable accommodations and excellent separation from the main living spaces. Both bathrooms were beautifully renovated in 2026, including a spacious primary bath with a double vanity and walk-in shower. A versatile office/flex space adds another dimension to the home and provides the extra room today’s buyers are looking for. This room could easily be enclosed to offer a dedicated home office, den, nursery, guest space, this flexible area can easily adapt as your needs evolve. The home’s best feature is the expansive private roof deck, accessed directly by a full interior staircase. With ample room for lounging, dining, and entertaining it extends the living space well beyond the walls of the home!

$1,899,000 Active

7 Upton Street 4 Boston, Massachusetts

2 Beds 2 Baths 1,620 SqFt 0.04 Acres

Located on a serene, tree-lined cul-de-sac and overlooking picturesque Sparrow Park with sweeping views of the Back Bay skyline, 68 W Rutland Square offers an elegant and expansive single-family residence boasting over 5,000 square feet of beautifully designed living space.Renovated from top to bottom, the home retains its original architectural details, such as soaring ceilings, decorative moldings, and grand bay windows, while offering every amenity for today’s discerning buyer. The layout includes a full-floor primary suite, 4 additional bedrooms, 3 full baths, and 3 half baths, providing generous space for both family living and entertaining. Enjoy THREE private outdoor spaces, a state-of-the-art home gym, a climate-controlled wine cellar, and a heated garage and driveway, something few South End brownstone homes can match. With Sparrow Park just outside your door, this is a rare opportunity to enjoy gracious city living with the indoor-outdoor lifestyle every Bostonian dreams of.

$6,795,000 Active

68 W Rutland Sq. Boston, Massachusetts

5 Beds 6 Baths 5,135 SqFt 0.04 Acres

Located on a tree-lined street in the South End, 13 Wellington Street is a single-family home offering 3,110 square feet across four floors, four bedrooms, and three baths, with exceptional ceiling height and dual east and west exposures that fill the home with light throughout the day. The first floor is anchored by a primary suite with a large walk-in closet and en-suite bath, along with a sitting room featuring built-in shelving and a bay window. The second floor adds two more bedrooms, a full bath, and a home office. The top floor opens entirely to living, with a kitchen, living room, dining area, and back deck with city views. The finished lower level offers flexible space well suited as a guest or in-law suite, complete with its own kitchenette and full bath. A wine cellar, laundry, and ample storage round out this level. A professionally landscaped patio, full-sized private parking, multi-zone air conditioning, and gas heat complete the home.

$3,299,000 Active

13 Wellington St Boston, Massachusetts

4 Beds 3 Baths 3,110 SqFt 0.05 Acres

Direct elevator access, full-sized tandem heated garage parking space #PS230/231 for 2 cars. 25 Savoy Street (Rollins Square) is a secure, well-lit garage with easy entrance and exit. The garage offers 24-hour video security and the option to install an electric car charger at your spot (owners’ cost). Buyer must be a South End resident.

$157,500 Active

25 Savoy Street #PS 230/231 Boston, Massachusetts

32 Milford 4 is a bright and spacious one bedroom penthouse located in the desirable Eight Streets neighborhood in the South End. Framed by vaulted ceilings at almost 10 feet and three front-facing windows, and skylights the home is filled with natural light and offers a refined open-concept living, anchored by an elegant decorative fireplace. The generously proportioned bedroom provides abundant closet space while in-unit laundry and updated bathroom make this a turn-key residence. An expansive private roof deck presents sweeping views across the South End and Back Bay—an exceptional setting for entertaining or outdoor retreat. Only 2 flights up to the home and ideally located moments from Restaurant Row, Ringgold Park, and Peter’s Park, this pristine condo offers a quintessential South End lifestyle in one of Boston’s most sought-after neighborhoods.

