Roxbury's Fort Hill Real Estate

Roxbury's Fort Hill Real Estate

Welcome to Fort Hill, a hidden gem nestled in the vibrant Roxbury neighborhood of Boston, Massachusetts. This historic area, rich in culture and community spirit, offers a unique blend of urban living and serene green spaces, making it an ideal place to call home.

Fort Hill is renowned for its stunning views of the Boston skyline and its lush landscapes, which include the picturesque Fort Hill Park. This beautifully maintained park serves as a perfect retreat for residents, offering walking paths, playgrounds, and picnic areas where families can enjoy the outdoors. The neighborhood is steeped in history, with many of its homes reflecting the architectural charm of the 19th century, showcasing the area’s storied past.

Culturally vibrant, Fort Hill is home to a diverse community that celebrates its rich heritage through various local events and festivals. The area boasts an array of dining options, from cozy cafes to renowned restaurants, where you can savor flavors from around the world. Additionally, residents enjoy easy access to public transportation, connecting them to downtown Boston and beyond, making commuting a breeze.

Education is a priority in Fort Hill, with several reputable schools and educational institutions nearby, ensuring families have access to quality learning environments. The neighborhood is also close to major hospitals and healthcare facilities, providing peace of mind for residents.

Whether you're looking for a quaint home with historic charm or a lively community with a strong sense of belonging, Fort Hill in Roxbury offers a delightful blend of both. Come discover your new home in this enchanting Boston neighborhood!

Newest Listings in Roxbury's Fort Hill

$400,000
2 Beds ⋅ 1 Baths ⋅ 73579026 MLS ⋅ ['Fort Hill Terrace Condominiums'] BLDG.
Located in highly sought after Fort Hill, this 2 bed, 1 bath condo is totally move in ready! Recent updates in 2025 and 2026 include new hardwood floors throughout the kitchen, living room and bedrooms, fresh paint throughout, a new hot water tank and new stainless steel kitchen appliances. This cozy unit is perfect for owner occupants or investors alike with functional space and great flow. The kitchen is open to the living room and has beautiful butcher block countertops with and overhang that comfortably seats two and plenty of cabinet space. The bedrooms are located on either side of the living room offering a sense of privacy and each has a double-wide closet. Enjoy the perks of a fabulous location, just .3 miles to Jackson Square on the orange line, and close to Rt. 93, Roxbury Community College, Northeastern University, the SW Corridor Bike Path, Highland Park and much more!

1 Centre Street Terrace Unit 4, Boston

Listing courtesy of Listing Agent: Elizabeth Bain from Listing Office: Commonwealth Standard Realty Advisors.
$1,800,000
12 Beds ⋅ 6 Baths ⋅ 73578206 MLS
Updated - Fort Hill - three-family with strong in-place income in one of Roxbury’s most desirable residential neighborhoods. Generating $12,870 per month and $154,440 annually in current gross rental income and 6.64% cap rate, 114-116 Thornton Street presents an exceptional opportunity to acquire a renovated, income-producing multifamily property with a proven rental history. Spanning 3,852 square feet, the property features three spacious 4-bedroom, 2-bath residences, creating an impressive 12-bedroom, 6-bath configuration with approximately 1,284 square feet per unit. Each residence offers a generous layout with a large living room, eat-in kitchen, refinished hardwood floors and updated finishes throughout. Kitchens feature granite countertops and stainless steel appliances. Additional features include gas heat, a large shared backyard and free common laundry in the basement with two washers and two dryers. Ideally situated in Fort Hill, approximately one mile from Northeastern University, the property offers convenient access to the Longwood Medical Area, area universities, public transportation, Downtown Boston and the surrounding Roxbury and Mission Hill neighborhoods. With all three residences currently grossing $12,870 a month, 114-116 Thornton Street combines strong in-place income, renovated interiors and a desirable rental configuration with long-term investment potential.

114-116 Thornton Street, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.
$2,650,000
17 Beds ⋅ 8 Baths ⋅ 73577592 MLS
Rare opportunity to acquire a fully renovated, condo-quality four-family investment property offering a 6.6% in-place cap rate with additional future upside. Ideally positioned between Nubian Square and Fort Hill, 34 Circuit Street offers convenient access to the Longwood Medical Area, Boston Medical Center, Northeastern University, Downtown Boston, public transportation, and the continued development throughout the Roxbury corridor. Spanning approximately 7,365 square feet, the property features four spacious, thoughtfully designed residences with condo quality finishes and desirable unit mix: one 2-bedroom, 2-bath apartment, one 4-bedroom, 1.5-bath apartment, and two expansive 5-bedroom, 2-bath apartments. Each residence features updated kitchens and baths, quality finishes, generous living spaces, and layouts designed for both livability and strong rental performance. Three off-street parking spaces. Currently generating $216,000 in annual gross rental income, the property is 100% occupied with all four units leased through August 31, 2027, providing exceptional income stability from day one. The property is projected to achieve a 7.1% capitalization rate in 2027, offering investors a compelling combination of immediate cash flow and future upside. The condo-quality renovations and strong unit mix make this a truly turnkey multifamily investment. Its larger floor plans, parking, and proximity to major employment, medical, educational, and transportation hubs support continued rental demand. Positioned between Nubian Square and Fort Hill, 34 Circuit Street is well situated to benefit from continued public and private investment throughout the surrounding area. A compelling opportunity for a 1031 exchange, portfolio expansion, or long-term investment, combining scale, stabilized income, quality renovations, parking, and future growth potential in one of Boston's evolving multifamily markets. Pro forma available upon request.

