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27 Dudley St, Boston
$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.
10-12 Rockledge St, Boston
$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.
22 Kenilworth St, Boston
$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.
21 Marcella St, Boston
$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.
27 Guild Street Unit 407, Boston
$1,000,000
3 Beds ⋅ 2 Baths ⋅ 73598751 MLS ⋅ ['Northampton Station Residences'] BLDG.
Welcome to Northampton Residences, a stunning new 28 unit condominium development ideally located in the heart of Fort Hill, Roxbury. Just minutes from Longwood Medical Area, Fenway, Back Bay, and Midtown, this prime location offers exceptional access to both the Silver and Orange Lines, making commuting effortless. Unit 407 features 3 bedrooms and 2 bathrooms, offering a thoughtfully designed open concept layout perfect for modern living. The stylish kitchen showcases two tone cabinetry, stainless steel appliances, and a sleek contemporary design that flows seamlessly into the living and dining areas. Generous bedroom sizes, large closets, and abundant natural light create a comfortable and inviting retreat. This fully amenitized building features a fitness center, two resident lounges, elevator access, and bicycle storage. Complete with in unit laundry hookup and a deeded garage parking space, Unit 407 delivers the perfect combination of luxury, convenience, and city living.

27 Guild Street Unit 407, Boston

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.
187 Highland St, Boston
$879,000
8 Beds ⋅ 2 Baths ⋅ 73476890 MLS
Elevate your portfolio with a rare 8-bedroom powerhouse in the heart of Historic Fort Hill. This isn’t just a two-family; it’s a strategic asset for the visionary who refuses to settle.Unit 1 offers a solid 3-bedroom foundation. Above, Unit 2 unveils a massive 5-bedroom bi-level sanctuary spanning the top two floors, bathed in natural light. Inside, the narrative is "Modern Grit meets Timeless Soul." Cool granite countertops and stainless steel kitchens meet century-old hardwoods. The custom river-rock rainfall shower adds a touch of spa-level luxury that commands premium attention.Situated moments from Roxbury Community College, the demand is relentless. Most will wait for a sign; the elite will recognize this as the deal of a lifetime. In a market this tight, the door is open—but it won’t stay that way. Seize the legacy before someone else does.

187 Highland St, Boston

Listing courtesy of Listing Agent: Alex E. Edwards from Listing Office: Thumbprint Realty, LLC.
16-18 Logan St, Boston
$875,000
4 Beds ⋅ 2 Baths ⋅ 73536299 MLS
Two-family home on a tree-lined street in Roxbury offering excellent value and versatility on a quiet side street on the Hill. Featuring off-street parking, a fenced backyard gorgeous yard with stone patio, and unbelievable sweeping city views. The owner's unit (delivered vacant) consists of a bright and sunny 2-bedroom apartment featuring an updated kitchen & private porch overlooking the City skyline. Conveniently located just a half block from a neighborhood park and close to Nubian Square's local shops, restaurants, hospitals, colleges, universities, and public transportation. Ideal for owner-occupants or investors seeking strong rents, location, and exceptional private outdoor space.

16-18 Logan St, Boston

Listing courtesy of Listing Agent: Julie Simmons from Listing Office: Conway - Dorchester.
27 Guild Street Unit 207, Boston
$730,000
3 Beds ⋅ 2 Baths ⋅ 73541799 MLS ⋅ ['Northampton Station Residences'] BLDG.
Welcome to Northampton Residences, a stunning new 28 unit condominium development ideally located in the heart of Fort Hill, Roxbury. Just minutes from Longwood Medical Area, Fenway, Back Bay, and Midtown, this prime location offers exceptional access to both the Silver and Orange Lines, making commuting effortless. Unit 207 features 3 bedrooms and 2 bathrooms, offering a thoughtfully designed open concept layout perfect for modern living. The stylish kitchen showcases two tone cabinetry, stainless steel appliances, and a sleek contemporary design that flows seamlessly into the living and dining areas. Generous bedroom sizes, large closets, and abundant natural light create a comfortable and inviting retreat. This fully amenitized building features a fitness center, two resident lounges, elevator access, and bicycle storage. Complete with in unit laundry hookup and a deeded garage parking space, Unit 207 delivers the perfect combination of luxury, convenience, and city living.

