Luxury homes for sale & real estate in Islesboro, ME

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ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Discover a unique opportunity in Mid-Island Islesboro, where history and potential converge in two remarkable buildings on one property. The Schoolhouse (300 Main Road): This was formerly the Pendleton School, Islesboro's main elementary school until the early 1950s. Currently operating as the Double Door Gallery during the summer, it features two large open rooms on the first floor with curved walls, bead board, wood paneling, and a half bath. The second floor offers a studio apartment with expansion potential, providing immediate income through gallery rentals and apartment leasing. This property is a piece of history with a bright future, ready for its next chapter as a vibrant art galle

$850,000

5 beds3 baths4,962 sq ft

292 & 300 Main Rd, Islesboro, ME 04848

Expansion potential • Wrap-around porch • Elegant staircase

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Escape to an island, down a wooded road to this secluded seasonal cabin retreat, set on over 10 acres with sunset views. View our video for a more immersive experience!

$1,200,000

0 beds1 bath360 sq ft

181 Oregon Rd, Islesboro, ME 04848

Over 10 acres • Sunset views • 10.7 acre lot

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
East Bay is a lovely coastal estate, an ideal summer retreat and a serene sanctuary for year-round living. Privately sited on 5 plus acres with 430 feet of accessible, pristine waterfront, the property is gracefully perched above a scenic pristine shoreline, where lush gardens and thoughtful landscaping frame cinematic views of Penobscot Bay and the islands. The residence unfolds along a gently sloping bluff, capturing sweeping vistas from nearly every room and outdoor space. Originally constructed as a post-and-beam home circa 2000, East Bay has since undergone a series of thoughtful transformations. Its final form, guided by the timeless coastal architecture of Royal Barry Wills, seamless

$6,750,000

6 beds7.5 baths9,449 sq ft

866 Pendleton Point Rd, Islesboro, ME 04848

Sweeping vistas • Pristine waterfront • Cinematic views

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Slip away to Seabox Cottage, your ideal summer retreat or year-round haven. Reminiscent of the gracious turn-of-the-century summer homes of Dark Harbor, Seabox blends timeless craftsmanship with modern comfort. A long gravel drive winds through the wooded property and opens to sunny, landscaped gardens, arriving at a circular turnaround that welcomes you to the home's charming wraparound covered porches. Inside, the home offers elevated views of East Penobscot Bay from both levels. At the heart of the first floor is an open-concept living space anchored by a stunning stone fireplace. The well-appointed cook's kitchen with pantry flows seamlessly into the dining and living areas, all opening

$899,000

3 beds3 baths3,801 sq ft

135 Rebel Hill Rd, Islesboro, ME 04848

3.73 acre lot • Built 2004 • Listed 130 days

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
East Shore Drive, Islesboro. Dark Harbor Village north along the shore dotted with grand waterfront summer cottages to your private haven. You will have your breath taken away as this stunning wildflower meadow reveals an unsurpassed view of the ocean and possibilities. 15 parkland acres edged with woods and 770 feet of bold shorefront and beach comprise commanding hillside building sites, deepwater dock, immaculate five-bedroom year-round primary or guest cottage ideal for entertaining with its expansive deck and meticulously landscaped grounds and thoughtful accents anchoring your environ to the highest expectation. Enjoy views of Charlotte's Cove with abundant wildlife activity. Watch ea

$3,950,000

5 beds4 baths2,400 sq ft

118 E East Shore Dr, Islesboro, ME 04848

15 parkland acres • Deepwater dock • Expansive deck

Property at 1317 Trim Ln, Islesboro, ME 04848, 1 bed, 1 bath

$2,000,000

1 bed1 bath936 sq ft

1317 Trim Ln, Islesboro, ME 04848

Property at 399 Hermit's Point Rd, Islesboro, ME 04848, 8 beds, 10 baths

$6,500,000

8 beds10 baths9,025 sq ft

399 Hermit's Point Rd, Islesboro, ME 04848

Property at 228 Gooseberry Point Rd, Islesboro, ME 04848, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,670 sq ft

