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$3,450,000
14 Beds ⋅ 11 Baths ⋅ 73478206 MLS
A rare turnkey 7-unit investment property with cultural significance, 27 Dudley Street was once home to Maurice Starr where New Kids on the Block and New Edition rehearsed and recorded. Fully gut-renovated in 2021, it delivers modern finishes including waterfall quartz countertops, central HVAC, in-unit laundry, hardwood floors, and 8+ off-street parking spaces, ensuring strong tenant demand. Generating $22,825/month with a 6.3% cap rate and a projected 7.3% cap rate by 9/1/26, it combines reliable cash flow with potential Opportunity Zone tax advantages. Positioned near public transit, universities, and Longwood Medical Area, this asset offers cultural legacy, premium quality, and growth potential in one of Boston’s fastest-growing neighborhoods. Ideal for 1031 exchange buyers or investors seeking a stable, high-performing asset with long-term appreciation potential. Full pro forma and unit breakdown available on request.

27 Dudley St, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.

$1,318,500
10 Beds ⋅ 5 Baths ⋅ 73528818 MLS
Turn-key Fort Hill two-family with vacant possession September 1, 2026 — owner-occupy, house-hack, or select your own tenants. Complete 2018 gut renovation in the Highland Park Architectural Conservation District: Pella windows, Hardie plank siding, central A/C and heating, dual Navien tankless, 200-amp electric, separately sub-metered utilities. Two mirrored five-bedroom units, each with stainless appliances, in-unit washer/dryer, granite counters, hardwood floors, and walk-in closets. 1st floor: 5BR/3BA. 2nd floor: 5BR/2BA. Deeded tandem two-car parking — a Fort Hill rarity. 10-min walk to Roxbury Crossing Orange Line and John D. O'Bryant exam school, minutes to Longwood Medical, Northeastern, downtown Boston, and I-93. Current gross rents $115,140/year with significant upside upon September lease restructure. Eligible for FHA 2-unit (3.5% down), conventional, or DSCR financing. Owner-occupants qualify for Boston residential exemption. Leases expire 8/31/2026.

10-12 Rockledge St, Boston

Listing courtesy of Listing Agent: Judy Joa from Listing Office: Centre Realty Group.

$1,250,000
3 Beds ⋅ 3 Baths ⋅ 73530822 MLS
Bring your vision & your desire for elevated living to this thoughtfully renovated brick residence in Boston’s historic Fort Hill neighborhood. This unique property offers 3 bed/2.5 baths, an open-concept layout, white oak floors, stylish kitchen, updated systems, designer finishes, generously sized bedrooms w/ custom closets, a stunning primary suite w/ beautifully appointed bath, a flexible bonus room ideal for an office/den/nursery, & a basement offering abundant storage & additional historic character. What truly sets this property apart is the attached architecturally rich brick structure, offering approx. 2,000 SF of space ready to be reimagined into something extraordinary. Whether you envision an ADU, artist studio, guest quarters, home office, wellness space, or income-producing opportunity, this remarkable space invites creativity & offers endless possibilities. Easy access to Longwood Medical area, Downtown, highways, universities, public trans & more. Lot zoned 3F-4000

22 Kenilworth St, Boston

Listing courtesy of Listing Agent: Bernice Osborne from Listing Office: Keller Williams Realty.

$1,150,000
8 Beds ⋅ 5 Baths ⋅ 73489301 MLS
Great opportunity to own a fully renovated two-family property located at 21 Marcella St, offering approximately 3,400+ sq ft of space. This expansive property features 8 total bedrooms and 5 total bathrooms, with each unit offering bi-level living potential, ideal for maximizing space, flexibility, and functionality.Both units have been thoughtfully updated with modern finishes throughout, including newly installed stone countertops, upgraded cabinetry, and stainless steel appliances, creating stylish and durable kitchens suited for everyday living and entertaining. In-unit washer and dryer in both units, providing added convenience for occupants. Residents can enjoy private decks with outdoor sitting areas, along with the benefit of off-street parking. This property presents a versatile investment profilewell-suited for owner-occupants seeking to offset expenses or for investors targeting long-term stability in an area with a consistent rental history.

21 Marcella St, Boston

Listing courtesy of Listing Agent: Hakim Sadler from Listing Office: MIG.

