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Federal Eyes on Real Estate: A 4-Part Insider’s Guide for Buyers and Sellers

Federal Eyes on Real Estate: A 4-Part Insider’s Guide for Buyers and Sellers

Federal Eyes on Real Estate:

A 4-Part Insider’s Guide for Buyers and Sellers

We are pulling back the curtain on how — and why — federal agencies like FinCEN, the FBI, Homeland Security, IRS-Criminal Investigations (IRS-CI), and CFIUS monitor real estate transactions in the U.S.

Whether you’re buying with cash, investing from abroad, transferring property to a family member, or just trying to close without a headache, you’ll want to know what can trigger federal scrutiny — and how to stay off the radar.

From flagged wire transfers and shell companies to gift-of-equity sales and land near military zones, this isn’t your average title-and-keys situation.

It’s real estate with a side of national security, tax enforcement, and financial crime prevention.

4-Part Series

PART 1

Is Big Brother Watching Your Home Sale?

fbi office

What Buyers and Sellers Should Know About Federal Oversight

You’re Not Paranoid — They Might Actually Be Watching
What you didn’t know on how federal agencies keep tabs on select real estate transactions.

PART 2

Your Closing Packet Could Be a Federal File

homeland security paperwork

How Your Paper Trail Might Raise Red Flags — And What You Can Do About It

What the FBI, IRS, and Homeland Security
Could See in Your Closing Docs
We’re unpacking what agencies might spot inside your deal’s fine print.

PART 3

Caught in the Crosshairs? What Triggers Federal Interest in Your Home Sale

cross hairs

The Top Red Flags That Could Invite a Closer Look from Washington

Cash, LLCs, or Land Near a Base? You Might Just Be a Target
The warning signs that put your deal on the government’s radar — and how to stay clear.

PART 4

Follow the Money: How the IRS Tracks Financial Crimes Through Real Estate

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From Unreported Income to Shell Game Schemes
— What IRS-CI Is Looking For

Your Closing Could Be an Audit Trigger — Here’s How the IRS Sees It
Explore the patterns, documents, and loopholes that turn ordinary deals into criminal cases.

Providing title, escrow, closing and settlement services to clients throughout Massachusetts and New Hampshire

From Our Clients

“As a realtor, the Rocheford team went above and beyond to make sure my client was not only protected from a legal standpoint but also operated in a timely manner to execute the sale of my client’s dream home.

Thank you for the great experience for myself and my client! Looking forward to our next deal together!”

Viktor Ryan

Realtor®

“I don’t usually use attorneys that often. But if an attorney is needed, I couldn’t recommend this law office enough. I always pride myself on responding quickly to emails and calls, but I was in awe of how fast paralegal Robert Heckman would respond to us. We sold our house a couple months ago and then did a two-part land swap with neighbors and my folks, and both transactions were seamless, including coming in to sign paperwork.

In short, if you need a law office that is responsive and attentive to detail, definitely consider them!”

John P.

Leominster, MA

“Excellent, conscientious and professional.

The communication throughout our Real Estate transaction was better than expected. We thought the fee to be very reasonable considering the work accomplished on our behalf. The law office handled the entire closing without us having to be in attendance….as we requested. I have had experience with very competent lawyers and law firms as the result of my previous profession. I would place this law office right up there among the best in their real estate field of expertise and surprisingly at very reasonable and affordable rates/fees.”

Tom M.

Buzzards Bay, MA

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What the FBI, IRS, and Homeland Security Could See in Your Closing Docs

What the FBI, IRS, and Homeland Security Could See in Your Closing Docs

What the FBI, IRS, and Homeland Security Could See in Your Closing Docs

How Your Paper Trail Might Raise Red Flags — And What You Can Do About It

Your Closing Packet Could Be a Federal File — Here’s Why

When you’re finalizing a real estate transaction, your focus is likely on the price, terms, and closing date — not on what a federal agency might find in your paperwork. But if certain conditions apply, your stack of signed documents could become part of a federal investigation.

From title fraud to suspicious wire transfers, real estate closings contain exactly the kind of data federal agencies use to detect fraud, money laundering, or foreign interference. Let’s break down the key documents that could raise red flags — and how to keep your transaction clean.

Settlement Statements (CD/HUD-1): Show Me the Money

These documents detail the financial anatomy of your transaction — where the money is coming from and where it’s going.

