Case StudiesHome Buying March 28, 2026

Case Study: Winning in Warrendale Before the Market Moves Past You

By Mike DelRose Jr. | Saturday, March 28th, 2026

I put these case studies together to give clients a real look at how deals actually play out. Real estate is a human-driven, emotional business. Every transaction is as unique as the personalities involved, and the same situation can play out differently every single time. That said, there are patterns that show up over and over again, and the goal here is to help you recognize them so you can navigate your own decisions with more clarity.

Quick Answer

If you are trying to buy in a competitive market like Waltham, MA, winning often comes down to how your offer is structured and how you respond under pressure. In this case, removing a home sale contingency, using a bridge loan, and making a decisive move in a final round secured the property, even in a tight multiple offer situation.

Context

This buyer was not exclusively targeting the Warrendale neighborhood, but they understood it was one of the more desirable areas in Waltham and were ready to act if the right opportunity came up.

Location, location, location. Warrendale continues to stand out because of its proximity to Newton, Watertown, and Belmont, along with the overall feel of the neighborhood.

I had also sold multiple homes in this area before, so I was very familiar with how properties tend to perform, how buyers respond to pricing, and how competitive things can get when the right house hits the market.

Inventory was tight and demand was strong, which made this a classic seller’s market setup.

The Real Challenge

The challenge was not whether the buyer could afford the home. It was how to position the offer in a way that would actually win.

They had a home to sell, and while we were confident it would move quickly, including a home sale contingency would have made their offer significantly less attractive.

On top of that, based on the activity and pricing, it was clear early on that the home would likely sell above their initial offer. Had they come in stronger from the start, there is a very good chance we could have avoided a final and best situation altogether.

This is something you see all the time. Buyers are careful upfront, which makes sense. No one wants to overpay or feel like they are bidding against themselves. Then the pressure of competition kicks in, and the numbers move quickly.

You only know the market you are currently in. Trying to predict where things will go and holding back because of that can sometimes put buyers in a worse position than just reacting to what is actually happening in front of them.

What We Did

We focused on removing the weaknesses in the offer and putting the buyer in a position to compete.

The client secured a bridge loan so they could remove the home sale contingency and present as a clean buyer. That alone changed how the offer was perceived.

We submitted a strong initial offer, knowing there was a high likelihood of multiple offers. When the property went to final and best, we had a very short window to respond.

At that point, the buyer was able to access additional funds from a relative and increase their offer in a meaningful way.

We also had a direct conversation about timing. Prices tend to rise as the year progresses, especially heading into the spring market. Waiting for the next opportunity does not always mean you are getting a better deal.

My role in that moment is always a balance. I want to protect the client and make sure they are not overextending, but at the same time the goal is to actually secure the house. It is easy to be conservative early and then have to stretch later under pressure.

How It Played Out

There were three offers total, and our client ended up tied for the highest price.

From there, it came down to overall strength and certainty. Because we had removed the contingency and presented a clean offer, the seller chose our client.

Result

The buyer secured a home in one of Waltham’s most competitive neighborhoods. Their previous home sold quickly after, just as expected.

What This Means

This is a good example of how early strategy impacts the entire process.

If the buyer had come in stronger upfront, they likely could have avoided the stress of a final round entirely. Instead, like many buyers, they adjusted under pressure.

Sometimes buyers need to lose one to understand the market. In this case, they understood it in time.

Buyers can end up chasing the market without realizing it. They try to be disciplined early, then have to stretch later anyway. In a market like Greater Boston, properties often surpass their purchase price in value within a relatively short period of time, which makes that early hesitation less impactful than it feels in the moment.

There is always another house, but that next house may come at a higher price, with more competition, or with compromises that were not necessary the first time around.

Key Takeaways

• Offer structure matters just as much as price
• Removing contingencies can significantly improve your position
• Strong upfront pricing can help avoid final and best scenarios
• Buyers often make bigger adjustments under pressure than they would initially
• You only know the market you are currently in, not the one you are trying to predict

If you are in this position, it is worth thinking about how your strategy early on is going to affect your options later. The goal is not just to make a safe decision, it is to put yourself in a position where you are not constantly reacting to the next move.

Click Here For A Real Estate Search With Your Guide, Mike DelRose Jr. 