$875,000 Active

32 Milford 4 Boston, Massachusetts

1 Beds 1 Baths 729 SqFt

$625,000 Active

473 Massachusetts Ave. 2 Boston, Massachusetts

1 Beds 1 Baths 767 SqFt 0.02 Acres

Distinctive parlor duplex at The Penmark, an architecturally significant South End residence thoughtfully converted from the historic Boston College High School. A semi-private entrance shared with just one other home gives this 2 bedroom, 2 bath condo an unusual sense of privacy from the moment of arrival. Inside, soaring 12-foot ceilings and dramatic arched windows define the main level, with leafy views and beautiful natural light adding to the remarkable volume of the space. Reclaimed wide-plank floors, crafted from old barn beams, add warmth and character throughout. The spacious living room flows naturally to a dining area with room for 6, and a recently renovated kitchen featuring quartz countertops, newer stainless appliances and gas cooking. Downstairs, both bedrooms are comfortably removed from the entertaining spaces, including an oversized primary suite with en-suite bath. A renovated second full bath, in-unit laundry, and ample storage complete the lower level. Set on a quiet South End street near neighborhood parks, The Penmark pairs historic architecture with a full-service lifestyle, including concierge services, elevator, fitness center, pet wash area, and elegantly renovated common areas. Garage parking for two cars (tandem) adds the ultimate convenience.

$1,195,000 Active

21 Father Francis Gilday St 109 Boston, Massachusetts

2 Beds 2 Baths 1,419 SqFt 0.03 Acres

Stunning New Construction 2 bed in charming South enclave bursting with historic charm. One of the first & oldest buildings in the South end, this historic treasure has been carefully rebuilt with a purposeful interior gut renovation, while the the stunning exterior restoration will bring it back to it's historic prominence, offering a rare street presence. The meticulously designed layout is excellent for entertaining with a wide open dining kitchen living arrangement & an amazing detail/ finish carpentry package. The dazzling kitchen boasts custom cabinetry, breakfast bar, Cafe Stainless Steel appliances with gas range. The Spacious Primary bedroom has breathtaking historic windows. Well sized 2nd bedroom. Situated in the heart of The South end, one if Boston's most vibrant neighborhoods, just steps to countless South end restaurant's, cafes, & Shops. Central air, w/d in Unit, nest, Marvin windows, white oak hardwood floors. Under Construction, Expected Completion Mid Winter. Rare Opportunity for some finish customizations !

$899,000 Active

6 E Springfield St 3 Boston, Massachusetts

2 Beds 1 Baths 752 SqFt

Exceptional four bedroom single family located in the heart of the South End! Victorian double parlor level with pocket doors plaster moldings, wood casings, & marble mantels. A beautiful entertaining space & intimate den with home theater & wet-bar. The kitchen, dining & living level has an open floor plan with convenient half bath & wet-bar. The custom Venegas design kitchen is a cook's delight! Finished with an oversized island, quartzite counters, Sub-Zero, Wolf appliances & great storage. The primary suite is an oasis. The spacious bedroom connects seamlessly through the spa style bath with glass enclosed shower, double vanity to the dressing room with laundry & office. A full staircase continues to the amazing roof-deck with 360 degree city views! Lower entrance with easy access for bikes & strollers. Two additional spacious bedrooms & full bath with laundry. Garden level family room with kitchenette & office leads to a beautiful private patio. Control 4 A/V, central a/c & more.

$4,395,000 Active

112 Appleton Street Boston, Massachusetts

4 Beds 3 Baths 3,678 SqFt 0.03 Acres

Rare opportunity to own a stunning South End condo that perfectly blends historic charm with modern convenience. This spacious home offers 2 bedrooms plus a versatile flex room approx. 82 sqft ideal for guest room, den, or office. The luxurious full bath features a relaxing Jacuzzi soaking tub, separate glass-enclosed shower and double vanity. Soaring ceilings, gleaming hardwood floors, crown molding, and a sun-drenched bay window create an inviting and elegant atmosphere throughout. The open-concept living, dining, and kitchen layout is perfect for everyday living and entertaining, centered around a beautiful decorative fireplace. Enjoy generous closets and a welcoming foyer entry. The tastefully updated kitchen boasts stainless steel appliances and breakfast bar seating. Complete with in-unit laundry and a private outdoor patio, this home checks every box. Unbeatable South End location near Boston Medical Center, Tufts Medical, Northeastern, acclaimed restaurants, Orange&Green line.