Agencies like the IRS Criminal Investigation Division (IRS-CI) and Homeland Security Investigations (HSI) use these to detect:

  • Undisclosed cash sources
  • Overstated or fake expenses
  • Unusual wire transfers or third-party contributions

IRS-CI investigates tax evasion and unreported income often spotted through property records.

Learn how IRS-CI tracks financial crimes through real estate

Power of Attorney or Signature Authority: Who’s Really Involved?

Documents granting someone else signing authority — especially in cash or trust purchases — can prompt FBI interest if:

  • The grantor isn’t properly identified or verified
  • A straw buyer is suspected (someone buying on behalf of an undisclosed party)
  • The purchase is connected to shell companies with no clear owner

These red flags are commonly tied to fraud and money laundering investigations.

Read the FBI’s guidelines on common real estate fraud patterns

Proof of Funds or Bank Letters: Show Your Work

Cash buyers are often asked to show proof of funds, but not all banks or letters are equal in the eyes of compliance officers.

Federal agencies may scrutinize:

  • Large transfers from offshore accounts
  • Lack of financial institution transparency
  • Inconsistencies between stated income and assets

Homeland Security Investigations (HSI) targets international financial crimes — especially involving real estate.

See how HSI investigates financial crimes tied to real estate

Entity-Based Transactions: LLCs, Trusts, and Shell Games

When a home is purchased through a legal entity — especially in cash — the title and closing documents must disclose the “beneficial owner.”
If they don’t, the transaction may:

  • Violate FinCEN Geographic Targeting Orders
  • Trigger FinCEN reporting requirements from title companies
  • Be flagged for money laundering or sanctions evasion

Review FinCEN’s current rules for real estate ownership transparency

Tax Documents: When Closings and Capital Gains Collide

The IRS reviews real estate closings for unreported capital gains, under-the-table transactions, or misuse of tax exemptions.

Closings can trigger audits when:

  • Sale proceeds are underreported
  • A home is falsely claimed as a primary residence
  • Form 1099-S isn’t issued when it should be

Sellers attempting to avoid tax obligations through title maneuvering or “gift-of-equity” deals should be cautious.

Understand when Form 1099-S is required in real estate transactions

What You Can Do (Besides Panic)

You don’t have to be laundering millions or working for a foreign government to attract unwanted attention. In most cases, red flags are raised by incomplete, inconsistent, or unexplained paperwork. Here’s how to stay ahead:

  • Work with a closing attorney who understands both the legal and compliance landscape
  • Avoid cutting corners on financial disclosures or title documentation
  • Be honest and thorough when structuring transactions involving trusts, foreign buyers, or LLCs

Want to Keep the Feds Out of Your Closing?

Our team at The Law Office of David R. Rocheford, Jr., P.C. ensures every “i” is dotted and every “t” is lawyer-checked. We review your paperwork with a compliance lens — so you don’t accidentally invite scrutiny.

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Providing title, escrow, closing and settlement services to clients throughout Massachusetts and New Hampshire

From Our Clients

“I would highly recommend David as a closing attorney. I have known David and have been using his office for many years. David’s professionalism when dealing with me, my closing department and most especially my clients has been always exemplary.”
DAVID BREMER

SENIOR LOAN OFFICER, SHAMROCK FINANCIAL SERVICES

“The Law Office of Attorney David R. Rocheford, Jr. is by far the most exceptional real estate law office that I have had the pleasure of working with. The professionalism is by far second to none.”
JACQUI KEOGH

SENIOR LOAN OFFICER, SALEM FIVE MORTGAGE SERVICES

“Attorney David Rocheford has provided settlement and title services for me and Greenpark Mortgage several years. He has assisted all of my clients, including my family and friends with mortgage closings. Always providing excellent service. Reliable and trustworthy!”
SANDRA MALDONADO

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Understanding Transfer Taxes (Tax Stamps) in Massachusetts

Understanding Transfer Taxes (Tax Stamps) in Massachusetts

Understanding Transfer Taxes (Tax Stamps) in Massachusetts

Massachusetts home sale paperwork including transfer tax terms and contract clauses.

When it comes to selling real estate in Massachusetts, one fee tends to catch sellers off guard: transfer taxes, also known as real estate tax stamps. At The Law Office of David R. Rocheford, Jr., P.C., we get a lot of questions about these costs — and we’re here to make sure you (and your clients) understand what to expect.

Who Pays the Transfer Tax in Massachusetts?

In nearly all cases, the seller is responsible for paying the transfer tax. However, during the negotiation process, the parties can agree to split the fee — or shift it entirely to the buyer. Like most things in real estate: it’s all negotiable.

