Jeffrey Pesarik

CourtUnited States Tax Court
DecidedFebruary 23, 2026
Docket23859-22
StatusUnpublished

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Bluebook
Jeffrey Pesarik, (tax 2026).

Opinion

United States Tax Court

T.C. Memo. 2026-20

JEFFREY PESARIK, Petitioner

v.

COMMISSIONER OF INTERNAL REVENUE, Respondent

__________

Docket No. 23859-22. Filed February 23, 2026.

Timothy J. Burke, for petitioner.

Patrick F. Gallagher, Christopher J. Richmond, and Erika B. Cormier, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION

URDA, Chief Judge: During 2020 petitioner, Jeffrey Pesarik, sold a property that he owned in Wakefield, New Hampshire (Wakefield Property), for $187,000, and another that he owned in Hull, Massachusetts (Hull Property), for $556,800. Mr. Pesarik did not report the gain from either sale on his 2020 federal income tax return. The Commissioner thereafter issued a notice of deficiency, which determined a deficiency in Mr. Pesarik’s 2020 income tax and an accuracy-related penalty.

In this Court Mr. Pesarik asserts that certain renovation expenditures and closing costs increased his basis in the Wakefield Property and limited his taxable gain to $55,799. He further contends that he was entitled to exclude the entirety of his gain from the Hull

Served 02/23/26 2

[*2] Property sale under section 121 1 because it had been his principal residence for more than two years. The Commissioner does not think that Mr. Pesarik has proved either point.

We conclude that Mr. Pesarik has provided sufficient substantiation of his Wakefield Property expenses to allow an estimate under the rule announced in Cohan v. Commissioner, 39 F.2d 540, 542– 44 (2d Cir. 1930). Mr. Pesarik fails to demonstrate that the sale of the Hull Property qualifies for the section 121 exclusion.

FINDINGS OF FACT

We tried this case in Boston, Massachusetts, and find the following facts based on the pleadings, stipulations of facts, and trial evidence. Mr. Pesarik lived in Portsmouth, New Hampshire, when he filed his petition.

I. Background

Mr. Pesarik grew up in New Hampshire. After earning a bachelor’s degree in business management and finance, he worked as a property manager in Seattle, Washington; Dallas, Texas; and Washington, D.C.

Mr. Pesarik maintained ties to the Granite State, buying a property in Epping, New Hampshire, in the mid-2010s. He moved back to New Hampshire in fall 2016 to arrange the affairs of his late mother.

Mr. Pesarik used his expertise in property management to renovate and sell his late mother’s house. By Mr. Pesarik’s estimate, his work increased the house’s value from $400,000 to $587,000, the price he remembered the property fetching when it was sold in 2017. 2

1 Unless otherwise indicated, statutory references are to the Internal Revenue

Code, Title 26 U.S.C. (I.R.C. or Code), in effect at all relevant times, regulation references are to the Code of Federal Regulations, Title 26 (Treas. Reg.), in effect at all relevant times, and Rule references are to the Tax Court Rules of Practice and Procedure. All amounts have been rounded to the nearest dollar. 2 Although Mr. Pesarik did not specify a sale year during his trial testimony,

we take judicial notice of online Portsmouth property records, which reflect that the Theresa N. Pesarik Revocable Trust sold a house in Portsmouth for $585,000 on March 27, 2017. See Fed. R. Evid. 201(b); Vision Government Solutions, Property Lookup, Portsmouth, NH, https://gis.vgsi.com/PortsmouthNH/Search.aspx (search in search bar for “214 Elwyn Ave.”) (last visited Feb. 11, 2026). 3

[*3] Mr. Pesarik and his two siblings each received $157,000 from this sale, with Mr. Pesarik also obtaining reimbursement for his expenses.

II. Property Purchases

A. Wakefield Property

Mr. Pesarik’s pursuits upon his return to New Hampshire were not confined to the rehabilitation of his late mother’s house. On November 17, 2016, Mr. Pesarik purchased the Wakefield Property (2110 Province Lake Road East, Wakefield) for $30,000.