Have a question about this situation or something personal to you? Call Me at 617.515.7715

Uncategorized March 18, 2026

Protecting Clients Is The Priority

Protecting Clients Is The Priority

By Jenna Figueiredo Expand

A profile picture of Jenna Jenna Figueiredo

Jenna Figueiredo

Sales Associate
REALTOR® ABR®
617.272.6126
Jenna@DelRoseMcShane.com

Belmont & Watertown Real Estate Professional Delivering Polished Service and Results-Driven Marketing

Jenna Figueiredo brings a strong foundation in technology sales and corporate relationship management to her real estate practice in Belmont and Watertown. Her background in the tech industry makes her highly efficient at marketing listings using advanced automation, digital distribution strategies, and data-driven targeting to maximize exposure and drive results. Having grown up in Belmont and now residing in Watertown, Jenna combines hyper-local knowledge with a modern, systems-oriented approach. She leverages cutting-edge marketing tools, streamlined communication processes, and strategic positioning to help sellers stand out in competitive markets and buyers move confidently through complex transactions. Her corporate experience shapes her polished professionalism, structured communication style, and ability to navigate negotiations with clarity and composure. Clients appreciate her responsiveness, strategic mindset, and ability to execute with precision from listing preparation through closing.

March 18th, 2026 | Watertown, MA

A strong offer isn’t just about price. It’s about smart strategy, minimizing risk, and ensuring you’re protected from financing surprises, low appraisals, and everything in between. Here are some of the key protections I regularly include when structuring buyer offers or in practice:

Financing Contingency – If something unexpected happens with underwriting, employment, or the lender, you’re protected and your earnest money isn’t at risk. Without this, buyers can lose significant earnest money if the loan falls through. Life happens. People lose their jobs, are relocated across the country, of have significant upheavals. Waiving the financing contingency is something we see once and a while, but comes with a lot of risk. 

Appraisal Protection – Ensures you’re not forced to overpay if the home doesn’t appraise at the contract price and/or allows for the option to renegotiate. Often included under the financing contingency, buyers need this protection when competing for offers. This becomes even more important in competitive markets when homes are consistently selling at 5%-10% over the listing price on a properly priced home. 

Clear Title Requirements – Guarantees you’re receiving true ownership with no hidden liens, debts, or legal claims attached to the property. 

Final Walkthrough Protection – Allows you to confirm the home’s condition and verify agreed-upon repairs right before closing. Things happen, and its not unheard of to find a flooded basement, or fixtures removed that the buyer expected to be in the home at the time of closing. I conduct walkthroughs as close to closing as possible to protect my clients. 

Appliances & Fixtures in Writing – If it’s not explicitly written in the contract, the seller may take it. We see this unfold with fixtures that are expected to stay. I ensure everything is clearly documented to avoid disputes at closing and potentially added costs.

HOA Document Review For Condominiums – Gives you time to review the association’s rules, fees, and financial health so there are no costly surprises later. This allows my buyers to understand exactly what they are investing in beyond their unit. Buyers are sometimes surprised to find conflicting rules to their preferences, and need protection is something is discovered that would prevent them from living at the property in the way they see fit. 

A strong offer isn’t just about the price – it’s about minimizing risk and protecting you from expensive surprises after closing. My job isn’t just to help you win the home of your dreams. It’s to help you win the right way to empower you, with confidence and guidance at every point during the home purchase journey.

Thinking about buying? Let’s connect, talk through your goals, and build a strategy!

Team News March 18, 2026

Meet Our Newest Team Member: Dimitri Konstantopoulos

Meet Our Newest Team Member

For roughly three decades and two generations, Dimitri Konstantopoulos has been one of our best clients. Originally, his Father worked with my Grandfather, Concenzio "Connie" DelRose, before working with Mike DelRose Sr. after he retired. With over a dozen transactions involving investment property over the years, Dimitri built a portfolio and learned the business of property management and development.

This all changed a few weeks ago. Already a licensed real estate agent, Dimitri wanted to pursue assisting others in their real estate journey. He understood the benefits of how property ownership could transform people's lifestyle. His mindset echoes the values and aspirations of our team. So when he told us that he wanted to join and be a part of what we do, we were ecstatic.

Dimitri brings a unique set of skills to the team. A native of both Cambridge and Watertown, the current Waltham resident knows and understands his local market and home values.  Over the years managing property, he has developed a vast network of professionals and contractors he relies on that service is own properties. When helping home buyers and sellers alike, he will be able to provide more accurate costs for upgrades and projects, and other situations that can impact a home's value.

Losing a client is not a good thing, but I guess we can make an exception if they'll be bringing value to our Team's clients for years to come. Welcome aboard Dimitri!

Home Buying February 2, 2026

First Time Home Buyers: Demystifying Upfront Costs

By Jenna Figueiredo
February 2, 2026. Watertown, MA

As we all know, purchasing a new home or investment property can come with a lot of uncertainty. However there are certainties that we can plan for and make sure we understand ahead of our home search and ahead of submitting an offer.