How Much Is It? 

The current transfer tax rate is $2.28 per $500 of the property’s sale price — that’s $4.56 per $1,000. This fee is paid to the state by purchasing tax stamps from the Registry of Deeds when the new deed is recorded.

Example: On a $500,000 home sale, the transfer tax would be $2,280.

You can review current rates and exemptions on the Massachusetts Department of Revenue website.

Massachusetts home sale paperwork including transfer tax terms and contract clauses.

Is It Deductible? 

Not exactly — transfer taxes are not tax-deductible on your income tax return. However, they do get added to the cost basis of the property, which may reduce your capital gains tax when the property is sold in the future.

Who’s Exempt? 

Some nonprofit organizations and federal agencies are exempt. Veterans Affairs (VA) and HUD transactions, for example, often qualify for exemption — but always confirm with the Registry and your closing attorney.

Additional Notes: 

  • The tax applies to any sale over $100.
  • The tax is separate from municipal excise taxes or local fees (if applicable).
  • The stamps are literally affixed to the deed — old school, but legally required.
Massachusetts home sale paperwork including transfer tax terms and contract clauses.

Small details. Big difference.

Whether you’re buying or selling, understanding transfer taxes is a small detail that can make a big difference at the closing table. We help our clients plan ahead and avoid last-minute surprises every step of the way.

REFERENCES

Contact

(255) 352-6258

1234 Divi St. #1000, San Francisco, CA 94220

Copyright © 2025 Divi. All Rights Reserved.

Won’t You Be My Neighbor? ADUs Now Permitted by Right in Massachusetts

Won’t You Be My Neighbor? ADUs Now Permitted by Right in Massachusetts

Won’t You Be My Neighbor? ADUs Now Permitted by Right in Massachusetts

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Accessory Dwelling Units (ADUs) — small, independent living spaces on the same property as a main home — just got a big green light in Massachusetts. Thanks to the Healey-Driscoll Administration’s “Affordable Homes Act,” homeowners can now build or convert ADUs by right in many communities, making it easier to add housing and income flexibility.

If you’re a Realtor®, lender, or homeowner, here’s what you need to know to make sense of the new rules — and how they impact your property or transactions.

What’s an ADU?

An ADU is a secondary living unit with its own sleeping, eating, cooking, and bathroom facilities. Think: a converted garage, a backyard cottage, or a finished basement with a separate entrance.

New Rules (Effective 2024):

The updated state law allows ADUs:

  • As detached structures
  • As additions to existing homes
  • As conversions of garages, attics, or basements

To qualify, the ADU must be:

  • Less than half the size of the primary residence or under 900 square feet
  • Located in a single-family zoning district
  • Code-compliant with a separate entrance
duplex housing in the city

Key Protections for Homeowners 

The new law, under MGL Chapter 40A, Section 3, overrides local zoning if the ADU meets minimum state standards:

  • Cities cannot ban single ADUs
  • Owner occupancy is not required
  • ADUs can be rented for long-term housing
  • Only one extra parking spot can be required

Local Nuances Still Apply: 

Municipalities can:

  • Ban short-term rentals (Airbnb, etc.)
  • Restrict ADUs in flood zones or historic districts
  • Require compliance with Title V septic and environmental regulations
Basement Apartment Housing

Zoning Still Matters

Each of Massachusetts’ 351 towns has its own zoning quirks. While ADUs are protected, local rules may shape your options. Thinking of building one? Start by calling your local planning board.

At The Law Office of David R. Rocheford, Jr., P.C., we help clients navigate land use, permitting, and local regulations with confidence. Whether you’re buying, building, or advising, we’re here to help.

REFERENCES

Contact

(255) 352-6258

1234 Divi St. #1000, San Francisco, CA 94220

Copyright © 2025 Divi. All Rights Reserved.

How to Prevent Delays at the Closing Table: Lessons from Recent MA & NH Transactions

How to Prevent Delays at the Closing Table: Lessons from Recent MA & NH Transactions

How to Prevent Delays at the Closing Table:

Lessons from Recent MA & NH Transactions

Closings should be the fun part — popping champagne, handing over keys, and celebrating the finish line. But anyone in real estate or lending knows that even the smoothest transaction can hit a snag at the eleventh hour. From unsigned documents to overlooked municipal requirements, the final stages of a home loan closing in Massachusetts and New Hampshire can turn from celebration to chaos quickly.

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Here are some common culprits behind last-minute delays and what loan processors, Realtors®, and mortgage teams can do to keep things on track.

