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$1,650,000
14 Beds ⋅ 5 Baths ⋅ 73530214 MLS
Introducing a rare, oversized Dorchester multi-family opportunity delivering scale, flexibility, and strong income in one of Boston’s most dynamic neighborhoods. This massive property offers 14 bedrooms and 5 bathrooms across four expansive units, including a complete finished apartment in the lower level; ideal for maximizing rental income. Each residence features generous layouts, hardwood floors, in-unit laundry, and updated systems, creating comfortable, modern living spaces attractive to today’s tenants & owners. With projected annual income upwards of $189,000, this asset is perfectly suited for investors seeking strong cash flow, a strategic 1031 exchange, or an owner-occupant looking to offset their mortgage with substantial rental income & immediate cash flow. Conveniently positioned near public transportation, neighborhood restaurants, shopping, and easy access to Downtown Boston, the location ensures long-term tenant demand. A high-yield Boston multi-family opportunity.

14 Everton St, Boston

Listing courtesy of Listing Agent: Markese Daise from Listing Office: Stony Brook & Lennox Realty Advisors.
$1,179,900
8 Beds ⋅ 4 Baths ⋅ 73525577 MLS
Take note of this modern, stunning and expansive 3613 sq ft (2 Family Home). 8 Bedrooms/ 4 Full Baths built in 1925; 2016 gut renovated offering refined living space with desirable open floorplans. This is a really special multifamily / forever home, with room for everyone. Perfect for owner occupants or 1031 exchange looking to invest and live in the city and do little to no work and deal with less tenant issues. Highly sought features include; 2026 HVAC's / Central Air, 9-foot ceilings, Hardwood floors, recessed lighting, chef's kitchens, terrazzo countertops & islands, beverage chillers, stainless appliances - complete with gas stove & griddle, in unit W/D hook ups. Bells & whistles adorn this owner occupant & solid income producing property including ensuites, marble floors, designer baths & showers, walk in closets, backyard w/ updated decks. Unit 1 delivering 3 bed, 2 full baths and Unit 2 boasting a bi level, approx. 2300 sq ft 5 beds / 2 full baths- currently rented for $5000/ month. 2016 plumbing, electrical, roof, walls & decks. 2023 Upgraded Foundation. The separate 2 car garage and clean full sized 7-foot ceiling basement await a potential ADU, workshop, lounge or additional future living space. To be delivered vacant.

41 Gleason St, Boston

Listing courtesy of Listing Agent: Cori Daddabbo from Listing Office: Coldwell Banker Realty - Canton.
$1,799,000
8 Beds ⋅ 5 Baths ⋅ 73528710 MLS
Extensively renovated and expanded, this exceptional Dorchester residence offers over 4,600 SF of thoughtfully designed living space in a quiet neighborhood setting. Classic colonial details, elegant millwork, and a grand staircase blend seamlessly with modern updates throughout. The main level features sun-filled living spaces, an exquisite fireplace, and a stunning chef’s kitchen with an oversized island, custom cabinetry, professional appliances, and designer finishes. Upstairs, the expansive primary suite is complemented by additional bedrooms and a second-floor living area opening directly to the upper deck. Featuring 8 bedrooms, 5 bathrooms, and a completed ADU, the layout is ideal for tiered living, work-from-home needs, and evolving lifestyles. Outdoor spaces include a two-story deck, patio, yard, and paved driveway. A rare offering combining timeless character, modern luxury, and versatility with exciting potential for Airbnb, rental income, or investment opportunities.

61 Wayland Street, Boston

Listing courtesy of Listing Agent: Jason Lisherness from Listing Office: The Agency Boston.
$995,000
6 Beds ⋅ 4 Baths ⋅ 73527312 MLS
Sitting prominently atop Upham's Corner, this oversized two-family is exactly what a seasoned investor or first-time buyer has been waiting for. Unit 1 spans two floors with 4 bedrooms and 2.5 baths, showcasing early 19th-century craftsmanship with wide staircases, soaring ceilings, intricate woodwork, and original hardwood floors throughout, complete with in-unit laundry, and central a/c. Unit 2 offers a comfortable 2 bedroom, 1 bath layout. Both units are lead compliant and self-sufficient with tenants paying their own gas and electric, landlord only pays water and sewer. Grossing $7,000 monthly currently with minimal overhead and no immediate capital expenses. Roof and fresh siding have been done in recent years. ADU potential adds another layer of upside for those looking to maximize the asset further. Ample parking on site, 15 minutes to Downtown Boston, and just 0.8 miles to the Savin Hill T Station. Reach out for a tour today!

