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Lot 7 Whispering Pines, Boothbay
$3,995,000
3 Beds ⋅ 4 Baths
Distinctive opportunity to live at the renowned Boothbay Harbor Country Club, recognized as the best golf and country club experience in Maine. This exceptionally designed and appointed home will be built with supreme quality and luxury, including a ground floor ensuite bedroom, and a spectacular primary bedroom suite upstairs with his & hers bathrooms, closets, and a study that could serve as an extra bedroom. The open concept kitchen and great room makes for satisfying everyday use, as does the abundanta outdoor living space, be it the screened porch, veranda, open deck, and granite patios. Sumptuously comfortable, the home offers owners an effortless club lifestyle, with golf cart access to Club amenities that feature the 18-hole course, lavish spa, family pool, fitness center, tennis & pickleball courts, dining facilities, and more. Club-maintained gardens & landscaping, municipal water & sewer, and other attributes make for ''lock and leave'' convenience, just up the hill from downtown Boothbay Harbor.

Lot 7 Whispering Pines, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

Lot 10 Whispering Pines, Boothbay
$2,995,000
2 Beds ⋅ 3 Baths
Distinctive opportunity to live at the renowned Boothbay Harbor Country Club, recognized as the best golf and country club experience in Maine. This exceptionally designed and appointed home will be built with supreme quality and luxury, including one-floor living with two ensuite bedrooms, an open concept kitchen & great room, and abundant outdoor living spaces. Sumptuously comfortable, the home offers owners an effortless club lifestyle, with golf cart access to Club amenities that include the award-winning 18-hole course, lavish spa, family pool, fitness center, tennis & pickleball courts, dining facilities, and more. Club-maintained gardens & landscaping, municipal water & sewer, and other features make for ''lock and leave'' convenience, just up the hill from downtown Boothbay Harbor.

Lot 10 Whispering Pines, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

1090 Pittston School St, Pittston
$6,000,000
4 Beds ⋅ 3 Baths
Tut Hill is a stunning 40-acre property with 19 buildings, including a Greek Revival-style home and a restored 1825 church. It offers limitless potential for events and businesses. The grounds are ideal for outdoor weddings, with ample space for ceremonies and receptions. The versatile indoor spaces, such as multi-bay garages and barns, can be customized for various needs. The picturesque setting, featuring mature plants and apple trees, is perfect for lasting photos. Tut Hill is also great for corporate retreats, with a serene atmosphere and rustic charm for team-building exercises and meetings. It has accommodations for overnight guests in apartments and homes. Car enthusiasts will appreciate the multi-bay garages, mechanic's garage, and spacious grounds for showcasing car collections. Tut Hill offers endless possibilities for events and businesses, with natural beauty, historic buildings, and versatile spaces. It can be tailored to suit your dreams, whether for weddings, retreats, starting a business, creating a campus, or simply calling it home.

1090 Pittston School St, Pittston

Listing courtesy of Summit Real Estate.

1 Ship St, Rockport
$4,495,000
4 Beds ⋅ 5 Baths
In one of the most extraordinary settings on Rockport Harbor, 1 Ship Street is a private harborfront enclave with two year-round residences, a private sandy beach, terraced gardens, and sweeping views across the harbor to Indian Island Lighthouse and beyond to Penobscot Bay and its islands. Offered for the first time since 1973, the property combines rare waterfront amenities, architectural distinction, and an intimate sense of privacy at the end of a dead-end street, all in the harbor Charles Kuralt once called ''the most perfect small harbor in America.'' The property comfortably sleeps up to eight guests and is especially well suited for family and guests with space to spread out and enjoy this quintessential coastal retreat. The main residence is a striking modern interpretation of a classic New England waterfront home, inspired by the owners' long admiration for renowned American architect Hugh Newell Jacobsen, with clean lines and light-filled interiors. The open main floor includes a vaulted living room with propane fireplace, a gourmet kitchen, and thoughtful custom details. The lower level offers two private bedroom suites, including a luxurious primary suite with a spa-like bath and sauna. At the water's edge, the year-round beach house, originally a 1940s boat-repair shop, provides additional accommodations with a full kitchen, two upstairs bedrooms, and one-and-a-half baths. The private sandy beach is an exceptional amenity on Rockport Harbor, creating a rare place for swimming, launching small watercraft, gathering by the water or beach fires. The Matthew Cunningham-designed grounds include terraced gardens, elegant stonework, mature plantings, and stone steps leading toward the shore. 1 Ship Street is a unique offering on Rockport Harbor in a design that honors coastal New England with fresh, sophisticated simplicity. Dead end road, absolutely no drive-bys.

1 Ship St, Rockport

Listing courtesy of LandVest, Inc..

29 Ferry Ln, Biddeford
$1,650,000
Set along the storied shores of the Saco River with direct access to the Atlantic Ocean, The John Tarr House, originally constructed in 1730, offers a unique opportunity to steward a piece of Maine's early history while shaping its future. Privately sited on beautifully elevated land, the property is notably high and dry. A recent survey reveals approximately 4.78± acres with an impressive 900+ feet of water frontage, creating a remarkable canvas of open river views, natural privacy, deep water dockage options and endless potential. The expansive setting invites a range of possibilities, including the potential for subdivision into two distinct parcels - subject to local approvals - offering flexibility for investment, legacy planning, or a multi-generational retreat. Rich in history yet ready for transformation, this legacy property is ideal for those with vision - whether restoring the existing antique structure, creating a bespoke waterfront estate, or designing a truly one-of-a-kind compound that embraces the beauty and serenity of coastal Maine. Bring imagination and seize the opportunity to craft an extraordinary waterfront treasure in one of Southern Maine's most compelling riverfront settings.

