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Explore Similar Apartments Within 2 Miles of Pleasantdale, ME

  • /89

    $638,500

    • 2 Baths
    • 1,689 Sq Ft

    Unlisted Address

    Investment, Lifestyle, and Location: Discover the Possibilities at 57 Jefferson Street.Welcome to Ferry Village, one of South Portland's most coveted and walkable seaside neighborhoods. Nestled on a sun-drenched corner lot, this beautifully maintained two-unit property is more than just an investment—it's a gateway to an unparalleled coastal Maine lifestyle. Step outside into your own private

    Teri Ouellette Keller Williams Realty

    Unlisted Address
  • /32

    $1,100,000

    • 3 Baths
    • 2,698 Sq Ft

    63 Vesper St, Portland, ME 04101

    Nestled in Portland's highly desirable Munjoy Hill neighborhood, this 3-unit multifamily offers an exceptional investment opportunity in one of the city's most historic and vibrant areas. Just steps from the Eastern Promenade, renowned restaurants, and the waterfront, the property combines classic New England charm with strong rental potential.Each unit is well-maintained, with

    Martin Macisso JR. Regency Realty Group

    63 Vesper St, Portland, ME 04101
  • /24

    $847,500

    • 3 Baths
    • 2,408 Sq Ft

    50 Hancock St, Portland, ME 04101

    Classic historic three family in the fantastic India Street area. Short walk to restaurants, shops, the Casco Bay Ferry terminal and the Old Port. Nice layout with three bedroom townhouse on the left side, and two 2-bedroom apartments on the right side. Potential expansion into unused attic area. Property has been carefully taken care of over the years, but leaves plenty of original details and

    Jeffrey Davis Town & Shore Real Estate

    50 Hancock St, Portland, ME 04101
  • /16

    $659,000

    • 3 Baths
    • 3,030 Sq Ft

    124 Sherman St, Portland, ME 04101

    Solid Bayside 3 unit with updated systems, convenient location just a few blocks from shopping and services.. This building has excellent rental history, income after expenses averages $70,000/year.

    Bryce Hamilton Coldwell Banker Realty

    124 Sherman St, Portland, ME 04101
  • /2

    $529,000

    • 2 Baths
    • 1,372 Sq Ft

    753 Main St, South Portland, ME 04106

    INVESTORS TAKE NOTICE!!Fantastic opportunity! Zoning and lot size allow for the addition of multiple units. per code office. Features a newer furnace and monitor heater. Long-term tenants already in place, with below market rent. Prime location with easy access to public transportation. In need of updating. Group showing 12 - 1pm Wed. 9/3.

    Phil Verrill Verrill Real Estate, Inc

    753 Main St, South Portland, ME 04106
  • /10

    $1,400,000

    • 10 Baths
    • 7,630 Sq Ft

    807 Congress St, Portland, ME 04102

    Congress Street 10-Unit Investment Property! Stable cash flow and some long-term tenants. Features include two lanes of off-street parking and an easy-to-own layout with onsite manager.Perfectly located near Maine Medical Center and Hadlock Field, and within walking distance to restaurants, coffee shops, and local amenities. A prime opportunity to own a solid investment! Group showing.

    Phil Verrill Verrill Real Estate, Inc

    807 Congress St, Portland, ME 04102
  • /23

    $1,390,000

    • 2 Baths
    • 2,764 Sq Ft

    42 Munjoy St, Portland, ME 04101

    Situated in Portland's desirable East End, this impeccably well-maintained two-family home offers a rare blend of character, modern efficiency, and prime location. The building consists of two multi-level units, one in front and one in the back, each with its own distinct appeal. The front features a bright, updated 2-bedroom layout, while the rear offers a spacious 3-bedroom unit, both enhanced

    Brit Vitalius Vitalius Real Estate Group, LLC

    42 Munjoy St, Portland, ME 04101
  • /30

    $1,395,000

    • 3 Baths
    • 2,646 Sq Ft

    67 North St, Portland, ME 04101

    Don't miss this opportunity to own a beautifully updated 3-unit property in Portland's highly sought-after Munjoy Hill neighborhood. Blending classic charm with modern updates, this building offers the perfect combination of character, convenience, and investment potential. Directly across from Fort Sumner Park, this property is bathed in sunlight on all sides and offers breathtaking Back Bay

