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Explore Similar Condos Within 2 Miles of Highland, ME

  • /31

    $749,000

    • 1 Bed
    • 1.5 Baths
    • 1,324 Sq Ft

    11 Mellen St Unit 4, Portland, ME 04101

    This rare, stand-alone carriage house blends timeless charm with modern luxury in one of Portland's most exciting neighborhoods. Set behind a grand historic home on Mellen Street, this chic city retreat lives like a private residence with the ease of condo living.Inside, soaring ceilings, antique details, and an open-concept layout create an elegant yet welcoming space. The refreshed

    Agent Photo

    Karen Schlegel

    Schlegel Realty

    (207) 521-9281

    11 Mellen St Unit 4, Portland, ME 04101
  • /46

    $3,190,000

    • 2 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    547 Congress St Unit 6, Portland, ME 04101

    The best private rooftop in Portland - just in time for summer. This luxurious loft-style condo offers you a unique blend of modern elegance in the heart of downtown Portland. The home boasts an expansive open concept kitchen, living room and dining area, designed with high end finishes, a gas fireplace, custom woodwork, and stunning floor to ceiling windows that flood the space with natural

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    David Banks

    RE/MAX By The Bay

    (833) 772-5790

    547 Congress St Unit 6, Portland, ME 04101
  • /39

    $989,000

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    22 Carroll St Unit 9, Portland, ME 04102

    Bathed in sunlight and brimming with character, this top-floor West End condo is a rare find. An architectural showpiece, the space features soaring ceilings, striking exposed beams, and an unforgettable brick statement wall that anchors the open-concept layout. Every inch of this 2,100+ square foot home radiates warmth, sophistication, and timeless style.Whether you're entertaining or unwinding,

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    Nova Tower

    Waypoint Brokers Collective

    (207) 305-9767

    22 Carroll St Unit 9, Portland, ME 04102
  • /6

    $2,095,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft

    383 Commercial St Unit 600, Portland, ME 04101

    Welcome to the top of the Old Port at Hobson's Landing, where city energy meets the rhythm of the sea, and every sunrise and sunset over Casco Bay is yours to take in. Perched above waterfront Commercial Street, Penthouse 600 is a perfect blend: a stylish corner unit with walls of windows, light that pours in from every angle, and a private 625 sq ft rooftop terrace that makes the Casco Bay

    Agent Photo

    Nova Tower

    Waypoint Brokers Collective

    (207) 492-4572

    383 Commercial St Unit 600, Portland, ME 04101
  • /27

    $645,000

    • 1 Bed
    • 1 Bath
    • 851 Sq Ft

    716 Chandlers Wharf, Portland, ME 04101

    Chandler's Wharf top floor pied a terre overlooks the fantastic cityscape, one of our favorite views of Portland. Ideal location for city living in the only gated community where you can park in your on site secure garage and wander the waterfront with it's renowned restaurants, shops and beautiful vistas. Listen to the summer live music from Portland Lobster Co, check out the lines at J's

    Christine Pemberton Pemberton Real Estate

    716 Chandlers Wharf, Portland, ME 04101
  • /42

    $695,000

    • 2 Beds
    • 2.5 Baths
    • 2,262 Sq Ft

    3 Cape Woods Dr, Cape Elizabeth, ME 04107

    Cape Woods Condominiums are well-sited along a tree-lined road that winds to a wooded cul-de-sac. Creating a well-landscaped, inviting setting, the condo community features 22 homes. This cape-style condo has been thoughtfully updated, and includes renovated kitchen with crisp, white cabinetry, black granite countertops, large center island and new appliances. Conveniently located, adjacent to

    Susanne Lamb Town & Shore Real Estate

    3 Cape Woods Dr, Cape Elizabeth, ME 04107
  • /50

    $869,000

    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft

    15 Brown St Unit 405, Portland, ME 04101

    Stunning Penthouse with Panoramic City & Water Views in Downtown Portland.Experience elevated urban living in this exceptional 2-bedroom, 2-bath penthouse perfectly situated in the heart of downtown Portland. Offering expansive, unobstructed views of the city skyline and Casco Bay, this one-of-a-kind residence combines historic charm with modern luxury.Step into a space filled