228 Gooseberry Point Rd, Islesboro, ME 04848

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NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Welcome to Ocean Ridge, a distinctively planned, 9 lot development in Coastal Maine, overlooking the Atlantic. ''Where the mountains meet the sea'', is a slogan common to this area of Maine and is most fitting here at Ocean Ridge. We are proud to introduce the newest Ecocor Energy Efficient Home by Ecocor's Design Expert. Luxury and style, with uncompromising quality, this sophisticated, chic home is an architectural masterpiece. With commanding ocean vistas and views of the mountains and hills, this property is like none you've ever imagined, becoming the place you call home. Boasting an innovative ecocor design and high-performance energy systems, this residence offers a seamless blend of

$1,795,000

4 beds2 baths2,262 sq ft

66 Ocean Ridge Rd, Northport, ME 04849

Screen porch • 1.21 acre lot • 2 garage spots

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Newly built 2,500 sq. ft. custom home is in the desirable Woodside at Saturday Cove subdivision. This 7-room single-family residence offers 4 bedrooms and 4 baths, featuring energy-efficient systems including a heat pump, solar power, and radiant in-floor heating. Amenities include a covered porch, detached 2-car garage, and first-floor primary bedroom with en-suite bath. Quality craftsmanship throughout with custom-built finishes. A perfect combination of comfort, energy efficiency, and modern design. Conveniently located between Camden and Belfast within walking distance of Saturday Cove public dock with ocean access.

$975,000

4 beds3 baths2,500 sq ft

185 Glenwood Ln, Northport, ME 04849

Covered porch • Custom home • Ocean access

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Exceptional opportunity in mid-coast Maine's beautiful seacoast town of Belfast. This wonderful property features 6 guest suites and a two bedroom apartment in the Inn as well as 13 rooms in the separate updated Lodge. The Lodge features a separate common kitchen which makes it ideal for extended stay rentals as well as a water view veranda on the second level. Situated on 3.49 acres on heavily travelled Route 1, it has spectacular views of Penobscot Bay, a huge lawn for special events and plenty of parking. The Inn building also has a large commercial kitchen space with a large porch for a possible restaurant seating. Also listed MLS#1642591

$1,390,000

6 beds8 baths5,174 sq ft

192 Northport Ave, Belfast, ME 04915

3.49 acres • Water view veranda • Huge lawn

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Ideal location in downtown Belfast! Renovations in 2008 for large addition includes: oversized two-car garage with second floor ideal for finishing into an apartment; primary bedroom with walk-in closet and full bathroom with handicapped accessible shower and private toilet with pocket doors. One-floor living at its finest! Drive-thru garage and private back yard. The old Carriage house/barn is perfect for storage or workshop area. This property is a stone's throw from the ocean, City Park, medical facilities, shopping, restaurants, Rail Trail and so much more. Enjoy the charm of the original property and the ease of the newer primary bedroom suite with this beautiful property! Seller

$950,000

3 beds2.5 baths2,818 sq ft

11 Durham St, Belfast, ME 04915

Private back yard • Shopping • Carriage house

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Developers and Investors take note this property is in a Prime Location! It's located on a Corner lot on Route 1 and Route 141, zoning allows many uses with planning board review. This is a combination of 2 lots, there is 3 phase power & Public sewer available, public water is already connected. The most recent average weekly traffic count is 22,695. The building on the property could be converted or removed. Possible owner financing if qualified. Just minutes to downtown Belfast. Call for an appointment.

