Roxbury's Fort Hill Real Estate

Welcome to Fort Hill, a hidden gem nestled in the heart of Roxbury, Boston! This vibrant neighborhood, steeped in rich history and culture, offers a unique blend of urban living and community spirit. With its picturesque streets and stunning views of the Boston skyline, Fort Hill is a place where tradition meets modernity.

Originally a prominent site during the Revolutionary War, Fort Hill has evolved into a thriving residential area that showcases a diverse array of architectural styles, from charming Victorian homes to contemporary condos. The community is known for its strong sense of belonging, where neighbors come together to celebrate local events and support each other.

Fort Hill is also home to several parks and green spaces, providing residents with ample opportunities for outdoor activities. The nearby Fort Hill Park offers a serene escape, perfect for picnics or leisurely strolls. Additionally, the neighborhood's proximity to public transportation makes commuting to downtown Boston a breeze, allowing residents to enjoy the best of both worlds—urban convenience and suburban tranquility.

Cultural enthusiasts will appreciate the rich tapestry of art and history that surrounds Fort Hill. The area boasts several museums, galleries, and historic sites, making it a hub for exploration and discovery. With a variety of local eateries and shops, residents can indulge in the diverse culinary scene that Roxbury has to offer.

Whether you're looking to buy your first home or seeking an investment opportunity, Fort Hill presents a captivating blend of community, culture, and convenience. Discover the charm of this remarkable neighborhood and become a part of its vibrant story!

Newest Listings in Roxbury's Fort Hill

$849,999

3 Beds ⋅ 2 Baths ⋅ 73590347 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 101 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 101 delivers the perfect combination of luxury, convenience, and city living.

27 Guild Street Unit 101, Boston

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.

$515,000

2 Beds ⋅ 1 Baths ⋅ 73590184 MLS

Step into this beautifully updated 2-bedroom, 1-bath home offering a bright, open-concept layout filled with natural light from oversized windows. Completely renovated from the studs-out in 2019, the residence combines comprehensive modern updates with comfortable city living, featuring a private entrance, hardwood flooring throughout, large bedrooms, a modern kitchen with an artisan tile backsplash, in-unit laundry, central air, and a gorgeous bathroom complete with a wet room- rain shower and oversized tub. Outside features multiple shared sitting areas with established gardens and large back yard. The spacious, sun-filled living area offers an easy flow for relaxing, entertaining, and everyday living. Ideally located minutes from downtown near Jackson Square T Station, with Marcella Playground directly across the street. You’ll also enjoy convenient access to Boston Medical Center, Longwood Medical Area, local universities, I-93, the Mass Pike/ I-90, and everything Boston has to offer. A wonderful opportunity for a family or young professionals alike.

77 Marcella St Unit 1, Boston

Listing courtesy of Listing Agent: Gregory Somar from Listing Office: Coldwell Banker Realty - Dorchester.

$978,000

3 Beds ⋅ 2 Baths ⋅ 73588641 MLS

Discover an unparalleled living experience at 27 Kenilworth St U:6, Boston, MA, a newly under construction condominium to be completed shortly. This sophisticated residence, encompassing 1460 square feet, offers a refined urban sanctuary designed for discerning tastes. This meticulously designed condominium features three well-proportioned bedrooms, one with an outdoor space. Add two full bathrooms with double-sinks and a floor through design is sure to enhance daily routines. Situated on the second floor, this residence offers seamless accessibility and an elevated perspective. We invite you to schedule a private viewing to fully appreciate the distinctive appeal of this exceptional Fort Hill condominium.Open House 10/11/26. 11-1pm

27 Kenilworth St Unit 6, Boston

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

$687,000

2 Beds ⋅ 1 Baths ⋅ 73588640 MLS

Under Construction, this sophisticated 858 square foot condominium, Unit 4 at 27 Kenilworth St. in Boston, MA, represents a prime opportunity for refined urban living. This second-floor residence encompasses two thoughtfully designed bedrooms, providing comfortable and private accommodations. Complementing these living spaces is a full bathroom, meticulously appointed to offer convenience and modern aesthetics. This unit presents a streamlined and accessible living experience. Discover the potential for an elevated lifestyle within this distinguished Boston neighborhood.

27 Kenilworth St. Unit 4, Boston

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

$649,999

2 Beds ⋅ 2 Baths ⋅ 73583853 MLS ⋅ ['Northampton Station Residences'] BLDG.

Welcome to The Lambert 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 Lambert 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 106, Boston

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.

$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! THIS PROPERTY QUALIFIES FOR THE CITY OF BOSTON COMMUNITY STABILIZATION PROGRAM. FTHBS LIVING IN BOSTON MAY BE ELIGIBLE FOR 10% IN DOWN PAYMENT ASSISTANCE. SEE ATTACHED FLYER.

1 Centre Street Terrace Unit 4, Boston

Listing courtesy of Listing Agent: Elizabeth Bain from Listing Office: Commonwealth Standard Realty Advisors.

$1,775,000

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.

$2,600,000

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.

$2,450,000

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.

$799,000

3 Beds ⋅ 2 Baths ⋅ 73576397 MLS

Space to spread out in historic Fort Hill! Offering 2,246 square feet across two levels, this upper-level residence features two oversized bedrooms, two full bathrooms, and a spacious finished bonus level with flexibility as a third bedroom, plus deeded off-street parking with EV charging. Whether you envision a guest retreat, dedicated home office, media room, or gym, the bonus level offers space to suit your lifestyle.Expansive living and dining areas provide plenty of room to entertain and flow into a beautifully appointed kitchen with brand-new appliances and abundant storage. The primary suite features a custom walk-in closet and an ensuite bath with a floating vanity and marble-tiled shower with bench seating.Hardwood floors, central air, in-unit laundry, and smart home technology add everyday comfort and convenience. Outside, enjoy a large shared backyard with patio space. A $200 monthly condo fee completes the package.Conveniently located near Nubian Square, with access to public transportation, the Longwood Medical Area, Boston Medical Center, and South Bay shopping and dining, this home combines generous living space, a flexible third-bedroom option, outdoor space, and deeded parking in Boston.

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. ** Please follow the link to learn more about this beautiful property and the recent renovations thoughtfully completed by the architect-owners: https://historicboston.org/a-new-era-for-the-spooner-lambert-house-a-peek-inside-recent-renovations-at-the-1782-home/ **

64 Bartlett St Unit 4, Boston

Listing courtesy of Listing Agent: Ken Sazama from Listing Office: Real Broker MA, LLC.

$3,750,000

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.

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