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$1,750,000
6 Beds 4 Baths 73554042 MLS
Perched proudly on Captains Row, this rare four-family, five story property with a two-story owner's residence on the top floors blends timeless architectural charm with breathtaking views of Boston Harbor and the downtown skyline from every apartment. Ideally located at 191 Webster Street, this exceptional property places you in the heart of one of Boston's most vibrant and culturally rich waterfront neighborhoods. Enjoy easy access to cafés, bakeries, and an array of diverse dining destinations. Directly across from historic Brophy Park and just a short stroll to Piers Park and the Jeffries Yacht Club, the location offers an unmatched waterfront lifestyle. Commuting is a breeze with the outstanding convenience of nearby MBTA Blue Line service and the East Boston Ferry, providing quick connections to downtown Boston, the Seaport, and beyond. Inside, apartments feature soaring ceilings, oversized windows, and beautiful period details that highlight the building's historic character. The property also offers separate utilities, fenced front and rear yards and the peace of mind that comes with a roof and skylight that are just two years old. Whether you're seeking a premier long-term investment, a prime condominium conversion opportunity, or an owner-occupant property with built-in rental income, this exceptional multi-family home presents a rare opportunity to own an historic, landmark property in one of Boston's most desirable waterfront neighborhoods.

191 Webster, Boston

Listing courtesy of Listing Agent: Susan Ferri from Listing Office: Chinatti Realty Group, Inc..

$1,150,000
9 Beds 3 Baths 73553914 MLS
Excellent investment opportunity! This fully occupied three-family property offers immediate cash flow with **$9,500/month** in rental income. All three units feature **3 bedrooms and 1 full bathroom** with spacious, functional layouts that consistently attract tenants. Units are occupied through housing voucher programs, providing stable tenancy, with Unit 3 under lease through **9/30/2026**. Freshly painted in **2025**, the property has been well maintained and features separate utilities with **3 gas meters, 4 electric meters (including a common panel), and three gas forced-air heating systems**. Additional amenities include hardwood floors, shared basement laundry, front and rear porches, a common backyard, and on-street parking. Conveniently located near shopping, restaurants, public transportation, and major commuter routes, this turnkey asset is an excellent opportunity for investors seeking reliable cash flow and long-term value. **48-hour notice required for all showings.**

109 Capen St, Boston

Listing courtesy of Listing Agent: Ciampa Group from Listing Office: Keller Williams Realty Boston Northwest.

$1,039,000
9 Beds 3 Baths 73553825 MLS
Presenting 317 Wood Ave in Boston’s Hyde Park, a beautiful income generating 3 FAMILY designed for sophisticated urban living and TURNKEY INVESTMENT ready for new ownership. The property features 3 three bedroom, 1 full bath units with young kitchens, baths and windows all renovated during current ownership. Hardwood floors gleam throughout. The property has been completely repainted inside and out in July 2026, with a new roof in 2020, separate water tanks and heating systems (2 in 2010 and 1 in 2018). Fully applianced kitchens with garbage disposals and dishwashers. Coin-op laundry in basement and 3 parking spaces. The first floor unit will convey rented for $3,300/month while units 2 & 3 are vacant. NO OPEN HOUSES UNTIL SATURDAY AUGUST 1ST. PRIVATE SHOWINGS OFFERED PRIOR. Schedule your appointment today for this rare opportunity!

317 Wood Ave, Boston

Listing courtesy of Listing Agent: Robert Hadge from Listing Office: eXp Realty LLC - Corporate Office.

$869,900
3 Beds 3 Baths 73553738 MLS
Opportunity knocks in East Boston with this well-located three-family offering three one-bedroom units and strong income potential. Each unit features a functional layout, hardwood flooring in many areas, and separately metered utilities. The first-floor unit includes an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances, while the additional units offer spacious rooms and flexible living areas. Outside, the property features rear decks and a fenced backyard, providing valuable outdoor space in the city. Major updates include a roof approximately four years old, replacement windows completed around ten years ago, and newer water heaters. Conveniently located near public transportation, shopping, parks, restaurants, schools, highway access, and the T. Some listing photos have been virtually edited to remove personal belongings and clutter.

259 Chelsea St, Boston

Listing courtesy of Listing Agent: The TrustPoint Group from Listing Office: eXp Realty LLC - Corporate Office.