In my experience working with buying clients, I am always asked “Jenna, how much cash should we be prepared to have available?” Let’s break it down – remember these costs are paid before closing or at closing:

  • Earnest Money Deposit (EMD)

    • Provided with an accepted Offer

    • Typically between $1,000 – $5,000

    • This amount is applied to your Down Payment at closing

  • Down Payment

    • Most buyers put down between 3% to 10% (some go as high as 20% to avoid private mortgage insurance)

    • On a $1M home (the current median in Greater Boston), that’s $30,000–$100,000

    • The amount of Downpayment will impact your monthly mortgage payment

  • Loan & Lender Fees

    • Loan Origination (about 1% of loan amount)

    • Underwriting & Processing Fee ($500 – $1,500)

    • Credit Report Fee (usually $25 – $75 per borrower)

  • Home Appraisal

    • Confirms the market value of the property for the lender

    • Typical cost $400-$800

  • Home Inspection

    • Typical Cost $600-$800 (average of a 2,500 sq/ft single family home in MA)

  • Title & Legal Fees

    • Protects ownership rights and completes transaction

    • Includes title search, recording fees, attorney fees, title insurance, etc.

    • $2,100 – $6,800+ depending on purchase price, title insurance choices, legal complexity

Overall, (in Massachusetts considering the average sale of a single family home being $1M and financing) expect to have between ~$30,000 and ~$115,000 cash available upfront before closing on your home.

Ultimately, these numbers will vary drastically depending on your own personal and specific situation. Every home search and financial preparation is different. Reach out to me, I would be happy to help you strategize and ensure you are preparing appropriately for your home purchase today!

ApartmentsLegal January 8, 2026

Massachusetts Rent Control On The 2026 Ballot

Introduction

We live in unprecedented times. 2025 was the longest 10 years of my life for so many reasons, and major shifts in the real estate landscape here in Greater Boston were certainly a part of that. Later this year Massachusetts voters will cast ballots to decide whether rent control will be implemented for the entire state after two decades since it was repealed by voters in 1994. 

As a REALTOR®, it is my responsibility to promote homeownership for buyers and the rights of property owners. That being said, this article is designed to educate voters on the history of rent control in Massachusetts and how it can affect different groups in the market. 

Laws and regulations of this magnitude will impact people differently, and it is extremely important to know how you personally would be affected. If you do not have strong feelings about the notion of rent control already, I want to provide an objective outlook so that you can make informed decisions for your own benefit. We will take a look at the history of Massachusetts policy, economic studies, and expert insight. I’ll include my opinion and thoughts at the end.

A Brief History of Rent Control In Massachusetts

It’s nothing new, relatively at least. Massachusetts has a long, contentious history with rent control1, which is marked by repeated cycles of implementation and repeal. The state first experimented with rent regulations during economic shocks, starting in 1920 following World War I and again in 1942 during World War II as the Federal Government under Roosevelt wanted to protect critical supply chain infrastructure. While federal price controls lapsed in 1953, Massachusetts lawmakers extended rent control locally through 1955, aiming to stabilize housing during turbulent times.

The most significant era of rent control emerged in the 1970s, when the state allowed cities like Boston, Cambridge, and Brookline to enforce their own rent regulation systems. These local rent control boards were given strong discretionary power; approving or denying rent increases, even for essential repairs. Over time, critics argued that the policy stifled new development, led to widespread property neglect, and benefited well-connected tenants, including affluent professionals rather than low-income residents. By the early 1990s, only three cities still had rent control, and voters repealed it statewide in 1994 through a ballot initiative brought to the table by landlords who felt they were being taken advantage of by affluent renters that could afford market rates. Cities like Boston, Brookline, and Cambridge were concerned that rental laws in their respective cities could be controlled by voters that lived all over the state. 

Since then, attempts to bring rent control back, either through legislation or local efforts, have been fiercely debated and consistently blocked. However, as housing costs have soared across the Commonwealth, a 2026 ballot initiative2 now proposes a strict statewide cap on rent increases, potentially reshaping this century-old conversation once again. The ballot initiative received nearly 50,000 more signatures than required to make it on the official ballot for this coming election cycle, signally strong and unified support for the idea. 

Why We’re Here

We are in a housing crisis and have been for quite some time. As simply as I can state it, there are far more people looking for homes than we have available. From my perspective the lengths at which my home buying clients have to go to put a home under agreement has become more costly and more risky. A problem that has become more and more exacerbated during my 15 plus years in the industry. 

My grandfather, a phenomenal real estate professional in his career, had always taught me that the middle class not being able to purchase homes would be catastrophic. Unfortunately, we’re at this point. First time home buyers I have traditionally worked with averaged in age from their mid to late 20s and are now closer to 40. It’s taking longer and costing more money. It’s a societal problem that is way more complicated and above my pay grade to manage.