$839,000
2 Beds ⋅ 2 Baths ⋅ 73476293 MLS ⋅ ['The Fort Hill E+ Condominium'] BLDG.
Sustainable style meets city living! This LEED-certified, energy-efficient Fort Hill 2 bedroom, 2 bathroom offers a single-family vibe with windows on all sides, skyline views, southwest light & forever-protected wooded scenery. Love JP? Fort Hill delivers the same charm, plus more space & value! Entertain with ease in the open layout, host dinners in the large dining room, unwind in the cozy living/media room, or sip morning coffee on your private 12x12 patio backed by a protected wooded area. The sunlit top-floor primary suite boasts a rain shower, walk-in closet & bonus nook for your Peloton or office. Custom storage throughout, plus EV charger, solar-power, a deep foyer closet for bikes. Nestled in a historic neighborhood near the iconic Cochituate standpipe, community gardens, Marcella Playground, the Southwest Corridor bike path, two Orange Line stops & the Silver Line. Minutes to JP, South End & downtown — the perfect mix of green living and urban convenience!

156-160 Highland St Unit 156, Boston

Listing courtesy of Listing Agent: O'Connor & Highland from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$760,000
3 Beds ⋅ 3 Baths ⋅ 73488194 MLS
This beautifully maintained 2014 residence offers the ideal blend of comfort, modern living and a ton of space for this price! The expansive duplex layout features an open-concept design with abundant natural light! Three generously sized bedrooms are complemented by a dedicated home office, ideal for today’s work-from-home lifestyle. Enjoy three full tiled bathrooms, including a spa-like bath with a jacuzzi tub. Outdoor space provides the perfect setting for grilling or unwinding, while additional highlights include off-street parking, central A/C, gas cooking, and in-unit laundry. Tucked away on a quiet, charming street, this home offers a peaceful retreat just moments from it all. Conveniently located near public transit, local shops, and grocery stores, with easy access to Jamaica Plain, the South End, and the Southwest Corridor’s scenic green spaces and parks. A rare opportunity to enjoy city living with a serene neighborhood feel, in this immaculate, owner occupied building!

51 Vale St. Unit 1, Boston

Listing courtesy of Listing Agent: Wilson Group from Listing Office: Keller Williams Realty.

$550,000
2 Beds ⋅ 2 Baths ⋅ 73550326 MLS
Set in Fort Hill within the Roxbury Highlands National Register Historic District, this bright 2-bedroom, 1.5-bath condo blends classic character with comfortable modern living. The open floor plan offers abundant natural light and an inviting flow for gathering, dining, and relaxing by the gas fireplace. The sunken primary bedroom opens directly to a private rear deck, while the second bedroom provides additional flexible space. In-unit laundry, deeded tandem parking, and generous deeded basement storage add everyday convenience. Enjoy morning coffee or fall dinners on the deck, plus a shared yard and front garden. A gas-fired boiler provides heat and hot water through an indirect-fired water heater. Just half a mile from the Orange Line, with convenient access to I-93 and the Mass Pike, downtown Boston, the Longwood Medical Area, local universities, and more.

31 Millmont St Unit 2, Boston

Listing courtesy of Listing Agent: Adams & Co. Team from Listing Office: Real Broker MA, LLC.

$429,000
1 Beds ⋅ 1 Baths ⋅ 73492393 MLS
Modern 1-bed, 1-bath condo in the historic Norfolk House, perfectly situated in the vibrant Fort Hill neighborhood. This bright third-floor unit features an open-concept layout with high ceilings, large windows, and hardwood floors throughout, seamlessly extending to a private terrace with amazing views of the city. The stylish kitchen boasts modern stainless steel appliances, a dishwasher, and a breakfast bar overlooking the living room, perfect for entertaining. Enjoy the convenience of central heat/AC, in-unit laundry, and secure access within a professionally managed elevator building that also offers a stunning shared roof deck with panoramic views of the Boston skyline. This incredible location is just steps from Nubian and Roxbury Crossing, Longwood Medical, Northeastern, and BU Med Center, offering modern city living at its finest.

10-18 John Eliot Sq Unit 3D, Boston

Listing courtesy of Listing Agent: Nichols Realty Team from Listing Office: MIG.

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