Vintage homes for sale & real estate in Fenway-Kenmore, MA

217 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Fenway-Kenmore, MA:
A spectacular one bedroom condo in great location where you can enjoy an urban setting while still being surrounded by green space. This top floor unit features an open style kitchen and living area, hardwood floors, 2 skylights, lots of closet space and high ceilings. The kitchen and baths have been tastefully updated. This wonderful building includes common laundry and bike storage. Conveniently nearby to the Longwood Medical area, Brookline Village, Fenway, E and D Green lines, parks, jogging trails and all that the city has to offer!

$489,000

1 bed1 bath555 sq ft

390 Riverway #24, Boston, MA 02115

Common laundry • Lots of closet space • 2 skylights

OPEN TODAY, 12PM TO 1:30PM

ABOUT THIS HOME
Vintage Home for sale in Fenway-Kenmore, MA:
Welcome to 705 Massachusetts Ave, a beautifully appointed penthouse corner residence set within an iconic South End brownstone. Thoughtfully updated and rich with natural light, this three-bedroom, one-and-a-half-bath home blends architectural character with contemporary comfort. The open kitchen, oversized windows, and refined finishes create an inviting sense of scale throughout. Additional features include in-unit laundry, central air with Nest, Andersen windows, and a recently installed HVAC system. A newly constructed roof deck offers an exceptional vantage point with sweeping Boston skyline views. Perfectly positioned near BU Medical, the Silver Line, and I-93, with effortless access

$750,000

3 beds1.5 baths950 sq ft

705 Massachusetts Ave., #8, Roxbury, MA 02118

In-unit laundry • Central air • Open kitchen

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Fenway-Kenmore, MA:
Sunny & bright 1 bedroom in a Worcester Square Brownstone offering location & value. Stately, well managed building with low condo fee that includes heat & hot water. Unit 4 has beautiful hardwood floors, a spacious bathroom with window, hi ceilings, 4 oversized windows & a modern kitchen. Perfect for investor with a strong rental history as it is steps from BU Medical, BU Dental & Boston Medical Center.

$419,900

1 bed1 bath445 sq ft

41 Worcester Sq #4, Boston, MA 02118

Low condo fee • Spacious bathroom • Modern kitchen

OPEN TODAY, 12PM TO 1:30PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Fenway-Kenmore, MA:
Back Bay Chic Meets City Convenience! Step into this sun-soaked, street-facing, pet-friendly 1BR condo perched on the 6th floor of The Charlesview! Enjoy beautiful southern exposure that fills the home with all-day natural light and offers classic Back Bay views. The updated open-concept kitchen is perfect for entertaining, featuring granite countertops, stainless steel appliances & a spacious peninsula island. You’ll love the hardwood floors, full bath & generous closet space throughout. Stay cool with CENTRAL AIR, and the bonus of HEAT, HOT WATER & AC INCLUDED in the condo fee. This professionally managed, ELEVATOR building was recently renovated and offers on-sit

$675,000

1 bed1 bath521 sq ft

534 Beacon St #602, Boston, MA 02215

Open-concept kitchen • Granite countertops • Central air

ABOUT THIS HOME
Vintage Home for sale in Fenway-Kenmore, MA:
A rare opportunity in Boston’s coveted St. Botolph neighborhood, perfectly situated between Back Bay and the South End. Few properties in the city offer the level of convenience and proximity that this classic brownstone provides, just steps from Copley Place, the Prudential Center, and the very best of both neighborhoods. Spanning over 4,000 square feet of living space, this quintessential Boston brownstone retains much of its original woodwork and architectural detail, offering the perfect canvas for a full redevelopment or luxury end-user restoration. The exceptionally large backyard - a rarity in this area - adds tremendous value and flexibility for outdoor space or potential expa

$4,250,000

4 beds4 baths4,068 sq ft

257 W Newton St, Boston, MA 02116

Architectural detail • Large backyard • Classic brownstone

Property at 20 David G Mugar Way, Boston, MA 02114, 5 beds, 4 baths

$5,295,000

5 beds4 baths4,474 sq ft

20 David G Mugar Way, Boston, MA 02114

Property at 160 Commonwealth #516, Boston, MA 02116, 1 bath

$749,899

0 beds1 bath463 sq ft

160 Commonwealth #516, Boston, MA 02116

Property at 30 Fenway #1, Boston, MA 02215, 1 bed, 1.5 baths

$649,000

1 bed1.5 baths2,100 sq ft

30 Fenway #1, Boston, MA 02215

Property at 548 Massachusetts Ave #3, Boston, MA 02118, 1 bed, 1 bath

$775,000

1 bed1 bath750 sq ft

548 Massachusetts Ave #3, Boston, MA 02118

Property at 75 Charles St Unit 4B, Boston, MA 02114, 1 bed, 1 bath

$675,000

1 bed1 bath523 sq ft

75 Charles St Unit 4B, Boston, MA 02114

Property at 23 Saint Stephen St Unit 23-3, Boston, MA 02115, 1 bed, 1 bath

$575,000

1 bed1 bath700 sq ft

23 Saint Stephen St Unit 23-3, Boston, MA 02115

Property at 357-359 Beacon St #2, Boston, MA 02116, 3 beds, 3 baths

$4,650,000

3 beds3 baths2,781 sq ft

357-359 Beacon St #2, Boston, MA 02116

Property at 6 Walnut St #3, Boston, MA 02108, 3 beds, 2 baths

$1,949,000

3 beds2 baths1,272 sq ft

6 Walnut St #3, Boston, MA 02108

Property at 362 Commonwealth Ave Unit 2E, 2F, Boston, MA 02115, 1 bed, 1.5 baths

$745,000

1 bed1.5 baths603 sq ft

362 Commonwealth Ave Unit 2E, 2F, Boston, MA 02115

Property at 131 Saint Botolph St #1, Boston, MA 02115, 3 beds, 2.5 baths

$2,799,000

3 beds2.5 baths1,991 sq ft

131 Saint Botolph St #1, Boston, MA 02115

Property at 51 Beacon St #3, Boston, MA 02108, 3 beds, 5 baths

$5,750,000

3 beds5 baths2,930 sq ft

51 Beacon St #3, Boston, MA 02108

Property at 30 Fenway #5, Boston, MA 02215, 0.5 baths

$849,000

0 beds0.5 baths1,476 sq ft

30 Fenway #5, Boston, MA 02215

Property at 15 Concord Sq Unit A, Boston, MA 02118, 1 bath

$525,000

0 beds1 bath435 sq ft

15 Concord Sq Unit A, Boston, MA 02118

Property at 12 Marlborough St #1, Boston, MA 02116, 2 beds, 2.5 baths

$3,900,000

2 beds2.5 baths2,357 sq ft

12 Marlborough St #1, Boston, MA 02116

Property at 1 Fairfield St, Boston, MA 02116, 6 beds, 5.5 baths

$10,950,000

6 beds5.5 baths5,700 sq ft

1 Fairfield St, Boston, MA 02116

Property at 128 Pembroke St Unit 2-3, Boston, MA 02118, 4 beds, 3.5 baths

$3,690,000

4 beds3.5 baths2,469 sq ft

128 Pembroke St Unit 2-3, Boston, MA 02118

Property at 466 Commonwealth Ave #305, Boston, MA 02215, 1 bath

$489,000

0 beds1 bath346 sq ft

466 Commonwealth Ave #305, Boston, MA 02215

Property at 15 Keswick St Unit B1, Boston, MA 02215, 1 bed, 1 bath

$419,999

1 bed1 bath436 sq ft

15 Keswick St Unit B1, Boston, MA 02215

Property at 19 Stanhope St, Boston, MA 02116, 15 beds, 13 baths

$14,650,000

15 beds13 baths14,787 sq ft

19 Stanhope St, Boston, MA 02116

Property at 10 Cumberland St Unit 10-4, Boston, MA 02115, 2 beds, 2 baths

$1,375,000

2 beds2 baths1,160 sq ft

10 Cumberland St Unit 10-4, Boston, MA 02115

Property at 692 Tremont St #6, Boston, MA 02118, 2 beds, 1 bath

$930,000

2 beds1 bath870 sq ft

692 Tremont St #6, Boston, MA 02118

Property at 190 Marlborough Unit C, Boston, MA 02116, 4 beds, 3 baths

$6,900,000

4 beds3 baths4,093 sq ft

190 Marlborough Unit C, Boston, MA 02116

Property at 330 Dartmouth Unit B1, Boston, MA 02116, 1 bed, 1 bath

$559,000

1 bed1 bath480 sq ft

330 Dartmouth Unit B1, Boston, MA 02116

Property at 321 Beacon St, Boston, MA 02116, 4 beds, 4 baths

$6,900,000

4 beds4 baths4,866 sq ft

321 Beacon St, Boston, MA 02116

Property at 109 Appleton St, Boston, MA 02116, 4 beds, 4.5 baths

$6,195,000

4 beds4.5 baths3,500 sq ft

109 Appleton St, Boston, MA 02116

Property at 193 West Springfield St, Roxbury, MA 02118, 4 beds, 4.5 baths

$3,325,800

4 beds4.5 baths2,560 sq ft

193 West Springfield St, Roxbury, MA 02118

Property at 107 Jersey Unit 21B, Boston, MA 02215, 2 beds, 1 bath

$599,000

2 beds1 bath750 sq ft

107 Jersey Unit 21B, Boston, MA 02215

Property at 69 E Berkeley St #1, Boston, MA 02118, 1 bed, 1 bath

$559,000

1 bed1 bath784 sq ft

69 E Berkeley St #1, Boston, MA 02118

Property at 231 W Newton St #3, Boston, MA 02116, 1 bed, 1 bath

$650,000

1 bed1 bath639 sq ft

231 W Newton St #3, Boston, MA 02116

Property at 41 Greenwich St, Boston, MA 02120, 4 beds, 1.5 baths

$899,000

4 beds1.5 baths1,614 sq ft

41 Greenwich St, Boston, MA 02120

Property at 35 Mt Vernon St #1, Boston, MA 02108, 2 beds, 1.5 baths

$1,249,000

2 beds1.5 baths1,192 sq ft

35 Mt Vernon St #1, Boston, MA 02108

Property at 44 Appleton St, Boston, MA 02116, 4 beds, 4 baths

$4,195,000

4 beds4 baths3,427 sq ft

44 Appleton St, Boston, MA 02116

Property at 577 Massachusetts Unit C, Roxbury, MA 02118, 2 beds, 1 bath

$999,000

2 beds1 bath973 sq ft

577 Massachusetts Unit C, Roxbury, MA 02118

Property at 362 Commonwealth Ave Unit 6D, Boston, MA 02115, 1 bed, 1 bath

$699,000

1 bed1 bath689 sq ft

362 Commonwealth Ave Unit 6D, Boston, MA 02115

Property at 39 Warren Ave Unit G, Boston, MA 02116, 1 bed, 1 bath

$699,000

1 bed1 bath940 sq ft

39 Warren Ave Unit G, Boston, MA 02116

Property at 1200 Washington St Unit 213A, Boston, MA 02118, 1 bed, 1 bath

$634,500

1 bed1 bath952 sq ft

1200 Washington St Unit 213A, Boston, MA 02118

Viewing page 1 of 6

Vintage Homes for Sale in Fenway-Kenmore

There are currently 217 vintage homes for sale in Fenway-Kenmore at a median listing price of $1.5M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Fenway-Kenmore stay on the market for 57 days and receive 1 offers. Popular neighborhoods include Dorchester, Jamaica Plain, Back Bay, Charlestown, and Beacon Hill. This map is refreshed with the newest listings in Fenway-Kenmore every 15 minutes.

In the past month, 64 homes have been sold in Fenway-Kenmore. In addition to houses in Fenway-Kenmore, there were also 459 condos, 34 townhouses, and 9 multi-family units for sale in Fenway-Kenmore last month. Find your dream home in Fenway-Kenmore 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 Fenway-Kenmore are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Fenway-Kenmore. If you're looking to sell your home in the Fenway-Kenmore area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Fenway-Kenmore with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Fenway-Kenmore, MA

Cities

Nearby Neighborhoods

Nearby Neighborhoods with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Fenway-Kenmore, MA

How to buy a house in Fenway-Kenmore, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.