The Wakefield Property was approximately 45 minutes north of Portsmouth by car. According to Mr. Pesarik, the Wakefield Property was “[b]asically . . . a chicken coop” and a “torn up” and “hammered” house in an “extremely rural” community when he purchased it. Unlike the relatively modest fine-tuning on his mother’s house, Mr. Pesarik testified that he “pretty much built a new house” at the Wakefield Property, which included “underground utilities, water, septic, [and] foundation work.”

B. Hull Property

On July 6, 2018, Mr. Pesarik purchased the Hull Property (59 B Street, Hull) for $394,750. The Hull Property, which sits two blocks from the beach, was a two-hour drive from Portsmouth, on the far side of Boston. Mr. Pesarik did not file Massachusetts state income tax returns during the time he owned the Hull Property, nor did he obtain a Massachusetts driver’s license.

C. Property Sales

Mr. Pesarik sold both properties during 2020. He first sold the Wakefield Property for $187,000 on March 30, 2020, 3 incurring $17,843 in closing costs. On October 7, 2020, he sold the Hull Property for $556,800, incurring $24,967 in closing costs. Shortly before the Hull Property sale closed, Mr. Pesarik provided an Arizona driver’s license to verify his identity as the owner of the Hull Property.

3 The parties stipulated that Mr. Pesarik disposed of the Wakefield Property

on or around March 30, 2020, and the deed conveying the property was also executed on this date. The settlement statement, however, includes a settlement date of March 31, 2020. Consistent with our Rules, we will treat the stipulated date as the date the property was sold. See Rule 91(e). 4

[*4] III. 2016–20 Financial Activity

During the relevant years, Mr. Pesarik relied on credit cards and a business bank account at Bank of America under the name of Internet Realty, a real estate brokerage and property management sole proprietorship that he owned. Specifically, in 2016 Mr. Pesarik used his Bank of America bank account, an American Express credit card, a Costco Citi card, and (starting in November 2016) a Home Depot credit card. The Home Depot card played a particularly prominent role, with Mr. Pesarik spending approximately $46,000 from November 2016 through September 2020. Mr. Pesarik also used a Lowe’s Synchrony Bank credit card, with statements showing that he spent approximately $8,000 on this card from July 2018 to November 2020.

The American Express statements in the record reflected an address for Mr. Pesarik in Manassas, Virginia, in the first half of 2016. In fall 2016 Mr. Pesarik’s mailing address changed, with his late mother’s address in Portsmouth serving as the mailing address for American Express card (and later the Home Depot card) statements, and a Portsmouth post office box serving as his mailing address for the Costco Citi card and Bank of America statements. By February 2017 all of Mr. Pesarik’s statements were addressed to the Portsmouth post office box, which continued until February 2020 when the mailing addresses changed to either the Hull Property or a post office box in Hull.

The 2016–20 statements show activity throughout New Hampshire and Massachusetts, with increasing frequency in Massachusetts during 2019 and 2020. The statements reflect numerous transactions at Home Depot, Lowe’s, and Tractor Supply Co. The store locations vary. The statements reveal that Mr. Pesarik sometimes engaged in transactions at or near Epping, Portsmouth, Wakefield, or Hull (or in the general vicinity of several of these locations).

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Welch v. Helvering
290 U.S. 111 (Supreme Court, 1933)
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515 U.S. 323 (Supreme Court, 1995)
Cohan v. Commissioner of Internal Revenue
39 F.2d 540 (Second Circuit, 1930)
Remy v. Commissioner
1997 T.C. Memo. 72 (U.S. Tax Court, 1997)
Gates v. Commissioner
135 T.C. No. 1 (U.S. Tax Court, 2010)
Dobra v. Commissioner
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Vanicek v. Commissioner
85 T.C. No. 43 (U.S. Tax Court, 1985)
Polyak v. Commissioner
94 T.C. No. 20 (U.S. Tax Court, 1990)

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