$1,699,000
8 Beds 3 Baths 73553476 MLS
PREMIER EAST SIDE SOUTH BOSTON THREE FAMILY OFFERED FOR THE FIRST TIME IN OVER 50 YEARS! THIS EXCEPTIONAL INVESTMENT OPPORTUNITY SPANS OVER 3,500 SQUARE FEET AND WILL BE DELIVERED VACANT. PROPERTY FEATURES THREE SPACIOUS UNITS CONFIGURED AS 3 BED, 3 BED, AND 2 BED, EACH WITH PRIVATE DECK ACCESS TO BACKYARD. POTENTIAL FOR CURB CUT OFFERING VALUABLE OFF-STREET PARKING IN ONE OF SOUTH BOSTON'S MOST SOUGHT AFTER NEIGHBORHOODS. IDEALLY SITUATED ON THE EAST SIDE, ON THE CORNER OF O STREET AND EAST FIRST STREET TWO BLOCKS TO FARRAGUT ROAD, CLOSE PROXIMITY TO BEACH, PARKS, AND DOG PARK, AND LOCATED DIRECTLY ON BUS ROUTE FOR EASY ACCESS TO ALL MAJOR TRANSIT. IDEAL OPPORTUNITY FOR SEASONED INVESTOR, DEVELOPER, OR AN OWNER-OCCUPANT. LEGAL ADDRESS IS 1-3 O STREET.

1-3 O St, Boston

Listing courtesy of Listing Agent: Joyce Lebedew from Listing Office: Joyce Lebedew Real Estate.

$849,000
5 Beds 2 Baths 73553131 MLS
Located in the highly desirable Fairmount Hill neighborhood of Hyde Park, this well-maintained two-family property offers an outstanding opportunity for both owner-occupants and investors. Nestled on a quiet, tree-lined street in one of Boston's most sought-after residential neighborhoods, the home combines spacious living with excellent income potential. Fairmount Hill is known for its suburban feel, historic homes, and convenient access to downtown Boston via the Fairmount Commuter Rail line.The first unit is a spacious 3-bedroom, 1-bath duplex offering generous living space and a functional layout ideal for families or those looking for extra room. The second-floor unit features 2 bedrooms and 1 full bath, making it perfect for rental income or extended family.Outside, enjoy a large fenced-in backyard with plenty of space for entertaining, gardening, or play, along with the convenience of off-street driveway parking. Whether you're looking to live in one unit while generating rental income from the other or to add a quality multi-family property to your portfolio, this Fairmount Hill gem is one you won't want to miss.

71 Tyler St, Boston

Listing courtesy of Listing Agent: Adam Sarbaugh from Listing Office: Cornerstone Real Estate.

$1,199,900
10 Beds 4 Baths 73552881 MLS
Welcome to 40-42 Coleman St. This property is a gem, well maintained and a rare find. Perfect for owner occupants or investors looking for a strong rental market. It's very rare to find a two-family home with 5 bedrooms and 1.5 baths per unit in the Dorchester area. The three season porches can be converted into a another room. The basement is clear and open and ready to be transformed into an ADU. Off street parking with this property is such a great convenience in this area. The half baths on both floors can easily be converted to full baths by adding a shower. The back yard is perfect for those special occasions, holiday cookouts and family gatherings. Whether you are looking for a place to grow into or a great investment opportunity, this property delivers with size and condition. There's also a community garden across the street for you, if you choose to use it. Come and see for yourselves and bring your imagination. The possibilities are endless.

40-42 Coleman St, Boston

Listing courtesy of Listing Agent: Paul A. Morrison from Listing Office: Keller Williams Realty.

$869,000
7 Beds 3 Baths 73552835 MLS
Discover the charm and flexibility of 35–37 Westminster Rd in Hyde Park, where classic character meets smart investment potential. Picture relaxed mornings on the front porch, evenings in a vibrant neighborhood, and the ease of multi-unit living that adapts to your lifestyle. This well-maintained two-family offers spacious, comfortable layouts perfect for owner-occupants or investors alike. Major updates provide peace of mind, including a roof approximately 15 years old and newer heating systems. Unit 1 is secured with a 3-year lease, offering immediate income stability, while the second unit which will be delivered vacant provides opportunity for personalization or additional revenue. Whether you're building wealth or creating a home with added flexibility, this property blends lifestyle, location, and long-term value.

35-37 Westminster St, Boston

Listing courtesy of Listing Agent: The Jenkins Group from Listing Office: Keller Williams Realty.

$749,000
6 Beds 2 Baths 73552775 MLS
Don't miss this opportunity to own a well-maintained two-family home in the heart of Mattapan. Will be delivered vacant at closing! Featuring an up-and-down layout, each unit offers 3 bedrooms, 1 full bathroom, and a functional floor plan, providing plenty of space for comfortable living.Each unit enjoys its own private patio, while the level shared backyard offers additional outdoor space for relaxing, entertaining, or everyday enjoyment. Whether you're looking for an owner-occupied property with rental income potential or a valuable addition to your investment portfolio, this duplex offers versatility and opportunity.Conveniently located near shopping, restaurants, parks, public transportation, and major commuter routes, this property provides easy access to everything Mattapan and the surrounding Boston area have to offer.

