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

222 homes

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ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
* * Own a Piece of Westbrook's History - Legal Two-Unit with Incredible Potential! * * Welcome to 84 Hillside Road, a legal two-unit property that offers both charm and opportunity. Originally built to welcome new workers to the historic S. D. Warren paper mill, this home is more than just an investment—it's a nostalgic piece of Westbrook's story. Unit 1 features four spacious bedrooms, a kitchen with a brand-new refrigerator, a dining room, and a living room with sliders that open to a private deck. Two beautiful stone fireplaces add warmth and timeless character. Unit 2 is a legal one-bedroom but includes two additional rooms that could potentially be converted to bedrooms&mdash

$345,000

5 beds2 baths3,051 sq ft

84 Hillside Rd, Westbrook, ME 04092

0.23 acre lot • Garage • Built 1911

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
This could be the opportunity you've been waiting for— a well-maintained two-unit in Portland. Each unit features its own kitchen, full bath, and comfortable living spaces with a mix of hardwood, tile, and laminate flooring. Heat pumps provide efficient year-round comfort, and thoughtful updates throughout give each unit a unique sense of style. The property also includes a private backyard. Whether you're looking for an investment or a chance to eventually live in one unit while renting the other, this property offers flexibility and function in a compact footprint. Conveniently located with easy access to the hospital, downtown Portland, local services, commuter routes, and amenitie

$525,000

3 beds2 baths1,234 sq ft

9 C St, Portland, ME 04102

2,613 sq ft lot • Built 1900 • Listed 52 days

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
With all the amenities within and around this property, this one should be on your list to see. The old farmhouse built in 1900 has been upgraded with the comforts and necessities of home. New pellet stove, 2015 septic system, air radon mitigation system, one bedroom on the first floor, with a beautiful year round sitting room, and an oversized deck outside the new room above the garage. with additional 1,832 sq ft of unfinished space. The land sits on . 66 acre in the enclosed back yard, you and your family are shielded from the outside world. The new construction is waiting for your final touches. You decide. So much around you here, Close to downtown Naples, restaurants, grocery stores,

$399,000

3 beds1.5 baths1,624 sq ft

414 Harrison Rd, Naples, ME 04055

Enclosed back yard • Oversized deck • New construction

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
Great opportunity to own this New England gem in Knightsville. Perfect for someone looking to have their business right below their residence. Three stories with nearly four thousand square feet are awaiting your clever plans! The location is incredible, stroll to local shops and Eateries, soak up the waterfront views from the third story deck. Welcome home!

$775,000

4 beds3 baths3,729 sq ft

13 Ocean St, South Portland, ME 04106

Waterfront views • Eateries • Third story deck

ABOUT THIS HOME
Vintage Home for sale in Cumberland County, ME:
Freshly painted exterior and full of charm, the Gilbert L. Bailey House offers a rare investment opportunity in the heart of Portland. Just a short walk to the Arts District, top restaurants, and entertainment, this property combines historic character with a prime location. Owner will consider selling 381 Cumberland Ave, a 12-spot parking lot, with the purchase of 379 Cumberland Ave. Per initial conversations with city officials, the lot may offer buildable potential. Buyer and agent to verify all information and conduct their own due diligence with the City of Portland regarding zoning, development, and permitted uses.

$915,000

4 beds3 baths2,576 sq ft

379 Cumberland Ave #3, Portland, ME 04101

Heart of portland • Prime location • 3,484 sq ft lot

Property at 930 Forest Ave, Portland, ME 04103, 4 beds, 2 baths

$625,000

4 beds2 baths1,940 sq ft

930 Forest Ave, Portland, ME 04103

Property at 222 N High St, Bridgton, ME 04009, 3 beds, 2 baths

$375,000

3 beds2 baths2,000 sq ft

222 N High St, Bridgton, ME 04009

Property at 296 Brighton Ave, Portland, ME 04102, 4 beds, 1.5 baths

$525,900

4 beds1.5 baths1,629 sq ft

296 Brighton Ave, Portland, ME 04102

Property at 7 Preston Way, Cumberland Center, ME 04021, 3 beds, 2 baths

$550,000

3 beds2 baths1,597 sq ft

7 Preston Way, Cumberland Center, ME 04021

Property at 30 Graffam Rd, West Baldwin, ME 04091, 3 beds, 2 baths

$649,000

3 beds2 baths2,025 sq ft

30 Graffam Rd, West Baldwin, ME 04091

Property at 105 Hillside Rd, Brunswick, ME 04011, 3 beds, 2 baths

$399,900

3 beds2 baths2,540 sq ft

105 Hillside Rd, Brunswick, ME 04011

Property at 44 Hersey St, Portland, ME 04103, 5 beds, 2.5 baths

$925,000

5 beds2.5 baths3,154 sq ft

44 Hersey St, Portland, ME 04103

Property at 14 Boynton St, Portland, ME 04102, 4 beds, 3 baths

$939,900

4 beds3 baths3,056 sq ft

14 Boynton St, Portland, ME 04102

Property at 85 Upper A St, Peaks Island, ME 04108, 2 beds, 1 bath

$579,000

2 beds1 bath1,000 sq ft

85 Upper A St, Peaks Island, ME 04108

Property at 445 Greely Extension Rd, Cumberland Center, ME 04021, 3 beds, 2 baths