$719,999 Active

617 Massachusetts Ave 1A Boston, Massachusetts

3 Beds 1 Baths 1,000 SqFt 0.02 Acres

Rarely available penthouse triplex just steps to the best of the South End and the Back Bay. Three plus bedrooms with two and a half baths, private outdoor space and a great layout. The gracious entry vestibule creates the perfect landing space for bikes, stroller, coats and shoes. One flight up, the main living level opens to soaring 11+ foot ceilings, beautiful hardwood floors, and abundant natural light. The living and dining areas showcase historic crown molding and custom built-ins. The chef’s kitchen features a Viking gas range, stainless-steel appliances, stone countertops and excellent storage, with direct access to a private deck—ideal for morning coffee, al fresco dining and entertaining. A convenient half bath completes this level. The next floor is dedicated to the primary suite, featuring a spacious full bath with beautiful tile and a large glass-enclosed shower. An adjoining flexible space offers exceptional versatility as a dressing room, nursery, sitting area or home office. The bedroom area has beautiful original detail and bed alcove. The top floor front bedroom includes an adjoining room that could serve as a home office, nursery or potential additional bedroom. The second bedroom features a wall of windows and lovely South End views. Garage rental parking is conveniently available at The Atelier 505, just a few steps away. Central air conditioning, hardwood floors throughout and an abundance of architectural character complete this truly special home.

$2,695,000 Active

43 Warren Avenue 2 Boston, Massachusetts

3 Beds 3 Baths 2,022 SqFt 0.05 Acres

The best of the South End with the benefits of a 5-unit Brownstone rebuilt with all new systems in 2019. This move-in-ready, full-floor Parlour-level 2-bedroom is set within a classic Victorian rowhouse that was extensively rebuilt from the studs in 2018/2019, including new infrastructure, electrical, plumbing, flooring, kitchens and baths—offering the character of a historic home with the confidence, efficiency and lower-maintenance ownership of newer construction. Inside, two remarkable 7' South End Landmark District-correct bay windows preserve the home’s architectural presence, while mini-split heating and cooling, in-unit laundry, hardwood floors and recessed lighting make everyday living effortless. The open kitchen and living space features tailored cabinetry, JennAir appliances and a waterfall granite counter. Just beyond, a rare 11' x 17' private roof deck sits directly off the living level and functions like an outdoor living room—an exceptional amenity in the South End! Two queen-size bedrooms feature Elfa closet systems. With major building work completed relatively recently, owners benefit from newer structure and systems and less exposure to the kinds of aging-infrastructure projects that can lead to costly repairs and special assessments in older buildings. Pet-friendly (2 pets allowed!) and ideally positioned on a tree-lined block, moments from the South End’s acclaimed restaurants, boutiques and galleries, with Back Bay, Symphony, cultural institutions, 12 minutes to Logan Airport, I-90 and I-93 all within easy reach. Historic South End beauty, thoughtfully rebuilt for modern ownership. This is the one you've been waiting for: Welcome home!

$790,000 Active

55 E Springfield St 2 Boston, Massachusetts

2 Beds 1 Baths 706 SqFt 0.02 Acres

The Marlowe introduces 44 new residences in Boston’s South End. This 2-bedroom plus a glass enclosed den/office, 2-bathroom, penthouse offers approximately 1,035 SF of open living space and a large private terrace. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, a statement island, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$1,500,000 Active

127 E Dedham St 605 Boston, Massachusetts

2 Beds 2 Baths 1,035 SqFt

The Marlowe introduces 44 new residences in Boston’s South End. This 1-bedroom plus a glass enclosed office/den space, 1-bathroom home offers approximately 945 SF of open living space. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, a statement island, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$1,000,000 Active

