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$1,275,000
5 Beds 3 Baths 73526199 MLS
Character, space, updates, and strong rental history — this well maintained two family checks all the boxes! Tucked away on a charming tree lined street, the home blends timeless detail with thoughtful improvements across three finished levels. Original hardwood floors, detailed moldings, classic wainscoting, and french doors bring warmth and charm throughout, while recent updates to the kitchens, bathrooms, lighting, paint, flooring, plumbing, and electrical add a more turn key feel. Unit 1 offers 2 bedrooms, an eat in kitchen, formal living and dining rooms, and 1 bath. Unit 2 spans two levels with an updated kitchen, living and dining rooms, two bedrooms, office, full bath, plus additional finished third-floor living space with another bedroom, full bath, and sitting area. Generating $7,350/month in rental income. Complete with a private backyard, driveway, garage, laundry in the basement and convenient access to Orient Heights station and Constitution Beach!

105-107 Saint Andrew Rd, Boston

Listing courtesy of Listing Agent: Madeleine Bain from Listing Office: Access.

$1,800,000
4 Beds 3 Baths 73526128 MLS
It’s rare to find a turnkey two-family that hits every mark, but this Charlestown gem on a quiet, sought-after street does exactly that. Whether you’re looking for a high-performing investment or a home with built-in rental income, this property delivers. Unit 1 is a modern one-bedroom retreat with a private deck. Upstairs, Unit 2 is a stunning duplex that masterfully balances contemporary updates with historic character. The main level flows seamlessly between the kitchen, dining, and living areas, while the top floor houses three sun-filled bedrooms and a stylishly renovated bath.The real "wow" factor? The private roof deck. It offers breathtaking, 360-degree unobstructed views of the city skyline—a true sanctuary in the heart of the neighborhood. With a proven track record for short-term rentals and a flexible layout, this is a standout opportunity in one of Boston’s most iconic locations.

19 Walker St, Boston

Listing courtesy of Listing Agent: Aranson Maguire Group from Listing Office: Compass.

$1,395,000
4 Beds 3 Baths 73526105 MLS
DEVELOPMENT OPPORTUNITY OF THE YEAR IN CENTRAL JP. Attention builders, developers, and investors—rarely does a parcel of this magnitude become available in prime Jamaica Plain. Sited on a massive 13,263 SF lot with approx 109’ of street frontage, this property is an absolute dream. Located in a 2F-7,000 zoning subdistrict, the expansive footprint offers incredible potential for a high-end multi-unit project. Tap into Jamaica Plain’s premium condo values, proven right in the immediate micro-market: look no further than the successful 4-unit townhouse development directly across the street (207-209 Chestnut) and the new construction directly behind it (23 Chestnut Sq). A+ central locale, just a short walk to Stony Brook T, SW Corridor Park, and the Brewery Complex. Buyer to perform all due diligence regarding project feasibility; broker and seller make no representations. Do not walk the lot without an appointment. No open houses.

212 Chestnut Ave, Boston

Listing courtesy of Listing Agent: Christian Iantosca Team from Listing Office: Arborview Realty Inc..

$1,875,000
9 Beds 3 Baths 73525869 MLS
Exceptional investment opportunity in Brighton! This well-maintained corner lot triple decker offers strong rental income and long-term upside in a prime location near Brighton Center. Spanning over 3,600 sq ft of living space, each sun-filled unit features 3 bedrooms, 1 bathroom, spacious living/dining areas, and fully renovated kitchens with quartz countertops, plus renovated bathrooms. Completely turnkey! Unit 1 is leased until 8/31/2027 for $3,600/month. Units 2 and 3 are leased until 8/31/2026 for $3,500/month each, offering flexibility for investors or owner-occupants. Additional highlights include side-by-side off-street parking accessible from both Union St and Snow St, a large shaded backyard, and a high-ceiling basement with direct access offering expansion or development potential. Conveniently accessible to BC, BU, Harvard, MIT, the Green Line, and Brighton Center's amenities. Don't miss your chance to invest in a prime neighborhood!

39 Union St, Boston

Listing courtesy of Listing Agent: Matt Gorman from Listing Office: EDGE Realty Advisors.

$8,250,000
6 Beds 7 Baths 73525662 MLS
A truly distinctive offering where timeless architecture, elevated design & flexible urban living converge. Set on one of the South End’s most coveted tree-lined streets, this home presents a rare opportunity to acquire two meticulously renovated residences within a classic bow-front brownstone, offered together as a cohesive multi-family property. Comprising a penthouse triplex & garden duplex, the building offers exceptional flexibility for multigenerational living, guest accommodations, income potential or future single-family conversion. The PH features 3+ beds, 3.5 baths, dramatic entertaining spaces, custom millwork, gas fireplaces, private roof deck & skyline views. The garden duplex offers 2 beds, 2.5 baths, study, private patio & refined finishes throughout. Complete w/ 2 direct parking spaces, designer kitchens & curated finishes. Moments from acclaimed dining, parks, SoWa, cafés & premier private schools, boutique shopping & renowned restaurants & galleries.

