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. Known for its rich history and diverse community, Fort Hill is a picturesque enclave that offers a unique blend of urban convenience and suburban charm.

Fort Hill’s streets are lined with beautifully preserved Victorian homes, showcasing the architectural elegance of a bygone era. The area is steeped in history, with roots dating back to the early 19th century, making it a fascinating place to live for history enthusiasts and culture seekers alike. Residents enjoy the close-knit community atmosphere, where neighbors greet each other with a smile and local events bring everyone together.

One of the standout features of Fort Hill is its breathtaking views of the Boston skyline. The elevated terrain offers stunning vistas, making it a perfect spot for those who appreciate both nature and city life. Parks and green spaces, such as the nearby Fort Hill Park, provide serene spots for relaxation, picnics, and outdoor activities.

Fort Hill is also conveniently located near public transportation, making it easy to access downtown Boston and beyond. With a variety of dining options, shopping venues, and cultural attractions just a stone’s throw away, residents have everything they need right at their fingertips.

Whether you’re a young professional, a growing family, or looking to retire in a vibrant community, Fort Hill in Roxbury offers a perfect blend of history, culture, and convenience. Discover the charm of this unique neighborhood and envision your future in this captivating corner of Boston!

Newest Listings in Roxbury's Fort Hill

27 Guild Street Unit 101, Boston
$849,999
3 Beds ⋅ 2 Baths ⋅ 73590347 MLS ⋅ ['Northampton Station Residences'] BLDG.
SELLER PAID 2:1 RATE BUYDOWN AVAILABLE 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.
77 Marcella St Unit 1, Boston
$505,000
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.
27 Kenilworth St Unit 6, Boston
$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.
27 Kenilworth St. Unit 4, Boston
$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.
27 Guild Street Unit 106, Boston
$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.
114-116 Thornton Street, Boston
$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.
34 Circuit Street, Boston
$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.
83-85 Highland Street, Boston
$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.
17 Akron St Unit 2, Boston
$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.
64 Bartlett St Unit 4, Boston
$595,000
3 Beds ⋅ 2 Baths ⋅ 73576173 MLS ⋅ ['Spooner Lambert House'] BLDG.
A rare opportunity to live in Boston’s Spooner-Lambert House circa 1782, this Roxbury Artillery Commander-built and architect-renovated Fort Hill residence combines the character and privacy of a historic home with the conveniences of contemporary condo living. With 1,267 square feet across multiple levels, a private entrance, off-street parking, in-unit laundry, central air, basement storage, and perpetually-in-bloom gardens, the condo offers an unusually house-like experience amidst the urban amenities of Boston. Inside, centuries-old character has been conserved and showcased through a thoughtful renovation. The light-filled living room is graced by original heart-pine floors, exposed beams, and preserved 18th century wallpaper. The new kitchen features custom cabinetry, stainless-steel countertop with integrated sink, panel-front dishwasher, induction cooking, and a walk-in pantry. Wood floors and distinctive architectural details continue in the two main level bedrooms, which boast a restored fireplace and custom closets. A stone vanity, custom cabinetry, and tiled shower surround give the bathroom a bespoke feel. Atop a custom-clad ’Pear Stair’, the expansive upper level offers a character-filled, flexible space for sleep, work, or play atop restored floorboards and under hand-hewn beams. A new half bathroom includes plumbing run for a potential future shower to make this a suite unto itself. The interior is conditioned by new ducted and wall-mounted mini-split heat pump units as well as baseboard heat for comfort in all seasons. Outside, a private entrance leads through the property’s lush grounds featuring mature plantings, raised garden beds, and a grilling and patio area. Highland Park and John Eliot Square are just steps away as are the numerous dining, retail, and cultural offerings of Mission Hill and Nubian Square. Both Orange and Silver line trains are within 10 minute walks to offer commuting flexibility. With the roof replaced, exterior paint refreshed, and shared front hall renovated within the past five years to go along with a healthy condo reserve, you can spend your time enjoying the charms of the house and gardens through the seasons. Historic, uniquely updated, and ideally situated, this property offers something seldom found: the character of an early New England home, the outdoor space and privacy of a single-family house, and the convenience of urban condo living.

64 Bartlett St Unit 4, Boston

Listing courtesy of Listing Agent: Ken Sazama from Listing Office: Real Broker MA, LLC.
36-38 Regent St, Boston
$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.
27 Guild Street Unit 202, Boston
$719,999
2 Beds ⋅ 2 Baths ⋅ 73573171 MLS ⋅ ['Northampton Station Residences'] BLDG.
SELLER PAID 2:1 RATE BUYDOWN AVAILABLE 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.
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