127 E Dedham Street 508 Boston, Massachusetts

1 Beds 1 Baths 945 SqFt

The Marlowe introduces 44 new residences in Boston’s South End. This 2-bedroom, 2-bathroom, corner penthouse with downtown city views, offers approximately 1,160 SF of open living space with a large private terrace. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, a statement island, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$1,550,000 Active

127 E Dedham St 601 Boston, Massachusetts

2 Beds 2 Baths 1,160 SqFt

The Marlowe introduces 44 new residences in Boston’s South End. This 1-bedroom, 1-bathroom home, with downtown city views, offers approximately 780 SF of open living space. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$925,000 Active

127 E Dedham St 501 Boston, Massachusetts

1 Beds 1 Baths 780 SqFt

Elegant and sunny parlor-level one bedroom home on desirable tree-lined Appleton Street, ideally located between Clarendon and Dartmouth streets. This beautiful property showcases the best of South End living: soaring ceilings enhanced by turn-of-the century decorative moulding, warm hardwood floors throughout and gracious bay windows at the front and rear of home that provide natural light throughout the day. Home also features a private rear balcony that overlooks a serene brick patio with mature plantings, an efficient galley kitchen with updated cabinets and countertops and stainless-steel appliances, a fresh and modern tiled bath and in-unit laundry. 114 Appleton #2 is located in a stately, well-maintained 4-unit building with low condo fees, and is perfectly situated between Back Bay's offices and parks and the South End's cafe, restaurants and galleries, while offering easy access to highways, MBTA and Amtrak stations, and Logan International Airport.

$815,000 Active

114 Appleton 2 Boston, Massachusetts

1 Beds 1 Baths 608 SqFt 0.23 Acres

The Marlowe introduces 44 new residences in Boston’s South End. This 2-bedroom, 2-bathroom, corner home offers approximately 1,148 SF of open living space. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, a statement island, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$1,295,000 Active

127 E Dedham St 102 Boston, Massachusetts

2 Beds 2 Baths 1,148 SqFt

The Marlowe introduces 44 new residences in Boston’s South End. This 2-bedroom plus a glass enclosed den/office, 2-bathroom home offers approximately 1,305 SF of open living space. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, a statement island, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$1,400,000 Active

127 E Dedham St 206 Boston, Massachusetts

2 Beds 2 Baths 1,305 SqFt

The Marlowe introduces 44 new residences in Boston’s South End. This 1-bedroom, 1-bathroom home offers approximately 740 SF of open living space. Originally built more than a century ago, the building has been thoughtfully transformed with a restored masonry facade, contemporary upper addition, and new rear expansion. Residences feature typical ceilings rising above 10 feet throughout most of the building, expansive windows, wide-plank European white-oak flooring, and a warm palette of natural wood and stone. The kitchen features custom cabinetry, a statement island, stone countertops, integrated paneled appliances and ample lighting. The bathroom includes a custom vanity, stone surfaces, textured tilework, frameless glass shower, and polished fixtures. The lobby features rich materials, sculptural lighting and a site-specific mural commissioned from Boston artist Cyrille Conan. An elevator serves every level, including the expansive common roof deck with views across the South End, Downtown Boston, and Back Bay. The roof deck also includes a grilling area, kitchenette, and dedicated powder room. Located in SoWa, near the emerging South End Exchange District, The Marlowe is close to galleries, studios, design showrooms, shops, restaurants, and markets, with convenient access to Back Bay, Downtown Boston, the Seaport, major highways, and Logan Airport. Developed by New Boston Ventures, with architecture and design by RODE Architects and construction by Holland Construction.

