Vintage homes for sale & real estate in Roslindale, MA

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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.

$620,000

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:
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

$2,150,000

8 beds4 baths4,562 sq ft

26 Tower St, Jamaica Plain, MA 02130

Triple decker • Two sizable lots • Pantries

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Tucked near the Jamaica Plain line, this bright 2-bed, 1-bath Roslindale condo offers effortless city living less than a mile from Forest Hills—ideal for first-time buyers, downsizers or investors. Perched on the second floor of a classic multifamily, the unit spans the full length of the building, with abundant natural light highlighting period details, hardwood floors & a freshly painted interior. A welcoming foyer, perfect as a drop-zone, opens to a living room that flows into a dining room with an original built-in & a spacious eat-in kitchen—ideal for cooking & gathering. The generous layout, with two well-proportioned bedrooms and a full bath, is ideal fo

$495,000

2 beds1 bath965 sq ft

348-350 Hyde Park Ave #2, Roslindale, MA 02131

Welcoming foyer • Original built-in • Hardwood floors

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
This move-in ready single-family alternative near the commuter rail is unique. It feels more like a single family than a condo. Great for a first-time home buyer or anyone looking to build equity with some minor changes over time. Also listed as condo: MLS # 73435962

$595,000

3 beds1.5 baths1,503 sq ft

15 Newburg St #1, Roslindale, MA 02131

3,187 sq ft lot • 2 parking spots • Built 1911

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Roslindale, MA:
Modern luxury meets unbeatable location in this custom-built showstopper just minutes from Roslindale Village, Centre Street, and the Commuter Rail. Originally crafted as the builder’s own home, it’s loaded with high-end finishes, smart Lutron Caseta lighting, and sleek contemporary style throughout. The open layout is all about flow—perfect for entertaining and effortless everyday living. A chef’s kitchen with custom cabinetry connects to a sunlit dining area and opens through French doors to a huge patio and private garden—your dream setup for indoor/outdoor living. Downstairs offers a flexible bedroom suite or media room with garden views. Upstairs, the spa-

$1,225,000

4 beds3 baths2,539 sq ft

276 Cornell St, Roslindale, MA 02131

Custom cabinetry • Huge patio • High end finishes

Property at 187 Florence St Unit 2L, Roslindale, MA 02131, 2 beds, 1 bath

$449,000

2 beds1 bath805 sq ft

187 Florence St Unit 2L, Roslindale, MA 02131

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 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 105 Neponset Ave #105, Roslindale, MA 02131, 3 beds, 2 baths

$715,000

3 beds2 baths1,334 sq ft

105 Neponset Ave #105, Roslindale, MA 02131

Property at 5 7 Hemman St, Roslindale, MA 02131, 5 beds, 3 baths

$1,125,000

5 beds3 baths2,318 sq ft

5 7 Hemman St, Roslindale, MA 02131

Property at 112 Roslindale Ave #2, Roslindale, MA 02131, 3 beds, 2 baths

$615,000

3 beds2 baths1,183 sq ft

112 Roslindale Ave #2, Roslindale, MA 02131

Property at 103 Neponset Ave #103, Roslindale, MA 02131, 3 beds, 2.5 baths

$690,000

3 beds2.5 baths1,313 sq ft

103 Neponset Ave #103, Roslindale, 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 103-105 Neponset Ave, Roslindale, MA 02131, 6 beds, 4.5 baths

$1,325,000

6 beds4.5 baths2,640 sq ft

103-105 Neponset 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 88 Gordon Ave #2, Hyde Park, MA 02136, 3 beds, 3 baths

$544,900

3 beds3 baths1,430 sq ft

88 Gordon Ave #2, Hyde Park, MA 02136

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

$539,900

2 beds2 baths945 sq ft

79 Robert St #3, Boston, MA 02131

Property at 375 Hyde Park Ave #3, Roslindale, MA 02131, 3 beds, 2 baths

$674,000

3 beds2 baths1,103 sq ft

375 Hyde Park Ave #3, Roslindale, MA 02131

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 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 142 Metropolitan Unit A, Roslindale, MA 02131, 4 beds, 3 baths

$989,000

4 beds3 baths1,950 sq ft

142 Metropolitan Unit A, Roslindale, MA 02131

Property at 64 Hyde Park Ave #3, Jamaica Plain, MA 02130, 3 beds, 1 bath

$525,000

3 beds1 bath1,042 sq ft

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

Property at 543 Hyde Park Ave #1, Roslindale, MA 02131, 2 beds, 2 baths

$585,000

2 beds2 baths1,101 sq ft

543 Hyde Park Ave #1, Roslindale, MA 02131

Property at 32 Jewett St, Roslindale, MA 02131, 4 beds, 3 baths

$849,000

4 beds3 baths2,047 sq ft

32 Jewett St, 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 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 11 Weld Hill St #2, Jamaica Plain, MA 02130, 2 beds, 1 bath

$599,000

2 beds1 bath1,127 sq ft

11 Weld Hill St #2, Jamaica Plain, MA 02130

Property at 75 Glendower Rd, Roslindale, MA 02131, 9 beds, 4 baths

$1,299,000

9 beds4 baths4,248 sq ft

75 Glendower Rd, Roslindale, MA 02131

Property at 142 Birch St #2, Roslindale, MA 02131, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths2,013 sq ft

142 Birch St #2, Roslindale, MA 02131

Property at 142 Birch St #1, Roslindale, MA 02131, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths2,013 sq ft

142 Birch St #1, Roslindale, MA 02131

Property at 103 Belgrade Ave #2, Roslindale, MA 02131, 3 beds, 2 baths

$705,000

3 beds2 baths1,473 sq ft

103 Belgrade Ave #2, 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

Property at 242 Belgrade Ave, Roslindale, MA 02131, 7 beds, 3 baths

$1,425,000

7 beds3 baths3,795 sq ft

242 Belgrade Ave, Roslindale, MA 02131

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Vintage Homes for Sale in Roslindale

There are currently 33 vintage homes for sale in Roslindale at a median listing price of $689K. 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 40 days and receive 2 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, 30 homes have been sold in Roslindale. In addition to houses in Roslindale, there were also 65 condos, 13 townhouses, and 17 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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