95 Woodhaven Street, Boston

Listing courtesy of Listing Agent: Patrick Willie-Bonglo from Listing Office: Dominion Realty Corp..

$1,450,000
6 Beds 4 Baths 73542890 MLS
Rare turn-key, roomy 2-family duplex on "triple-size" lot with 5+ off-street parking in quiet part of high-demand neighborhood - Mission Hill. Built in 1988 with upgrades over the years. 2 apartments used as 4 bedrooms each with leases in place til September 2027 at $10,000 rent/month starting September 2026, with increases possible in September 2027. Delightful 2-level suburban-feel living with a bonus 3rd level to the house: a finished walk-out lower level that is not included in the City's living-area records. Open kitchen/dining areas and good-size yard. This is an easy-to-lease income property with hardly any maintenance - no shared common area in the building. All separate utilities including 2 water meters, paid for by the tenants. Easily converted to condos as-is, with the possibility of getting approvals to build additional units.

77-79 Wensley St, Boston

Listing courtesy of Listing Agent: Eric D. Berke from Listing Office: Eric Berke.

$1,299,000
8 Beds 3 Baths 73551760 MLS
Prime opportunity at the top of highly sought-after Jones Hill! This classic triple-decker is a turnkey investment meticulously maintained by a long-term owner with a stellar rental history. Perfect for an owner-occupant or savvy investor, Units 1 and 2 are vacant and recently renovated with sleek stainless steel appliances. Unit 2 features a modern open layout, while Unit 3 offers traditional charm with stunning city views. Unbeatable location: a short walk to the Red Line, minutes to downtown Boston, and steps from vibrant local dining. With endless potential to buy and hold, condo-convert, or maximize market rents, this is a premier Boston investment you don't want to miss!

22 Rowell St, Boston

Listing courtesy of Listing Agent: Nichols Realty Team from Listing Office: MIG.

$940,000
4 Beds 3 Baths 73551319 MLS
This versatile multi-family property is perfect for savvy investors or owner-occupants looking for strong rental income. The first-floor unit features two bedrooms, while the second-floor unit also offers two bedrooms. Both units boast fresh paint, gleaming hardwood floors, and beautiful kitchens equipped with brand-new appliances and private balconies that welcome abundant natural light. The fully finished basement provides excellent extended living space, complete with two additional bedrooms and a full bathroom featuring a standing shower. For even more flexibility, the walk-up attic. Nestled in a quiet neighborhood, this home also boast backyard, off-street parking, and easy access to local schools, shopping, public transportation, and major highways. Don’t miss this incredible opportunity! Sold as-is.

391 Poplar St, Boston

Listing courtesy of Listing Agent: Johnson Folorunso from Listing Office: DOSU Realty LLC.

$1,575,000
6 Beds 4 Baths 73550870 MLS
Fully renovated three-family brick in South Boston's coveted City Point, delivered turnkey and stabilized with new September leases. 6 bedrooms and 4 bathrooms across three units, generating a $10,650/month gross rent roll ($127,800/year) with upside at the next renewal cycle ($3,850 + $3,400 + $3,400).Unit 1 is a spacious 2-bed/2-bath duplex with a private deck and mini-split system; Units 2 and 3 are each 2-bed/1-bath. Every unit shines with updated kitchens and baths, vinyl flooring, and in-unit laundry.Unbeatable location — two blocks to M Street Beach and Pleasure Bay, three blocks to East Broadway's shops and restaurants. MBTA bus routes 7, 9, and 11 reach Broadway Station on the Red Line (~10 min to South Station), and the Seaport is a 5-minute drive. Turnkey income and a lifestyle address in one — don't miss the second chance!

595 East 5th Street, Boston

Listing courtesy of Listing Agent: GPG Team from Listing Office: Grove Property Group.