$825,000 Active

127 E Dedham St 205 Boston, Massachusetts

1 Beds 1 Baths 740 SqFt

$925,000 Active

127 E Dedham Street 207 Boston, Massachusetts

1 Beds 1 Baths 850 SqFt

$1,825,000 Active

69 Rutland St 3 Boston, Massachusetts

2 Beds 3 Baths 1,607 SqFt 0.04 Acres

SHOWINGS BY APPOINTMENT ONLY. Located on a picturesque tree-lined street in the South End of Boston, this pretty light-filled 2-bedroom condominium has been extensively renovated and blends the charm of the original brownstone features with contemporary upgrades. Soaring ceilings, refinished floors, and recessed lighting create a bright and inviting atmosphere. The living room features a fireplace and charming bow window, opening to a stylish chef’s kitchen with a quartz peninsula, contemporary cabinetry, and stainless-steel appliances including a gas range. The primary bedroom offers a walk-in closet, a beautifully appointed quartz and tile bathroom and direct access to a private deck. The second bedroom also opens to the deck. Modern upgrades include a new HVAC system with 3 mini-splits, in-unit washer/dryer, updated lighting and electrical. This 5-unit, pet friendly association offers low condo fees. Ideally located near the SW Corridor Park, Back Bay, Copley and the South End's renowned restaurants and cafes.

$1,250,000 Active

209 W Canton St 3 Boston, Massachusetts

2 Beds 2 Baths 835 SqFt 0.02 Acres

Rarely available, fully renovated parlor and second-floor duplex offering a thoughtfully designed layout and beautiful architectural detail throughout. The east-facing living room features soaring ceilings, detailed moldings, a handsome fireplace, and hardwood floors. An adjacent dining area provides direct access to a private deck, while the renovated kitchen is appointed with stainless steel appliances and gas cooking. A guest bath completes the main level. Upstairs are two generously sized bedrooms, including a spacious primary suite with an en suite bath. Additional features include in-unit laundry, central air conditioning, and one tandem parking space. Set within an intimate, three-unit, self-managed association.

$1,995,000 Active

44 Rutland Sq 2 Boston, Massachusetts

2 Beds 3 Baths 1,290 SqFt 0.03 Acres

Available for the first time in over 25 Years – this well-appointed 1 bedroom 1 bathroom floor-through at the corner of Dartmouth and Montgomery Streets has been meticulously cared for. Overflowing with natural light, this property features a southeastern exposure in the bedroom, and a northwestern exposure from the large 2nd floor private deck overlooking picturesque Montgomery Street. Built-in shelving surrounding the fireplace, along with a kitchen breakfast bar keep the space functional. Unique front-facing bedroom with carpeted floors, custom closet and windows. With newly refinished hardwood floors, an updated kitchen and bath, custom sliding glass door, soaring 10+ foot living room ceilings, in-unit laundry, abundant closet storage, as well as additional deeded storage. Close proximity to restaurants and quaint shops of the South End– just bring your furniture, and settle right in.

$849,000 Active

24 Dartmouth 2 Boston, Massachusetts

1 Beds 1 Baths 690 SqFt

Renovated Venetian Gothic beauty located on a much sought after South End Square – Rutland Square designed in the 19-Century around an English-style central garden park. This beautiful low stoop single family developed with a 4-story glass extension is comprised of 5 bedrooms (4 on the top two levels – a rare find), 4 bathrooms and 2 powder rooms, open concept kitchen flows naturally to the living/dining room, expansive family room, sitting room and separate library & office. Distinguishing features include 3 gas fireplaces, custom cabinetry & millwork, wired for home audio/surround sound, custom closets (tremendous amount of storage), designer/custom window treatments & rugs, 2 wet bars, high ceilings, 2 laundry locations, deck off the kitchen, roof deck, patio and direct access parking for 2 cars.