    Craig Miller Portside Real Estate Group

    15 Brown St Unit 405, Portland, ME 04101
  • /39

    $699,000

    • 3 Beds
    • 1.5 Baths
    • 1,370 Sq Ft

    16 Tate St Unit 2, Portland, ME 04102

    Nestled in Portland's desirable West End, this beautifully remodeled condo blends historic charm with modern convenience. Spanning two spacious levels, the unit feels more like a single-family home than a traditional condo. With 3 generous bedrooms and 1.5 baths, the layout is thoughtfully designed for both comfort and functionality.Flooded with natural light, the home features skylights,

    Shea McGonigal Beacon Realty

    16 Tate St Unit 2, Portland, ME 04102
  • /40

    $649,000

    • 1 Bed
    • 1 Bath
    • 770 Sq Ft

    709 Chandlers Wharf Unit 709, Portland, ME 04101

    Experience the epitome of coastal urban living in this exceptional 1-bedroom, 1-bath condominium at Chandler's Wharf—Portland's premier waterfront address. This single-level unit offers a private deck with sweeping easterly views of Casco Bay, where you'll enjoy spectacular sunrises and a front-row seat to the working waterfront. Just outside your door is immediate access to the historic Old Port

    Tom Landry Benchmark Real Estate

    709 Chandlers Wharf Unit 709, Portland, ME 04101
  • /40

    $699,500

    • 3 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    21 Pine St Unit 2, Portland, ME 04102

    Historic Character Meets Elevated LivingIn the heart of Portland's iconic West End, discover a residence that's equal parts refined retreat and hidden gem. With three bedrooms, two and a half baths, and over 1,700 square feet of thoughtfully designed living space, this exceptional walk-up offers the best of both worlds: tucked away tranquility just steps from the city's best dining, arts, and

    Amanda Vigue Waypoint Brokers Collective

    21 Pine St Unit 2, Portland, ME 04102
  • /49

    $765,000

    • 2 Beds
    • 2 Baths
    • 1,430 Sq Ft

    149 Fort Rd Unit 6, South Portland, ME 04106

    This 1 floor condo offers spectacular panoramic views of Casco Bay, and offers over 1400sqft of living with 2 spacious bedrooms, 2 full baths, open concept living, kitchen and dining area with direct access to the outside deck, for morning coffee over looking the bay. The office & laundry room offers great space for in home office and all offer stunning hardwood & title floors, fireplace and

    John Harmon John Carroll EXP Realty

    149 Fort Rd Unit 6, South Portland, ME 04106
  • /51

    $799,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    16 Holbrook Farms Way Unit 2, Scarborough, ME 04074

    Brand new luxury House-O-Miniums in Scarborough with Limited Time Builder Incentive - offering a 15K RATE BUY-DOWN CREDIT to lower your monthly mortgage payment - contact broker for details. The last four houses are now being built in popular Holbrook Farms with its ultra-convenient location - just 10 mins to Portland or Jetport. Enjoy the flexibility of a private house + the convenience of

    Deborah Meek Keller Williams Realty

    16 Holbrook Farms Way Unit 2, Scarborough, ME 04074
  • /59

    $2,295,000

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft

    387 Commercial St Unit 613, Portland, ME 04101

    Experience living in one of the most desirable small cities in the country, walk to award-winning restaurants, the working waterfront & private marinas, amazing art galleries & museums, and talent filled music venues. Hobson's Landing was built for those looking for luxury living in a thriving city on the water. This 6th floor penthouse unit offers an association with all the community &

    Peter Molloy Town & Shore Real Estate

    387 Commercial St Unit 613, Portland, ME 04101
  • /22

    $355,000

    • 1 Bed
    • 1 Bath
    • 616 Sq Ft

    104 Grant St Unit 403, Portland, ME 04101

    Welcome to your dream condo nestled on the picturesque peninsula of Portland, where city living meets serene comfort. This modern 1-bedroom, 1-bath home on the 4th floor comes with sweeping treetop views and floods of natural light through stunning floor-to-ceiling windows. Inside, you'll find sleek European-style design with energy-efficient features throughout, from quartz countertops to