While I don’t personally have a one-size-fits-all answer to solving the housing crisis, I did spend years working in PropTech to develop a platform that allowed home buyers to shop for homes based on their monthly budget. Housing affordability is important in my world. As the cost of living rose just as quickly as housing prices, I often wonder how anyone is surviving financially. It’s so profound that Governor Healy has created a comprehensive housing plan to address the problem3, results to be determined. The State has a strong understanding of what the problems are, stating that 222,000 homes need to be produced to slow housing costs enough that wages can catch up. Housing stock has been negatively impacted by climate change, deed restriction expiration, year-round units converted to short-term leases, and zoning restrictions. A Home For Everyone, is a plan that deserves more attention. It is a profound example of problems being identified with realistic solutions to solving them over the long-term. It won’t be easy, and the administration makes note of the challenges. 

Charts and data displaying information on housing affordability for renters in Massachusetts 2026

Data From The National Low Income Housing Coalition

Summary Of Ballot Initiative

Summary of the 2026 Rent Control Ballot Initiative

Purpose

The stated goal of the initiative is to provide housing stability and reduce displacement across Massachusetts by limiting how much landlords can increase rent each year.

Who It Applies To

The policy applies to most residential rental units statewide, with a few key exemptions:

  • Owner-occupied buildings with four or fewer units
  • Units already regulated by a public housing authority (tenants with mobile vouchers are not considered exempt)
  • Short-term rentals leased for less than 14 consecutive days
  • Units in nonprofit, religious, or educational housing
  • Newly built units (less than 10 years old), which are exempt for their first 10 years after receiving a certificate of occupancy

Rent Increase Limits

Annual rent increases are capped at the lower of:

  • 5% per year, or, the annual change in the Consumer Price Index (CPI)
  • The cap applies even if the tenant moves out and a new tenant moves in (i.e., vacancy does not reset the rent)
  • The rent level in place as of January 31, 2026 becomes the baseline (or the most recent rent charged for vacant units)
  • If a unit hasn’t been rented in five years or has no rent history, the first post-2026 rent becomes the baseline going forward

Compliance Requirements

For exempt units, landlords must provide tenants with written notice of exemption:

  • With the lease (for written agreements)
  • Or before the first rent payment (for tenants-at-will with no lease)

Enforcement and Penalties

  • Violations are treated as unfair and deceptive practices under Massachusetts consumer protection law (Chapter 93A)
  • Tenants may pursue legal remedies under Chapter 93A, including damages
  • The Attorney General may also take enforcement action, including civil penalties and injunctive relief

Other Considerations

The measure does not change or override any existing state or federal tenant protections

Initiative Petition For A Law

Below is the full text of the petition, formatted from its original document on the State’s Ballot Initiatives website. 

An Initiative Petition to Protect Tenants by Limiting Rent Increases

Be it enacted by the People, and by their authority:

The General Laws are hereby amended by striking out chapter 40P and inserting in place thereof the following:

CHAPTER 40P. LIMITING RENT INCREASES4

Section I. Purpose. 

The purpose of this act is to provide housing stability for tenants, landlords, and communities across the commonwealth, and curb displacement as a result of the housing shortage and affordability crisis in Massachusetts.

Section 2. Definitions.

For the purposes of this chapter “covered Dwelling Units” shall mean all dwelling units leased for residential, but not commercial, use, except:

(a) Dwelling units in owner-occupied buildings with four or fewer units.

(b) Dwelling units whose rents are subject to regulation by a public authority; provided, however, that occupancy by a tenant with a mobile housing voucher does not constitute being regulated by a public authority.

(c) Dwelling units that are rented primarily to transient guests for a period of less than 14 consecutive days.

(d) Dwelling units in facilities operated solely for educational, religious, or non-profit purposes.

(e) Dwelling units for which the first residential certificate of occupancy is less than 10 years old, for a period of 10 years from the date at which such certificate of occupancy was issued.

Section 3. Rent increase limits.

This chapter shall establish a limit on any annual rent increase for a covered dwelling unit in the

commonwealth, which shall not exceed the annual increase in Consumer Price Index or 5%, whichever is lower, in any 12-month period. This limit shall apply whether or not there is a change in-tenancy during the relevant 12-month period.

For purposes of this chapter, the rent amount in place on January 31, 2026, shall serve as the base rent upon which any annual rent increase shall be applied. If a covered dwelling unit is vacant on the date of adoption, the last rent amount charged shall serve as the base rent. If there was no previous rent amount, or if no rent has been charged for at least the previous five years, for a covered dwelling unit the rent amount the owner first charges following the date of adoption shall serve as the base rent. Where dwelling units are exempt, a notice of exemption must be provided with the lease for all tenancies. If there is no written lease for such dwelling units, the tenants-at-will must be provided with a written notice of exemption prior to the acceptance of the initial rent payment.