29 Ferry Ln, Biddeford

Listing courtesy of Landvest, Inc..

245 Arundel Rd, Kennebunkport
$1,550,000
3 Beds ⋅ 3 Baths
A rare estate located in the countryside of Kennebunkport, just minutes from Goose Rocks Beach. Nestled on approximately 7 idyllic acres abutting conservation land, this exceptional property offers privacy, beauty, and unlimited potential. The centerpiece is a beautifully renovated 10,000+ square foot barn featuring spacious living quarters with 3+ bedrooms, 3 baths, soaring open spaces, and distinctive architectural character. Two additional barns provide endless opportunities for collectors, hobbyists, workshops, equestrian pursuits, or future creative uses. Expansive fields, a picturesque pond, abundant parking, and a serene natural setting create an extraordinary backdrop unlike anything else on the market. Whether you're seeking a remarkable private retreat, multi-use property, or legacy estate, this one-of-a-kind offering presents an unparalleled opportunity in one of Kennebunkport's most desirable countryside locations.

245 Arundel Rd, Kennebunkport

Listing courtesy of Pack Maynard and Associates.

3 Canter Ln, Cape Elizabeth
$3,390,000
7 Beds ⋅ 10 Baths
A Luxury Residence inspired by Nature: Sited on 14 private acres in the heart of Cape Elizabeth, Great Woods Lodge at 3 Canter Lane offers a rare blend of seclusion and convenience. Bold architecture meets warm, livable elegance throughout. The home unfolds with a gourmet kitchen, refined library, living and sitting rooms, four bars, six bedrooms, two offices, a gym, sauna, steam room, and a private movie theater. Thoughtfully appointed baths, multiple fireplaces, and a detached carriage house complete the estate. Outside, curated grounds feature exquisite hardscaping, fountains, and lush landscaping, along with deeded access to a peaceful pond. Canter Lane connects directly to sidewalks leading to village shops, schools, dining and abutting preservation land trails bring you to the Atlantic Ocean. This extraordinary estate offers endless exploration opportunities! Just moments from Portland International Jetport (PWM) and the celebrated dining, art, and music scene of Portland, Maine - this is a lifestyle of both retreat and refinement!

3 Canter Ln, Cape Elizabeth

Listing courtesy of Legacy Properties Sotheby's International Realty.

20 Sailors Way, Vinalhaven
$1,795,000
3 Beds ⋅ 3 Baths
A rare offering on Winter Harbor, this exceptional waterfront property captures the essence of life on Vinalhaven. Set in one of Maine's most celebrated sailing and boating destinations, the property enjoys a one-of-a-kind vantage point overlooking Ames Cove, with protected nearby islands just beyond and a remarkably preserved viewscape. Winter Harbor is one of Vinalhaven's most coveted waterfront settings--an area where properties are rarely offered and surrounding estates have often remained in the same hands for generations. With over 260 feet of private waterfront, the setting is both striking and serene. A substantial dock offers access at all tides, while a small rocky beach, open fields, mature and fruit trees, and a rear garden framed by historic stone walls create a landscape of rare character and timeless coastal charm. A barn adds utility and visual appeal. Set on 4.18± acres, the 3-bedroom, 2.5-bath residence was thoughtfully designed to complement its surroundings, with warm natural materials, enduring craftsmanship, and water views woven throughout nearly every room. Red birch flooring runs throughout the home, while custom tiled baths, solid fir doors, granite stone steps, and refined finishes speak to the quality of its construction. The main living spaces are bright and welcoming, centered around a beautifully appointed kitchen with granite countertops, a farmhouse sink, stainless appliances, generous cabinetry, and a large center island that flows into the dining and living areas. Expansive windows and glass doors draw in natural light and frame the harbor beyond, while generous decking extends the living space outdoors. Upstairs, the primary suite offers vaulted ceilings, deck access, and a soaking tub positioned to take in the view. Private, peaceful, and deeply connected to the rhythms of the coast, this is an exceptional opportunity to own a legacy waterfront property in one of Maine's treasured island communities.

20 Sailors Way, Vinalhaven

Listing courtesy of Rock Coast Realty.

15 Sleepy Hollow Rd, Windham
$4,200,000
7 Beds ⋅ 5 Baths
This is a rare opportunity to experience luxury lakefront living in this extraordinary, furnished waterfront residence on pristine Sebago Lake. Take in spectacular Mt. Washington views, breathtaking sunsets, abundant natural light and 113 feet of private shoreline.This area of Sebago's Jordan Bay is closest to the airport, the arts, world class restaurants and the ocean. Also just five minutes from local coffee shops, supermarkets, shopping and local restaurants. Multiple premier ski destinations are within an easy drive making this a true four season gem. Share what you will come to love about the Lakes Region with friends and family. Two attached guest suites/apartments seamlessly expand the home's living space for larger gatherings. Each has its own entrance and parking.The main level features a great room, an expansive kitchen, large island with seating for 6, a private office or formal dining room, and a luxurious primary suite complete with a walk-in closet and laundry. The spa-inspired ensuite bath includes a spacious steam shower with dual shower heads and jetted soaking tub. The fully finished walk-out lower level expands the home's possibilities with a dedicated media/theater room, an additional family room with kitchenette, bedroom and full bath--ideal for guests or extended family. Upstairs, you'll find another comfortable living area, two large bedrooms, a full bath, and an expansive deck where you can relax while enjoying panoramic views.Situated on 2.1 acres, the property features mature landscaping with fruit trees, an expansive lawn, playground, outdoor speakers, and a spacious patio with a fire pit--perfect for entertaining family and friends. Exceptional waterfront amenities include a permanent lakeside deck with seating, storage, and direct swimming access. The deep-water dock features a generous 12 x 20 ft seating area, Jet Ski lift, storage for lake toys, and a boat mooring with room for additional moorings.