    Yasmine Habash Keller Williams Realty

    104 Grant St Unit 403, Portland, ME 04101
  • /50

    $1,600,000

    • 3 Beds
    • 3.5 Baths
    • 2,394 Sq Ft

    749 Congress St Unit 5, Portland, ME 04102

    Among the nicest homes ever built in Portland, this 3-bedroom, 3.5-bathroom townhouse set in a quiet alcove off Congress Street has it all: Chef's kitchen, elevator, three outdoors spaces, two-car garage, gym space, office space, air-conditioning, three en-suite bathrooms, gorgeous finishings, deck views of Back Cove and the White Mountains, nearly soundproof walls, low HOA fees, potentially

    Jason Singer Keller Williams Realty

    749 Congress St Unit 5, Portland, ME 04102
  • /44

    $455,000

    • 2 Beds
    • 1 Bath
    • 1,068 Sq Ft

    3 Walker St Unit 4, Portland, ME 04102

    First time on market in 20 years. Located in Portland's iconic West End, this top-floor-2-bedroom, 1-bath condo blends historic charm with modern updates. Beautifully maintained, the home features gleaming hardwood floors throughout, a custom-designed kitchen, and a sunroom that doubles perfectly as a second bedroom or home office. The spacious primary bedroom is a true retreat, complete with

    Matthew Robedee Excellence Realty

    3 Walker St Unit 4, Portland, ME 04102
  • /51

    $590,000

    • 2 Beds
    • 1 Bath
    • 730 Sq Ft

    148 Breakwater Dr Unit 809, South Portland, ME 04106

    This top floor Penthouse unit with a one of a kind view is breathtaking. With Casco Bay at your fingertip, you could literally sit and watch the inner workings of the ships channel and all Portland Harbor activities.This two-bedroom unit features 762 square feet, fresh painted, new carpeted & new stainless appliances could make this an entirely fresh beginning. Breakwater at Spring Point is a

    Thomas Ranello RE/MAX Shoreline

    148 Breakwater Dr Unit 809, South Portland, ME 04106
  • /48

    $490,000

    • 1 Bed
    • 1 Bath
    • 584 Sq Ft

    148 Breakwater Dr Unit 808, South Portland, ME 04106

    Breathetaking views from this top floor Penthouse unit with a one of a kind exposure to all of the natural beauty of Portland harbor and Casco Bay.Framed by the city skyline, FortGorges and the inner harbor islands. Freshly painted and newly carpeted this unit is a blank canvas awaiting your final touches..Breakwater at Spring Point is a largecondominium building set between

    Thomas Ranello RE/MAX Shoreline

    148 Breakwater Dr Unit 808, South Portland, ME 04106
  • /27

    $399,900

    • 1 Bed
    • 1 Bath
    • 564 Sq Ft

    179 Pine St Unit 1B, Portland, ME 04102

    Incredible location and opportunity to live full time or part time in the beautiful and historic West End! This lovely, refreshed, 1 level, ground floor unit is amenity laden and centrally located to anything and everything Portland affords. Perfectly placed for your convenience and ease, nothing to do but move in and enjoy! Unit floors and interior painting redone June 2025, the location of

    Jennifer Sweeney Portside Real Estate Group

    179 Pine St Unit 1B, Portland, ME 04102
  • /19

    $275,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    25 Minott St Unit 9, South Portland, ME 04106

    Affordable South Portland condo that abuts the Green Belt! All new appliances ,flooring, paint and overall updates. Can't beat the location - easy to walk to South Portland's vibrant downtown and into Portland.This property is ready to move in or rent.Designated parking and guest parking available.Close to schools , airport , mall and waterfront

    Brian Mayhew Landing Real Estate

    25 Minott St Unit 9, South Portland, ME 04106
  • /39

    $1,900,000

    • 2 Beds
    • 2 Baths
    • 1,601 Sq Ft

    387 Commercial St Unit 527, Portland, ME 04101

    STUNNING corner condo with panoramic water views!This spacious 2-bedroom, 2-bath condo boasts 1,600 square feet of luxurious living space with breathtaking water views in every room. Thoughtfully designed with custom built-ins, elegant crown moldings, and a modern gas fireplace, this condo perfectly combines comfort and style. The well-appointed kitchen includes a pantry, while both