Section 4. Penalties.

Any violation of this chapter shall be deemed an unfair and deceptive act under chapter 93A of the General Laws. Any person claiming a violation of this chapter may pursue remedies under section 9 of chapter 93A. The attorney general is hereby authorized to bring an action under section 4 of chapter 93A to enforce this provision and to obtain restitution, civil penalties, injunctive relief, and any other relief awarded pursuant to said chapter 93A.

Section 5. Interpretation of This Chapter.

Nothing in this section shall be construed to interfere with any existing rights or protections afforded to tenants under current state or federal law.

 

According to Rent Cafe5 via The Cost of Living Index published by the Council for Community and Economic Research (C2ER), rent in Massachusetts is 48% higher than the national average. 

 

What Do Economists Say About Rent Control?

The short answer is that there are a lot of factors and a situation that are hard to measure when often additional policies affect pricing. What I have learned from researching the topic of whether or not rent control is good policy or bad policy is that there is so much nuance. Many economists say long-term rent control does not solve a housing affordability crisis6. It can actually exacerbate the supply problem. What rent-control policies can help with is the displacement of low-income households, something it can be extremely effective at, which I find notable and an important facet to consider. The root-cause of the housing crisis is supply, and with more people needing to rent than currently renting, economists push for relaxation to zoning laws and regulations that prohibit new development. I have noted consistent messaging through various studies that credit rent control’s short-term benefit with immense tradeoffs down the road. 

A paper published by Economist Konstantin Kholodilin7 with the German Institute for Economic Research concludes that while the policy measure appears effective for households in controlled units, it comes with undesired effects that equate to higher rates in uncontrolled units, lack of mobility, and reduced residential construction. Kholodilin also notes that other regulations, policy, and external economic factors will complicate the outcome and evaluation of a policy’s perceived success.

An Interesting Note About Rental Inventory In Our Market

2025 saw an interesting change in Greater Boston’s rental market, at least for the communities I primarily serve. In April of last year a few dozen international students at local universities had their visas revoked. Massachusetts has roughly 450,000 international students, contributing $4B to the local economy in 20248. That’s almost 1 in five students, with Massachusetts hosting the 4th largest international student population in the country. Nationally, studies have shown that international students are now avoiding the United States, with a 6% drop in enrollment for undergraduate programs, and 19% for graduate students respectively9

With college students representing a huge portion of the leasing population in the area, how will that impact rental rates and the real estate market as a whole? Anecdotally, rental inventory has been up on the Multiple Listing Service (MLS), and our apartments have been more difficult to lease. Condominiums that have previously been attractive options for investors have also seen a decline in demand in some cases. Either way, we have seen repercussions from this shift in National Policy. 

Annecdotal Observations

A story I often hear from my network, and especially from those renting are situations in which a tenant is informed that their rent is being raised significantly. They find a new place at a predictably higher cost but lower than their current residence, and move out to discover that their original unit was listed at $100 higher than what they were paying. An increase the tenant would have been willing to pay. Other times, I hear of decrepit college apartments that don’t need to be maintained due to their scarce supply and students that need an apartment for only one year. My contractors have shared horror stories of some of the safety issues they have encountered. I hate this about our apartment sector. 

The rental industry, especially here in Greater Boston is dysfunctional. I haven’t even mentioned the rampant discrimination that has occurred and how easy it is when tenants do not have advocates on their side. That is a discussion that deserves its own article. For these reasons as well as sky-rocking costs I am all ears to potential solutions to fix the myriad of problems that tenants face. I represent their interests as well as landlords. 

I fully support sound policy and protections from disadvantaged groups. You’ll be hard-pressed to find a bigger advocate of Fair Housing Laws in our marketplace, a cause I am fervent about. While My personal opinion may not matter in the grand scheme of things, I’ll provide what I like and dislike about the ballot initiative. Maybe it helps you understand a different perspective than your own.

What I Like About The Ballot Initiative  

Like an effective protest, it turns heads. Sure, it may be extremely controversial any way you slice it, but it’s presented by people that want to accomplish something positive that helps people. I celebrate that. Instead of buying into the system, one that is clearly failing, awareness has been raised and there can be conversations. Perfectly sound or an idea so crazy it would never work, I want to hear it and I applaud the effort. There are people struggling out there and I’m all for protections for those groups. Some of you may disagree with the sentiment, and that’s more than okay too. 

Where The Ballot Initiative Needs Improvement

While the intentions behind the proposed rent control measure are understandable, protecting tenants from steep increases during a housing crisis, the policy, as written, doesn’t address the root cause of the problem: a lack of housing inventory. Nor does it have the ability to on its own. Without working in tandem with a plan to meaningfully increase the supply of available units, we risk applying a short-term fix to a long-term structural issue.