15 Sleepy Hollow Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

17 Pepperell Way, York
$1,950,000
4 Beds ⋅ 4 Baths
Nestled privately among the Western Point neighborhood in York, this exquisite residence is a true testament to the elegance of Maine's shingled cottage style, seamlessly combined with modern flair. Spanning 2.63 acres, the property offers a sense of seclusion and tranquility. As you arrive, a pathway from the three-car garage leads you to impressive granite stone steps, highlighting the superior craftsmanship evident throughout the residence. Built in 1989, among the thoughtful renovations, recent updates to the kitchen and primary suite create a luxurious and inviting atmosphere. The heart of the home is a chef's kitchen with custom-built cabinetry, white quartz countertops, an eight-burner range with double ovens, and radiant heat underfoot. The L-shaped breakfast nook, with its built-in seating, invites family gatherings. Step into the great room, a stunning two-story space that captivates with its sophisticated details with access to the awning-covered bluestone patio overlooking perennial gardens and the fenced backyard. The great room and adjoining media room feature custom cherry bookcases and cabinetry, anchored by twin stone wood-burning fireplaces. The primary suite wing offers a serene retreat, complete with cathedral ceilings, access to a private patio, and a custom walk-in closet. The pièce de résistance is the remodeled spa-like bath. Here, the interplay of warm-toned vanities against striking green tile, and a herringbone marble floor is captivating. An inviting freestanding soaking tub beckons relaxation, while exposed plumbing enhances the contemporary design of the freestanding shower. Two staircases lead upstairs to the three guest rooms, one ensuite, plus an art studio/office overlooking the great room. A finished room on the third level makes for a terrific gym. At the rear of the home are thoughtfully designed outdoor spaces including a bluestone terrace, established perennial gardens, elegant hardscaping, and a charming garden shed.

17 Pepperell Way, York

Listing courtesy of Anne Erwin Sotheby's International Realty. 207-363-6640

5 Salem St, Portland
$1,774,000
4 Beds ⋅ 4 Baths
A rare opportunity to own a truly distinctive contemporary residence in Portland's coveted West End, now newly priced. Custom-built with an emphasis on architecture, natural light, sustainability, and year-round comfort, 5 Salem Street is a one-of-a-kind home unlike anything else on the Peninsula. Be sure to watch the new property film to experience the architecture, light, and exceptional indoor-outdoor living this home offers. Designed across three levels, the home features 3 bedrooms, 2 full baths and 1 half bath, soaring ceilings, dramatic translucent elements, and a striking two-story light shaft that fills the interior with natural light. Therma-Steel insulated panels, Marvin windows, Boral siding, and Azek trim contribute to its energy efficiency and distinctive design. The spectacular 2026 kitchen features rift-cut oak cabinetry, integrated storage, a statement island, paneled refrigerator, black granite countertops and backsplash, and premium Thermador appliances, including a new natural gas range. An appliance garage, coffee station, custom dining credenza, motorized blinds, and new washer and dryer add thoughtful function. The top floor is crowned by a sun-drenched winter garden beneath skylights and a translucent roof system, capturing abundant natural light and glimpses of Casco Bay. Six covered porches extend the living space outdoors, while an enclosed backyard provides rare private outdoor space. The ground level includes a studio with kitchen, full bath, private entrance, and outdoor space- offering flexibility for guests, a home office, creative studio, or rental use. A climate-controlled garage is a rare Peninsula amenity. Just moments from Portland's restaurants, the Old Port, and waterfront, 5 Salem Street offers an extraordinary opportunity to own a modern architectural masterpiece in one of Portland's most desirable neighborhoods.

5 Salem St, Portland

Listing courtesy of Peninsula Real Estate LLC.

4 Ledge Rd, Cumberland
$2,575,000
5 Beds ⋅ 5 Baths
Welcome to 4 Ledge Road, located on one of the most picturesque streets in Cumberland Foreside, running parallel to Casco Bay and offering exceptional water views and access, this impeccably maintained 5-bedroom, 4.5 bath home is perched on an elevated lot, blending coastal beauty with thoughtfully designed spaces for everyday living and entertaining. Inside, this sun filled home reveals itself with a sense of warmth and connection. The main level features a front-to-back living room, an updated custom kitchen , along with a dining area, spacious family room, and versatile bonus room with vaulted ceilings. The upper levels feature the primary suite, along with 2 additional bedrooms. The finished lower level features the 5th bedroom, a full bath, and provides additional space for recreation, hobbies, or a home gym. Offering flexible living options, this home provides generous space for guests, work-from-home needs, or multi-generational living. Step outside to the expansive front porch to take in the sweeping water views or unwind on the covered back patio overlooking beautifully landscaped grounds, including hidden garden areas, stone pathways, and landscaping beds all enhanced by an irrigation system. A 4-car garage offers ample storage for vehicles and outdoor gear. With deeded beach access, this impressive property offers a rare opportunity to enjoy the very best of coastal Maine living.

