luxury real estate for sale Brooksville, United States

Discover an exceptional coastal compound on the peaceful north end of Islesboro, where expansive acreage, shoreline access, and privacy come together in a truly uncommon offering. Spanning 13 acres with approximately 514 feet of open waterfront, the property provides direct, easy access to the beach without stairs. Abutting conservation land and reached by a long private drive, the setting feels secluded and removed from the everyday. At the heart of the compound is a beautifully threebedroom crafted log-style residence completed in 2025. The approximately 2,200-square-foot home combines rustic warmth with a bright, contemporary layout. Adding another dimension to the property is the original 1968 residence, a comfortable fourbedroom, two-bath home designed for year-round use. All of the living space is conveniently located on a single floor, and the home retains plenty of character. There is a separate two-car garage provides ample room for vehicles, equipment, and storage, as well as a boat house. Outdoor living is an integral part of the compound. A covered porch and waterside fire pit provide inviting places to gather, unwind, and enjoy the shoreline. Both residences have fenced yards with gated paths leading directly to the beach. For those interested in gardening or a more self sufficient lifestyle, the property also includes a newly installed greenhouse and 10 young fruit trees. With two distinct homes, substantial acreage, protected surroundings, and rare open waterfront, this Islesboro compound offers remarkable versatility for extended family, private retreats, and generations of shared summers. Offered separately. See MLS 1679400 & 1679401.

Discover a private coastal escape on the quieter northern end of Islesboro, where expansive acreage, immediate waterfront access, and new construction come together in an exceptional setting. The property encompasses eleven acres with approximately 260 feet of shoreline, offering the rare convenience of level access to the beach directly from the groundsno stairs or difficult terrain required. Completed in 2025, the 2,200-square-foot log-style residence was designed to make the most of its natural surroundings. The heart of the home is an airy kitchen and living space defined by soaring cathedral ceilings and a broad expanse of windows that captures abundant daylight and views toward the water. A covered rear porch extends the living area outdoors, providing an inviting place to gather while overlooking the shoreline. Two bedrooms are located on the main level, including a generous primary suite with a walk-in closet and direct access to a screened porch. Upstairs, a spacious third bedroom and private bath provide comfortable accommodations for visitors or family members. Privacy is a defining feature of the property. The home is reached by a lengthy private drive, creating a peaceful sense of separation from the surrounding island community. A recently completed detached garage with room for two vehicles adds valuable storage and everyday functionality. Offered as a move-in-ready waterfront property, this Islesboro retreat combines contemporary comfort with the timeless appeal of island living. An expanded 13-acre purchase is also available for those interested in creating a larger family compound or multi-generational estate. That offering includes an additional four-bedroom, year-round residence, providing an uncommon opportunity to establish a substantial private coastal property.

Set on two private acres on the northeast side of Islesboro, this thoughtfully updated coastal retreat offers an idyllic setting overlooking East Penobscot Bay. Originally conceived as a classic Maine camp, the property has evolved into a comfortable four season home that combines its original character with the conveniences of modern island living. The single-story interior is designed for easy everyday living, centered around an inviting open living space and framed by a dramatic glass enclosed entry. Beyond, a covered porch provides an exceptional spot to take in the water views and enjoy the changing landscape throughout the seasons. The home includes four bedrooms, including a bright built-in bunk room, along with two full bathrooms. Practical updates include a new washer and dryer and 1GB high-speed internet. The waterfront setting is equally appealing. A gradual path leads toward the shore, creating an easy place to launch a kayak, swim, or simply spend time beside the bay. Above the approximately 120+/- foot long seawall, a stone terrace and fire pit provide a natural gathering place for long afternoons, evening fires, and waterfront dinners featuring lobster from the local fleet. The grounds have been designed with both recreation and privacy in mind, including a fenced area. Just across the driveway, a substantial boathouse and workshop offer ample room for equipment and storage, with ceiling mounted hoists making it convenient to store kayaks and smaller boats. Additional improvements include a recent property survey along with enhancements to the easement and driveway. Located on peaceful Pripet Woods Lane, the property enjoys a quiet, low-traffic setting with nearby access to Islesboro Island Trust trails. Private, waterfront, and surrounded by the natural beauty of coastal Maine, this is an inviting island escape with the flexibility to serve as a seasonal getaway or a year-round home. Septic not designed for 4 bedrooms.