    Jessica Wallimann Vitalius Real Estate Group, LLC

    67 North St, Portland, ME 04101
  • /74

    $1,200,000

    • 2 Baths
    • 1,728 Sq Ft

    44 Myrtle Ave, South Portland, ME 04106

    Rare Willard Beach opportunity!Just steps to the beach and a short walk to Scratch, Scoops and area restaurants, this home sits in one of the most sought after neighborhoods in the area and has partial views of the water. Feel the sea breeze and smell the salt air, this sunny, corner-lot property has so much to offer! Currently arranged as a two-unit with a strong rental history, it could

    L Kate Hodgson Locations Real Estate Group LLC

    44 Myrtle Ave, South Portland, ME 04106
  • /34

    $1,175,000

    • 4 Baths
    • 3,492 Sq Ft

    22 Madison St, Portland, ME 04101

    **Back on the market at no fault of the building!** Rare East Bayside 4-unit with buildable lot! This classic triple-decker style building features bright spacious layouts and a deck overlooking an adorable courtyard with raised beds in the rear. An additional lot that fronts on Monroe Street currently serves as parking for the building, but ultimately could be built upon, potentially

    Brit Vitalius Vitalius Real Estate Group, LLC

    22 Madison St, Portland, ME 04101
  • /47

    $749,000

    • 2 Baths
    • 1,587 Sq Ft

    310 Pine St, South Portland, ME 04106

    Charming Two-Unit Property in the Heart of South Portland's Meetinghouse HillWelcome to 310 Pine Street a rare opportunity in the highly desirable Meetinghouse Hill neighborhood of South Portland. This well-maintained two-unit property offers flexibility, character, and incredible potential, whether you're looking to owner-occupy, invest, or convert to a single-family home.The first-floor

    Joshua Caron Maine Community Real Estate

    310 Pine St, South Portland, ME 04106
  • /23

    $579,000

    • 2 Baths
    • 1,844 Sq Ft

    83 Brackett St, Portland, ME 04102

    This West End neighborhood 2-unit has a funky charm that reflects Portland housing built before the fire of 1866. It is move-in ready with a vacant unit on the 2nd floor with more living/storage on the 3rd. 83 Brackett Street is an outstanding location - convenient and central to all that Portland has to offer - while also being private on this quiet end of the street. The backyard is a highlight

    Brit Vitalius Vitalius Real Estate Group, LLC

    83 Brackett St, Portland, ME 04102
  • /9

    $850,000

    • 5 Baths
    • 3,404 Sq Ft

    10 Walker St, Portland, ME 04102

    Welcome to 10 Walker Street, a stunning historic home located in the heart of Portland, ME. Built in 1905, this three-story property boasts timeless charm and exquisite craftsmanship. With a total finished area of 3,500 sq.ft., this spacious home offers ample room for comfortable living. The property features 5 bathrooms, adding convenience and luxury to everyday life. The lot size of 0.05 acres

    DANIEL DEMERS Sell Your Home Services

    10 Walker St, Portland, ME 04102
  • /16

    $799,900

    • 2 Baths
    • 3,286 Sq Ft

    24 Marshall St, Portland, ME 04102

    Fantastic investment or owner-occupant opportunity located on a quiet 1-way street in Portland's sought-after West End neighborhood, just a short walk to MaineHealth Maine Medical Center Portland Campus, local restaurants and shops of downtown. This classic two-unit building features two spacious 4-bedroom, 1-bathroom units with charming original details and modern updates. The first-floor unit

    Mark Small Landmark Realty

    24 Marshall St, Portland, ME 04102
  • /13

    $799,000

    • 4 Baths
    • 3,568 Sq Ft

    3 Crescent St, Portland, ME 04102

    Perched on a sunny corner in Portland's West End, just steps from the Western Promenade, this 3-family property offers unique historic character and urban convenience. With its bay windows, detailed millwork, the apartments are generously sized with high ceilings and flexible layouts. So much to offer, yet still plenty of potential to add value through sweat equity, all within walking distance to

    Brit Vitalius Vitalius Real Estate Group, LLC

    3 Crescent St, Portland, ME 04102
  • /53

    $970,000

    • 4 Baths
    • 2,607 Sq Ft

    34 Deering Ave, Portland, ME 04101

    Welcome to the heart of Portland, Maine! This 4-unit building located on the Portland peninsula is the perfect investment opportunity for those seeking to break into the thriving real estate market of this coastal city. Situated in a prime location, this property offers residents easy access to all that Portland has to offer. With a walkability score of 93 out of 100, you'll find that Maine

    Dominik Porobic Keller Williams Realty

    34 Deering Ave, Portland, ME 04101
  • /39

    $715,000

    • 3 Baths
    • 3,653 Sq Ft

    50 Alder St, Portland, ME 04101

    Be part of Bayside's exciting transformation—one of Portland's fastest redeveloping neighborhoods. This spacious, move-in ready duplex sits in the heart of the Peninsula within the dynamic B2b business zone, offering both immediate cash flow and long-term upside. The detached garage includes a workshop—pefect for a creative or trade business—and off-street parking adds daily convenience.