$1,495,000

3 beds2 baths2,577 sq ft

445 Greely Extension Rd, Cumberland Center, ME 04021

Property at 55-57-59 St Lawrence St, Portland, ME 04101, 13 beds, 7 baths

$2,250,000

13 beds7 baths9,600 sq ft

55-57-59 St Lawrence St, Portland, ME 04101

Property at 244 Sebago Rd, Sebago, ME 04029, 3 beds, 2 baths

$330,000

3 beds2 baths1,302 sq ft

244 Sebago Rd, Sebago, ME 04029

Property at 242 Valley St, Portland, ME 04102, 2 beds, 1.5 baths

$499,000

2 beds1.5 baths1,281 sq ft

242 Valley St, Portland, ME 04102

Property at 35.5 Bath Rd, Brunswick, ME 04011, 3 beds, 1 bath

$283,000

3 beds1 bath1,144 sq ft

35.5 Bath Rd, Brunswick, ME 04011

Property at 338 Ocean St, South Portland, ME 04106, 5 beds, 2 baths

$650,000

5 beds2 baths2,092 sq ft

338 Ocean St, South Portland, ME 04106

Property at 117 Blackstrap Rd, Falmouth, ME 04105, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths3,010 sq ft

117 Blackstrap Rd, Falmouth, ME 04105

Property at 107 Haskell Ave, Raymond, ME 04071, 2 beds, 1 bath

$364,999

2 beds1 bath540 sq ft

107 Haskell Ave, Raymond, ME 04071

Property at 126 Winter St #1, Portland, ME 04102, 1 bed, 1 bath

$359,000

1 bed1 bath810 sq ft

126 Winter St #1, Portland, ME 04102

Property at 189 Gray Rd, Falmouth, ME 04105, 3 beds, 2 baths

$550,000

3 beds2 baths1,644 sq ft

189 Gray Rd, Falmouth, ME 04105

Property at 61 Shore Rd, Sebago, ME 04029, 3 beds, 3 baths

$489,900

3 beds3 baths1,200 sq ft

61 Shore Rd, Sebago, ME 04029

Property at 162 Merrill Rd, Pownal, ME 04069, 3 beds, 1.5 baths

$1,199,999

3 beds1.5 baths2,400 sq ft

162 Merrill Rd, Pownal, ME 04069

Property at 7 Dyer Ln, Cape Elizabeth, ME 04107, 3 beds, 2 baths

$2,685,000

3 beds2 baths1,715 sq ft

7 Dyer Ln, Cape Elizabeth, ME 04107

Property at 106 Cumberland Ave #101, Portland, ME 04101, 2 beds, 2 baths

$549,900

2 beds2 baths1,170 sq ft

106 Cumberland Ave #101, Portland, ME 04101

Property at 5 Eastern Promenade, Portland, ME 04101, 2 beds, 2 baths

$3,190,000

2 beds2 baths1,942 sq ft

5 Eastern Promenade, Portland, ME 04101

Property at 103 Basin Rd, Windham, ME 04062, 2 beds, 1 bath

$1,000,000

2 beds1 bath813 sq ft

103 Basin Rd, Windham, ME 04062

Property at 35 Jefferson St, South Portland, ME 04106, 3 beds, 1 bath

$515,000

3 beds1 bath1,322 sq ft

35 Jefferson St, South Portland, ME 04106

Property at 4 Sarah Ln, Standish, ME 04084, 2 beds, 1 bath

$425,000

2 beds1 bath624 sq ft

4 Sarah Ln, Standish, ME 04084

Property at 44 Pleasant Ave, Portland, ME 04103, 5 beds, 2 baths

$700,000

5 beds2 baths2,442 sq ft

44 Pleasant Ave, Portland, ME 04103

Property at 364 Island Ave, Peaks Island, ME 04108, 3 beds, 2 baths

$1,260,000

3 beds2 baths1,720 sq ft

364 Island Ave, Peaks Island, ME 04108

Property at 850 Lawrence Rd, Pownal, ME 04069, 2 beds, 1 bath

$599,000

2 beds1 bath1,301 sq ft

850 Lawrence Rd, Pownal, ME 04069

Property at 187 Pequawket Trl, East Baldwin, ME 04024, 4 beds, 2 baths

$210,000

4 beds2 baths1,988 sq ft

187 Pequawket Trl, East Baldwin, ME 04024

Property at 147 Pleasant Ave #2, Portland, ME 04103, 1 bed, 1 bath

$395,000

1 bed1 bath610 sq ft

147 Pleasant Ave #2, Portland, ME 04103

Property at 31 Allen Range Rd, Freeport, ME 04032, 2 beds, 1 bath

$450,000

2 beds1 bath1,194 sq ft

31 Allen Range Rd, Freeport, ME 04032

Property at 987 Naples Rd, Harrison, ME 04040, 3 beds, 1 bath

$339,900

3 beds1 bath1,296 sq ft

987 Naples Rd, Harrison, ME 04040

Property at 16 Davis Ave, Windham, ME 04062, 2 beds, 1 bath

$300,000

2 beds1 bath1,297 sq ft

16 Davis Ave, Windham, ME 04062

Property at 61 Sawyer Rd, Chebeague Island, ME 04017, 7 beds, 4.5 baths

$2,175,000

7 beds4.5 baths4,677 sq ft

61 Sawyer Rd, Chebeague Island, ME 04017

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Vintage Homes for Sale in Cumberland County

There are currently 222 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 45 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, 4 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.

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