The Bluff House is a gracious 19th Century Greek Revival ship captain's house, set high on the north end of the island with inviting views over its nearly 18 private and mostly wooded acres with trails leading to over 700 feet of sandy beach on the eastern shore of Islesboro. As the back of this stately home opens to a sprawling lawn with the views over tree tops east to Penobscot Bay, the Bluff House's privacy, quiet neighborhood, and bucolic feel beckon a time long ago. Set up island, this home is in close proximity to the island's community center, places of interest, and activities. This 1800's, 4 bedroom, 3 bath property has many renovations and updates complete with new engineered European White Oak flooring, new structural support system under the kitchen, new lighting in the kitchen and bathrooms, and new plumbing stubbed and ready to go. Currently the kitchen and two of the bathrooms are ready for your own touch and completion! There are generous yet comfortable spaces to enjoy - family room, living room, dining room, library/study - at the Bluff House with its architectural elements echoing an age of simplicity and elegance, while its systems and structures have been updated during thoughtful and meticulous renovation creating a distinguished, historic home of notable character with modern convenience, including a two car garage - with sub flooring in place and could be finished as an office, studio, or other space -, 10kw generator, and high speed internet. A perfect island home ready for year round living or seasonal retreat.

Experience the magic of coastal living at this seasonal camp, set on 7 acres of level land and offering 1,400 feet of accessible shoreline and beach. Whether you choose to enjoy the camp as it is or build your dream retreat, this property provides the ideal setting to enjoy island life. Imagine long summer days filled with swimming, boating, and beach combing, capped off by breathtaking sunsets over the water. When you're ready to explore, take a stroll up the beach to Islesboro Island Trust's Turtle Head Preserve, where rocky cliffs, panoramic views, and fascinating geological history await. Or head out to explore all the island has to offer. The property is being offered as is.

Set atop the sought-after heights of Caterpillar Hill, this exceptional 20? acre estate enjoys sweeping views across Eggemoggin Reach and offers a rare combination of privacy, acreage, and timeless Maine craftsmanship. Built by acclaimed local builder Michael Hewes, the residence encompasses over 3,800? square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, and 2 half baths across three levels. The home's dramatic central staircase and soaring wall of glass frame water views and fill the interior with natural light. A large ceiling fan keeps the main living cool during the summer months. Rich wood finishes, custom built-ins, and warm architectural details create an inviting atmosphere throughout. Multiple living and entertaining spaces include formal and informal gathering rooms, a dining room, library, and lower-level recreation room, offering flexibility for both everyday living and hosting guests. The spacious primary suite provides a private retreat with elevated views, while additional bedrooms and guest accommodations comfortably welcome family and friends. Radiant heat, extensive storage, and an attached two-car garage provide year-round comfort and functionality. Outside, the landscape captures the essence of Downeast Maine with a blend of open meadows, mature forest, and established blueberry grounds. Stone walls, multiple decks, and a screened porch create inviting spaces to enjoy summer sunsets over Eggemoggin Reach, abundant wildlife, and the changing seasons. A few minute drive to the public beach and boat launch at Walker Pond offer easy access to swimming, fishing, kayaking, and boating throughout the summer season. Perched high above the coast, the property offers remarkable privacy while embracing the beauty of its natural surroundings. Located just minutes from the villages of Sedgwick, Blue Hill, and Deer Isle, this custom and private estate places world-class sailing, protected harbors, acclaimed arts communities.

