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14 Winchester Drive, 
Cutler, ME 04626

$639,000


3

Beds


3

Baths


2,357

Sq Ft


Single Family

Active Under Contract

Better Homes & Gardens Real Estate/The Masiello Group, nballrealestate@gmail.com

Last updated:

September 15, 2026, 09:19 AM

MLS#

1678360

Source:

ME MREIS

About This Home

14 Winchester Drive

Little Machias is an intimate coastal community that echoes the quiet history of generations who have made their homes along the protected waters of this secluded Atlantic bay. Recently refreshed to feel like new, this impeccable home offers an abundance of thoughtful updates, attractive details, new appliances, a new roof, and more--creating a move-in-ready retreat designed for relaxed coastal living. Trek down to 150 feet of sandy beachfront, where you can take a brisk, salty swim, launch a kayak, or simply settle in and enjoy the ever-changing beauty of the Maine coast. Spend sunny afternoons on the oversized deck, listen for seals calling among the lapping waves, watch eagles ride the prevailing winds overhead, and linger beneath the stars in evenings. This home fits Maine to a T--a wonderful setting for reunions, entertaining, getaways, or year-round living. Thoughtfully designed, the 1st floor includes a well-appointed laundry room and versatile spaces, including the option for a 1st-floor bedroom. One wing offers its own entrance and is excellent potential for an accessory dwelling unit. Water views grace nearly every room. The spacious living room features a fireplace woodstove and flows naturally to the open dining room and kitchen with seated island. A full, well-lit basement provides abundant storage and opportunity for additional living space if desired. Outside is ample parking and an oversized detached two-bay garage with dedicated work area. There's a storage shed with power and the property's original ''camp home,'' relocated to its current setting now an open workspace, offers flexibility as additional storage, a studio, or creative space. Adding to the property's unique Maine character, the original ''duplex'' outhouse remains intact and now serves as 2 charming storage sheds. Rarely does a property combine this--with sandy beach, abundant wildlife, sweeping water views, and the quiet rhythm of one of Maine's truly special coastal communities

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1998

Price Summary

639,000

$271 per Sq. Ft.

MLS #:

1678360

Last Updated:

September 15, 2026, 09:19 AM


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2


Structure

Structure

Architectural Style:

Cape Cod, Contemporary, Shingle

Building Area:

2,357 Sq. Ft.

Year Built:

1998


Lot

Lot Size (Sq. Ft):

56,627


Finances & Disclosures

Finances

Price:

$639,000

Price per Sq. Ft:

$271 per Sq. Ft.

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MREIS Multiple Listing Service™ systemListing data is derived in whole or in part from the Maine IDX & 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

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.