Gary Kittredge | Coastal Maine and Island Properties

Gary Kittredge, Dwelling in Maine Real Estate

Based out of Thomaston, Maine, and serving clients seeking luxury primary residences and second homes throughout Knox, Lincoln, and Cumberland counties.

Gary brings his skills of leadership, effective communication, and skillful negotiations from his executive level career in printing and publishing to his role as REALTOR® with Dwelling In Maine. Following years as a corporate nomad with travels throughout the U.S., Europe and Southeast Asia, Gary has returned to his Maine roots and now calls Thomaston his home.

Whether searching for a new home in Maine for retirement or those interested in a second home along the coast or one of the many inland lakes, Gary enjoys sharing his own experiences with clients settling in this beautiful and healthy environment.


What I like most about Maine:

  • Architecture I enjoy the range of residential architectural styles, from the Gilded Age shingle-style cottages along the rugged coast of Penobscot Bay to the stunning and sleek contemporary homes of Casco Bay.
  • Food Being a self professed foodie, I love the fresh local seafood, grilled scallops, Muscongus Bay oysters, and of course, a seemingly endless supply of lobster. And, there’s not much better than working the tide to dig a hod of fresh clams.
  • Gardening For the gardening geek in me, MidCoast Maine has the perfect climate for cultivating native conifers such as pinus banksiana “Schoodic”, and other Zone 5 plants.
  • Photography As a lifelong photographer, I’m drawn to the dramatic landscapes of Coastal Maine and its people. With our proximity to Acadia National Park, this is the perfect setting for large format photography or shooting the night sky.

Waterfront Homes in Maine

5 Beds 2 Baths
This classic home and guest cottage are set on nearly seven acres, toward the end of a private road on the western shore of Islesboro, boasting spectacular sunsets and 355 feet of shore frontage. The property is a perfect island getaway! The main home features an open concept living area opening up to an expansive porch and deck, with retractable awning, overlooking established perennial gardens out to the bay. On the first floor is the living room with fireplace, dining room, kitchen, and breakfast area. There are two bedrooms with potential for a third bedroom in a room that is currently set up as an office and craft room. There is a full bath and laundry closet. The first floor is approximately 1,566 sf. There is also an attached 2-car garage with unfinished storage space above. The second floor has approximately 1,292 sf of unfinished space with insulation and electricity, and is ready for your finishing! Across the lawn, there is a self-sufficient two story guest cottage which has a deck overlooking the water. It's just right for guest overflow or rental income. 2 bedrooms, 1 full bath. Enjoy this property's sprawling lawn, or head off over a little bridge over the creek and explore the woods. The beach is perfect for strolling, beach combing, wading. Boaters will love this home as it is an ideal spot for sailors and motor boaters. Bay Shore Lane is a private road with almost no traffic. This property has 1GB fiber optic broadband internet with booster for good coverage in both home and cottage, wired for phone (land line), TV antenna for local channels and Direct TV dish. Some accessibility features too.

246 Bay Shore Lane, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

3 Beds 4 Baths
Seaside serenity resides at this beautifully landscaped .93 acres with 102 ft. of private waterfront overlooking Little Island and out to the Mussel Ridge Channel. The morning sunrises wash this 1,600 sq. ft. completely renovated 1960's cottage with morning light and the promise of a momentous day. Nearly every inch of this home has been renovated to capture the authentic feel of a fond family oceanside camp with all the modern conveniences including year-round heating, internet, updated lighting, modern appliances, new bathrooms, and a chef's kitchen. The interior features pickled pine walls and beadboard wood ceilings in every room and an abundance of windows to capture the spectacular ocean views from nearly every room. There is plenty of room for friends and family with three ensuite bedrooms, plus a half bath. The kitchen's old-fashioned decor is balanced with a layout that any serious cook will be unable to resist including a large pantry, large farmers sink with windows overlooking the waterfront, a gas range and leathered granite counters. Your kitchen ''spectators'' will have plenty of room to participate around the soap stone island or chill out at the dining table. The front sitting room boasts a spectacularly large window to enjoy the views in any weather, any season especially with the comfort of the robust gas, fireplace to keep you cozy. Best of all - you are only a few granite steps away from an expansive rocky beach. The majority of the furniture will convey with the sale.

76 Bayview Terrace, Owls Head

Listing courtesy of Camden Coast Real Estate.

7 Beds 10 Baths
A rare opportunity to own a breathtakingly beautiful 230 acre property with over a mile of shorefront on Long Cove and Hurricane Sound. Two stunning year-round homes, a deepwater dock, large barn, multiple accessory buildings, several walking paths, and a varied terrain of open fields, woods, and dramatic granite outcroppings for exploring. The ''Water House'' has a beautiful great room with a large granite fireplace, dining room with fireplace, a chef's kitchen with Aga Stove and high end appliances, dining area with wood stove, first floor powder room, first floor en suite bedroom and 3 ensuite bedrooms on the second level. Outside is a wrap around porch with granite steps to the boathouse and deepwater dock. The ''Red Barn'' is privately sited at a higher elevation and is a Timber Frame built with wood from the property. It includes the same attention to detail as the ''Water House'' and also has radiant heat on both levels. Inside is a gracious entry, first floor ensuite bedroom, cherry kitchen with Aga stove and high end appliances, dining area, living room with large granite fireplace, office area, powder room and laundry room. Upstairs is a library and two ensuite bedrooms. The property is currently used as a sheep farm and has two wells, a water collection system, 2 frost-free filed faucets, 2 generators, small pond, apple trees, and 2 soil tested lots for future development. Transferring with the sale are all appliances, a ramp and float, several Merino sheep, 32-HP tractor, John Deere gator, tow behind mower, and various sheep handling equipment. This is a once in a life time opportunity to own one of the largest estates on the Fox Islands.

137&187 Long Cove Road, Vinalhaven

Listing courtesy of Davidson Realty.

3 Beds 4 Baths
Conceptualized by a renowned ship builder, this true post and beam home was crafted from timbers that were felled and milled from the property. The beams have chamfered edges and are one example of the care that was taken in every detail of the house. Set on 1.52+/- acres with 150 ft+/- of waterfront, with protected views of west Penobscot Bay, the protected lands of Turtle Head and Sears Island, this 3-bedroom, 3.5 bath home has space and elegance and comfort. The open floor plan includes a chef's kitchen, large hearth and chimney built from local island stones and offers multiple sitting areas all with water views. Radiant heat throughout the house warms the Brazilian slate floors on the first floor and wood floors of the second floor. The large deck is perfect for entertaining and offers the opportunity to watch both the sunrise and sunset. The grounds have been cared for and there is a walking path that leads you down to a pebble and stone beach.Plenty of privacy is offered by the up-island location and the thoughtfully crafted protective easements for view and vegetation. The northern side of the property abuts 24 acres of conservation land. The private dirt roads that lead you to the property are well maintained.Stay connected with fiber optic broadband internet with 1 gibibyte connection speeds.Used as a successful seasonal and year round rental in previous years, consider the opportunities. Islesboro is a 20-minute ride from the mainland town of Lincolnville, accessed by a public car ferry, water taxi or private boat or small airplane.No drive by please.

195 Beach Drive, Islesboro

Listing courtesy of Cates Real Estate.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2023 Maine Real Estate Information System, Inc. All Rights Reserved.

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