34 Circuit Street, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.
$2,475,000
15 Beds ⋅ 6 Baths ⋅ 73577201 MLS
Rarely available at this scale, this substantial Fort Hill three-family offers 15 bedrooms, 6 bathrooms, nearly 5,750 square feet of rentable living area, strong in-place income, and a current 6.76% cap rate in one of Boston’s most strategically located rental markets. Each of the three expansive residences features 5 bedrooms and 2 full bathrooms, with renovated kitchens and 2 full bathrooms and the added convenience of in-unit laundry. Fully leased through August 31, 2027, the property currently generates $16,725 per month and $200,700 in annual gross rental income, providing immediate, stabilized cash flow with a projected 7.28% cap rate by September 1, 2027. Ideally positioned in historic Fort Hill, the property combines neighborhood character with exceptional access to some of Boston’s largest employment, educational, and medical centers. Located between the Jackson Square and Roxbury Crossing Orange Line stations, with additional public transportation nearby, the property offers convenient connectivity throughout Boston and is close to Northeastern University, Wentworth, MassArt, and the Longwood Medical and Academic Area. Longwood, just down the road, is home to Brigham and Women’s Hospital, Boston Children’s Hospital, Beth Israel Deaconess Medical Center, Dana-Farber Cancer Institute, Harvard Medical School, and numerous other healthcare, research, and academic institutions. With three large 5-bedroom residences, renovated interiors, in-unit laundry, strong existing income, long-term leases, and proximity to transit, universities, and Longwood, this is a compelling opportunity to acquire a stabilized, high-capacity income-producing asset in a well-connected Boston neighborhood.

83-85 Highland Street, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.
$824,000
2 Beds ⋅ 2 Baths ⋅ 73576397 MLS
This newly constructed upper-level residence offers 2,246 square feet of versatile living space, featuring two oversized bedrooms and a finished bonus level ideal as a home office, media room, guest suite, gym, or third bedroom. The chef's kitchen is appointed with brand-new appliances, abundant storage, and flows seamlessly into the expansive living and dining areas. The primary suite serves as a private retreat with a custom walk-in closet, floating vanity, and marble-tiled shower with bench seating.Additional features include hardwood floors throughout, central air, smart home technology, in-unit laundry, EV charging, and access to a large shared backyard with patio space. Ideally located near Nubian Square, the Longwood Medical Area, Boston Medical Center, South Bay Shopping Center, and public transportation, this home offers exceptional space, flexibility, and convenience in one of Boston's most connected neighborhoods

17 Akron St Unit 2, Boston

Listing courtesy of Listing Agent: Penney Gould Team from Listing Office: Compass.
$615,000
3 Beds ⋅ 2 Baths ⋅ 73576173 MLS ⋅ ['Spooner Lambert House'] BLDG.
An amazing three-bedroom condo in the heart of historic Fort Hill, just steps from beautiful Highland Park, this one-of-a-kind home blends centuries of character with thoughtful modern living. Enter through your own private door and discover a home that unfolds beautifully across three levels within the historic Spooner Lambert House. The main level features a generous living room with 18th-century heart pine floorboards, exposed beams, and preserved historic wallpaper, creating a warm, distinctive setting for relaxing or entertaining. The home flows naturally into the dining area and beautifully renewed kitchen, featuring 2025 custom millwork cabinetry, stainless steel countertops, an integrated sink, induction cooking, and a walk-in pantry with integrated shelving. A bedroom with an 18th-century fireplace, 19th-century cast-iron insert, and 2025 tile surround continues the home’s historic character. Custom millwork closets, a renovated full bath with a stone countertop, wood wainscoting, and a tiled shower surround, plus a 2025 stacked washer and dryer add modern convenience. Upstairs, the attic-level third bedroom is a unique retreat with original heart pine floors, hand-carved beams, a skylight, and 2026 custom millwork paneling and stair rail. An updated half bath includes new fixtures and plumbing, with space and plumbing run for a future shower. Outside, enjoy shared grounds with plantings, raised garden beds, a grill, and a patio seating area, while Eliot Square and Highland Park are just moments away. Exposures in all four cardinal directions and cross-ventilation in most rooms bring abundant natural light and fresh air throughout. Central air, three heat pumps, a 2024 roof, one assigned and deeded off-street parking space, and private lockable basement storage add everyday ease. Here, history becomes part of daily life. Come experience the light, character, and charm for yourself.