4 Ledge Rd, Cumberland

Listing courtesy of Town & Shore Real Estate. 207-773-0262

57 Andersen Rd, Raymond
$2,200,000
3 Beds ⋅ 3 Baths
Sebago Lake Life! This state-of-the-art retreat awaits its new owners. Formed 14,000 years ago by retreating glaciers, this extraordinary setting of granite boulders and pristine shoreline frames Maine's 2nd-largest lake. Built into that landscape in 1984, the home has been thoughtfully enhanced during the current owner's stewardship with purposeful, creative improvements that honor both the architecture and its remarkable surroundings.Among them are structural steel beams reinforcing the cantilevered design, high-end HVAC, an on-demand water-cooled generator, new balconies and stairs, custom railings, roof, and electric skylights with rain sensors - bringing together innovation, comfort, and craftsmanship. Throughout the home, artful interiors flow seamlessly into the landscape, while an exterior staircase with balconies and decks cascades through the boulders to the waterfront below.A newly designed front entry opens to a practical mudroom before unfolding into the main living space, where a chef's kitchen, informal dining area, and inviting sitting room are all oriented toward the panoramic beauty of Jordan Bay. This level also includes a guest bedroom, bath, and laundry. Above, the cathedraled primary suite is a private sanctuary overlooking the lake, complete with a spa-inspired bath. Below, a fireplace living area leads to the lower level, designed for effortless lakeside living, featuring a kitchenette, a full bar, and a Murphy bed for family and guests.At sunrise, the home is bathed in light from every angle, with the calm inlet shimmering just beyond and the surrounding landscape revealing its quiet magic. Don't miss the moss heart accents on the boulders. Three docks create your waterfront experience, from swimming and boating to rowing, kayaking, or simply relaxing. Completing the property is a garage with a fully equipped 579-square-foot studio apartment above, also with HVAC, along with ample electrical capacity for a true workshop.

57 Andersen Rd, Raymond

Listing courtesy of Legacy Properties Sotheby's International Realty.

3 Morning St, Scarborough
$3,450,000
3 Beds ⋅ 3 Baths
Rare opportunity to own one of Higgins Beach's most iconic oceanfront residences, offering breathtaking panoramic views stretching from Cape Elizabeth and Richmond Island to Biddeford Pool. Featured in Maine Home + Design, this exceptional coastal retreat was thoughtfully reimagined to blend timeless New England architecture with sophisticated seaside living. Perfectly positioned on a rare double lot in one of Maine's most coveted beachfront communities, the home captures the beauty of the Atlantic from nearly every room. Expansive walls of glass frame ever-changing ocean vistas, flooding the interiors with natural light and creating a seamless connection to the surrounding landscape. Custom millwork, carefully curated finishes, and impeccable craftsmanship are showcased throughout, while multiple gathering spaces provide the perfect setting for both relaxed family living and effortless entertaining. Step outside to enjoy the sights and sounds of the ocean, with direct access to Higgins Beach and endless opportunities for swimming, surfing, beach walks, and coastal exploration. Whether enjoying sunrise over the water, watching boats pass along the coastline, or entertaining guests against a backdrop of spectacular ocean views, this home offers a lifestyle that is truly unparalleled.. A once-in-a-generation offering, this extraordinary property combines privacy, architectural significance, and an irreplaceable oceanfront setting in one of Maine's most treasured seaside neighborhoods.

3 Morning St, Scarborough

Listing courtesy of Legacy Properties Sotheby's International Realty.

386 Lake House Rd, Naples
$2,295,000
6 Beds ⋅ 4 Baths
Discover a rare 10+ acre waterfront property encompassing two separate residences with over 1,400 feet of frontage on Sebago Cove, offering exceptional privacy and direct access to Sebago Lake. The main residence showcases a modern passive solar design with striking post-and-beam construction, featuring 3 brms and 2 full bths. A dramatic iron spiral staircase adds architectural character, while the open-concept kitchen features high-end appliances, a waterfall island, and expansive views of the cove through oversized windows. Radiant flr heating throughout provides year-round comfort. The 1st floor primary suite offers a spacious en-suite bath. The walk-out lower level features a large family rm that opens directly onto an expansive patio--perfect for outdoor dining, relaxing in the hot tub, or stepping into the yard for easy access to wooded trails and the shoreline. A beautifully converted post-and-beam barn serves as a separate guest cottage with 3 brms and 2 full bths. A custom-crafted staircase built from oversized solid wood planks creates a stunning focal point, while natural wood walls fill the space with the rich character. An inviting loft den centered around a freestanding gas stove, its own outdoor hot tub beneath the covered porch, and a welcoming fire pit gathering area beside the full glass garage door seamlessly blend indoor and outdoor living. Currently operating as a successful Airbnb, the property offers the opportunity to continue the established vacation rental business and branding or transform it into an extraordinary private estate. Offered fully furnished, the sale also includes a dock, kayaks, and paddleboards, allowing you to begin enjoying the waterfront lifestyle immediately. This is a truly one-of-a-kind offering where privacy, waterfront living, proven rental income, exceptional future development potential, and the serenity of nature come together on the shores of Sebago Cove.