    Whitney Harvey Town & Shore Real Estate

    387 Commercial St Unit 527, Portland, ME 04101
  • /33

    $569,500

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    32 State St Unit 5, Portland, ME 04101

    Spacious and sunny 3 bedroom, 1 bath condo unit with water views on the coveted Portland Peninsula! This condo has been thoughtfully updated while preserving its original character - hardwood floors, a built-in china cabinet, stained glass, and ornamental mantels alongside an updated kitchen with quartz countertops, peninsula seating and a fabulous original butler's pantry. The condo offers a

    Jennifer Tabb Portside Real Estate Group

    32 State St Unit 5, Portland, ME 04101
  • /33

    $460,000

    • 2 Beds
    • 1 Bath
    • 1,142 Sq Ft

    16 Guilford Ct Unit B1, Portland, ME 04101

    Discover comfort and convenience in this nearly brand new 2-bedroom + office, 1-bath condo located in the heart of downtown Portland. Perfect as a primary residence or second home, this property offers a seamless move-in opportunity in one of New England's most desirable cities. The open-concept layout includes a spacious eat-in kitchen, inviting living area, and a dedicated office nook—ideal for

    Elise Loschiavo Vitalius Real Estate Group, LLC

    16 Guilford Ct Unit B1, Portland, ME 04101
  • /30

    $295,000

    • 1 Bed
    • 1 Bath
    • 595 Sq Ft

    18 Sherman St Unit 4, Portland, ME 04101

    LOW MONTHLY ASSOCIATION FEE! PARKING SPOT INCLUDED! PET AND RENTER FRIENDLY! Welcome to 18 Sherman Street, a charming top floor condo in the heart of the West End in Portland, Maine! This special, inner city spot offers historic charm as well as modern upgrades, making it an ideal spot for those looking for easy, enjoyable city living. The unit features an updated kitchen with many windows that

    Mandy Wheeler U&R Real Estate

    18 Sherman St Unit 4, Portland, ME 04101
  • /18

    $375,000

    • 2 Beds
    • 1 Bath
    • 854 Sq Ft

    20 West St Unit 3, Portland, ME 04102

    Located in the heart of Portland's walkable West End, this affordable condo is within an historic brick building on desired West Street. The 795± square foot, two level unit is situated on the building's first and lower floors providing ideal access for groceries and pets. The open floorplan living/dining area with high ceilings and kitchen are on the first floor main entry level. A large bedroom

    John Saint-Amour LandVest, Inc.

    20 West St Unit 3, Portland, ME 04102
  • /28

    $420,000 Open Sun 11AM - 12:30PM

    • 1 Bed
    • 1 Bath
    • 695 Sq Ft

    66 Spruce St Unit 1, Portland, ME 04102

    This immaculate West End condo underwent a total renovation in 2018 with no space underutilized! You don't need to bring much furniture with an abundance of built-in custom cabinetry throughout. The gracious kitchen area features plenty of pantry and storage space and a custom dining table. The living space is quiet and bright, with high ceilings and lots of historic charm. Enjoy assigned parking

    Elise Loschiavo Vitalius Real Estate Group, LLC

    66 Spruce St Unit 1, Portland, ME 04102
  • /27

    $590,000

    • 3 Beds
    • 3 Baths
    • 1,523 Sq Ft

    1 Teal Point Dr Unit 1, Scarborough, ME 04074

    Come take a look at this charming condo in the highly sought-after Teal Point Condominium Association. It's back on the market after a short break! This condo offers - * Open first-floor layout with vaulted ceilings in the living room, dining area, and kitchen.* Two first-floor bedrooms and two full baths.* Inviting three-season porch with a view of the private backyard.* Second-floor loft,

    Jennifer A. Allen Regency Realty Group

    1 Teal Point Dr Unit 1, Scarborough, ME 04074
  • /30

    $449,000

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    17 Pine St Unit 1, Portland, ME 04102

    First-floor condo in Portland's historic West End blends period charm with modern convenience—all at an exceptional value. Enjoy soaring ~10' ceilings, hardwood floors, and abundant natural light throughout. The updated kitchen and bath, in-unit laundry, and efficient mini-splits for heating and cooling make this home truly move-in ready. With rare deeded off-street parking, low/low condo fees,