$8,400,000
46 Beds 24 Baths 73550688 MLS
Rare opportunity to acquire a 24-unit, Cash Flowing Multifamily Asset in the Heart of Dorchester (one of Boston's most desirable rental markets). This Well-Maintained property generates $60,200 in monthly gross rental income (approximately $722,400 annually), featuring a highly sought after unit mix of 22 (2bd 1bth) units and 2 (1bd 1bth) units. Major capital improvements include updated plumbing and electrical systems completed within the past five years and a roof replaced approximately ten years ago. Additional features include separately metered utilities (Gas & Electric), ample off-street parking, and strong in-place cash flow with opportunities for long-term appreciation. Centrally located near Ashmont Station and Ruggles Station. Whether completing a 1031 exchange or expanding an investment portfolio, this turnkey asset offers immediate income, proven stability, and exceptional upside in one of Greater Boston's strongest multifamily markets. Pro Forma available.

7-11 Abbot St., Boston

Listing courtesy of Listing Agent: The Boston ONE Team from Listing Office: Serhant.

$1,075,000
9 Beds 3 Baths 73550526 MLS
Investor Opportunity – MOTIVATED SELLER!! For this Value-Add 3-Family in 02125 zip code with ADU Potential! This spacious 3-family property offers strong rental potential and room for growth. Each floor features 3 bedrooms, with the 2nd floors currently used as 4-bedroom room rentals. The 1st and 3rd floor is vacant. A major value-add opportunity exists with the potential to add an ADU (Accessory Dwelling Unit) in the basement, effectively converting this into a 4-unit building and significantly increasing cash flow. Recent updates include newly constructed back porches completed just a few years ago. With solid bones, great unit layouts, and strong rental demand in the area, this property is an ideal addition to any investor’s portfolio or a perfect opportunity for an owner-occupant landlord seeking extra income. Being sold As-Is” Work needed for this diamond in the rough.

45 Brookford St, Boston

Listing courtesy of Listing Agent: Paige Thompson from Listing Office: eXp Realty LLC - Corporate Office.

$1,199,000
6 Beds 3 Baths 73550409 MLS
Fantastic opportunity for owner occupier or savvy investor. Meticulously maintained classic three decker in one of Dorchester’s hottest neighborhoods. Each unit features 2 bedrooms, living room, dining room, full kitchen and bath. Rear decks overlook a massive, landscaped yard. Total area of 6300 square feet. Considering a condo conversion? Off street parking adds value immediately. Want to live in one unit and rent the others? Unit 3 awaits with newer kitchen and bath. Positioned for growth with releasing at current market rents. Current long term tenants are open to staying with new leases. There have been multiple upgrades for all units and building. Conveniently located within a short distance to the T, shopping, YMCA, local parks & restaurants. Don't miss this chance to add to your portfolio!

15 Bailey Street, Boston

Listing courtesy of Listing Agent: Tara O Riordan from Listing Office: Coldwell Banker Realty - Dorchester.

$2,350,000
9 Beds 4 Baths 73550321 MLS
Introducing a premier investment at 1011 Tremont Street - a fully renovated three-family brownstone across from Northeastern’s new 1,370-bed residence hall. Located at the nexus of the South End and Roxbury Crossing, steps from Ruggles and Mass Ave T stops, the MFA and Longwood Medical, this asset offers rare access to Boston’s top educational and medical hubs. This corner building with a secondary entrance on 4 Burke Street features enhanced natural light and three thoughtfully updated 3-bedroom units, including a 3-bed, 2-bath duplex with central AC and laundry, plus two 3-bed, 1-bath units with efficient split-vent systems. All units feature hardwood floors, modern kitchens with quartz counters and stainless appliances, and updated baths. With upgraded systems, strong in-place income and ample future upside, this turnkey asset is ideal for investors seeking long-term appreciation and low-maintenance stability in one of Boston’s most resilient rental markets. Full proforma available.

4 Burke St, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.

$1,369,000
9 Beds 4 Baths 73550177 MLS
Discover an exceptional investment opportunity, a massive, versatile multi-family property located in Meetinghouse Hill. This 4,446 square feet of living space has endless potential. 9 beds 4 baths, this spacious open-concept layout of this property is perfect for savvy investors or an owner-occupant looking for long term wealth and residual income. In addition to a fully unfinished basement, this property offers a total of 0.16 of yard space for agriculture or ADU (extremely rare in the city). Off street parking for 4 cars. Location is also key, with this home convenient located with easy access to the redline, commuterail, several bus routes and easy access to 93. Parks and schools located within walking distance to property. Great neighborhood. SOLD AS IS. Buyer/buyer's agent to do their Due Diligence.Two floors currently occupied one floor to be delivered vacate. Annual gross income of $118,400.OPEN HOUSE 7/18 12PM-1:30PM offers due 7/20 at 5pm.

90 Homes Ave, Boston

Listing courtesy of Listing Agent: Patrice Williams from Listing Office: Thumbprint Realty, LLC.

