SoldOct 30, 2025

Listed and Bought with Maureen DeLeo from Keller Williams Realty

Source: Maine Real Estate Information System, Inc. #1623559

14 Oak Street, Kennebunk, ME, 04043

$2,000,000

8
5
5173 sq. ft.
13939.2 sq. ft.

SingleFam

•

30+ days on the market

Sold: Oct 30, 2025

What's around 14 Oak Street

About this property

Once a cherished guest cottage of the iconic Wentworth Hotel, this enchanting 1920s shingled cottage invites you to experience the grace and elegance of a bygone era. Perched atop a gentle knoll just steps from coveted Mother's Beach, the KBIA and a short bike ride to the shops, galleries and restaurants of famed Dock Square, this home offers sweeping, unobstructed views of the Webhannet Golf Club and seasonal peeks of the ocean - an exceptional blend of historic charm and a prime seaside location. With 8 bedrooms and 4.5 baths, this spacious home is an ideal retreat for gatherings large or small. Thoughtfully designed interiors include the expansive ''Pine Room'' with an abundance of natural light, and inviting dining and living rooms featuring cozy wood-burning fireplaces that spill outdoors to an enviable wrap around porch made for morning coffee, afternoon naps, and everything in between. Timeless details abound - rich wood floors, exposed beams, and a beautifully crafted 3-story central staircase radiate the warmth and character of the home's heritage. A whimsical nod to its storied past, the former guest check-in office has been transformed into a swanky walk-in bar, ideal for mixing cocktails, wine tasting or set up as a barista style coffee station. Lovingly maintained throughout the years, the home combines preserved character with meaningful updates, such as refreshed bathrooms and improvements to the electrical panel, roof, and windows. Whether you're entertaining generations of family, hosting seaside weekends, or simply savoring quiet mornings by the shore, this is a place to make lasting memories. For nearly half a century, one family has filled these rooms with laughter, love, and the rhythm of summer tides, a legacy now ready to be shared. Welcome home!

Looking for more information on 14 Oak Street?

Explore comparables, sales history and growth for this property.
Learn more

Other properties sold by Keller Williams Realty

SoldOct 30, 2026
$1,425,000
9 Walkers Lane
Kennebunkport ME 04046
3
3
2
Single-Family
Listing courtesy of Keller Williams Realty and Portside Real Estate Group
SoldSep 30, 2026
$525,000
1/30 Merrill St
Portland ME 04101
1
1
Condo
Listing courtesy of Portside Real Estate Group and Keller Williams Realty
SoldSep 18, 2026
$2,505,000
149 Main Street
Kennebunkport ME 04046
3
4
1
Single-Family
Listing courtesy of Pack Maynard and Associates and Keller Williams Realty

Browse properties sold in nearby areas

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

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent