Vintage homes for sale & real estate in Roslindale, MA

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ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Prime three-family opportunity with strong upside potential. Public record reflects 5 beds / 3 baths, while the current layout offers 7 beds / 3 baths (buyer to do due diligence). Ideal for investors or owner-occupants seeking flexible living and income potential. Conveniently located near MBTA Forest Hills with easy access to bus routes, the Orange Line, and downtown Boston. Situated on Main Street, the property features a large lot with ample off-street parking and a spacious backyard, a rare find for a multi-family in this location. The basement offers potential for an ADU (subject to zoning and city approval), providing additional value and future expansion possibilities. A well-located

$1,125,000

6 beds3 baths3,343 sq ft

3886-3888 Washington, Roslindale, MA 02131

Large lot • 5,906 sq ft lot • Built 1890

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Welcome to 50 Southbourne Road, a solid 3-bedroom, 1-bath home located on a tree-lined street in Jamaica Plain. This property offers a classic layout with a living room, dining room with built-in hutch, and an enclosed front porch. The home has good bones, with recent roof and exterior work completed. Interior features include original details, generous windows, and three second-floor bedrooms. The basement provides additional storage space. Conveniently located near public transportation, schools, parks, and local amenities. This home is being sold as is and presents an opportunity for a buyer looking to bring their vision to a well-structured property in a desirable neighborhood.

$580,000

3 beds1 bath1,120 sq ft

50 Southbourne Rd, Jamaica Plain, MA 02130

Recent exterior work • Recent roof work • Tree-lined street

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Welcome to 103 Belgrade Ave, Residence 2 - a recently renovated duplex offering almost 1500 sqft in the heart ofRoslindale Square. This spacious condo features 3 beds, 2 full baths, in-unit laundry, assigned parking & additionalprivate storage in basement. The sun-drenched living room features a bay window, recessed lighting, high ceilings, andseamlessly leads into a spacious eat-in kitchen with elegantly appointed white shaker cabinets, granite countertops, andstainless steel appliances. One bedroom & full bathroom complete this level. The second level offers 2 bedrooms, 1 fullbathroom & laundry room. With two heating & cooling zones, hardwood floors throughout, an

$695,000

3 beds2 baths1,473 sq ft

103 Belgrade Ave #2, Roslindale, MA 02131

Bay window • In unit laundry • Assigned parking

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Looking for a strong investment? Welcome to Hemman Street - a rare opportunity in Roslindale. Currently operating at a mid–6% cap rate, this partially updated 3-family features modern, condo-quality finishes in Units 1 and 2, while Unit 3, though unrenovated, is leased at a strong rental rate through 8/31/2026. Units 1 and 2 offer updated kitchens and baths, hardwood floors, private outdoor space, and in-unit conveniences that appeal to today’s renters. Unit 3 provides excellent long-term value with its high existing income stream. Situated on a residential street minutes from Roslindale Village, the commuter rail, shops, and dining, this property delivers strong cash flow, turn

$1,095,000

5 beds3 baths2,318 sq ft

5 7 Hemman St, Roslindale, MA 02131

Fully renovated • In-unit conveniences • Updated kitchens

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
INVESTORS and END-USERS! UNIQUE OPPORTUNITY to own a TRIPLE DECKER w/ ATTACHED AND VERSATILE ANNEX situated on Two Sizable Lots! Well-maintained and spacious, these units have a variety of features including Hardwood Floors, High Ceilings, Beautiful Woodwork, Pantries, Built-In Hutches, Stained Glass, French Doors, Ceiling Fans, Recessed Lighting & Rear Decks. There are 3 NEW, HIGH EFFICIENCY HEAT UNITS. The Basement has plenty of storage and Common Laundry. Also included are separate utilities & 3 off-street parking. The MODERN Two-Level ANNEX has great flexibility as an Art Studio, Meeting Room, Office, Gym, Rec Room or Bonus Room for guests, nannies, or family. It's is equip

$2,050,000

8 beds4 baths4,562 sq ft

26 Tower St, Jamaica Plain, MA 02130

Triple decker • Two sizable lots • Pantries

Property at 178 Hyde Park Ave #3, Jamaica Plain, MA 02130, 3 beds, 2 baths

$499,900

3 beds2 baths1,653 sq ft

178 Hyde Park Ave #3, Jamaica Plain, MA 02130

Property at 79 Robert St #3, Boston, MA 02131, 2 beds, 2 baths

$525,000

2 beds2 baths945 sq ft

79 Robert St #3, Boston, MA 02131

Property at 95 Newburg St, Roslindale, MA 02131, 4 beds, 1.5 baths

$660,000

4 beds1.5 baths2,000 sq ft

95 Newburg St, Roslindale, MA 02131

Property at 18-20 Northbourne Rd #18, Boston, MA 02130, 2 beds, 1.5 baths

$789,000

2 beds1.5 baths1,302 sq ft

18-20 Northbourne Rd #18, Boston, MA 02130

Property at 55 Metropolitan Ave, Roslindale, MA 02131, 5 beds, 3.5 baths

$995,000

5 beds3.5 baths2,622 sq ft

55 Metropolitan Ave, Roslindale, MA 02131

Property at 26 Bradfield Ave #3, Roslindale, MA 02131, 2 beds, 1 bath

$515,000

2 beds1 bath745 sq ft

26 Bradfield Ave #3, Roslindale, MA 02131

Property at 1 Catenaccia Way #47, Jamaica Plain, MA 02130, 1 bed, 1 bath

$390,000

1 bed1 bath581 sq ft

1 Catenaccia Way #47, Jamaica Plain, MA 02130

Property at 34 Averton St, Roslindale, MA 02131, 9 beds, 3 baths

$1,549,900

9 beds3 baths4,393 sq ft

34 Averton St, Roslindale, MA 02131

Property at 15 S Fairview St #3, Roslindale, MA 02131, 3 beds, 1 bath

$649,000

3 beds1 bath1,475 sq ft

15 S Fairview St #3, Roslindale, MA 02131

Property at 25 Crandall St, Roslindale, MA 02131, 6 beds, 2 baths

$949,900

6 beds2 baths2,308 sq ft

25 Crandall St, Roslindale, MA 02131

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OPEN SAT, 12PM TO 2PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Beautifully modernized 1780 antique Colonial blending historic charm with updates. This 2-bedroom, 1.5-bath has it all. The 1st floor features an upgraded kitchen with stainless steel appliances, roomy living room with a wood burning fireplace and built in shelving from the original wood floors, a spacious dining room, half bath and a mudroom with driveway access. The second floor has vaulted ceilings and skylights throughout and offers 2 bedrooms and a modern bath with walk-in shower. Enjoy a private fenced yard with 18×11 grapevine covered pergola and patio, oversized driveway, 16×12 storage shed, newer roof and siding, and transferable solar panels. Quiet side street location

$579,900

2 beds1.5 baths1,103 sq ft

38 Colonial Dr, Dedham, MA 02026

Built in shelving • Upgraded kitchen • Vaulted ceilings

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Opportunity is knocking. .. Actually is pounding on the door for this adorable and affordable cape located on popular tree lined street. With high ceilings and hardwoods floors, we are the best value in town. The "cliche" of why rent when you can own, is exactly why you should buy 60 Meagher Ave. Roll up your sleeves, bring your creative paintbrush and make this one shine! All conveniently located to all Great things Milton! Come take a look and see for yourself.

$665,000

2 beds1.5 baths1,306 sq ft

60 Meagher Ave, Milton, MA 02186

4,199 sq ft lot • Garage • Built 1925

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Your new home awaits you! Newly remodeled 2-bedroom condo in Boston offering modern comfort and style. The updated kitchen features brand new stainless steel appliances, ample cabinetry, and a dedicated pantry. Beautiful hardwood floors run throughout the unit, complemented by overhead and recessed lighting. Generously sized bedrooms provide excellent closet space, while the expansive living and dining areas offer flexible layouts ideal for entertaining or working from home. A well-appointed home in a convenient Boston location. || Open House Sat 13 & Sun 14 from 12pm-1:30pm || HOA Fees are approximate.

$519,000

2 beds1 bath1,150 sq ft

16 Clarkwood St #2, Mattapan, MA 02126

Dedicated pantry • Updated kitchen • Recessed lighting

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Your new home awaits you! Newly remodeled 1-bedroom condo in Boston offering modern comfort and style. The updated kitchen features brand new stainless steel appliances, ample cabinetry, and a dedicated pantry. Hardwood floors run throughout the unit, complemented by overhead and recessed lighting. The spacious bedroom offers excellent closet space, while the open living and dining areas provide a flexible layout ideal for entertaining or working from home. A well-appointed home in a convenient Boston location. || Open House Sat 13 & Sun 14 from 12pm–1:30pm || HOA fees are approximate.

$409,000

1 bed1 bath660 sq ft

16 Clarkwood St #3, Mattapan, MA 02126

Dedicated pantry • Updated kitchen • Recessed lighting

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Discover the potential of 104 Greaton Road, a versatile two-unit multifamily home in a prime West Roxbury location, ideally situated near Centre Street shops, Hynes Playground park, and Independence Village in Chestnut Hill. The living and dining rooms feature large windows and effortless flow, perfect for relaxation and entertaining. The semi-finished attic invites creativity, offering potential for two additional bedrooms or a luxurious primary suite. Original woodwork, hardwood floors, and built-ins grace the home, adding warmth and character throughout. Multiple 3-season enclosed porches are perfect for enjoying the changing seasons and a detached garage provides ample storage space. Th

$1,100,000

4 beds2 baths2,640 sq ft

104 Greaton Rd, West Roxbury, MA 02132

Semi finished attic • Original woodwork • 5,000 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
PLEASE SUBMIT ALL OFFERS BY 12/26 @ 5:00 PM. Fantastic investment opportunity in Mattapan! 95 Deering Rd is a multi-family property set on a generously sized lot, offering excellent value-add potential for both new and seasoned investors. With multiple units ready for updating or repositioning, this property is ideal for those looking to create long-term value and maximize rental income. The spacious lot provides added flexibility for outdoor space or future improvements. Conveniently located just minutes from the MBTA and highway access - this is a prime chance to invest in a growing Boston neighborhood.

$799,000

6 beds3.5 baths3,434 sq ft

95 Deering Rd, Mattapan, MA 02126

Multiple units • Generously sized lot • Value-add potential

Property at 58 Oak St, Hyde Park, MA 02136, 4 beds, 1.5 baths

$889,900

4 beds1.5 baths2,295 sq ft

58 Oak St, Hyde Park, MA 02136

Property at 145 Lagrange St, West Roxbury, MA 02132, 5 beds, 4 baths

$1,350,000

5 beds4 baths2,419 sq ft

145 Lagrange St, West Roxbury, MA 02132

Property at 115 Windham Rd, Hyde Park, MA 02136, 3 beds, 2.5 baths

$590,000

3 beds2.5 baths1,224 sq ft

115 Windham Rd, Hyde Park, MA 02136

Property at 8 Pine St #4, Hyde Park, MA 02136

$599,000

0 beds— baths1,805 sq ft

8 Pine St #4, Hyde Park, MA 02136

Property at 152 Stratford St, West Roxbury, MA 02132, 4 beds, 3.5 baths

$1,750,000

4 beds3.5 baths2,792 sq ft

152 Stratford St, West Roxbury, MA 02132

Property at 107 West St, Hyde Park, MA 02136, 4 beds, 2 baths

$510,000

4 beds2 baths2,156 sq ft

107 West St, Hyde Park, MA 02136

Property at 55 South St, Jamaica Plain, MA 02130, 8 beds, 2.5 baths

$2,900,000

8 beds2.5 baths3,996 sq ft

55 South St, Jamaica Plain, MA 02130

Property at 175 Clare Ave Unit B3, Hyde Park, MA 02136, 1 bed, 1 bath

$254,900

1 bed1 bath435 sq ft

175 Clare Ave Unit B3, Hyde Park, MA 02136

Property at 1139 Hyde Park Ave, Hyde Park, MA 02136

$600,000

0 beds— baths2,000 sq ft

1139 Hyde Park Ave, Hyde Park, MA 02136

Property at 42 Raldne Rd #1, Hyde Park, MA 02136, 3 beds, 2.5 baths

$580,000

3 beds2.5 baths1,446 sq ft

42 Raldne Rd #1, Hyde Park, MA 02136

Property at 12 Hiawatha, Mattapan, MA 02126, 16 beds, 6 baths

$2,170,000

16 beds6 baths4,989 sq ft

12 Hiawatha, Mattapan, MA 02126

Property at 34 Ridlon Rd, Hyde Park, MA 02136, 4 beds, 1.5 baths

$620,000

4 beds1.5 baths1,812 sq ft

34 Ridlon Rd, Hyde Park, MA 02136

Property at 16 Concord Ave #1, Milton, MA 02186, 2 beds, 1 bath

$475,000

2 beds1 bath920 sq ft

16 Concord Ave #1, Milton, MA 02186

Property at 519 Metropolitan Ave, Hyde Park, MA 02136

$1,400,000

— beds— baths— sq ft

519 Metropolitan Ave, Hyde Park, MA 02136

Vintage Homes for Sale in Roslindale

There are currently 15 vintage homes for sale in Roslindale at a median listing price of $690K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Roslindale stay on the market for 60 days and receive 1 offers. Popular neighborhoods include Hyde Park, Dorchester, Jamaica Plain, Chestnut Hill, and West Roxbury. This map is refreshed with the newest listings in Roslindale every 15 minutes.

In the past month, 18 homes have been sold in Roslindale. In addition to houses in Roslindale, there were also 49 condos, 13 townhouses, and 12 multi-family units for sale in Roslindale last month. Find your dream home in Roslindale using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Roslindale are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Roslindale. If you're looking to sell your home in the Roslindale area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Roslindale with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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