189 W Brookline St, Boston

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.

$1,945,000
9 Beds 6 Baths 73525052 MLS
Presenting a rare opportunity to acquire a fully occupied 6-unit multifamily property just moments from Revere Beach. Situated on a level lot with two driveway entrances and ample off-street parking, this investment offers strong in-place income with future upside. Current monthly rent roll is $12,100 with as-is pro forma rents projected to be at least $14,400/month, plus there is an approximately $2,000 annually in laundry income. Property features potential expansion for 2 additional units on the top level. Conveniently located near public transit with train access to Boston, major highways, shopping, dining, and a playground 1 block away on the same street. Excellent opportunity for investors seeking cash flow, appreciation, and long-term value add potential. Sellers reserve the right to accept an offer at anytime.

120 Dolphin, Revere

Listing courtesy of Listing Agent: Justin Brown from Listing Office: Three Hills Real Estate Service, LLC.

$3,195,000
14 Beds 8 Baths 73524168 MLS
Presenting 275 Webster Street — a rare, fully leased four-family asset situated in the heart of Jeffries Point, East Boston’s most coveted and rapidly evolving neighborhood. Just steps from Piers Park, the Harborwalk, and Maverick MBTA Station, this turn-key building has been meticulously rebuilt from the studs with extensive capital improvements including 4 new HVAC systems, full insulation, all-new windows, doors, and sliders, upgraded 200AMP electrical, a full sprinkler system, Hardie Plank siding, new hardwood floors, a rear granite patio, and reconstructed front steps. Each spacious unit showcases contemporary finishes, in-unit laundry, and strong tenant appeal. An exceptional opportunity for investors seeking a low-maintenance, high-performing property in one of Boston’s most competitive submarkets. A perfect fit for 1031 exchange buyers looking for stabilized income and long-term upside in a supply-constrained rental market.

275 Webster, Boston

Listing courtesy of Listing Agent: Mike Preston from Listing Office: Aura Realty Advisors.

$1,900,000
6 Beds 5 Baths 73524076 MLS
A rare blend of historic craftsmanship and contemporary design defines this architectural gem. Unit 1 is a 5 bed, 2.5 bath residence that was initially a stand-alone single family spreading across three expansive floors. Rich in original detail; the ground floor showcases four entirely different parquet floor patterns — creating a striking first impression that guests never forget. Period fireplaces, elegant coffered ceilings, and timeless Victorian character are thoughtfully paired with modern updates throughout. The anchor of the first unit is a stunning eat-in kitchen addition built in 2021, simultaneous with the construction of Unit 2. Equipped with Central AC & an open floor plan, the second unit sits as a present-day juxtaposition to the history-filled original structure. This two-family's long list of attractions is rounded out by several outdoor spaces, a long driveway, basement storage and solar panels that are owned outright to help reduce utility bills.

42 Atherton St., Boston

Listing courtesy of Listing Agent: Aidan Flanagan from Listing Office: Coldwell Banker Realty - Hingham.

$799,986
6 Beds 2 Baths 73523937 MLS
Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!

50 Main St, Winthrop

Listing courtesy of Listing Agent: Matt Tasgin from Listing Office: United Brokers.

$1,599,000
8 Beds 3 Baths 73523150 MLS
South Mission Hill opportunity! Well maintained multi-family property located in a prime Jamaica Plain location with strong access to public transportation, major hospitals, universities, and local amenities. Positioned near both the Green and Orange Lines, this property offers convenience for commuters, medical professionals, and tenants alike. Located across from a school, the property benefits from added openness and fewer direct neighboring residences. Each unit features hardwood floors, central air, and private rear decks providing ideal outdoor space. Off street parking adds additional value and convenience. Separate utilities with tenants paying their own heat and electric make for an efficient investment setup. Whether you’re looking to expand your portfolio or secure a property in one of Boston’s most desirable rental markets, 12 Schiller St checks all the boxes.

12 Schiller St, Boston

Listing courtesy of Listing Agent: The J. Pavao Team from Listing Office: Keller Williams South Watuppa.