27 Guild Street Unit 207, Boston

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.
27 Guild Street Unit 103, Boston
$665,000
2 Beds ⋅ 2 Baths ⋅ 73501266 MLS ⋅ ['Northampton Station Residences'] BLDG.
Northampton Residences brings 28 beautifully designed condos to one of Boston's most exciting neighborhoods, Fort Hill in Roxbury, where a tight-knit community feel meets unbeatable city access. The Silver and Orange Lines are right outside your door, and Longwood Medical Area, Fenway, Back Bay, and Midtown are all just minutes away. Unit 102 is a spacious 2 bed, 2 bath with an open-concept layout that feels both stylish and lived-in. The kitchen features two-tone cabinetry and stainless steel appliances that flow naturally into the living and dining areas, a great setup for entertaining or unwinding. Generous bedrooms, large closets, and plenty of natural light round out the interior. The building delivers everything you'd want: fitness center, two resident lounges, elevator, bike storage, and in-unit laundry hookup. A deeded garage parking space is also included. Roxbury's momentum is real and Northampton Residences is built right in the middle of it!

27 Guild Street Unit 103, Boston

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.
49 Norfolk Street, Boston
$660,000
3 Beds ⋅ 2 Baths ⋅ 73557328 MLS
Welcome to 49 Norfolk Street, where historic Boston charm meets modern comfort in the heart of Roxbury's coveted Fort Hill neighborhood. This beautifully maintained attached single-family home is the perfect blend of timeless architectural character & today's most sought-after amenities, offering a move-in-ready lifestyle you'll love coming home to. From the moment you step inside, you'll be greeted by rich period details, soaring ceilings, beautiful millwork & an abundance of natural light that fills every room with warmth & character. Thoughtfully updated while preserving its original charm, this home offers three spacious bedrooms & two full bathrooms designed for comfortable everyday living. The primary suite is a true retreat, featuring an incredible walk-in closet that provides exceptional storage & organization - a rare find in the city. Whether you're starting your day or winding down in the evening, this peaceful space offers the perfect place to recharge. The home's inviting layout flows effortlessly for both everyday living & entertaining. Step outside to your private deck, an ideal spot to enjoy your morning coffee, host summer barbecues, or simply unwind after a busy day while taking in the neighborhood atmosphere. Modern conveniences abound, including central air conditioning to keep you comfortable year-round, energy-efficient solar panels to help reduce utility costs & two coveted off-street parking spaces...an invaluable luxury in Boston. Perfectly positioned in the historic Fort Hill section of Roxbury, you'll enjoy easy access to parks, local cafés, restaurants, public transportation, the Longwood Medical Area, Northeastern University, Roxbury Crossing, the Museum of Fine Arts & downtown Boston. Whether commuting for work, exploring the city's vibrant culture, or enjoying everything the neighborhood has to offer, this location offers exceptional convenience & connectivity. If you've been searching for a home that beautifully balances historic elegance, modern updates, energy efficiency & city living, your search ends here. Welcome home to 49 Norfolk Street—a place where character, comfort & a little everyday bliss come together. Come fall in love with this timeless beauty!

49 Norfolk Street, Boston

Listing courtesy of Listing Agent: Kellyanne Swett from Listing Office: Allison James Estates & Homes of MA, LLC.
101 Cedar St Unit 3, Boston
$560,000
2 Beds ⋅ 1 Baths ⋅ 73530154 MLS
Experience timeless Boston living at 101 Cedar St #3, a charming 1,161 sq ft condo blending historic character with modern comfort. This inviting home features 2 spacious bedrooms and 1 full bath, offering a functional and well-balanced layout with classic architectural details throughout. Ideally located near Hale Elementary School, O’Bryant School of Math and Science, and Boston Latin Academy. Enjoy close proximity to Franklin Park and Roxbury Heritage State Park for outdoor recreation. A great opportunity for both homeowners and investors seeking convenient city living in a well-connected Boston location.

101 Cedar St Unit 3, Boston

Listing courtesy of Listing Agent: Juan Lopera-Martinez from Listing Office: eXp Realty.
31 Millmont St Unit 2, Boston
$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.
10-18 John Eliot Sq Unit 3D, Boston
$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.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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