$1,849,000
11 Beds 6 Baths 73549729 MLS
PRICE ADJUSTMENT! Exceptional investment opportunity in the heart of Jamaica Plain! This turnkey 3-family currently generates $11,680/month ($140160/year) and features two spacious 4-bed/2-bath units and one 3-bed/2-bath unit with separate heating and cooling systems, central air, hardwood floors, oversized decks, and strong in-place rental income. Since purchasing, the owner has completed significant capital improvements, including a new roof (2023), approximately $60,000 in basement improvements, updated bathrooms, kitchen cabinetry, new refrigerators, ranges, microwaves, recent HVAC improvements, and coin/card-operated common laundry. Ideally located just steps to the Green Street MBTA Orange Line, parks, restaurants, shopping, Longwood Medical Area, and major commuter routes. A rare opportunity for investors or 1031 exchange buyers seeking strong cash flow, quality improvements, and long-term appreciation.

39 Glen Rd, Boston

Listing courtesy of Listing Agent: Bhamin Mukesh Chhatrapati from Listing Office: eXp Realty LLC.

$889,000
4 Beds 4 Baths 73549596 MLS
A Roslindale two-family with a built-in advantage: a home for you and a second unit that helps carry it. Each unit runs a smart, flexible plan, with an updated kitchen and a convenient half bath, a formal dining area and living room, and a sunroom off the living space that works as a home office or exercise room. A central hallway connects the bedrooms and full bath, with a bedroom anchoring the rear. The upper unit adds a bonus room, ideal as a third bedroom or study. Both units are clean, bright, and well kept, with thoughtful updates throughout. Outside, a sizeable yard offers room to garden, gather, or expand down the road. Off-street parking behind the buildings for two to three cars, plus convenient on-street parking. Recent improvements include fresh exterior paint, a sealed and repointed foundation, masonry front steps, and a roof under 10 years old. Close by: Roslindale Village, the commuter rail, and green space at Bellevue Hill, Stony Brook Reservation, and Turtle Pond.

21-23 Averton St, Boston

Listing courtesy of Listing Agent: The Boston Home Team from Listing Office: Gibson Sotheby's International Realty.

$1,099,000
5 Beds 3 Baths 73549445 MLS
Incredible investment opportunity in the heart of central South Boston! This spacious semi-detached three-family property offers 5 bedrooms and 3 bathrooms across 2,088 square feet. Featuring high ceilings, the home provides an open and inviting atmosphere. Well-maintained with a newer roof and updated heating systems, this property is ready for your personal touches and cosmetic updates. Delivered vacant and in "as is" condition, you have the flexibility to renovate and maximize its potential. With a projected total rent of $10K per month after updates, this is a must-see for investors and buyers seeking a promising income property. Don’t miss your chance to own this centrally located gem!

48 H Street, Boston

Listing courtesy of Listing Agent: Jackie Rooney Team from Listing Office: Rooney Real Estate, LLC.

$1,789,000
8 Beds 3 Baths 73549427 MLS
Don’t miss this incredible opportunity in the heart of South Boston! This large-scale, detached three-family home offers 8 bedrooms and 3 bathrooms across 3,412 square feet of living space. Soaring high ceilings and a big garden add a sense of openness and outdoor enjoyment. The property sits on a spacious 3,588 SF lot, providing room for expanded living space or outdoor activities. While the home is well-maintained with a newer roof and updated heating systems, it’s ready for your cosmetic updates to really make it shine. Delivered vacant, with the potential for a total rent of $15K/month after updates, this is a prime investment opportunity in a central location.

46-R H St, Boston

Listing courtesy of Listing Agent: Jackie Rooney Team from Listing Office: Rooney Real Estate, LLC.

$3,699,000
24 Beds 18 Baths 73549277 MLS
Rare opportunity to own a turnkey 9-unit brick apartment building in the desirable Egleston neighborhood of Jamaica Plain. This well-maintained asset features an ideal unit mix of six 3-bedroom, 1.5-bath units and three 2-bedroom, 1.5-bath units, offering broad tenant appeal. Solid brick construction provides long-term durability and low maintenance.Ideally located just minutes from major universities, renowned hospitals, downtown Boston, and the Orange Line, the property attracts a diverse tenant base of students, healthcare professionals, and working professionals. Currently generating $228,600 in gross annual income with three vacant units, this asset presents significant upside proforma through lease-up and rental growth.A rare opportunity to acquire a high-quality Boston multifamily asset with immediate value-add potential and long-term appreciation.

3146-3150 Washington St, Boston

Listing courtesy of Listing Agent: Derek Young from Listing Office: Longwood Residential, LLC.

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