3 Ware St, Boston

Listing courtesy of Listing Agent: Brian Quijada from Listing Office: EVO Real Estate Group, LLC.
$5,000
6 Beds ⋅ 3 Baths ⋅ 73525373 MLS
An incredible opportunity to rent a spacious, unfurnished 6-bedroom, 3-bath apartment in a prime Dorchester location. With generous room sizes and a flexible layout, there's plenty of potential for roommates, or plenty of space for home offices, guest bedrooms, or just extra breathing room you won't find in most Boston rentals. The main level features a bright living room with large windows, a separate dining/flex space, a walk-out balcony, two large bedrooms, a full bath, and a well-equipped kitchen with modern appliances. Upstairs, you'll find four additional bedrooms, including a large master with an en-suite bath. Hardwood floors throughout, on-site laundry, a shared backyard, and on-street parking with no permit required. Conveniently located with easy access to transit, dining, and everything Dorchester has to offer.

11 Bowdoin Avenue Unit 2, Boston

Listing courtesy of Listing Agent: Rachel Chang from Listing Office: Century 21 Cityside.
$5,300
6 Beds ⋅ 3 Baths ⋅ 73525369 MLS
An incredible opportunity to rent a beautifully furnished apartment in a prime Dorchester location! This spacious 6-bedroom, 3-bath home offers the flexibility you need — whether you're working from home, hosting guests, or simply want extra space for dedicated home offices. Enter through an inviting front entrance to a sunny living room with large windows, a separate dining/flex space, and a walk-out balcony. The main level also features two large bedrooms, a full bath, and a modern kitchen with updated appliances. The upper level offers four bedrooms, including a massive master suite with en-suite bath — plus an additional room perfect for a home office or guest space. Hardwood floors throughout, on-site laundry, on-street parking (no permit required), and a large shared backyard for summer entertaining. Fantastic location with easy access to everything you need.

11A Bowdoin Avenue Unit 2B, Boston

Listing courtesy of Listing Agent: Rachel Chang from Listing Office: Century 21 Cityside.
$1,350,000
9 Beds ⋅ 3 Baths ⋅ 73522682 MLS
Charming all-brick, three-family investment property in a highly desirable neighborhood.beautifully updated. Each spacious unit features contemporary high-end finishes, newly renovated bathrooms, modern recessed lighting, and stylish tile work throughout. Open layouts maximize natural light and flow, offering comfortable living spaces for tenants or owners.Well-maintained exterior, strong curb appeal, and thoughtful upgrades make this a low-hassle, high-return opportunity. Ideal for investors or owneroccupiers seeking reliable income in a sought-after location schedule a showing today.

22-A Crawford St, Boston

Listing courtesy of Listing Agent: Anthony Jean-Baptiste from Listing Office: Bohio Realty LLC.
$1,499,900
9 Beds ⋅ 6 Baths ⋅ 73501320 MLS
Fully gut-renovated in 2022, this turnkey multi-family property offers modern living with all major systems and finishes completely updated. Featuring a full sprinkler system for enhanced safety, this home blends quality construction with peace of mind. Each unit showcases bright, open-concept layouts with stylish kitchens, quartz countertops, stainless steel appliances, and updated baths, all in-unit washer+ dryer. Enjoy good ceiling heights, central HVAC. Exterior highlights include private outdoor spaces with balcony, deck, and patio—perfect for relaxing or entertaining. Only 10 minutes walk Shawmut and Ashmont MBTA Red Line, local restaurants, parks, and major routes, this property offers both strong rental potential and ideal owner-occupant flexibility. A rare opportunity to own a fully renovated, income-producing property in a prime Dorchester location.