    David Marshall EXP Realty

    50 Alder St, Portland, ME 04101
  • /67

    $1,495,000

    • 4 Baths
    • 5,619 Sq Ft

    101 - 107 Congress St, Portland, ME 04101

    Offered for the First Time in 47 Years - A Rare Munjoy Hill Icon.Located at the pinnacle of Portland's sought-after Munjoy Hill, 101-107 Congress Street is a distinctive Italianate-style building offering a rare investment or live/work opportunity in one of the city's most vibrant neighborhoods.This mixed-use property features four well-maintained 2-bedroom, 1-bath apartments on the upper

    David Marsden Marsden Real Estate

    101 - 107 Congress St, Portland, ME 04101
  • /8

    $1,300,000

    • 3 Baths
    • 2,490 Sq Ft

    115 Congress St, Portland, ME 04101

    Rare opportunity to own a three family apartment building on the top of Munjoy Hill. Future potential for condo conversion or redevelopment. Property is located on the iconic Donatelli Square.

    Vince Ciampi Porta & Company

    115 Congress St, Portland, ME 04101
  • /21

    $886,000

    • 4 Baths
    • 3,825 Sq Ft

    232 Brighton Ave, Portland, ME 04102

    Large, classic 3-decker with over 3,800 SF of living area, a driveway and garage. All of the units are similar but with interesting differences: an updated kitchen on the 1st floor creates an open living space and a unique 3bd/2bath setup. The 2nd floor is spacious with an enclosed porch for additional storage. The 3rd floor includes a bonus bedroom in the front (making it a 3 bd) plus a

    Brit Vitalius Vitalius Real Estate Group, LLC

    232 Brighton Ave, Portland, ME 04102
  • /51

    $1,950,000

    • 4.5 Baths
    • 3,667 Sq Ft

    123 Cumberland Ave, Portland, ME 04101

    This redesigned downtown three-unit is a rare gem—where historic charm blends with contemporary design. Step through the classic double doors and into a foyer with a modern twist. Up the curved staircase, a 3 bedroom, 2.5 bath owner's penthouse awaits with unobstructed views of Back Cove. Waterfall countertops on the island, Wolf appliances, expansive windows, and intricate tile work display

    Randy Ferrell Portside Real Estate Group

    123 Cumberland Ave, Portland, ME 04101
  • /45

    $1,495,000

    • 5 Baths
    • 4,732 Sq Ft

    160 Washington Ave, Portland, ME 04101

    Turnkey 5-Unit Investment in Prime Munjoy Hill Location! Seasoned investors know the value of location, layout, and low-maintenance assets—this property checks all the boxes. Situated at the base of Munjoy Hill, one of Portland's most desirable and appreciating neighborhoods, this well-maintained five-unit building offers a solid, income-generating opportunity. All five units are two-bedrooms,

    Fred Andrews Spectrum Real Estate

    160 Washington Ave, Portland, ME 04101
  • /32

    $1,150,000

    • 6,393 Sq Ft

    243 & 245 High St, Portland, ME 04101

    16 room lodging house in downtown Portland. Property features long term tenants; two kitchens and five bathrooms, updated electrical panel, rear decks, and driveways on both sides of building. Huge upside potential with ability to increase rents to subsidized tenants. Also listed Commercial MLS #1618280.

    Jeffrey Davis Town & Shore Real Estate

    243 & 245 High St, Portland, ME 04101
  • /26

    $1,350,000

    • 4 Baths
    • 3,686 Sq Ft

    68 Pleasant St, Portland, ME 04101

    Known as the Nathan Nutter House, this historic 2.5 story home was built in 1840 for a local Portland merchant. The original 3,686± square foot Greek Revival building was converted into a two-family dwelling in 1924 and then most recently into four one-bedroom apartment units. Recognized by Greater Portland Landmarks, the property is publicly on the market for the first time in 38 years. The

    John Saint-Amour LandVest, Inc.