$1,799,999
6 Beds 3 Baths 73522561 MLS
Exceptional opportunity to own a three-family property in the heart of South Boston’s East Side neighborhood. 607 East 7th Street offers strong investment potential, owner-occupant flexibility, and long-term upside in one of Boston’s sought-after locations. The property features classic South Boston charm, excellent natural light, and the rare benefit of 5 parking spaces recognized by the City of Boston, an incredible asset in this neighborhood. Conveniently located near Castle Island, Carson Beach, the Seaport District, restaurants, shopping, public transportation, parks, and major highways. Surrounded by ongoing growth and development, this property presents an outstanding opportunity for investors, developers, or buyers looking to secure a prime multi-family asset in a thriving urban market. Easy access to downtown Boston and the waterfront further enhances the value and appeal of this exceptional offering. Plus, it has Austria parking according to the deed 5 spots

607 E 7th St, Boston

Listing courtesy of Listing Agent: Melvin A. Vieira Jr. from Listing Office: RE/MAX Real Estate Center.

$1,225,000
9 Beds 3 Baths 73522069 MLS
WELCOME HOME! Beautiful 2 family home located in the heart of Boston. This newly remodeled gem is city living at its finest. First floor apartment is composed of a stunning living and dinning room with built in fireplace, updated kitchen, full bathroom, and 3 bedrooms. Second floor is a rare find in Boston; consisting of 6 bedrooms. This remodeled unit as well, exemplifies townhouse living. First floor includes an elegant living and dinning room, updated kitchen with pantry, full bathroom, and 3 bedrooms. Second floor boasts an additional three bedrooms and full bath. Home is nestled on a quiet side street, yet is just a stone's throw away to major high, area shopping, and public transportation.

102 Radcliffe St, Boston

Listing courtesy of Listing Agent: Jeffrey Jacques from Listing Office: CM Realty Associates.

$1,499,000
11 Beds 5 Baths 73521547 MLS
Rare opportunity to own a turnkey 3-family in a strong Dorchester location near Talbot Ave commuter rail. The property has undergone extensive renovations and system updates within the last 10 years, including major electrical, plumbing, heating, and interior improvements, with select kitchens and bathrooms renovated within the last year. Deleaded units with compliance documentation available. The layout offers spacious units, including a first-floor unit with additional finished lower-level space and separate entrance, a large second-floor unit, and a top-floor unit featuring a primary suite. Additional features include updated systems, off-street parking, strong commuter access to downtown Boston, and architectural shingles replaced approximately 7 years ago on the pitched portion of the roof. Property will be delivered vacant, offering a strong opportunity for market-rate lease-up and stabilization.

36 Spencer St, Boston

Listing courtesy of Listing Agent: Nilton Depina from Listing Office: Wisepath Realty Advisors LLC.

$1,845,099
12 Beds 5 Baths 73520828 MLS
Well maintained 100% occupied income-producing Multi-Family in Brighton THE PERFECT INVESTMENT PROPERTY IN BRIGHTON-Turnkey 3-unit w parking a charming brick building ideally located in the heart of Brighton with long term tenants in place through 8/31/26. Situated on a tree-lined residential street, steps from Cleveland Circle, Washington Square, Brookline, Boston College, and multiple Green Line T stops (B, C and D for an easy commute downtown. Residents enjoy close proximity to local cafés, restaurants, parks, shopping, and Chestnut Hill Reservoir. The property features 12+ bedrooms,5 bath, two exterior back decks for unit 2&3. Professionally managed. 2026 Gross Income $145,400 with NOI $81,875- cap rate 4.7%. Showings by appointment only. Property management must be onsite for all showings. Units are tenant occupied, and would like to renew leases. At least 24 hours’ notice is required. See feature sheet and expenses attached to MLS listing.

8 Colliston Rd, Boston

Listing courtesy of Listing Agent: Lexi Crivon from Listing Office: Coldwell Banker Realty - Boston.

$2,595,000
8 Beds 3 Baths 73520401 MLS
Rare mixed-use investment opportunity in the heart of Jamaica Plain’s vibrant South Street corridor. This three-unit condominium building features a well-established bakery/café operating since 2004 with a licensed 20x20 patio, alongside two spacious four-bedroom residential units with covered porches. Property offers flexible use and strong income potential, with projected rents of $15,000–$18,000/month with business in place. Commercial space includes walk-in freezer and high-ceiling basement with expansion potential. Additional highlights include updated 400-amp electrical, FHA gas heat, two-car garage, and option to deliver with or without business. Business can be relocated and residential units can be delivered vacant. Plans for four units plus rear townhouse to transfer. Prime location near the Monument, Arboretum, and local shops. Ideal for investors, end users, or redevelopment.

55 South St, Boston

Listing courtesy of Listing Agent: Riley Walters from Listing Office: .

$1,250,000
10 Beds 4 Baths 73519387 MLS
RECENTLY BACK ON MARKET!... Coveted Wellington Hill area in Mattapan, this oversized well cared for updated multi-family presents a rare opportunity for both owner-occupants and investors! Configured as a 2-family with an additional finished 3rd unit in the lower-level full walk out basement, the property offers a bi-level 5 bed/2 bath, a spacious 3 bed/1 bath, and a 2 bed/1 bath garden unit delivering flexibility, scale, and strong income potential. Owner-occupants can live comfortably in one unit while offsetting their mortgage with rental income, while investors can capitalize on the high bedroom count & layout efficiency to maximize cash flow. New roof, updated 200AMP electrical, updated plumbing, yard space, central air, & parking! Located near Mattapan’s vibrant shops, restaurants, and retail corridors with easy access to transit and Downtown Boston. Amazing neighborhood growth and strong demand for this street! This property offers both immediate income and long-term upside!