    Tom Landry Benchmark Real Estate

    17 Pine St Unit 1, Portland, ME 04102
  • /13

    $385,000

    • 1 Bed
    • 1 Bath
    • 520 Sq Ft

    21 Dow St Unit 4, Portland, ME 04102

    Newly renovated Condo in Historic brick building. Roofs rights above the double garage with a possibility of adding a private deck. Includes rare garage parking space for each unit. In the Arts District of the West End of Portland. Close to Maine Medical Center and walk-able to downtown and the old Port.

    Sheldon Ashby Ashby Real Estate

    21 Dow St Unit 4, Portland, ME 04102
  • /45

    $2,900,000

    • 2 Beds
    • 2.5 Baths
    • 1,672 Sq Ft

    387 Commercial St Unit 710, Portland, ME 04101

    Luxury means living in one of the most desirable small cities in the country, within walking distance of award-winning restaurants, the waterfront, galleries, museums, musical venues and private marinas. Luxury means easy access to an international airport, and first-class medical facilities. Luxury means proximity to recreational activities such as hiking, skiing, boating, fishing, kayaking and

    Sandra Johnson Town & Shore Real Estate

    387 Commercial St Unit 710, Portland, ME 04101
  • /22

    $549,000

    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft

    773 Congress St Unit 3, Portland, ME 04102

    You will be glad that you put this one on the top of your your list! Sunfilled second floor condo located in the West end. 2 BEDROOMS, 2 FULL BATHS, 2 dedicated OFF STREET PARKING SPACES, Truly it is MOVE IN READY. Eat in kitchen with stainless appliances and granite countertops . Wood floors that are throught the entire unit as well. A dedicated washer and dryer for this unit located on first

    Holly Stickney EXP Realty

    773 Congress St Unit 3, Portland, ME 04102
  • /20

    $1,360,000 New Construction

    • 2 Beds
    • 2 Baths
    • 1,510 Sq Ft

    387 Commercial St Unit 430, Portland, ME 04101

    Luxury Living at it's best, unit features hardwood throughout, 9 ft. ceilings, gas fireplace, radiant heat in master bathroom and private decks. Amenities include lobby with concierge, clubroom with a fireplace, deck, and full kitchen, fitness room, dog wash, reservable guest suite, shared Tesla and bikes, and spacious courtyards. Deeded Garage parking is available at $35000. Take this

    Sandra Johnson Town & Shore Real Estate

    387 Commercial St Unit 430, Portland, ME 04101

Why Live in Highland

Highland in South Portland features forested cul-de-sacs and curved roads leading to clapboard cottages and brick-trimmed estates. Raised ranches with driveways and two-car garages are common, often with wooden fences enclosing backyards that include inground pools and patios. The neighborhood is quiet, ideal for biking and walking, though it lacks sidewalks, requiring caution. Homes range from 1940s Cape Cods and Colonials to 1970s split-levels and ranch-style homes. Wainwright Sports Complex, a large community athletic facility, connects to the Greenbelt Walkway, a nearly 6-mile path leading to Bug Light Park, popular for winter sports and summer swimming at Willard Beach. The South Portland Recreation Center offers a pool and fitness center without membership fees. Nearby, the Maine Mall features numerous stores, Urban Air Trampoline Park, and a movie theater. Dining options include Indy’s Sandwich and Coppersmith Tavern & Table on Route 1, with more upscale choices like North 43 Bistro offering river views. Mill Creek Park hosts community events such as Winterfest and a summer concert series. Highland is conveniently located 5 miles from downtown Portland and 6 miles from the Portland International Jetport. Public transit is available via South Portland Bus Service. The neighborhood falls within the South Portland Public Schools district, with Dyer Elementary and South Portland High nearby.

Home Trends in Highland, ME

Housing Trends

Median Sale Price
$348,450
Median Single Family Sale Price
$460,605
Average Price Per Sq Ft
$305
Number of Homes for Sale
10
Last 12 months Home Sales
18
Months of Supply
6.70
Median List Price
$457,605
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-2%
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