Rent control may offer immediate relief for some, but it can unintentionally create new challenges for others, especially small-scale, independent landlords. I work with many of these “mom and pop” owners who rely on a single rental unit, often a condo, as their retirement plan. Unlike corporate investors, they typically avoid frequent rent hikes, opting instead to prioritize long-term, respectful relationships with their tenants. For landlords who have kept rents stable for years, a blanket cap on increases, even after a long-term tenant vacates, feels disproportionately punitive.

Policy should aim to balance the needs of tenants and property owners alike, and in this case, I worry the pendulum may swing too far in one direction as we have seen historically. If we want to create a healthier housing market, we need solutions that expand access, encourage responsible ownership, and promote long-term affordability, not just freeze pricing in place. That starts with building more homes, not just regulating the ones we already have.

Is There An Alternative?

What about options such as short-term rent control fixes for a couple of years, subsidies for those that need help the most, tax breaks for landlords that do not increase their rents on an annual basis, etc. 

Again, I am the wrong person to provide the solution, but an agreeable one will likely require leaders from different interest groups coming together to form an amiable solution. If that’s even possible. 

In Final Thought

It was rewarding to take a deep dive into some of the data and history behind the rent control policy. Especially since its not a side of the industry I spend the most amount of time in. The challenge I see with any sort of policy change is that for many of the groups that would be affected, or seeking relief for that matter, are immensely challenged one way or another. While I’ll stop short of encouraging a vote one way or another this fall, My hope is that I have presented enough information for the reader to either; invest more time in understanding the issue, or providing a different perspective that can create meaningful conversation.

Home BuyingHome Selling January 6, 2026

New England Winter – Don’t Miss Out!

By Jenna Figueiredo
January 6, 2026. Watertown, MA

When most people think about real estate moves, spring and summer may be the initial thought of the “right time”. The truth is, winter is one of the most strategic times of the year to purchase personal and investment property. Why?:

1. Less Competition = Stronger Negotiation Power

The winter months naturally bring fewer active buyers. With reduced competition, investors often have more room to negotiate, secure better terms, and avoid bidding wars that drive prices up.

2. Motivated Sellers

Homes listed during the winter typically belong to sellers who NEED to sell, not just those who are “testing the market.” This creates opportunities for buyers and investors to secure properties at agreeable prices.

3. A Clearer Picture of a Property’s State

Winter weather exposes issues that might stay hidden during warmer months. Such as:

  • HVAC performance

  • Insulation quality

  • Roof condition

  • Drainage and land behavior

4. Faster Closings and Easier Due Diligence

Lenders, appraisers, inspectors, and title companies are often less backed up during the winter. That means you benefit from quicker timelines and smoother transactions.

5. (Investors) Positioning Yourself for Spring Rental Demand

Buying in winter allows investors to make improvements and have the property ready for peak rental or resale season in early spring allowing for a maximum return on investment.

Overall, the winter real estate market quietly holds some of the best opportunities of the year for buyers willing to act while others wait for the warmer months to roll around. If you’re considering making a move. expanding your investment portfolio, or simply exploring opportunities in the Greater Boston market, I would love to connect, share experience and discuss strategy.


A profile photo of Jenna Figueiredo wearing a white blazer and a soft white background

JENNA FIGUEIREDO
REALTOR® | Accredited Buyer’s Representative (ABR®)
Coldwell Banker Realty
130 Concord Ave, Belmont, MA, 02478
C. (617) 272-6126 | O. (617) 266-4430

Home Buying November 24, 2025

Gather & Give Thanks: How Homeownership Makes Friendsgiving Even Sweeter

A profile picture of Jenna Jenna Figueiredo

Watertown, MA. November 24th, 2025

By Jenna Figueiredo


November is a time to reflect and be grateful for the lives we live! As I take a moment to myself, I am blessed to be sitting around a table of my closest friends. What makes this year extra special is my best friends are hosting the festivities at their new home. They have created a warm home, weaving their charm, style, and personalities into every corner of their space. As their trusted advisor and Realtor, I had the privilege of guiding them through the journey of purchasing their first home, making this Friendsgiving celebration even more meaningful.

Homeownership is a beautiful opportunity, it’s a choice, it’s a financial commitment, it’s a journey. It requires patience, strategy and long-term value planning for future growth and appreciation. It’s a dedication to building a residence and roots, it’s an immense privilege! Watching my friends step into homeownership this year has been a powerful reminder of how meaningful this journey can be. 

In 2025, first-time home buyers have been active but up against a competitive landscape. With Greater Boston’s high prices and limited inventory, professional real estate guidance is critical to success. Ultimately, preparation is key: Getting a  pre-approval, understanding closing costs, and working with a local agent who understands and has a pulse on the market realities. 