Smoke Certificates & Local Requirements (Massachusetts Specific)

In Massachusetts, sellers are responsible for obtaining a smoke and carbon monoxide detector certificate from the local fire department before closing. But fire departments don’t always have next-day appointments — and some towns have inspection backlogs.

Solution: Schedule inspections early in the process. Share this state smoke alarm compliance guide with sellers and keep your transaction timeline padded.

Title Surprises

A missing mortgage discharge or a surprise lien can halt everything. These issues are especially common with older properties, estate sales, or refinances. Even unpaid water bills in NH can delay closings.

Solution: Have the title attorney conduct a thorough title search early, and follow up on payoff letters or missing discharges well before the closing date.

Funds Not Cleared or Missing Documentation 

Sometimes buyers assume that a wire transfer or certified check guarantees immediate access. Not always. Banks may hold large deposits, and underwriters may require additional documentation — right at the finish line.

Solution: Prep buyers on timelines for cleared funds and triple-check lender requirements ahead of the final week.

“Surprise” Repairs or Walkthrough Issues 

If a final walkthrough reveals an incomplete repair or unexpected damage, it can cause stress and even stall the closing.

Solution: Set a walkthrough 24–48 hours before closing, not the morning of. This allows time to resolve any issues or negotiate credits.

Missing People 

Closings can’t happen without the right people — including sellers, buyers, and notaries. In the age of remote work and travel, someone’s vacation can mean a reschedule.

Solution: Confirm everyone’s availability well in advance and plan for powers of attorney or remote notarization when allowed (and legal — more on that in a future blog!).

Real Estate Closings Done Right — Every Time.

At The Law Office of David R. Rocheford, Jr., P.C., we’ve seen nearly everything that can go wrong at a closing. And more importantly — we know how to make it go right.

REFERENCES

Providing title, escrow, closing and settlement services to clients throughout Massachusetts and New Hampshire

From Our Clients

“As a realtor, the Rocheford team went above and beyond to make sure my client was not only protected from a legal standpoint but also operated in a timely manner to execute the sale of my client’s dream home.

Thank you for the great experience for myself and my client! Looking forward to our next deal together!”

Viktor Ryan

Realtor®

“I don’t usually use attorneys that often. But if an attorney is needed, I couldn’t recommend this law office enough. I always pride myself on responding quickly to emails and calls, but I was in awe of how fast paralegal Robert Heckman would respond to us. We sold our house a couple months ago and then did a two-part land swap with neighbors and my folks, and both transactions were seamless, including coming in to sign paperwork.

In short, if you need a law office that is responsive and attentive to detail, definitely consider them!”

John P.

Leominster, MA

“Excellent, conscientious and professional.

The communication throughout our Real Estate transaction was better than expected. We thought the fee to be very reasonable considering the work accomplished on our behalf. The law office handled the entire closing without us having to be in attendance….as we requested. I have had experience with very competent lawyers and law firms as the result of my previous profession. I would place this law office right up there among the best in their real estate field of expertise and surprisingly at very reasonable and affordable rates/fees.”

Tom M.

Buzzards Bay, MA

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Bill H.245: Chapter 93 of the General Laws Amended

Bill H.245: Chapter 93 of the General Laws Amended

Bill H.245: Chapter 93 of the General Laws (Amended)

An Act protecting consumer rights in purchasing safe and habitable homes

PDF: HOUSE No. 245 Filed

Below is our summary of significant legislative development that impacts our industry. The Massachusetts General Court has introduced a bill titled “An Act protecting consumer rights in purchasing safe and habitable homes.” This bill, presented by Representative Brian M. Ashe and others, aims to enhance consumer protection by ensuring that buyers have the right to conduct home inspections when purchasing residential properties. Below, I have provided a detailed summary of the key provisions and implications of this bill for real estate professionals.

KEY POINTS

Purpose:

The bill aims to ensure that buyers have the right to home inspections when purchasing residential properties, including houses and condominiums.

Inspection Definition:

An inspection involves a licensed home inspector evaluating various components of the property, such as heating, cooling, plumbing, electrical systems, structural components, foundation, roof, and more.

Buyer’s Rights:

  • Buyers have the right to have the property inspected within 10 days of the seller accepting their offer, unless a different period is agreed upon in writing.
  • Sellers cannot condition the acceptance of an offer on the buyer waiving their right to an inspection, except in certain cases like auctions or sales to close family members.

Offer to Purchase:

Every offer to purchase must include a clause informing the buyer of their right to an inspection and the conditions under which they can revoke the offer if significant defects are found.

Seller’s Obligations:

  • Sellers must comply with the inspection rights and cannot accept offers that waive these rights unless specific exceptions apply.
  • Violations by sellers can result in damages to the buyer and civil penalties.

Enforcement:

An inspection involves a licensed home inspector evaluating various components of the property, such as heating, cooling, plumbing, electrical systems, structural components, foundation, roof, and more.

This bill is designed to protect consumers by ensuring they have the opportunity to identify any significant issues with a property before finalizing the purchase.

Implications:

The legislation has several implications for for real estate agents, brokers and Realtors:

Disclosure and Compliance:

  • Real estate agents must ensure that all offers to purchase include the required language informing buyers of their right to a home inspection.
  • Agents must be aware of the 10-day inspection period (or longer if agreed upon) and ensure that this is communicated clearly to both buyers and sellers.

Offer Conditions:

  • Agents cannot advise or encourage sellers to condition the acceptance of an offer on the buyer waiving their right to an inspection, except in specific cases like auctions or sales to close family members.
  • They must ensure that sellers do not accept offers from buyers who indicate an intention to waive the inspection right, unless the exceptions apply.

Legal and Financial Implications:

  • If a seller violates the provisions of this bill, the real estate agent could be implicated in any resulting legal actions or penalties. This includes potential civil penalties and damages to the buyer.
  • Agents need to stay informed about the legal requirements and ensure their practices comply with the new regulations to avoid liability.

Consumer Protection:

  • The bill enhances consumer protection, which may increase buyer confidence in the real estate market. Agents can use this as a selling point to assure buyers that their rights are protected.
  • Agents should be prepared to guide buyers through the inspection process and help them understand their rights and options if significant defects are found.

Overall, real estate professionals will need to adapt their practices to ensure full compliance with the new regulations, prioritize transparency, and protect the interests of their clients. This may involve additional training and adjustments to standard operating procedures.

Statutory Offer to Purchase Language

According to the bill each offer to purchase a residential structure or residential condominium unit shall include the following language:

“Buyer is entitled under section 115 of chapter 93 of the General 33 Laws to choose to have the premises inspected at Buyer’s expense within 10 days, or longer as Seller and Buyer may agree in writing, of Seller’s acceptance of Buyer’s offer to purchase. Unless one of the exceptions in said section 115 applies, neither Seller nor Buyer may make acceptance of this offer to purchase contingent upon waiver, limitation or restriction of Buyer’s right to choose to obtain a home inspection. Should Buyer choose to have the premises inspected, if it is the inspector’s opinion that the premises contain serious structural, mechanical or other defects and if the repair of such defects would cost Buyer in the aggregate more than the amount indicated by the Buyer herein ($________), then Buyer shall have the option of revoking this offer to purchase by written notice to the Seller or Seller’s agent within 5 business days of the date of the inspection, or longer as Seller and Buyer may agree in writing. Such notice shall be accompanied by a copy of the inspector’s opinion and a copy of cost estimates obtained by Buyer.”

Understanding and complying with this new legislation is crucial for all real estate professionals. By staying informed and adapting practices, we can better serve our clients and uphold the integrity of our industry. If you have any questions or need further clarification on this bill, please do not hesitate to reach out to one of our Real Estate Attorneys.

Providing title, escrow, closing and settlement services to clients throughout Massachusetts and New Hampshire

From Our Clients

“I would highly recommend David as a closing attorney. I have known David and have been using his office for many years. David’s professionalism when dealing with me, my closing department and most especially my clients has been always exemplary.”
DAVID BREMER

SENIOR LOAN OFFICER, SHAMROCK FINANCIAL SERVICES

“The Law Office of Attorney David R. Rocheford, Jr. is by far the most exceptional real estate law office that I have had the pleasure of working with. The professionalism is by far second to none.”
JACQUI KEOGH

SENIOR LOAN OFFICER, SALEM FIVE MORTGAGE SERVICES

“Attorney David Rocheford has provided settlement and title services for me and Greenpark Mortgage several years. He has assisted all of my clients, including my family and friends with mortgage closings. Always providing excellent service. Reliable and trustworthy!”
SANDRA MALDONADO

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You’ve found your dream home in Massachusetts or New Hampshire. The offer is in, the inspection went smoothly, and closing day is in sight. But then—bam!—a title defect surfaces, and suddenly your seamless transaction feels more like a nightmare. At The Law Office of...

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