Highland Park, MA homes for sale & real estate

Highland Park, MA Homes for Sale

Attention investors and owner-occupants alike. Check out this spacious bi-level Roxbury condo, just steps away from the Fort Hill area and offering stunning views of the Back Bay skyline! Boasting 4 generously sized bedrooms and 2 bathrooms, this condo is ideally located near all the best of Boston. Situated on a highly sought-after street, it features hardwood floors, an excellent floor plan, multiple private off-street parking spots, a charming exterior, skyline views, and a relatively new roof. Commuting is a breeze with Roxbury Crossing on the Orange Line, bus lines, and highway access nearby. Northeastern University, the Longwood Medical area, South Bay, Downtown Boston, Back Bay, and

Highland Park, MA Homes for Sale

Welcome to this beautiful updated 2-family residence located in the heart of historic Roxbury. Boasting 6 spacious bedrooms, this rare find sits on a massive corner lot and blends timeless character with modern upgrades- perfect for homeowners and investors alike. Each unit has new bathrooms with contemporary fixtures. Each bedroom has ample closet space with high ceilings. The new dormer adds additional space to the master bedroom. The master has two massive closets and a new modern bathroom with ample natural light. New and updated kitchens with all new appliances. This home has a new 30 year architectural shingle roof, new vinyl siding, new electrical service to code, new pressure treate

Highland Park, MA Homes for Sale

Spacious, light-filled 3-bed 2-bath top unit in a 2-family on a cul-de-sac street by Fort Hill. Private entry reveals living room with recessed lighting, dining room with bay windows, and kitchen with open sightlines, pantry, and granite countertops. Hardwood floors flow to 2 bedrooms + 1 full bath; and a secluded master suite with full bath and Boston skyline views. Large closets, in-unit laundry, keyless entry, central AC, and elevated private porch. Walk-out basement with exclusive storage room (currently home gym). Tall attic offers extra storage and future potential. New 2023 building envelope boasts new siding/trim/decking and new acoustic windows for privacy. New 2024 aluminum fence

Highland Park, MA Homes for Sale

Nowhere else in the city can you find a two-story penthouse with two deeded garage parking spots and a private oversized deck at this price! This loft delivers the space, style & convenience that city buyers crave in a professionally managed elevator building. With a quirky past as a former pickle factory, this home blends historic character with modern ease. The sun-splashed layout features an open living/dining area w/ hardwood floors and open concept kitchen. The spacious primary suite offers two walk-in closets and a large en-suite bath. You'll also enjoy central heat and A/C, in unit laundry, private storage, Amazon lockers, and bike storage—all just around the corner from

Highland Park, MA Homes for Sale

This rarely available rowhouse offers the perfect blend of comfort, space, and convenience in the heart of Roxbury. Built in 2005 and lovingly cared for by its original owner, this home is in excellent condition. Inside, you'll find HW floors throughout and a functional layout with generous closet space & storage. The main level features a bright living room, a well-appointed kitchen, a separate dining area, and a convenient half bath. Upstairs, the primary suite has a large walk-in closet & private full bath. Two additional bedrooms, a 2nd full bath, and a walk-in hall closet complete the upper level. A full basement provides excellent potential for future expansion/storage. Ad

Highland Park, MA Homes for Sale

Fully renovated three-family in Boston’s highly sought-after Mission Hill, just 0.3 miles to the Orange Line and minutes to the Green Line, 39 & 66 buses. Steps from the Longwood Medical Area and top universities—Northeastern, Wentworth, MCPHS, MassArt, and Simmons—ensuring strong, stable rental demand. Starting 9/1/25, gross rent will be $16,500/month, with a projected 6.7% cap rate by 9/1/26. Unit 1 is a 4 bed, 2 bath duplex with dual living rooms. Unit 2 offers 3 beds and 1.5 baths with an open layout. Unit 3 is a top-floor 3 bed, 2 bath with vaulted ceilings and exceptional natural light. All units feature quartz counters, stainless steel appliances, glass-enclos