If buying or selling a home is on your mind, especially in Greater Boston’s competitive market, I’d love to be your guide. Together, we can navigate the process. I standby leading with confidence, strategy and integrity so you can focus on building the life you envision. Let’s connect and start the conversation, your dream home could be closer than you think!

Team News November 20, 2025

The Day I Almost Quit

A profile photo of Mike DelRose Jr. with a landscaped green background

By Mike DelRose Jr.

Belmont, MA .Thursday, November 20, 2025


It still sits with me, more than ten years later.

I’ve finally found the clarity and courage to share an experience that nearly drove me out of real estate for good. This post isn’t a masterclass or a marketing piece. It’s a catharsis. But if you’re in this business or have worked with someone who is, there are important lessons here worth sharing.

A Detour That Became a Calling

In 2009, I graduated with a degree in marketing and minors in sports management and business administration. At the time, joining the family real estate business was the furthest thing from my mind.

I was all-in on a career in professional sports. I even paid for one last academic credit after graduation just to intern with the Kraft Sports Group. That summer was meant to be my launchpad. But the economy had other plans.

It was the aftermath of the financial crisis. Companies were slashing marketing budgets left and right, and landing a job in sports, or anywhere near it, wasn’t looking good. Sales roles were available, but they weren’t in the direction I was aiming.

Around the same time, real estate was evolving. The internet was shifting from a helpful tool to a mission-critical platform. I pitched an idea to Mike Sr. Let me modernize the business; systems, branding, marketing, and then I’d move on to “Mike Jr.” things.

Only I didn’t.

What started as a stopgap turned into a passion. I discovered I loved guiding people through life-changing decisions. It gave me purpose. It was emotional, intense, and deeply rewarding. 

But a few years in, one situation made me question whether it was worth continuing.

The Knock on the Door

It was a normal day at the office. I wore a suit every day back then and took calls on a desk phone—both rarities now. A local homeowner called and asked me to provide a broker price opinion. They knew our family and wanted to hear what we thought.

When I arrived, the owner shared something that immediately raised red flags: they had recently gone through a major medical issue and weren’t thinking clearly. My instincts kicked in. This person didn’t need just representation. They needed advocacy.

We walked the property and talked options. Then someone knocked on the door.

A person was standing there with a purchase contract in hand. No prior appointment. Just… there.

My first thought: was I too late?

Too late to earn the business? Maybe. But more importantly, was I too late to help protect this person?

What most of my clients know about me is this: I’m not attached to being the one who gets the listing. I’m attached to doing the right thing. And in this case, that meant ensuring someone vulnerable had professional eyes on a major decision.

Doing the Right Thing and Getting Burned

Before I left, I asked for the name of the owner’s attorney and gave them a call. I explained the situation, not to interfere, but to flag that someone who explicitly told me they were mentally compromised was about to make a significant financial decision.

I told the attorney, paraphrased:

“Your client just told me they’re not thinking clearly due to medical reasons. They’ve received an offer on their home. I’m not inserting myself into the deal, but they need someone looking out for them, and they named you.”

I hung up that call thinking I did the right thing.

I was wrong.

The Fallout

Later that day, or maybe it was the next, I got a call from the seller. What followed was one of the most brutal phone calls of my career. I was berated, insulted, and mocked, with personal details from my background thrown back at me.

Apparently, the buyer had told them I was clueless, didn’t know what I was doing, and dug into my public bio online for ammunition. I was blindsided.

I explained that I hadn’t interfered with the transaction. I didn’t ask for business. I simply alerted their legal representative with their permission because I thought they needed help. That’s it.

And still, I got torched.

The hardest part? Realizing that trying to do the right thing could end up hurting you.

In that moment, I questioned everything. Not just my actions, but my entire career. Was it even worth it?

The Aftermath

A few days later, the seller called back and genuinely apologized.

The buyer, likely a local contractor, did end up purchasing the home months if not a couple of years later. He probably still thinks I’m an idiot. That’s fine.

Because even now, more than a decade later, I’m okay knowing that I did everything I could to protect someone who might have been taken advantage of.

The Takeaway

So what’s the lesson?

No good deed goes unpunished? You can’t win them all? Maybe. Or maybe there’s no lesson at all, just the reality that doing the right thing doesn’t always feel good or end well.

But here’s what I do know:

I’m not going to change.

I’m not entitled to anyone’s business. But when someone asks for my help, they’ll get the full extent of my care, my expertise, and my advocacy. No shortcuts. No apologies.

Over the years, there have been other moments that tested my resolve. That comes with the territory in this business. But the difference now? I expect those moments. And they won’t derail me.