386 Lake House Rd, Naples

Listing courtesy of Waypoint Brokers Collective. tyson@waypointbrokers.com

19 Tiger Lily Ln, Cape Elizabeth
$2,995,000
7 Beds ⋅ 9 Baths
Nestled within Cape Elizabeth's desirable Cross Hill neighborhood, 19 Tiger Lily Lane is a remarkable estate property. Built by renowned Maine custom builder Russ Doucette, this exceptional residence showcases timeless craftsmanship, architectural elegance, and meticulous attention to detail throughout. Privately situated on 1.65 acres of beautifully landscaped grounds, the home offers thoughtfully designed living spaces featuring six bedrooms, multiple gathering areas, and luxury amenities designed for both comfortable family living and sophisticated entertaining. The shingle-style architecture reflects classic New England charm, while the interior blends warmth and refinement with truly custom millwork, expansive living spaces, and high-end finishes. The backyard is a private oasis, its deck overlooking an in-ground gunite pool and spa, surrounded by beautiful hardscaping and mature landscaping creating a secluded retreat. A charming carriage house further enhances the property, offering guests a private residence complete with a full kitchen, living room, and separate bedroom. Thoughtfully designed with one-of-a-kind finishes, every element of this exceptional property reflects a commitment to quality, comfort, and privacy. Ideally located just minutes from Cape Elizabeth's scenic beaches, the Portland International Jetport, and Portland's acclaimed culinary, arts, and cultural destinations, this home offers the perfect blend of convenience and coastal elegance. A rare offering in one of Southern Maine's most sought-after communities, this is an extraordinary place to call home.

19 Tiger Lily Ln, Cape Elizabeth

Listing courtesy of Legacy Properties Sotheby's International Realty.

1 River Rd, Kennebunkport
$2,150,000
4 Beds ⋅ 3 Baths
PEAR TREE FARM is a rare opportunity to own a distinctive circa-1800 farmhouse set on nearly an acre in one of Kennebunkport's most desirable locations. Overlooking the fairways of Cape Arundel Golf Club and just a short distance from Dock Square, the property offers privacy, character, and exceptional potential. The current owner has thoughtfully demonstrated what is possible through the renovation of the primary suite, featuring vaulted ceilings, exposed beams, a beautifully appointed bath, and updated heating and cooling. Additional improvements include a charming covered entry with an oversized custom Dutch door, an updated wet bar, and three mini-split systems providing efficient heating and air conditioning. Rich with original architectural details, multiple fireplaces, exposed brick, and period craftsmanship, the home is ready for its next steward to continue the restoration and modernization while preserving its historic character. With four bedrooms, three bathrooms, and flexible living spaces, the possibilities are substantial. A defining feature of the property is the remarkable barn, offering approximately 2,500 square feet of open space on the main level, additional loft space above, and drive-in access below. Whether envisioned as an entertaining venue, workshop, studio, collector's space, or future enhancement opportunity, the barn is a truly exceptional asset. For buyers with vision, Pear Tree Farm presents the opportunity to create significant value while enjoying golf course views, western sunsets, walkability to town, and the timeless charm of one of Kennebunkport's historic homes.

1 River Rd, Kennebunkport

Listing courtesy of Keller Williams Realty.

190 Mills Rd, Kennebunkport
$4,999,000
4 Beds ⋅ 4 Baths
Welcome to a truly one-of-a-kind property where history, character, and opportunity come together across more than 37 acres of breathtaking coastal countryside. Ideally located between the charming fishing village of Cape Porpoise and the sandy shores of Goose Rocks Beach in Kennebunkport, this exceptional estate offers a rare chance to own a generational property with multiple residences, expansive acreage, and future potential in one of Southern Maine's most desirable coastal settings. At the heart of the property sits a charming antique farmhouse featuring 4 bedrooms, oversized living spaces, beautiful, beamed ceilings, and three fireplaces that create warmth and timeless character throughout. Rich in history and architectural detail, the home offers the perfect blend of rustic charm and comfortable living. Complementing the main residence are two separate guest cottages, ideal for extended family, guests, rental income, or caretaker accommodations. One cottage offers a cozy one-bedroom layout, while the second provides two bedrooms and additional flexibility for a variety of uses. A substantial barn adds even more possibilities, whether for agricultural pursuits, storage, workshops, events, hobbies, or future creative ventures. The 37+ acre setting is truly remarkable, featuring open fields, natural landscapes, and small development potential for those seeking to explore additional opportunities. Enjoy peaceful marsh views and distant ocean vistas that provide a stunning backdrop, and a sense of privacy rarely found in such a convenient coastal location. Whether you envision a family compound, working farm, investment property, hospitality venture, or a private retreat to be enjoyed for generations, this extraordinary offering presents a unique opportunity to create your legacy in Kennebunkport's coveted coastal corridor.

190 Mills Rd, Kennebunkport

Listing courtesy of Pack Maynard and Associates.

547 Congress St Unit 6, Portland
$2,950,000
2 Beds ⋅ 3 Baths
Welcome to The Penthouse on Congress--an incredible opportunity in the heart of downtown Portland's Art District, with 360-degree views of the ocean to the mountains, architectural pedigree, and elevated design converge. Set on the top three levels of The Winslow Lofts, this residence lives like a work of art--layered in natural materials, bathed in light, and framed by the ever-changing beauty of the water beyond. Soaring ceilings and dramatic floor-to-ceiling windows create an immediate sense of scale, drawing the outdoors in and showcasing panoramic views of Casco Bay from the main living space. A striking fireplace anchors the room, adding warmth and intimacy to an otherwise expansive, light-filled setting--perfect for both quiet evenings and unforgettable entertaining. The primary suite is a true retreat, offering tranquil water views over Back Cove, a private balcony, a generous walk-in closet, and a spa-like bath with radiant heat floors, designed for indulgence. A second fireplace adds an additional layer of comfort and romance, making this suite feel like a boutique hotel sanctuary high above the city. Arrive via a secure elevator, underscoring the exclusivity and ease of penthouse living. Two dedicated parking spaces--including one within a heated garage--complete the offering, a coveted amenity in downtown Portland. This is not just a residence--it's a statement. A true penthouse lifestyle defined by privacy, design, and breathtaking vantage points. From intimate evenings by the fire to unforgettable gatherings on the rooftop deck with city and water views, this home offers a front-row seat to Portland's most iconic scenery. A living art piece suspended above the city, where luxury, light, and location converge.

