Vintage homes for sale & real estate in Cumberland County, ME

211 homes

Sort:

Recommended

NEW 9 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
The new zoning for this bungalow in the sought after Stroudwater area of Portland offers investors an income stream opportunity. 1549 Westbrook Street zoning allows someone the option of building an additional structure on the back of the lot, up to 4 units total on the lot. Conveniently located, this move-in ready sweet home has a breathtaking backyard with a large bellowing willow tree. The bungalow with charming built-ins on both floors and hardwood floors is bubbling over with character. Bright and clean, the layout is unique. The actual living space is twice the above grade square footage with the kitchen, dining room, half bath/laundry room and 1 bedroom on the lower level and 2 addit

$435,000

3 beds1.5 baths1,314 sq ft

1549 Westbrook St, Portland, ME 04102

Charming built-ins • High end finishes • Granite countertops

NEW 17 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
Discover a rare opportunity in one of Portland's most sought-after neighborhoods. This four-unit offers strong investment potential along with the timeless charm of period architectural details throughout including original millwork, hardwood floors, high ceilings, and built-ins. Each unit offers well-proportioned living spaces and strong rental appeal. The property also provides a valuable in-town amenity: private off-street parking for up to four vehicles. With its historic character, consistent rental demand, and prime location near the Old Port, shops, restaurants, parks, and public transit, this property presents an excellent addition to any Portland investment portfolio.

$1,799,000

6 beds4 baths3,582 sq ft

105 Pine St, Portland, ME 04102

High ceilings • Original millwork • Hardwood floors

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
Priced to account for the work needed, this 3BR/1.5 BA mid-century ranch offers convenient one-level living in a sought-after location close to town amenities and schools. With the right vision and sweat equity, this property could become a strong rental investment, a profitable flip, or your next home. Highlights include hardwood floors, updated kitchen and first floor bathroom, sizable backyard with deck access from dining area, and a 1-car garage. This is a probate estate sale and the property is being sold as-is by the Personal Representatives of the estate who have limited knowledge of the property. The property has been professionally pre-inspected and the full report is available for

$325,000

3 beds1.5 baths1,196 sq ft

97 Stroudwater St, Westbrook, ME 04092

0.29 acre lot • Garage • Built 1960

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
Priced below assessed value! Complete the bathroom renovation already started, and gain quick equity! Steps from Willard Beach, this is your opportunity to live in this desirable South Portland coastal neighborhood, with Dora Small Elementary School behind this spacious peaceful backyard with room to expand if desired. Newer wrap around composite decking. Don't miss this rare opportunity, priced less than a condo for a single family home. No HOAs! Great Value near SMCC, Bug Light, and the Beach. Broker has an ownership interest.

$386,000

1 bed— baths594 sq ft

52 Smith St, South Portland, ME 04106

Bathroom renovation • 6,098 sq ft lot • Built 1949

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
Welcome to this beautifully renovated ranch in the heart of downtown Westbrook! The main level offers a bright and modern three-bedroom, one-bath home, while the fully finished basement provides a separate two-bedroom, one-bath apartment with its own private entrance—perfect for rental income, guests, or multigenerational living. Sitting on over half an acre, this property is ideal for anyone looking for a move-in-ready home that can help pay the mortgage, or an investor seeking a promising addition to their portfolio. With plenty of space and a fantastic location, there may even be potential to add more units in the future. Buyers should verify all possibilities with the appropriate