$7,450,000 Active

21 Rutland Square Boston, Massachusetts

5 Beds 6 Baths 4,315 SqFt 0.03 Acres

A renovated South End penthouse with something few homes of its size can offer: an expansive private roof deck with 360-degree views of the city. Located at 331 Shawmut Avenue in a prime South End location, this two-bedroom, one-bathroom corner home benefits from three exposures, filling the interiors with natural light. An open, well-proportioned layout provides generous space for both living and dining, while thoughtful renovations throughout balance classic South End character with a fresh, considered approach to design. The newly expanded kitchen features custom cabinetry, open shelving, abundant storage, stone countertops, warm wood accents, brass details and counter seating, creating a natural gathering point for everyday living and entertaining. Refinished hardwood floors carry throughout the home, complemented by updated electrical and thoughtfully selected lighting. Rich materials give the newly renovated bathroom a distinctive feel, with deep green tile, marble accents, warm brass fixtures, a teak wood vanity, deep soaking tub and radiant heated floors. Both bedrooms are well proportioned, including a primary with a custom built-out walk-in closet offering exceptional storage. A second bedroom provides flexibility for guests, a home office or both, while in-unit laundry adds everyday convenience. Above it all, the expansive private roof deck is directly accessible from the residence and offers extraordinary 360-degree views over the South End and across the Boston skyline, complete with water and electrical hookups. Generous proportions allow for distinct areas for outdoor dining, lounging and entertaining, creating a true extension of the home and a rare amount of private outdoor space in the heart of the city. Set along one of the South End’s most recognizable residential corridors, the location puts some of the neighborhood’s best restaurants, cafés, shops and parks within easy reach. Restaurant Row, SoWa’s galleries, markets and design destinations, and the neighborhood’s historic streets and squares are all close by, with Back Bay and downtown Boston easily accessible. It is a location that offers the residential character of the South End while keeping the best of the city remarkably close.

$1,250,000 Active

331 Shawmut Ave 4 Boston, Massachusetts

2 Beds 1 Baths 822 SqFt 0.02 Acres

Fully renovated garden duplex complete with private patio and 1 full direct access parking space! Located on Dartmouth St at Montgomery St, moments to Back Bay station and Copley Square, this centrally located property is also adjacent to Tremont St and Restaurant row offering easy walking access to many of Boston's most desirable restaurants, shops, galleries & historical sites. A private entrance from Dartmouth St leads into a double entry and the bedroom level of the home. A large front facing bedroom is complete with ample storage, a decorative fireplace and access to a full bath. An en suite bedroom on the back of the building overlooks the homes private garden. The lower level is has a large kitchen with stone island, stainless steel appliances and island with breakfast bar! The large well designed kitchen is open to the living area with windows overlooking the garden areas and offering access to the private patio and to 1 full direct access parking space. This floor also offers a small alcove at the bottom of the stairs that can be used as a separate dining area or interior study. Laundry, abundant storage, wine cellar, half bath, central air, in-unit laundry, newly renovated, electric car charger, pet friendly, and ready for immediate occupancy!

$1,350,000 Active

25 Dartmouth St 1 Boston, Massachusetts

2 Beds 3 Baths 1,727 SqFt 0.04 Acres

An entire South End brownstone. One remarkable home. A truly distinctive opportunity in a market defined largely by condominium living, this offering presents the chance to own an entire classic bow-front brownstone on one of the South End’s most beautiful & coveted tree-lined streets. Currently configured as two meticulously renovated residences, a penthouse triplex & garden duplex, the property has been transformed to near-new construction standards, bringing together timeless architecture, tailored interiors & exceptional flexibility under one roof. For those seeking the scale, privacy & permanence of a true townhome, the property offers the opportunity to combine both residences into one substantial single-family home, with conversion plans available for review. The existing configuration also provides immediate flexibility for multigenerational living, extended family, guests, an au pair or the ability to occupy one residence while generating income from the other. The approximately 2,518 SF penthouse triplex offers 3+ beds & 3.5 baths across three beautifully considered levels. Soaring ceilings, abundant natural light, custom millwork, gas fireplaces & refined finishes define the interiors, while a designer kitchen with custom cabinetry & high-end appliances anchors the main entertaining level. A private balcony extends from the kitchen, while an expansive private roof deck offers Boston skyline views, a built-in grill, integrated sound & fire pit. The approximately 1,802 SF garden duplex offers 2 beds & 2.5 baths across two generous levels, with beautifully proportioned living & dining spaces, a gas fireplace, custom cabinetry, integrated storage & curated finishes throughout. The living space opens directly to a substantial private patio for seamless indoor-outdoor living. Together, the residences provide approximately 4,320 SF of finished interior space, private outdoor living at both the garden & rooftop levels & 2 direct-access parking spaces. Moments from acclaimed dining, cafés, parks, SoWa, boutiques, galleries & premier private schools, this is a rare opportunity to move beyond the traditional condo & own an entire South End brownstone, ready to live beautifully today or become one extraordinary home for the future.