Rarely does a property like this become available in Islesboro's storied and much-loved summer colony, Sabbathday Harbor. Perfectly sited, up high on the shores of East Penobscot Bay, this classic cottage offers sweeping easterly water views extending to Cape Rosier and approximately 100 feet of bold, accessible shoreline. The first floor features a living room with a wood stove and doors that open to a spacious water view deck, a functional galley kitchen, and a full bath. The generous wrap-around deck provides the perfect vantage point for sunrise coffee, afternoon reading, or evening gatherings with the bay as your backdrop. Upstairs, three charming bedrooms capture the light and sea breezes. A separate simple structure could make for a fun getaway space. Steeped in tradition and rich in natural beauty, this property invites you to create lasting memories for generations to come in one of Maine's most cherished summer enclaves.

Perched above the timeless beauty of Snow's Cove, this exceptional one-acre homesite offers an opportunity to create a bespoke coastal Maine retreat in a truly captivating setting. Fully surveyed and soils tested, the property is thoughtfully prepared for future development and enjoys sweeping views across iconic blueberry barrens, with the potential for seasonal water vistas beyond. Just minutes from the village of Blue Hill, one of Maine's most cherished coastal communities, residents will enjoy convenient access to fine dining, local markets, art galleries, boutique shopping, healthcare services, and a vibrant year-round cultural scene. Whether envisioned as a private sanctuary or a legacy property for generations to come, this offering embodies the tranquility, natural beauty, and authentic character that define Downeast Maine. Build your dream home and experience a lifestyle shaped by open skies, coastal breezes, and the enduring charm of Blue Hill Peninsula living.

On an island in Maine sits this sweet cottage with room to expand or build on the elevated point looking West over Penobscot Bay. Explore 14 acres and 1,288 feet of shore front and beach.

This three-bedroom, two-full-bath property features an updated and remodeled kitchen and bathrooms. Additional highlights include a wood stove for supplemental heating, a whole-house generator, and a private deck offering peaceful field views with Blue Hill Mountain as the backdrop.The home is conveniently located near Blue Hill, Bucksport, and Castine, with numerous hiking and water recreation opportunities nearby.

From the moment you enter the main house, you see views of the Benjamin River and Eggemoggin Reach. These 2 beautifully landscaped homes provide rental opportunities and histories in both AIRBNB for the Cottage and local rental markets for the Main House. They were originally purchased for rentals and that lasted until the owner fell in love with them and moved in 2020 for a full-time life in Maine. The Main House has a spacious chef friendly kitchen, dining room and 4 separate sitting areas, a library, living room, sitting room and studio that allow a number of people to be in the home and find private space. 3 bedrooms, with the studio as a possible 4th, make it a wonderful place to have guests. The kitchen addition has radiant floor heating and is quite welcoming on colder days. The Cottage is also the perfect place to put family or guests so that they have their own space and can open and close their days on their own. It is a favorite on AIRBNB since 2019 with a 4.94 rating. If income is an issue, this provides a great option. The houses can be sold with most of the furnishings, excluding art, if so desired. The property is being sold 'As Is' and the homes have both been cared for by the best contractors you can find in the area. The owner has been intent old into easy.

Nestled in a serene countryside setting, this expansive 10 acre parcel of land offers the perfect blend of tranquility and convenience. Located just a short drive away from the charming towns of Brooklin, Blue Hill, and Deer Isle, this property provides easy access to a variety of amenities while still maintaining a sense of seclusion. As you step onto the land, you'll be greeted by a picturesque landscape that showcases its natural beauty. Towering trees create a peaceful and private atmosphere, making it an ideal retreat for those seeking solace. Imagine waking up to the gentle sounds of nature, sipping your morning coffee on a sun-drenched porch, and enjoying views of the surrounding landscape. The property boasts ample space for various outdoor activities, whether you're looking to build your dream home, set up a garden, or simply enjoy the great outdoors. With its generous size, this land presents endless possibilities for building your dream home or creating a serene getaway. If you're looking to escape the city permanently or seeking a peaceful retreat for weekends and holidays, this 10 acre parcel of land offers the perfect canvas for creating your own slice of paradise. Don't miss out on this opportunity to own a piece of tranquility in this sought-after location.

