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$1,650,000
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Property Description
Introducing a prime investment opportunity: the iconic Miss Wakefield Diner-an institution for over three decades at its current location, with roots dating back to 1948 in New York. This impeccably renovated Jerry O'Mahony diner offering features two income-producing units: the celebrated diner plus an additional retail space (Gracie's Country Store), with potential to convert the retail area into expanded dining/seating. The property offers significant outdoor seating on a deck and additional front seating-ideal for maximizing seasonal revenue. A destination for locals and travelers alike, Miss Wakefield Diner is widely respected and has welcomed celebrities and politicians, including those on and off the campaign trail. The diner has been featured in multiple news stories, on NH Chronicle, and in a television commercial for PSNH (now Eversource). Situated on over 5 acres with level parking well-suited for large events, the site benefits from very high traffic counts and approximately 884 feet of road frontage for exceptional visibility. Additional ancillary income is generated from multiple on-site billboards. A rare opportunity for restaurant, retail, and street-retail investors seeking a landmark property with strong presence and multiple revenue streams.
Full Property Details
Full Property Details for 7 Windy Hollow Rd
General
- Price: $1,650,000
- Taxes: $7,022 (2025)
- Status: Active
- Type: Commercial
- Source: PrimeMLS
- MLS ID: 5076890
- Updated: 4/16/2026
- Added to Site: 117 day(s) ago
Additional Information
- Equipment: Central Vacuum, Indoor Air PLUS Package, Sprinkler System, Whole BldgVentilation
Parking
- Parking: Off Street, Parking Spaces 21+, Paved, Unpaved
Location
- County: Carroll
- Driving Directions: White Mountain Highway (Rt 16) to Windy Hollow Rd on east side just north of rt 109. Miss Wakefield Diner visible from road
Heating & Cooling
- Cooling Type: Central AC
- Heating Type: Forced Air
Utilities
- Sewer: 1500+ Gallon
Structural Information
- Basement Entrance: Interior
- Basement Desc.: Concrete Floor, Crawlspace, Full, Interior Stairs, Unfinished
- Roof: Architectural Shingle
- Square Feet: 5,058
- Year Built: 1992
Lot Features
- Lot Size (Acres): 5.18
- Lot Size (Sq. Ft.): 225,641
- Frontage: Yes Road Frontage
- Frontage Feet: 884
- Zoning: B&CBUS
Financial Considerations
- Price Per Sq. Ft.: $326.22
- Assessment Year: 2025
- Assessment Amount: $806,200
- Tax Amount: $7,022
- Tax Year: 2025
Timeshare
- Fractional Own: Adequate
Listed by BHHS Verani Wolfeboro, Michael Travis
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Schools
Schools serving 7 Windy Hollow Rd
School District:Wakefield School District, Wakefield, NH
| Name | Grades | Distance |
|---|---|---|
Paul Elementary School 60 Taylor Way, Wakefield, NH 03872 | PK-8 | 0.7 mi |
Spaulding High School 130 Wakefield Street, Rochester, NH 03867 | 9-12 | 17.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 7 Windy Hollow Rd
Date
Details
Price
Change
Source
2/18/2026
Listed
$1,650,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 7 Windy Hollow Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,022
16%
$806,200
—
2024
$6,063
10%
$806,200
—
2023
$5,522
-8%
$806,200
65%
2022
$5,978
-1%
$488,000
—
2021
$6,022
—
$488,000
—
2020
$6,041
-1%
$488,000
—
2019
$6,085
11%
$488,000
—
2018
$5,495
15%
$488,000
29%
2017
$4,772
-2%
$377,200
—
2016
$4,868
-1%
$376,200
—
2015
$4,913
3%
$376,200
—
2014
$4,793
4%
$376,200
—
2013
$4,620
—
$376,200
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 7 Windy Hollow Rd
7 Windy Hollow Road, Wakefield, NH 03872 (MLS# 5076890) is a Commercial property. 7 Windy Hollow Road is currently listed for $1,650,000 and was received on February 18, 2026. Want to learn more about 7 Windy Hollow Road? Do you have questions about finding other Commercial real estate for sale in Wakefield? You can browse all Wakefield real estate or contact a Coldwell Banker agent to request more information.