$7,750,000 Active

189 W Brookline St Boston, Massachusetts

6 Beds 7 Baths 4,320 SqFt 0.04 Acres

A highly tailored penthouse, intentionally designed on one of the South End’s most beautiful & coveted tree-lined streets. Occupying the upper three levels of a classic South End bow-front brownstone, this exceptional home spans approximately 2,518 SF with 3+ bedrooms & 3.5 bathrooms, bringing together remarkable scale, architectural character & a distinctly modern point of view. Created in collaboration with Markel Interiors, the residence is thoughtfully curated with custom millwork, refined materials, sophisticated lighting & elevated finishes throughout. The main entertaining level is defined by soaring ceilings, abundant natural light & beautifully proportioned living & dining spaces. A gas fireplace anchors the living room, while custom millwork adds warmth & character. At the heart of the home, the integrated kitchen combines custom cabinetry, high-end appliances & carefully selected finishes with a layout equally suited to everyday living & entertaining. A generous private balcony directly off the kitchen, equipped with gas, water & electrical connections, extends the living experience outdoors. The primary suite occupies its own private level, creating a serene retreat with an intimate sitting area & built-ins, two custom walk-in closets & a spacious four-piece bath. Just off the suite, an additional flexible room provides valuable space for a private office, den or nursery. Two additional bedrooms, each with an en-suite bath, provide private accommodations for family or guests, while a separate family room with gas fireplace creates another inviting place to gather. Crowning the residence is an expansive private roof deck overlooking the Boston skyline & historic South End streetscape. Complete with a built-in grill, integrated sound system & fire pit, it offers an exceptional setting for outdoor dining, entertaining or quiet evenings above the neighborhood. One parking space completes this distinctive home, moments from acclaimed restaurants, cafés, parks, boutiques, SoWa & premier private schools.

$4,750,000 Active

189 W Brookline St PH Boston, Massachusetts

3 Beds 4 Baths 2,518 SqFt

A garden residence of remarkable scale, where tailored design meets effortless South End living. Spanning approximately 1,802 square feet across two beautifully considered levels, this sophisticated 2-bedroom, 2.5-bath garden duplex pairs the timeless character of a classic South End brownstone with the finish, comfort and ease of near-new construction. Thoughtfully designed with an emphasis on both form and function, the home is distinguished by custom millwork, integrated storage, curated lighting, hardwood floors, a gas fireplace and elevated finishes throughout. Generous living and dining spaces create an inviting setting for everyday living and entertaining, flowing naturally into a beautifully appointed kitchen with custom cabinetry, high-end appliances and carefully selected materials. The interiors feel warm and tailored, with thoughtful architectural details and built-ins adding character while maximizing functionality. The living areas extend directly to a substantial private patio, creating a seamless connection between indoors and out with ample room for dining, entertaining, gardening or simply relaxing in a private setting. The bedroom level offers a quieter, more intimate retreat. The serene primary suite features generous storage, a beautifully finished bath and an adjoining sitting area that adds valuable flexibility to the space. A well-proportioned second bedroom with its own en-suite full bath provides comfortable and private accommodations for family or guests. A powder room, additional storage and thoughtful details throughout further enhance the home’s effortless day-to-day livability. Complete with one direct-access parking space, this distinctive residence offers an increasingly rare combination of sophisticated design, substantial private outdoor space, generous proportions and everyday convenience. Ideally positioned on one of the South End’s most coveted tree-lined streets, the home is moments from acclaimed restaurants, cafés, neighborhood parks, boutiques, SoWa and some of Boston’s premier private schools.

$2,750,000 Active

189 W Brookline St 1 Boston, Massachusetts

2 Beds 3 Baths 1,802 SqFt

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