$585,000

5 beds2 baths1,892 sq ft

315 Conant St, Westbrook, ME 04092

Renovated ranch • Private entrance • Fantastic location

Property at 44 Jones Creek Dr, Scarborough, ME 04074, 1 bed, 1 bath

$895,000

1 bed1 bath560 sq ft

44 Jones Creek Dr, Scarborough, ME 04074

Property at 40 Belfort St, Portland, ME 04103, 4 beds, 1.5 baths

$485,000

4 beds1.5 baths1,395 sq ft

40 Belfort St, Portland, ME 04103

Property at 5 Tenney Hill Rd, Casco, ME 04015, 3 beds, 2 baths

$275,000

3 beds2 baths1,250 sq ft

5 Tenney Hill Rd, Casco, ME 04015

Property at 20 Bowdoin St, Brunswick, ME 04011, 2 beds, 1 bath

$423,000

2 beds1 bath1,302 sq ft

20 Bowdoin St, Brunswick, ME 04011

Property at 18 Ash Point Rd #18, Harpswell, ME 04079, 3 beds, 2.5 baths

$659,000

3 beds2.5 baths2,111 sq ft

18 Ash Point Rd #18, Harpswell, ME 04079

Property at 16 Ash Point Rd #16, Harpswell, ME 04079, 3 beds, 2.5 baths

$559,000

3 beds2.5 baths1,728 sq ft

16 Ash Point Rd #16, Harpswell, ME 04079

Property at 6 Gilman Rd, Standish, ME 04084, 3 beds, 3 baths

$1,750,000

3 beds3 baths2,502 sq ft

6 Gilman Rd, Standish, ME 04084

Property at 147 Spring St, Westbrook, ME 04092, 3 beds, 1 bath

$365,000

3 beds1 bath1,152 sq ft

147 Spring St, Westbrook, ME 04092

Property at 7 Cherry St, Portland, ME 04102, 8 beds, 3 baths

$740,000

8 beds3 baths2,923 sq ft

7 Cherry St, Portland, ME 04102

Property at 107 W Gray Rd, Gray, ME 04039, 2 beds, 1 bath

$330,000

2 beds1 bath768 sq ft

107 W Gray Rd, Gray, ME 04039

Property at 79 Whites Point Rd, Standish, ME 04084, 4 beds, 3.5 baths

$1,800,000

4 beds3.5 baths2,880 sq ft

79 Whites Point Rd, Standish, ME 04084

Property at 114 Narragansett St, Gorham, ME 04038, 3 beds, 1 bath

$360,000

3 beds1 bath950 sq ft

114 Narragansett St, Gorham, ME 04038

Property at 37 Swan Rd, Windham, ME 04062, 3 beds, 1 bath

$419,900

3 beds1 bath1,938 sq ft

37 Swan Rd, Windham, ME 04062

Property at 29 Parris St #3, Portland, ME 04101, 2 beds, 1 bath

$319,000

2 beds1 bath940 sq ft

29 Parris St #3, Portland, ME 04101

Property at 13 Quest Ave, Sebago, ME 04029, 5 beds, 1.5 baths

$749,500

5 beds1.5 baths1,900 sq ft

13 Quest Ave, Sebago, ME 04029

Property at 10 Kasseys Way #1, Westbrook, ME 04092, 2 beds, 1 bath

$299,900

2 beds1 bath722 sq ft

10 Kasseys Way #1, Westbrook, ME 04092

Property at 1155 Washington Ave #2, Portland, ME 04103, 2 beds, 1 bath

$399,000

2 beds1 bath1,296 sq ft

1155 Washington Ave #2, Portland, ME 04103

Property at 1155 Washington Ave #1, Portland, ME 04103, 2 beds, 1 bath

$399,000

2 beds1 bath1,296 sq ft

1155 Washington Ave #1, Portland, ME 04103

Property at 1155 Washington Ave, Portland, ME 04103, 4 beds, 2 baths

$799,000

4 beds2 baths2,592 sq ft

1155 Washington Ave, Portland, ME 04103

Property at 562 Island Ave, Peaks Island, ME 04108, 2 beds, 1 bath

$850,000

2 beds1 bath750 sq ft

562 Island Ave, Peaks Island, ME 04108

Property at 311 Ocean St, South Portland, ME 04106, 7 beds, 3 baths

$895,000

7 beds3 baths3,996 sq ft

311 Ocean St, South Portland, ME 04106

Property at 184 Central St, Westbrook, ME 04092, 3 beds, 1.5 baths

$412,900

3 beds1.5 baths1,172 sq ft

184 Central St, Westbrook, ME 04092

Property at 1 Holbrook St, Portland, ME 04103, 2 beds, 1 bath

$420,000

2 beds1 bath788 sq ft

1 Holbrook St, Portland, ME 04103

Property at 1097 Pequawket Trl, Steep Falls, ME 04085, 2 beds, 1 bath

$315,000

2 beds1 bath1,624 sq ft