    68 Pleasant St, Portland, ME 04101
  • /35

    $849,000

    • 3 Baths
    • 1,729 Sq Ft

    12 Romasco Ln, Portland, ME 04101

    Second Floor Unit Now Vacant! In a city where the old meets the bold, 12 Romasco Lane stands at the intersection. This isn't your typical Munjoy Hill multi. It's sharper. Smarter. Built for the investor who wants both return and refinement, or the owner-occupant who refuses to compromise.Two units, fully remodeled, running lean and green. The first-floor unit—a crisp, uncomplicated 1-bedroom,

    Kim Tarbox FIV Realty Co Maine, LLC

    12 Romasco Ln, Portland, ME 04101
  • /10

    $2,250,000

    • 3 Baths
    • 4,896 Sq Ft

    104 Monument St, Portland, ME 04101

    Developers Take Notice! This oversized lot is approved for development of 7 condo units. Stunning views overlooking the ocean and located in the highly-desirable Munjoy Hill neighborhood on a quiet street. This lot is just waiting for the right developer to bring their vision and be part of the booming development of Portland Maine!

    Alexander Munsell Real Broker

    104 Monument St, Portland, ME 04101
  • /44

    $1,495,500

    • 6 Baths
    • 5,376 Sq Ft

    21 Merrill St, Portland, ME 04101

    OWNER FINANCING AVAILABLE. Developers and Investors take notice. Large 6 unit located on the ultra desirable East End (Eastern Promenade) of Portland. This is a rehab project perfect for basic or high end rentals, or you could condo the units and sell them off individually. on site parking for up to 5 cars. Don't miss this exciting opportunity.

    Sheldon Ashby Ashby Real Estate

    21 Merrill St, Portland, ME 04101
  • /92

    $1,895,000 Open Sun 12PM - 2PM

    • 4.5 Baths
    • 5,751 Sq Ft

    49 Deering St, Portland, ME 04101

    A Rare Opportunity to own a distinguished stand alone brick building in the heart of Downtown Portland. This 3 unit property combines historic architecture with modern versatility. Offering three beautiful residences plus professional office space in the lower level. Highlights include: Timeless craftsmanship with original stained-glass windows and architectural details. Flexible office space

    Catherine Nekoie Gardner Real Estate Group

    49 Deering St, Portland, ME 04101

Why Live in Pleasantdale

Pleasantdale, a neighborhood in South Portland, offers residents close proximity to both nature and urban amenities. Located just 3 miles from Portland, it is even closer to South Portland's stores and restaurants, including Taco Trio. The South Portland Greenbelt Pathway connects Pleasantdale to Bug Light Park, known for its boat launch and annual car show. The neighborhood features a mix of home styles, from 19th-century Queen Annes and Victorian-era houses to early 20th-century Foursquares and mid-20th-century Cape Cods, all set on grassy lawns with gardens and trees. While the area borders industrial sites like the CITGO South Portland Terminal, which can lead to increased noise levels, it remains a residential area with a variety of modest and larger homes. Pleasantdale is adjacent to Knightville, South Portland’s retail hub, offering shops like Nonesuch Books and Bull Moose, as well as dining options such as Cia Cafe and Q Street Diner. Grocery shopping is convenient with Shaw’s and Hannaford nearby, and the South Portland Farmers’ Market provides fresh produce year-round. Major retailers like Home Depot, Walmart, and Target are within 5 miles. The neighborhood is part of the South Portland Public Schools system, with schools receiving moderate ratings. For things to do, residents can enjoy events like Art in the Park at Mill Creek Park and the Classic Car Show at Bug Light Park. Outdoor activities are plentiful with the South Portland Greenbelt Pathway, Yerxa Park, Willard Beach, and the Winnick Roads trail all within a short drive. The area is largely car-dependent but offers bike-friendly roads and paths. Portland International Jetport is about 5 miles away, and Maine Medical Center is the nearest emergency room, located 3 miles from Pleasantdale.

Home Trends in Pleasantdale, ME

Housing Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$505,000
Median 1 Bedroom Sale Price
$210,000
Average Price Per Sq Ft
$340
Number of Homes for Sale
0
Last 12 months Home Sales
9
Months of Supply
0.00
Median List Price
$499,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
11%
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