72 Wellington Hill St, Boston

Listing courtesy of Listing Agent: Markese Daise from Listing Office: Stony Brook & Lennox Realty Advisors.

$1,299,000
9 Beds 3 Baths 73519103 MLS
A rare, fully turn-key Mattapan multi-family delivering scale, flexibility, and immediate income in a high-demand Boston market. This oversized 3-family features three expansive 3 bed/1 bath units, each with layouts that can easily function as 4-bedroom apartments maximizing rental potential. Designed for today’s buyer, the property offers central air, updated electrical, hardwood floors, modern kitchens & baths, new siding, newer rubber roof, & decks throughout. The building is well-maintained with a strong in-place rent roll, creating a true plug-and-play investment or an ideal opportunity for an owner-occupant to offset their mortgage with substantial income. ***NOTE***Additional upside: the identical neighboring property at 19 Hosmer St is also available...purchase one or secure both for a scalable $240K+ gross annual rent play. Positioned near public transit, retail, and many amenities, this is a high-performing Boston multi-family with long-term appreciation and income growth!

21 Hosmer St, Boston

Listing courtesy of Listing Agent: Markese Daise from Listing Office: Stony Brook & Lennox Realty Advisors.

$1,299,000
9 Beds 3 Baths 73519092 MLS
A rare, fully turn-key Mattapan multi-family delivering scale, flexibility, and immediate income in a high-demand Boston market. This oversized 3-family features three expansive 3 bed/1 bath units, each with layouts that can easily function as 4-bedroom apartments maximizing rental potential. Designed for today’s buyer, the property offers central air, updated electrical, hardwood floors, modern kitchens & baths, new siding, newer rubber roof, & decks throughout. The building is well-maintained with a strong in-place rent roll, creating a true plug-and-play investment or an ideal opportunity for an owner-occupant to offset their mortgage with substantial income. ***NOTE***Additional upside: the identical neighboring property at 21 Hosmer St is also available...purchase one or secure both for a scalable $240K+ gross annual rent play. Positioned near public transit, retail, and many amenities, this is a high-performing Boston multi-family with long-term appreciation and income growth!

19 Hosmer St, Boston

Listing courtesy of Listing Agent: Markese Daise from Listing Office: Stony Brook & Lennox Realty Advisors.

$1,495,000
7 Beds 4 Baths 73519052 MLS
Exceptional two-family opportunity in Boston's highly desirable Brighton neighborhood. This beautifully maintained and landscaped property is ideal for an owner-occupant seeking rental income or for investors looking for a strong portfolio addition. The second-floor unit features four spacious bedrooms and two full bathrooms, offering generous living space, abundant natural light, and a flexible layout ideal for larger households or roommates. The first-floor unit offers three bedrooms and two full bathrooms, featuring comfortable accommodations and well-proportioned living areas. Additional highlights include lower-level laundry, a private backyard, driveway parking for up to six vehicles with individual access, and a detached two-car garage. A rare Brighton convenience: street parking on Donnybrook Road does not require a resident permit. Quick access to the Mass Pike, Storrow Dr, and downtown Boston. A rare opportunity to own a versatile income-producing property.

39-41 Donnybrook Rd, Boston

Listing courtesy of Listing Agent: Paul McCormick from Listing Office: Gibson Sotheby's International Realty.

$1,299,900
9 Beds 3 Baths 73518556 MLS
Welcome to 1661 North Shore Rd a rare opportunity to own a fully renovated and well-maintained three-family property in one of Revere’s most sought-after beachside neighborhoods. Each spacious unit offers 3 bedrooms updated kitchens and bathrooms modern finishes, and separate utilities making this property ideal for investors or owner-occupants seeking strong rental income potential.Conveniently located just minutes from the MBTA Blue Line residents enjoy easy access to both Revere Beach and Beachmont stations for a quick commute to Downtown Boston as well as nearby access to Route 1A and Logan Airport. The neighborhood is known for its walkability public transportation, and close proximity to Revere Beach, along with a growing selection of local restaurants coffee shops and retail options.Whether you’re looking for a turnkey investment property or a home with excellent income potential in a prime commuter location this property offers the best of convenience lifestyle and opportunity.

1661 North Shore Rd, Revere

Listing courtesy of Listing Agent: Afonso Realty Group from Listing Office: REMAX Andrew Realty Services.

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