64 Bartlett St Unit 4, Boston

Listing courtesy of Listing Agent: Ken Sazama from Listing Office: Real Broker MA, LLC.
$3,800,000
23 Beds ⋅ 12 Baths ⋅ 73573397 MLS
A rare opportunity to acquire a fully renovated, institutional-quality multifamily asset with a 7.4% cap rate in place. Roxbury is one of Boston's fastest-growing neighborhoods. Ideally located between Nubian Square and Fort Hill, 36-38 Regent Street offers exceptional access to the Longwood Medical Area, Downtown Boston, major universities, public transportation, and the rapidly evolving Roxbury corridor. A comprehensive down-to-the-studs renovation was completed in 2025, this turnkey investment consists of six luxury, condo-quality residences totaling approximately 7,950 square feet. The unit mix includes five 4-bedroom, 2-bath apartments and one 3-bedroom, 2-bath apartment, each thoughtfully designed with modern finishes, efficient layouts, and amenities that continue to drive exceptional rental demand. Virtually every major building system was replaced, including new electrical, plumbing, HVAC, roofing, windows, insulation, and high-end interior finishes, allowing an investor to acquire a virtually new asset with minimal anticipated capital expenditures for years to come. The property is 100% occupied, with all six apartments leased through August 31, 2027, generating approximately $26,925 per month in gross rental income while providing exceptional income stability from day one. Perched above the neighborhood, the property also enjoys beautiful city views, further distinguishing it from competing rental properties and enhancing its long-term appeal. Elevated setting with impressive neighborhood and city views. Turnkey multifamily assets of this quality, scale, and yield rarely become available in Boston. Whether you're completing a 1031 exchange, expanding a multifamily portfolio, or seeking a long-term generational investment, 36-38 Regent Street offers an exceptional combination of strong in-place cash flow, long-term lease stability, and virtually maintenance-free ownership in one of Boston's most dynamic neighborhoods.Proforma available upon request.

36-38 Regent St, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.
$719,999
2 Beds ⋅ 2 Baths ⋅ 73573171 MLS ⋅ ['Northampton Station Residences'] BLDG.
Welcome to The Tremont at 27 Guild St, a stunning corner unit offering the best of modern Fort Hill living. This thoughtfully designed home features an open-concept kitchen and living area bathed in natural light from multiple exposures, with generous two-tone cabinetry and stainless steel appliances that flow naturally into the living area, a great setup for entertaining or unwinding. The Tremont offers spacious bedrooms, a master suite, and large closets throughout. 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. 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!!!

27 Guild Street Unit 202, Boston

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.
$584,000
1 Beds ⋅ 1 Baths ⋅ 73570543 MLS
Introducing 27 Kenilworth, a boutique collection of nine new-construction condominiums in Roxbury’s historic Fort Hill neighborhood. This three-story, all-electric building offers thoughtfully designed one- to three-bedroom residences, including spacious flats and dramatic loft-style penthouses, ranging from approximately 730 to 1,860 square feet. Homes feature open layouts, oversized windows, and floor-to-ceiling glazing in select residences. Top-floor homes include skylights and full-height mezzanine spaces suited for an office, studio, or lounge. Residences are offered from $584,000 to $1,256,000Each residence pairs contemporary design with high-performance construction. The advanced building envelope incorporates natural, low-VOC TimberHP wood-fiber insulation, carefully detailed air sealing, and triple-glazed European windows designed to support year-round comfort, energy efficiency, and sound reduction.Kitchens feature modern cabinetry, premium LG and Bosch appliances, and durable Cosentino Dekton countertops and backsplashes, with waterfall islands in select homes. Bathrooms are finished with Hansgrohe fixtures and full-height Porcelanosa tile. Select residences also offer private balconies.The brick façade and Dekton exterior accents bring a refined, contemporary presence to the streetscape. Every home includes dedicated basement storage.Located approximately five minutes from Nubian Square and ten minutes from Roxbury Crossing and the Orange Line, 27 Kenilworth offers convenient access to public transportation, neighborhood amenities, and downtown Boston. The building is adjacent to the new Dudley–Kenilworth Pocket Park, bringing green space, mature trees, and locally commissioned public art to the block.

27 Kenilworth St Unit 2, Boston

Listing courtesy of Listing Agent: Scott Webster from Listing Office: Wright Realty, LLC.
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