$989,500

5 beds2 baths2,248 sq ft

2 Swan Lake Ave, Belfast, ME 04915

Public sewer • 3 phase power • Corner lot

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Islesboro, ME:
Pond House - A Forever Home and Smart Retirement Investment Just two miles from Lincolnville Beach and minutes from Camden, Pond House combines Scandinavian design, ultra-efficient construction, and year-round beauty with excellent income potential. The perfect forever home and a smart retirement plan. Designed for Living and Entertaining Step through a tiled foyer into a sun-filled living room with floor-to-ceiling windows overlooking your private pond and waterfall. NO HOA Fees or Restrictive Covenants. Floating decks with cascading levels create the perfect spot for morning coffee or evening sunsets, while the 7-foot gas fireplace anchors gatherings year-round. A quiet reading room off

$989,000

3 beds2.5 baths2,300 sq ft

11 Iron Bluff Rd, Lincolnville, ME 04849

Private pond • 2.38 acre lot • 2 garage spots

Property at 208 High St, Belfast, ME 04915, 5 beds, 3.5 baths

$1,300,000

5 beds3.5 baths6,239 sq ft

208 High St, Belfast, ME 04915

Property at 33 Sea View Dr, Lincolnville, ME 04849, 12 beds, 11.5 baths

$1,450,000

12 beds11.5 baths7,548 sq ft

33 Sea View Dr, Lincolnville, ME 04849

Property at 19 Glenview Ln, Belfast, ME 04915, 4 beds, 3.5 baths

$1,925,000

4 beds3.5 baths3,245 sq ft

19 Glenview Ln, Belfast, ME 04915

Property at 155 Bayside Dr, Belfast, ME 04915, 5 beds, 3.5 baths

$1,625,000

5 beds3.5 baths3,824 sq ft

155 Bayside Dr, Belfast, ME 04915

Property at 6 Whitetail St, Belfast, ME 04915, 5 beds, 2.5 baths

$899,000

5 beds2.5 baths2,048 sq ft

6 Whitetail St, Belfast, ME 04915

Property at 440 Belfast Rd Unit Inio E2, Camden, ME 04843, 2 beds, 2 baths

$1,350,000

2 beds2 baths1,360 sq ft

440 Belfast Rd Unit Inio E2, Camden, ME 04843

Property at 16 Cottage St, Belfast, ME 04915, 3 beds, 2.5 baths

$1,195,000

3 beds2.5 baths2,816 sq ft

16 Cottage St, Belfast, ME 04915

Property at 51 Bridge St, Belfast, ME 04915, 4 beds, 4 baths

$1,295,000

4 beds4 baths2,729 sq ft

51 Bridge St, Belfast, ME 04915

Property at 440 Belfast Rd Unit Naan.D1, Camden, ME 04843, 3 beds, 2 baths

$1,400,000

3 beds2 baths1,720 sq ft

440 Belfast Rd Unit Naan.D1, Camden, ME 04843

Property at 555 Belfast Rd, Camden, ME 04843, 4 beds, 3.5 baths

$1,975,000

4 beds3.5 baths3,268 sq ft

555 Belfast Rd, Camden, ME 04843

Property at Lot 26 Mariner's Watch Rd, Northport, ME 04849

$1,500,000

— beds— baths— sq ft

Lot 26 Mariner's Watch Rd, Northport, ME 04849

Property at Lot 50-2 Serene Dr, Northport, ME 04849

$2,500,000

— beds— baths— sq ft

Lot 50-2 Serene Dr, Northport, ME 04849

Property at M17 L15 Battle Ave, Castine, ME 04421

$850,000

— beds— baths— sq ft

M17 L15 Battle Ave, Castine, ME 04421

Luxury Homes for Sale in Islesboro

There are currently 8 luxury homes for sale in Islesboro at a median listing price of $693K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Islesboro stay on the market for 156 days. This map is refreshed with the newest listings in Islesboro every 15 minutes.

In the past month, 1 home has been sold in Islesboro. Find your dream home in Islesboro 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 Islesboro are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Islesboro. If you're looking to sell your home in the Islesboro area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Islesboro with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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