547 Congress St Unit 6, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

1 Colonial Mast Rd, Naples
$9,800,000
4 Beds ⋅ 1 Baths
A truly rare offering, this 117± acre waterfront estate presents a once-in-a-generation opportunity on the shores of Maine's highly sought-after Long Lake. Currently operated as the family-owned Colonial Mast Campground for 48 years, the property boasts more than 2,500 feet of pristine waterfront, expansive sandy beaches, and an extensive docking system with 72 boat slips. Licensed for 110 RV campsites, including some year-round sites, the property features an impressive collection of existing infrastructure, including an indoor pool facility, camp store with commercial kitchen, recreation hall, bathhouse, garages, and a waterfront owner's residence. Many of these structures are grandfathered within the shoreland zone, creating significant value and flexibility that would be difficult to replicate today. With over 7,000 feet of combined road frontage along Kansas Road, Bove Road, and Colonial Mast Road, this property offers exceptional access and development potential. Whether envisioned as a continued campground operation, a large-scale residential development, a luxury waterfront community, or an extraordinary private family compound, the possibilities are unmatched. Enjoy direct access to 11 miles of boating and recreation on Long Lake, with navigable access to Brandy Pond and Sebago Lake. Ideally located in the heart of Maine's Lakes Region, the property is just minutes from the Naples Causeway, 15 minutes to Pleasant Mountain Ski Resort, and only 45 minutes from Portland. Opportunities of this scale, with this amount of waterfront, acreage, infrastructure, and development potential, rarely come to market. Own one of the largest and most significant waterfront properties in the Lakes Region to hit the open market.

1 Colonial Mast Rd, Naples

Listing courtesy of Oberg Insurance & Real Estate Agency, Inc..

37 Alliquippa Rd, Phippsburg
$4,690,000
6 Beds ⋅ 5 Baths
A rare and truly generational opportunity to own an extraordinary piece of Maine's coastline, this exceptional oceanfront estate offers the chance to create a lasting legacy for years to come. Perched high above the rugged rocky shore, the property commands glorious southwesterly views and unforgettable sunsets over the water. Encompassing nearly 8 acres of remarkable privacy, the setting is nothing short of extraordinary, with a sandy beach, deep-water dock, and sweeping ocean vistas. The magnificent shingle-style residence is a timeless expression of Maine coastal architecture, distinguished by impeccable craftsmanship and enduring materials. Stucco and hand-selected stonework lend character and distinction to the façade, while a grand stone chimney anchors two wood-burning fireplaces, creating inviting spaces for gathering in every season. With six bedrooms and five beautifully appointed bathrooms featuring custom tilework and refined finishes, the home is thoughtfully designed for comfortable living and entertaining. The main-floor primary suite offers a private retreat, while expansive living spaces are filled with natural light and framed by panoramic ocean views. Here, the true luxury extends beyond the home itself. It is the opportunity to spend summers on the beach, launch a boat from your own deep-water dock, gather around the fire on cool coastal evenings, and create cherished memories and traditions that endure for generations. Every detail reflects a commitment to quality, from the exceptional construction and bespoke finishes to the seamless connection between indoor living and the spectacular natural surroundings. Despite its extraordinary privacy, the estate is just minutes from the restaurants, shops, and amenities of Bath, with the treasured Small Point community and Popham Beach nearby. Properties offering this rare combination of oceanfront beauty, acreage, privacy, and a legacy-quality residence seldom come to market.

37 Alliquippa Rd, Phippsburg

Listing courtesy of Town & Shore Real Estate. 207-773-0262

66 Dans Cottage Rd, Bristol
$1,900,000
2 Beds ⋅ 2 Baths
Stunning ocean front property! Watch fishing boats work and enjoy views out to Monhegan Island. At night you'll see lighthouses in the distance and stars in the sky over the ocean. This beautiful summer cottage is at the end of a peaceful road on ''the jagged edge of America''. Included is deeded access to a deep water dock in protected Back Cove and a quarter interest in Little Island just off shore. Completely updated and refurbished in 2014, the interior has been simply and tastefully decorated and is designed to accomadate gatherings but at the same time comfortable for when you don't have company. The Primary Suite has ocean views to wake up to as does the open concept Living/Dining Room and Kitchen. The second bedroom and office are at the back of the cottage. There is a large garage for cars or boat storage and a delightful outdoor shower. Although the property shares a driveway with a neighboring cottage, privacy is almost complete. Very well maintained and ready for you to enjoy this season.

66 Dans Cottage Rd, Bristol

Listing courtesy of Keller Williams Realty.