Commanding extraordinary ocean views across the Benjamin River and Eggemoggin Reach, this newly constructed hilltop coastal residence pairs refined design with more than five private acres with flexibility for modern Maine living.Thoughtfully designed with fine finishes, high-end appliances, and energy-efficient systems, the three-bedroom, three-bath home offers generous, light-filled spaces oriented toward the surrounding landscape and water. The main level features an expansive open living, dining, and kitchen area, along with a first-floor guest bedroom and full bath. A covered porch extends the living space outdoors, providing a peaceful vantage point for watching abundant birdlife and wildlife while taking in the ever-changing river views.Upstairs, the primary suite is a private retreat with an en-suite bath and walk-in closet, complemented by conveniently located second-floor laundry.Adding to the property's appeal is the original 2017 structure, now completely transformed to incorporate a one-bedroom apartment with additional finished space into the newly finished addition. This flexible configuration allows the property to function beautifully as a single-family residence, accommodate extended family and guests, or provide the opportunity to live in one portion while generating rental income from the other.Walk to the public boat dock. The Town of Sedgwick offers mooring permits.Privately situated and designed for comfortable year-round living, this distinctive Benjamin River ocean view property brings together new construction, elevated finishes, modern efficiency, remarkable water views, and uncommon versatility.

An Island Life with Room to Create | Come to Islesboro and live a little differently. Long known for its thriving arts community, the island offers a blend of creative energy, natural beauty, and a welcoming spirit. This historic three-bedroom Maine sea captain's house features wood floors, abundant natural light, and views toward Mill Creek Cove and Gilkey's Harbor. Open living, kitchen, and dining spaces flow to a screened porch, while the kitchen features cherry countertops and a handcrafted Maine Monson slate sink. A first-floor primary suite opens to the deck. Outside, more than 60 heirloom fruit trees surround a fenced garden, spring-fed pond, firepit, and outdoor shower. Stairs lead to the shore of Mill Creek Cove, providing direct access for launching a kayak or paddleboard. A separate artist studio with electricity and loft space overlooks the pond, offering a peaceful setting for inspiration and creativity. A lovely deck extends to the water's edge, perfect for morning coffee or a quiet moment of reflection. A historic former village post office serves as a seasonal guest cottage or flexible retreat, with a full bath and screened porch. The property borders acres of undisturbed wilderness, creating a wonderful sense of privacy and connection to nature. Golf, trails, the ferry, island market, community center, seasonal farmers market, bakery, and other island amenities are all nearby. Ideal for seasonal living, with potential for year-round use with additional improvements, this is a distinctive island property with room to create, garden, gather, and enjoy life on Islesboro.

There are properties that sit near the water, and then there are properties like this one. With 400+ feet of direct Penobscot Bay frontage, a private deepwater mooring, and a whole-house generator, 220 Shore Road is as complete a waterfront package as the mid-coast offers.Every room has been renovated with intention. The kitchen shines with butcher block counters, a hands-free faucet, new lighting, and custom storage. The living room anchors around a fireplace with built-in shelving. The primary suite features a custom window seat and a fully updated bath with new shower, flooring, and a statement Fandelier. Downstairs, a finished lower level delivers a custom built-in den, Whirlpool laundry, and a second fully renovated bath.Outside: fresh blacktop driveway, a cedar fence with solar lighting enclosing the entire yard, and a refinished deck with new railing and 180 degree views! Whole-house generator. Private mooring. Nothing left on the to-do list.

This rare and exceptional waterfront parcel is located on Golf Club Road, just a short stroll from the Tarrantine Club's golf course. Spanning 1.9 private acres, the property boasts stunning westerly views across the cove and bay, along with 320 feet of accessible shoreline. It is also ideally positioned up and outside of the flood zone.

Occupying a privileged position along one of the most celebrated stretches of the Maine coast, this distinguished waterfront residence commands 200 ft of private frontage on Eggemoggin Reach, with an extraordinary perspective toward the iconic Deer Isle-Sedgwick Bridge. The four-bedroom, three-and-a-half-bath residence has been thoughtfully oriented to its remarkable setting, with expansive views of the Reach from nearly every room. The interiors have been thoughtfully refreshed under the direction of an interior designer, introducing a sophisticated and cohesive sensibility while preserving the warmth and ease appropriate to a Maine waterfront residence. Generously proportioned living spaces invite both intimate everyday living and larger gatherings, with ample accommodations for family and guests. A long private drive creates an immediate sense of arrival and seclusion, revealing a property that feels wonderfully removed from the outside world. The attached two-car garage and full basement provide substantial additional space and practicality for effortless year-round living. Beyond the residence, the shoreline of Eggemoggin Reach provides a vantage point from which to experience one of Maine's most storied waterways. Schooners and sailboats pass through the Reach, working vessels trace familiar routes between island communities, and the Deer Isle-Sedgwick Bridge provides an architectural landmark against the horizon. With a sense of privacy, the property is ideally positioned for enjoying the cultural, recreational, and culinary offerings of the Blue Hill Peninsula, placing some of the region's most beloved coastal villages within easy reach. More than a waterfront residence, this is a property defined by its setting: substantial shorefront, exceptional privacy, beautifully considered interiors, and a view that could not be replicated. An uncommon opportunity to own a refined year-round retreat overlooking one of the defining landscapes of the Maine coast.

Set well back from the road on 3.7 wooded acres, this three-bedroom farmhouse offers privacy, space, and an opportunity for the next owner to bring new life to a property with plenty of potential. The first floor features a spacious eat-in country kitchen, living room with fireplace, and a primary bedroom with a generous walk-in closet and adjoining full bath. Two additional bedrooms are located on the second floor, with attic space providing additional storage. For those looking for workspace, hobbies, or projects, the property includes an attached workshop with additional storage above, as well as a separate one-car garage. A paved, tree-lined driveway leads from Route 15 to the home, creating a wonderful sense of separation and privacy. Additional features include a private well and septic system, mature landscaping, a newer standing seam metal roof, and a deck overlooking the wooded surroundings. This home is ready for updates and improvements, making it an appealing handyman special for someone looking to create a year-round residence, Maine getaway, or investment property. Enjoy the peace and quiet while remaining convenient to area schools, shopping, and amenities. Bring your ideas and make this Maine farmhouse your own.

This delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Enjoy soaking up Summer days on the deck surrounded by honeysuckle, peonies, and mature rhododendrons and playing out on the lawn. Inside, are cozy living spaces with a bedroom tucked upstairs. A detached storage shed provides convenient space for garden tools and gear. Located close to many of the island's year-round activities, including community center, gym, and school. Offered mostly furnished. In addition to this property offering, if you are looking for a larger or compound-style property, consider the abutting property at 115 Babbidge Road Road which is also for sale.

This property offering includes an historic Arts and Craftsman-style Foursquare house - thought to be one of the first houses built in Dark Harbor - set on a sunny and open lot, as well as an additional vacant wooded lot both, just a short walk from the charm and amenities of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Brimming with original character and island warmth, the residence offers the best of both community connection and personal retreat. Ascend granite steps and enter through the welcoming formal front door beneath a gracious covered porch, perfect for waving to neighbors or enjoying a quiet cup of coffee. Inside, a central hall anchors the home, with a lovely parlor and dining room on one side, and a cozy study, powder room, and laundry area on the other. The kitchen, complete with pantry, is located to the center rear of the house, adjacent to a small sunlit room which leads out to a back deck, an ideal spot for relaxed outdoor dining. There is also a mudroom that opens to the covered back porch. The second floor includes three bedrooms and a full bath. An additional flexible use room has a staircase to a spacious, unfinished attic which offers expansion potential and includes glimpses of the water. The detached barn is closely adjacent to the house and is suitable for storing outdoor furniture. Located close to many of the island's year-round activities, including community center, gym, and school. Offered partially furnished.