Winter Harbor, Maine

House Hunting? Start your search here with all homes, condos and land for sale in Winter Harbor. Worried about missing out on your dream home? Don't be! Get email alerts alerts for new properties that meet your criteria. Questions? Contact me to begin your home buying journey.

Have a Winter Harbor home to sell? Check out our helpful information for sellers, find out what your home is worth with a free home value estimate, or contact me to find out the first steps for getting your home SOLD.

Latest Listings in Winter Harbor

$265,000

2 Beds ⋅ 2 Baths

Turnkey & comfortable Winter Harbor home with 2 beds & 2 baths. On a large parcel with an in-town location. The master suite includes its own bathroom and walk-in closet. A rear deck and a wonderful private backyard. Full basement with a newer furnace. Plus, a spacious garage with a second floor. Plenty of living & storage space. Enjoy the very quiet street while being close to everything in town. This home has been updated over the years, and the improvements are too numerous to itemize here. Come take a look and see if this meets your needs.

61 Hillcrest Dr, Winter Harbor

Listing courtesy of Portside Real Estate Group.

$239,000

3 Beds ⋅ 1 Baths

3bedroom rustic cottage/Bungalow on the Schoodic Peninsula. Located on a quiet dead end road. Great rental opportunity. Minutes to Acadia National Park/Schoodic Point.

2 Crane Rd, Winter Harbor

Listing courtesy of The Winter Harbor Agency.

$445,000

3 Beds ⋅ 2 Baths

Welcome to your private Maine retreat, ideally located just minutes from downtown Winter Harbor, Schoodic Woods Campground, Birch Harbor Mountain, and the Winter Harbor Marina. Set on nearly 8 acres, this charming home offers the perfect blend of privacy, comfort, and convenience. As you arrive, you're welcomed by a beautiful lawn, an expansive covered front porch, an attached two-car garage, and a peaceful setting surrounded by nature. Step inside and you'll instantly feel at home. Warm wood walls and rustic accents create the cozy Maine charm you've been looking for, making every space feel inviting and comfortable. This property abuts Schoodic Acadia National Park and is conveniently located just 35 minutes from Ellsworth, hospitals, shopping, restaurants, and everyday amenities. You are 50 minutes from Acadia National Park, and you also have the option to take the ferry across to Bar Harbor for a fun and scenic adventure. This property offers easy access to some of Maine's most treasured destinations while still providing the tranquility of country living. Don't miss your opportunity to own this stunning Maine home!

161 Birch Harbor Rd, Winter Harbor

Listing courtesy of NextHome Experience.

$595,000

5 Beds ⋅ 4 Baths

A distinguished offering in the heart of Winter Harbor, this exceptional property encompasses two turnkey residences on a single parcel, thoughtfully positioned to capture views of the harbor while enjoying the convenience of village living. Held by the same owners for more than two decades, the property presents a compelling opportunity for investment, multi-generational living, or a private coastal retreat with income-producing potential. The primary residence is a beautifully maintained turn-of-the-century home offering three bedrooms and two baths, rich in character and timeless New England charm. Complementing the main house is a separate two-bedroom, two-bath residence that has generated a strong and consistent vacation rental history over the past fifteen years. Just a short stroll from the village's shops, restaurants, public boat launch, and everyday conveniences, both residences offer an enviable lifestyle in one of Downeast Maine's most authentic coastal communities. Live in one home and rent the other, establish a family compound, or continue operating both as income-producing properties. This residence is ideally situated near the Schoodic Peninsula and Acadia National Park, with access to miles of scenic hiking trails, rugged granite shoreline, and some of Maine's most breathtaking coastal scenery. As a turnkey offering in one of Downeast Maine's most desirable waterfront communities, it combines historic character, proven income potential, and an exceptional location. This is a legacy property ready for its next chapter.

20 Rand Ln, Winter Harbor

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,595,000

6 Beds ⋅ 5 Baths

LANDMARK PROPERTY in the heart of Winter Harbor! Five buildings on three-quarters of an acre right in town. 2,775-square-foot beautifully maintained and upgraded HOUSE with two-bay, two-story GARAGE housing two studio spaces on the second level. Guest COTTAGE new in 2004 is artistically designed and furnished and will be sold turn-key. Retail SHOP with another garage bay is ready for your imagination. An additional small antique STUDIO is adorable! So many possibilities for all this wonderful space! Directly across from well-known Hammond Hall, performing arts center of Schoodic Arts for All, this cluster of unique buildings has been known for decades as the the beloved Works of Hand Gallery and Giftshop. The in-town style house has almost 3,000 square feet of amazing layout--even a surprise hidden workshop/studio behind an upstairs door. New kitchen, old wood floors, many built-ins, quality cabinetry, new appliances, whole-house generator. Landscaped with lovely perennial beds, fruit trees and hardscaping--with a sizable potting shed for the gardener! The guest cottage is a dream--so many artistic touches only these owners could have created. Wood floors, new appliances. This property is a perfect place to live and enjoy so many amenities, or a wonderful spot to live out your dream of having shops, spaces for multiple artists, or let your imagination lead you! Room count and square footage includes both the Main House and Cottage. Year Built is for Main House.

430 Main St, Winter Harbor

Listing courtesy of The Christopher Group, LLC.

Start Your Search

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. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.