251 Mount Pleasant St, Rockport
$2,795,000
3 Beds ⋅ 4 Baths
New Photos! New Matterport Virtual Tour! Perched atop Spruce Mountain, this stunning estate commands a phenomenal, nearly 360-degree panorama where the world unfolds before you: Penobscot Bay and its islands, Cadillac Mtn, the Presidential Range and Mt Washington. The architecturally dramatic interior seamlessly blends fine craftsmanship with a view-drenched open floor plan centered around a soaring, fitted-stone hearth with two gas fireplaces and an authentic wood-burning pizza oven. This striking focal point is surrounded by a well-appointed kitchen and flowing living spaces, all framed by vast banks of windows. Whether watching boats sail the bay, clouds blanket the islands below, satellites trace the Milky Way, or a winter storm march across the viewscape, every vista is captivating. The luxurious primary suite boasts a spa bath and expansive walk-in closet. Glass sliders lead to the hot tub and deck, nestled amid stone outcrops. The upper level with full bath features a large, open space currently used as an airy bedroom—though it is equally well-suited as an inspiring studio or creative retreat overlooking the living areas below. An open bridgeway leads to a guest bedroom with private balcony. The lower level provides both formal and casual entrances with garage access. A powder room, sauna, recreation room, workshop and storage. Designed for longevity, the main open-well central staircase is built to accommodate a future elevator. Privately nestled just down the driveway, a separate unfinished cottage offers boat storage below and designs for living quarters above. With nearby Camden's restaurants, harbor, lakes, boating, hiking, skiing, the state park, enchanting villages to the north and south, and the convenience of the regional airport just 12 miles away, this exquisite home and setting assure an unparalleled coastal mountain lifestyle. No Drive-bys please.

251 Mount Pleasant St, Rockport

Listing courtesy of Camden Real Estate. info@camdenre.com

49 Ocean Ave, Kennebunkport
$3,495,000
3 Beds ⋅ 4 Baths
Nestled in the heart of iconic Dock Square, this exceptional antique riverfront residence offers a truly rare opportunity to own one of the area's most distinctive and coveted properties. Rich in character and timeless charm, this 3,200± square foot home seamlessly blends historic architectural details with spacious, comfortable living. The residence features three generously sized bedroom suites, expansive gathering spaces, and two fireplaces that create warmth and ambiance throughout the seasons. Antique craftsmanship and period details are showcased throughout the home, while two inviting sunporches and rear deck provide the perfect vantage point to enjoy river views and changing tides. Outside, a quaint riverside backyard offers a peaceful retreat overlooking the water, while the property's private dock provides direct access to the river--a remarkable amenity rarely found in Dock Square. Beautiful curb appeal, mature landscaping, and a one-car attached garage further enhance this special offering. Leave your car behind and enjoy an easy stroll to Dock Square's renowned shops, galleries, restaurants, and waterfront attractions. Combining an unparalleled location, private waterfront access, and authentic antique charm, this is a one-of-a-kind property that seldom becomes available. An extraordinary opportunity to own a landmark riverfront home with a private dock in one of Maine's most sought-after coastal destinations.

49 Ocean Ave, Kennebunkport

Listing courtesy of Pack Maynard and Associates.

2319 Harpswell Island Rd, Harpswell
$2,390,000
5 Beds ⋅ 2 Baths
Privately tucked away on coveted Bailey Island, this exceptional waterfront retreat captures the essence of refined coastal living. Set on a rare parcel with its own beach and extensive ocean frontage, the property enjoys breathtaking 180-degree water views across a protected cove and out to the Atlantic beyond. From its elevated vantage point, the ever-changing seascape becomes the backdrop to daily life, offering a remarkable sense of privacy and connection to the Maine coast. Thoughtfully renovated to blend timeless cottage charm with modern comfort, the home is designed to embrace its extraordinary surroundings. A wraparound porch provides the perfect setting for morning coffee, afternoon sea breezes, and spectacular sunsets over the water. Inside, the residence offers a versatile and inviting floor plan featuring a first-floor bedroom and three additional bedrooms on the second level, including a spacious primary suite with a private balcony overlooking the water--an ideal perch for taking in the coastal scenery. Enhancing the property's appeal is the detached Sea Shed, a charming and flexible space well suited for guests, a studio, home office, recreation room, or additional sleeping quarters. With private beach ownership, direct access to the shoreline, and panoramic coastal views from nearly every angle, this is a rare opportunity to experience one of Maine's most treasured island settings.

2319 Harpswell Island Rd, Harpswell

Listing courtesy of Legacy Properties Sotheby's International Realty.

24 Emerald Point Dr, Frye Island
$2,150,000
4 Beds ⋅ 4 Baths
Where else on Sebago Lake can you enjoy the convenience of a golf cart ride to a championship golf course, pickleball and tennis courts, swimming pool, fitness center, youth summer camp, and athletic fields for baseball, soccer, and lacrosse,all surrounded by breathtaking views of the White Mountains & Mount Washington from the island and wonderful sunrises from property? Start your mornings picking wild blueberries for fresh pancakes before spending the day on the crystal-clear waters of Sebago Lake. This exceptional property offers a rare combination of privacy, luxury, recreation, and investment potential. Set on a spectacular 1.3-acre private lot with 280 feet of pristine lake frontage, the property features its own sandy beach, dock, mooring, and boat lift-creating the ultimate waterfront retreat. The custom-built 4,850-square-foot home is being offered completely furnished and beautifully decorated, allowing you to move in and immediately begin enjoying lake life. Expansive lake views can be enjoyed from nearly every room. The thoughtfully designed interior features a gourmet kitchen with a spacious dining area, a formal dining room for entertaining, a large walk-in pantry, and a built-in butler's pantry. Every detail has been crafted for comfort, functionality, and gathering with family and friends. Outdoor living is equally impressive, with a large patio perfect for al fresco dining, relaxing with a morning coffee, or hosting summer gatherings. As the sun sets, gather around the fire pit for s'mores, stories, and unforgettable evenings under the stars. Whether you're seeking a family retreat, or an investment opportunity, this property offers it all. The extensive amenities available on the island make it one of the most sought-after rental destinations on Sebago Lake, providing exceptional appeal for investors looking to capitalize on the strong vacation rental market. This is more than a home-it's a lifestyle unlike any other on Sebago Lake

24 Emerald Point Dr, Frye Island

Listing courtesy of Sunset Lakes Real Estate.