1097 Pequawket Trl, Steep Falls, ME 04085

Property at 212 Main St, Freeport, ME 04032, 3 beds, 2 baths

$549,000

3 beds2 baths1,571 sq ft

212 Main St, Freeport, ME 04032

Property at 7 Wabun Rd, Cape Elizabeth, ME 04107, 3 beds, 2 baths

$850,000

3 beds2 baths1,767 sq ft

7 Wabun Rd, Cape Elizabeth, ME 04107

Property at 15 Sea Cove Rd, Cumberland Foreside, ME 04110, 5 beds, 3 baths

$1,295,000

5 beds3 baths3,812 sq ft

15 Sea Cove Rd, Cumberland Foreside, ME 04110

Property at 32 Melbourne St, Portland, ME 04101, 3 beds, 1 bath

$1,195,000

3 beds1 bath1,617 sq ft

32 Melbourne St, Portland, ME 04101

Property at 307 Church Rd, Brunswick, ME 04011, 3 beds, 1 bath

$325,000

3 beds1 bath982 sq ft

307 Church Rd, Brunswick, ME 04011

Property at 10 Walker St, Portland, ME 04102, 8 beds, 4.5 baths

$650,000

8 beds4.5 baths3,988 sq ft

10 Walker St, Portland, ME 04102

Property at 207 State St, Portland, ME 04101, 6 beds, 4.5 baths

$1,050,000

6 beds4.5 baths3,104 sq ft

207 State St, Portland, ME 04101

Property at 45 Harding Rd, Brunswick, ME 04011, 4 beds, 3.5 baths

$695,000

4 beds3.5 baths2,865 sq ft

45 Harding Rd, Brunswick, ME 04011

Property at 21 Mill Rd, Falmouth, ME 04105, 4 beds, 3.5 baths

$1,200,000

4 beds3.5 baths2,400 sq ft

21 Mill Rd, Falmouth, ME 04105

Property at 41 Haskell Ave, Raymond, ME 04071, 3 beds, 2 baths

$995,000

3 beds2 baths1,787 sq ft

41 Haskell Ave, Raymond, ME 04071

Property at 15 Read Rd, Windham, ME 04062, 3 beds, 1 bath

$375,000

3 beds1 bath1,784 sq ft

15 Read Rd, Windham, ME 04062

Property at 29 Parris St #4, Portland, ME 04101, 1 bed, 1 bath

$224,900

1 bed1 bath440 sq ft

29 Parris St #4, Portland, ME 04101

Viewing page 1 of 6

Vintage Homes for Sale in Cumberland County

There are currently 211 vintage homes for sale in Cumberland County at a median listing price of $599K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Cumberland County stay on the market for 55 days and receive 2 offers. This map is refreshed with the newest listings in Cumberland County every 15 minutes.

In the past month, 525 homes have been sold in Cumberland County. In addition to houses in Cumberland County, there were also 359 condos, 18 townhouses, and 86 multi-family units for sale in Cumberland County last month. Find your dream home in Cumberland County 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 Cumberland County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Cumberland County. If you're looking to sell your home in the Cumberland County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Cumberland County 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 Cumberland County, ME

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Cumberland County, ME

How to buy a house in Cumberland County, ME

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 Maine

Portland homes for sale
$697,000
Scarborough homes for sale
$625,000
South Portland homes for sale
$529,000
Falmouth homes for sale
$1,172,500
Cape Elizabeth homes for sale
$1,325,000
Bangor homes for sale
$289,900
Kittery homes for sale
$1,067,000
Kennebunk homes for sale
$545,000
Brunswick homes for sale
$390,000
Yarmouth homes for sale
$825,000
Saco homes for sale
$507,500
Kennebunkport homes for sale
$1,899,000
Camden homes for sale
$725,000
Freeport homes for sale
$474,000
Bar Harbor homes for sale
$795,000

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.