14 Oak Street

Kennebunk ME 04043

5173 sq. ft.

13939.2 sq. ft.

Single-Family

Last sold for $2,000,000

Maureen DeLeo, last sold this property on 30 October 2025 after -308 days on market.

Overview

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!

Features

8 bedrooms

5 bathrooms

5173 sq. ft. floor area

13939.2 sq. ft. lot size

Single-Family

Estimated Value

We need at least 3 similar 8 bedroom single-family properties sold in Kennebunk over the last 12 months.

Property history for 14 Oak Street

2025

Sold

$2,000,000

30 Oct 2025 by Maureen DeLeo, of Keller Williams Realty

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