Oceanfront Family Compound!
Set on the serene north end of Islesboro, this rare coastal compound offers the kind of privacy, flexibility, and natural beauty that's increasingly hard to find. With 13 acres, 525 feet of open shoreline, and direct, stair-free access to the water, this property stands apart from nearly every other waterfront offering on the island.

The centerpiece is a stunning 2025 built log style home, thoughtfully designed with over 2,200 square feet of warm, inviting living space. Cathedral ceilings and a wall of windows flood the open kitchen and living area with natural light, creating an airy yet cozy gathering space. The first floor features two spacious bedrooms, including a primary suite with a walk-in closet and sliding doors leading to a screened-in porch, perfect for quiet mornings or summer evenings. Upstairs, a large third bedroom with its own bath provides a private retreat for guests or family. A detached two-car garage adds convenience and storage.


The second home, built in 1968, is a well-maintained, year-round residence offering four bedrooms and two baths, all on one level. Full of character and functionality, it includes a charming bunk room with built-in beds and clever storage, making it ideal for hosting. A covered porch and waterside fire pit create easy spaces for relaxation and entertaining.
Included are 10 fruit young trees and a new greenhouse, perfect for those looking to embrace a more self sufficient or garden focused lifestyle. Both homes enjoy fenced backyards with gated access to the beach.

The setting is exceptionally private, tucked at the end of a long drive and bordered by conservation land.

Whether you're seeking a multi-generational retreat, an income-producing opportunity, or a private island escape, this property delivers unmatched versatility. Offered as a complete compound or the 2025 home with 5.77 acres, (See separate listing )

Set on the peaceful north end of Islesboro, this exceptional waterfront property offers a rare combination of privacy, modern construction, and effortless access to the shore. With 5.77 acres and 262 feet of open shoreline, you can enjoy one of the island's most sought-after features: direct, stair-free access to the water, allowing you to walk right from your yard to the beach.

Built in 2025, this beautifully crafted log-style home offers 2,200 square feet of thoughtfully designed living space. Cathedral ceilings and a dramatic wall of windows fill the open-concept kitchen and living area with natural light, creating a bright, welcoming atmosphere that brings the outdoors in, and opens to a covered back porch facing the shoreline.

The first floor features two spacious bedrooms, including a primary suite with a walk-in closet and sliding doors that open to a screened-in porch, the ideal spot to relax and take in the coastal air. Upstairs, a large third bedroom with its own bathroom offers a private retreat for guests or family.

Tucked at the end of a long private road, the setting is both quiet and secluded. A newly built detached two-car garage adds practicality and convenience, completing this turnkey island retreat.

This property is a rare opportunity to own a newly constructed waterfront home in one of Islesboro's most peaceful and private locations. For those seeking additional space or a multi-generational compound, there is also the option to purchase the full 13-acre offering, which includes a separate, well-maintained 4-bedroom, year-round home, creating a truly unique and versatile coastal estate.

Charming three bedroom home, recently renovated with care from top to bottom. With new windows, wiring, plumbing, and insulation, it is practically a brand new house while still offering classic character.

The primary bedroom is conveniently located on the first floor, making single level living an easy option. Beautiful cherry wood floors add warmth and richness, and the bathroom features radiant heat beneath the tiled floor for everyday comfort.A whole house generator provides added peace of mind.

Come take a look and fall in love with living in Stonington.

Owner prefers an October 2026 closing date.

Two detached living spaces set on a picturesque 4.06-acre parcel with a small pond. The property features a 3-bedroom, 1-bath Cape in need of updating, offering great potential to customize, along with a move-in-ready 2-bedroom, 1-bath ranch. Ideal for multi-generational living, rental income, or guest accommodations. The property also includes a detached two-car garage and ample outdoor space for privacy and enjoyment.

Island Living with Room to Grow!

Set on 5.85± acres along Main Road, this classic red New England home offers the perfect blend of comfort, character, and future potential. Surrounded by mature trees, established landscaping, and a recently added raised bed garden ready for your next growing season. Plenty of open space, the property enjoys wonderful curb appeal and a peaceful setting in one of Maine's most treasured island communities.

Originally the homestead of Jason W. Ladd, this inviting red home has been part of the Islesboro landscape for well over a century. The original 1900 residence, with its hand-hewn beams and fieldstone foundation, was expanded and renovated in 1968, creating the single floor three-bedroom, one-bath home enjoyed today.


A detached two-story barn/garage provides abundant storage, workshop space, or room for hobbies.

The value of this property extends beyond the home. With approximately 5.85 acres, there is potential for subdivision, subject to local and state approvals, making this an attractive opportunity for buyers looking to invest in Islesboro's future while enjoying the property today.

Just a scenic ferry ride from the mainland, Islesboro offers a rare coastal lifestyle with miles of shoreline, quiet roads, a close knit year-round community, and easy access to boating, hiking, and the natural beauty of Penobscot Bay. Whether you're searching for a year round residence, a seasonal retreat, or a property with long term investment potential, 804 Main Road is ready for its next chapter.

Showings by appointment with 24-hour notice required.

This is the one buyers are constantly searching for and rarely find -- an absolutely delightful single level cottage tucked away on a quiet street just two blocks from the water and an easy stroll to downtown shops, restaurants, and the waterfront.

Full of charm and easy living, this inviting home offers two bedrooms, an updated kitchen and bath, convenient first floor laundry, and bright comfortable spaces designed for a relaxed coastal lifestyle. The full dry basement provides exceptional storage and plenty of room for hobbies, gear, or future possibilities.

Outside, the beautifully maintained corner lot feels like a private retreat, complete with a fenced backyard, off street parking, a wonderful 10 x 16 workshop with electricity and built in benches, plus an additional garden shed for even more storage.

Properties like this are becoming increasingly hard to find: A quiet neighborhood setting, true one floor living, walkability to town, and the water just around the corner. Whether you are downsizing, searching for the perfect Maine cottage, simplifying life, or looking for a smart investment opportunity, this home offers the rare combination of charm, convenience, and location that everyone wants.

Looking for a Lifestyle? Searching for an affordable place to keep your horses? Looking for organic farmland? This is the place!

In addition to the farmstead and the 1.74 acre lot, you also get a 1/6 undivided interest in the surrounding acreage of the Twin Springs Land Association, which is between 120-150 acres and encompasses hayfields, garden space, an orchard, a swimming hole, and long frontage on Quiggle Brook.

Sometime after the Revolutionary War, James St. Claire walked from New Hampshire and built a cabin by a stream, and remains as the magnificent post and beam cape with attached gambrel barn he built over the years.

The farm became the Twin Springs Farm Land Association in the 1980s, when the last surviving heir- who still farmed with horses- passed the baton to a group of conservation-minded farmers, some of whom still farm the land. There are six shares in the farm, and each shareholder owns their own house lot with plus or minus 2 acres, and a 1/6 undivided share in the remaining farmland. All the farmland has always been organic.

Landowners hunt, fish in Quiggle Brook, harvest apples from the orchard, ski, graze animals, cut firewood, and live the good life.

There are some restrictions to use, which are listed in the attached By-Laws, but this is an incredible opportunity for those looking for open space or farmland with a low overhead and low taxes.

Many systems have been upgraded, such as electrical, heat pump hot water heater, kitchen windows and back door, water system, oil furnace and tank. The barn foundation needs some work, and the house needs some exterior work. However, the home interior is tastefully renovated, super-cozy, and you're convenient to all the amenities of the Midcoast.

If you've been searching for a classic New England farm, this is the place. Big House, Little House, Back House, Barn!