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 offers a unique blend of urban living and suburban tranquility that captivates both residents and visitors alike.

Fort Hill boasts a distinctive landscape characterized by its elevated terrain, providing stunning views of the Boston skyline and surrounding areas. The neighborhood is steeped in history, with roots tracing back to the 17th century, making it a fascinating place for history enthusiasts. As you stroll through the tree-lined streets, you'll encounter beautifully preserved Victorian homes and charming brownstones that reflect the architectural diversity of the area.

One of the most appealing aspects of Fort Hill is its strong sense of community. The neighborhood is home to a diverse population, fostering an inclusive atmosphere that celebrates cultural heritage. Local events and community gatherings are commonplace, allowing residents to connect and engage with one another.

Fort Hill is also conveniently located near public transportation, making it easy to access downtown Boston and its plethora of attractions, including world-class dining, shopping, and entertainment options. For those who enjoy outdoor activities, nearby parks and green spaces provide a perfect setting for relaxation or recreation.

Whether you’re looking to settle down in a historic neighborhood rich with character or seeking an investment opportunity in a thriving community, Fort Hill in Roxbury is an ideal choice. Discover the charm and warmth of this remarkable neighborhood, where history and modern living beautifully intertwine.

Newest Listings in Roxbury's Fort Hill

$679,999

2 Beds ⋅ 2 Baths ⋅ 73574387 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.

$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, Boston

Listing courtesy of Listing Agent: Scott Webster from Listing Office: Scott Webster.

$649,900

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.

$699,900

3 Beds ⋅ 1 Baths ⋅ 73551785 MLS

Welcome to 51 Norfolk Street, where historic charm, modern updates & city convenience come together beautifully in Roxbury's sought-after Fort Hill neighborhood. This sun-drenched attached single-family home offers the perfect blend of timeless character & everyday comfort, creating a space that feels warm & inviting. From the moment you arrive, you'll appreciate the classic architectural details that give this home its unique personality. Inside, beautiful period features have been thoughtfully preserved while tasteful updates provide the conveniences today's homeowners are looking for. Natural light pours through the oversized windows, filling every room with warmth & creating an airy, welcoming atmosphere throughout. The spacious main living areas are ideal for both everyday living & entertaining, offering a seamless flow with plenty of room to gather. Whether you're hosting holiday dinners, enjoying a quiet evening at home, or working remotely, the flexible layout adapts beautifully to your lifestyle. The home features three comfortable bedrooms, each offering abundant natural light & inviting spaces to relax & recharge. Every room reflects the perfect balance of historic character and modern livability, making this home as functional as it is charming. One of the true luxuries of city living is having your own off-street parking & 51 Norfolk Street delivers just that—making daily life that much easier. Whether you're commuting into downtown Boston, heading to neighborhood restaurants & cafés, or exploring nearby parks & cultural attractions, you'll love the convenience of this exceptional location. Adding to the appeal is an additional lot, creating an exciting opportunity for homeowners & investors. Whether you're looking to expand your investment portfolio, explore future possibilities, or simply enjoy the added space, this unique offering presents exceptional value. Buyers are encouraged to perform their own due diligence regarding any future use or potential. Fort Hill is one of Boston's most treasured historic neighborhoods, known for its tree-lined streets, distinctive architecture, vibrant community & close proximity to the Longwood Medical Area, Northeastern University, downtown Boston, public transportation, shopping, dining & major commuter routes. Full of warmth, character & timeless appeal, 51 Norfolk Street offers more than just a place to live-it offers a place to grow, invest & create your next chapter. Come experience the bliss!

51-53 Norfolk Street, Boston

Listing courtesy of Listing Agent: Kellyanne Swett from Listing Office: Allison James Estates & Homes of MA, LLC.

$919,000

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.

$499,000

2 Beds ⋅ 2 Baths ⋅ 73534324 MLS ⋅ ['Marcella Condominiums'] BLDG.

Vaulted ceilings, exposed brick, and a private deck make this Fort Hill brownstone feel far larger than its footprint. Just minutes from the Orange Line, .3 miles from closest T stop, a beautifully renovated residence in Boston’s Fort Hill neighborhood.

134 Marcella Street Unit 1, Boston

Listing courtesy of Listing Agent: Matthew Jonah from Listing Office: Venture.

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