61 Shepton St, Boston

Listing courtesy of Listing Agent: Rebecca Huang from Listing Office: William Raveis R.E. & Home Services.
$3,149,000
13 Beds ⋅ 8 Baths ⋅ 73492888 MLS
A rare offering featuring two buildings on a quiet cul-de-sac with five total units and 8+ off-street parking spaces ideal for the savvy investor or condo conversion. The fully gut-renovated front building showcases modern design and high-end finishes, with each unit offering two full baths, brand new central HVAC, in-unit laundry, and tankless hot water systems. Interiors shine with recessed lighting, new windows, hardwood floors, and sleek quartz countertops complemented by stainless steel appliances and slab quartz backsplashes. Unit 3 features a private deck with great views, while Unit 1 enjoys a patio. The basement provides ample storage. The rear building includes two additional units with a charming wraparound porch, both updated with new countertops and appliances. A true turnkey opportunity ready for immediate occupancy or portfolio expansion.

66-66R Stanley St, Boston

Listing courtesy of Listing Agent: Tara Dynan from Listing Office: Seaport Realty Group.
$1,175,000
10 Beds ⋅ 3 Baths ⋅ 73487162 MLS
Fantastic opportunity to own a solid 3 family in an up and coming area in Dorchester. Units are in good condition, hardwood floors, tile baths, front and back porches, all separate utilities. Long term tenants.

36 Floyd Street, Boston

Listing courtesy of Listing Agent: Wendy Rist from Listing Office: Jamaica Plain Realty.
$960,000
6 Beds ⋅ 2 Baths ⋅ 73470153 MLS
**Back on the Market – No Fault of the Seller!** Previous buyer was unable to complete the purchase after their home did not sell before the contingency deadline and financing was not secured prior to the agreement expiration.**Now competitively priced to reflect today's market**, this is your opportunity to own a spacious and versatile two-family home in one of Dorchester's most convenient locations. Whether you're an owner-occupant looking to offset your mortgage with rental income or an investor seeking a strong long-term asset, this property offers exceptional value.Each unit provides generous living space with functional layouts, abundant natural light, and the flexibility today's buyers are looking for. Conveniently located near public transportation, major highways, shopping, restaurants, parks, schools, and downtown Boston.The seller has already navigated the inspection and transaction process, making this an excellent opportunity for a motivated buyer ready to move forward. With the recent price adjustment, this property is positioned to attract immediate interest.**Don't miss your second chance—schedule your private showing today!**

60 Thetford Ave, Boston

Listing courtesy of Listing Agent: Jermaine Dowdell from Listing Office: eXp Realty LLC - Corporate Office.
$2,225,000
12 Beds ⋅ 6 Baths ⋅ 73451541 MLS
THIS IS THE ONE! This is the massive almost 7,000+ SQ FT modern multi-family across 4 finished units that you have been waiting for in the Boston/Dorchester area! A true turnkey investment or premier owner-occupant opportunity, this impressive property can generate up to $170,000 annually in gross rents—or live in one of the four levels and let the others pay your mortgage. Featuring 4 spacious units including a masterfully finished lower level, this property showcases brand-new central air, updated plumbing and updated electrical, new roof, siding, and gutters, refinished hardwood floors, plus a 2-car powered garage W/ additional parking. Every detail reflects quality and care. Enjoy a central location near Franklin Park, the golf course, public transit, and easy access to the Orange and Red Lines. Minutes to Downtown Boston, universities, restaurants, and shops. A must-see modern TROPHY BUILDING—live, invest, and build wealth! This property is turn key & is well taken care of!

69 Greenwood St, Boston

Listing courtesy of Listing Agent: Markese Daise from Listing Office: Stony Brook & Lennox Realty Advisors.
$1,799,000
17 Beds ⋅ 6 Baths ⋅ 73440102 MLS
Unlock this prime investment opportunity in one of Dorchester’s fastest-growing neighborhoods.This six-unit multifamily features five 3-bed/1-bath units and one 2-bed/1-bath unit, offering strong value-add potential investors can increase cash flow through cosmetic updates and strategic improvements.Minutes from Four Corners/Geneva and Upham’s Corner commuter rail stations, the location attracts renters seeking convenience and transit access. Nearby grocery stores, shops, and restaurants support strong rental demand.Private decks, a fenced backyard, and direct access to an adjacent playground add to tenant appeal. This property combines the opportunity to enhance cash flow with a desirable, rapidly developing location. Video walkthrough/virtual tour available.

252-254 Magnolia St, Boston

Listing courtesy of Listing Agent: Ashmael Brun from Listing Office: EVO Real Estate Group, LLC.

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