7 Loon Ln, South Bristol
$2,245,000
3 Beds ⋅ 3 Baths
7 Loon Lane is a classic waterfront property in a peaceful wooded setting, with broad westerly views over the upper branch of the Damariscotta River and south towards the open ocean. Located in a desirable neighborhood enclave in South Bristol, the property includes 4.4± acres, a charming and versatile three-bedroom house, a rustic water's-edge cabin, a one-car garage, and 276± feet of shorefront with a deep-water dock, ramp, and float. The property also offers the potential to add one additional building, such as a guest house or barn, providing flexibility for future use or to create a family compound. The main house is designed for comfortable year-round use, with open living and dining spaces, a stone fireplace, built-ins, sliding glass doors, and a wraparound deck oriented toward the view. A main-floor primary suite with an adjoining office offers flexibility, while the lower level includes two additional bedrooms, a full bath, and a family room. The wooded landscape features lawn and garden areas, mature flowering shrubs, a natural sense of privacy, and a wooden walkway leading to attractive ledge shorefront where there is a rustic water's-edge cabin ready for improvement. With excellent access to the protected harbors, coves, and sailing waters of the Damariscotta River and Midcoast Maine, the property offers a rare combination of privacy, acreage, shorefront, and deep-water access in one of South Bristol's most sought-after neighborhoods.

7 Loon Ln, South Bristol

Listing courtesy of LandVest, Inc..

866 Pendleton Point Rd, Islesboro
$5,750,000
6 Beds ⋅ 9 Baths
East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands. The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication. Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite with a private sitting room and office, multiple guest suites, inviting sitting rooms, a library, additional office spaces, a wine cellar, exercise room, updated mechanical systems, air conditioning, a generator, and a carport. The outdoor amenities are equally impressive. A heated swimming pool, hot tub, and sauna are perfectly positioned to maximize the breathtaking waterfront setting and views, while a custom-built staircase provides direct access to the property's private beach. Evoking the charm and grandeur of Islesboro's historic summer cottages, East Bay is a rare legacy property--an extraordinary expression of Maine's rugged coastal beauty, enduring craftsmanship, and timeless elegance. Explore the 3D tour and floor plans for a fully immersive experience of this remarkable estate.

866 Pendleton Point Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

914 Union Rd, Appleton
$1,500,000
2 Beds ⋅ 2 Baths
Set amid the rolling countryside of Appleton, this remarkable 142-acre property captures the core essence of Maine living. A diverse landscape unfolds across open vistas, sweeping meadows, and mixed-species forests, creating a setting rich in natural beauty, wildlife, and year-round recreational opportunities. The land stretches to approximately one-half mile of frontage along the St. George River and includes another 500 ft of frontage on Sennebec Pond--a picturesque shoreline perfect for swimming, paddling, fishing, or simply enjoying the tranquility of the water. Perched prominently above the forests and meadows is a gentleman's hunting and fishing camp, built in the 1990s. Thoughtfully sited to take advantage of the property's commanding vantage point, the camp serves as an ideal retreat for sportsmen, outdoor enthusiasts, or those seeking an escape into the natural world. The barn provides additional utility for equipment storage, agricultural pursuits, or future expansion of the property's capabilities. Whether envisioned as a private family compound, sporting retreat, working farm, or legacy estate, this extraordinary holding offers a rare combination of acreage, water frontage, recreational amenities, and scenic beauty in the Midcoast Maine rolling hills. This is a place where fields meet forest, river meets pond, and generations of memories await.

914 Union Rd, Appleton

Listing courtesy of Legacy Properties Sotheby's International Realty.

1 Fieldstone Estates Rd, York
$1,795,000
3 Beds ⋅ 2 Baths
Seller will be doing a leaseback as his new construction will be completed in Spring 2027. Originally constructed in 1998 and purpose-built to accommodate both residential occupancy and commercial operations, this unique property provides outstanding flexibility. The residential portion of this unique property provides a warm and inviting living environment thoughtfully designed for comfort, functionality, and flexibility. Finished with pine flooring throughout, the home showcases rustic character and craftsmanship, highlighted by custom wainscoting in the den and abundant natural light from multiple skylights. This well-functioning kitchen features granite countertops, ample cabinetry, and a full complement of appliances, creating an ideal space for both everyday living and entertaining. A wood-burning stove provides warmth and ambiance in the main living area, while central air conditioning ensures year-round comfort throughout the home. The custom-designed bathroom has been thoughtfully upgraded in 2018 with an oversized walk-in shower, bidet, and quality finishes that reflect the owner's attention to detail. The upper levels provide 3 bedrooms, full bath, generous living space, laundry facilities, and flexible areas well suited for home offices, hobbies, guests, or creative pursuits. Extensive improvements over the years include a new roof, upgraded HVAC systems, replacement water heater, and continued maintenance throughout ownership. Combining comfort, character, and versatility, this distinctive residence presents a rare opportunity to enjoy spacious living accommodations with the added benefit of exceptional mixed-use flexibility. The commercial space is currently zoned R1-3. The first-floor features four workshop/commercial spaces and a dedicated shipping and receiving bay with oversized garage door access. The building is serviced by three-phase power, municipal water, central air conditioning, and a buried 500-gallon propane tank.

1 Fieldstone Estates Rd, York

Listing courtesy of Gosselin Realty Group.

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