Because I didn’t get into this for easy wins. I’m here to do right by people. Even when it’s hard.

Home BuyingHome SellingTeam NewsUncategorized October 31, 2025

Greater Boston Real Estate: Fall Market 2025

A profile photo of Mike DelRose Jr. with a landscaped green background


By Mike DelRose Jr.

Friday, October 31st, 2025. 10:34 AM

Belmont, MA


Happy Halloween!  What a strange time to be in real estate, or life for that matter, but I digress. Market shifts are expected, cyclical, an often have reflected long-term trends. This market now is ambiguous at best. When I first started in the industry in 2009 the market was non existent. Properties sat for months, buyers didn’t really have the money to purchase homes, and lenders were hesitant to spot you $5 for coffee. I remember getting a client a great Cape in Metro West for a price around $250,000! What a great year to graduate from college by the way (Work hard they said. Study hard they said. Great opportunity they said). But even in that market the data was persistent and the sentiment remained true for the next two years before taking a turn that was clearly palpable.

Many sellers that inadvertently listed too late in the Summer this year came to the harsh realization that pricing wasn’t what it was a couple of months prior. Remember that listing data is always 60-90 days old. But even when the market took a breather at times over the last couple of years, things were still going strong. Throughout much of 2025 we professionals were being told from lenders issuing pre approvals and applications that they were getting busier. Even though inventory was coming up year over year, business was still strong based on so much demand spillover. The promise of the reduction in mortgage interest rates was also short lived. But we’re in Greater Boston, we’ll be fine….

The oddest part about the Fall right now, is that every indication of market strength or weakness is being seen on a case-by-case basis. Locations, property types, price points, and even specific properties are all having their own experiences. Earlier this month, a client of mine successfully beat out 9 other offers to secure a home they had been searching for over the last year. The trade-up market in that community had been extremely competitive over the past 24 months. A listing of mine in the same community in a slightly, but not drastically lower price point, received only a couple of offers.  Despite a great selling price with competition, and happy clients to boot, buyers noticeably took their time after the first weekend of open houses before expressing interest in presenting offers. Of the dozen or so buyers through the open houses or interest expressed via their agent showing serious interest, only a few took the next steps. The house was immaculate by the way. The 80-20 power rule, otherwise known as the Pareto Principle, was on full display here, with 20% of the traffic submitting offers, and causing 80% of our potential opportunity to sell.


 

Thumbnail For a Belmont Massachusetts Real Estate Report PDF file

Belmont, Massachusetts September 2025 Real Estate Report

Thumbnail image of the September 2025 Watertown, MA real estate report linking to the full PDF file

Watertown, Massachusetts September 2025 Real Estate Report

 


 

If you take a look at the Belmont report for example, you will see an increase in supply of homes, a decrease in number of homes sold, and a correlated decrease in absorption rate to reflect the two figures. I love the absorption rate because despite the lagging data, you really can get a feel for what a potential search is going to look like or more accurately predict activity on an upcoming listing. In Belmont and Watertown, our two primary market with office locations, that figure still remains in the mid-20% range. Listings still have a slight edge, but buyers are playing ball instead of overbidding.

When we’re thinking about pricing a listing or preparing a market analysis in terms of gauging a solid offer price, we provide values in ranges to account for varying preferences and subjective tendencies. However, when we’re analyzing the market as a whole across all price points, we really want to avoid averages and focus on the median. With traditionally lower inventory, one $3M+ property can throw off our perception of price points between $800,000 and $1.5M. In our analysis here, its clear that prices have still risen over the past 12 months, but have come back down to earth after a big boom at start the year.


On to a more depressing reflection on our current market; Wonder why the rental market has absolutely tanked? Watertown, at time of writing has 94 rental properties listed through MLS. Belmont has 37. After removing 1 listing from the total for having a $17,000/month rent. We’re looking at an average monthly rent just shy of $3,400/month, with days on market a hair under 2 months. Yikes. Mind you, while I personally avoid the rental game, I don’t remember the last time I rented a unit in Watertown or Belmont that didn’t have dozens of potential applicants.

Well no wonder the market is ambiguous! Investors and landlords have been sidelined which takes competition and demand from other residential listings. In Greater Boston we have desirable educational systems, higher education, hospitals, and biotech that has attracted people from all over the …. oh…. Could our current market economics be tied to the cancellations of visas? It may not be the only reason but it sure looks like it isn’t helping. I’m not sure of the amount of people avoiding coming here at time of writing, but I would not be surprised to see the fear from sectors like education may be spilling over to other industry as well. Regardless of the reason, the rental market is soft. With new state regulation that requires brokerages to only take fees or commission from those they actually represent, any positive impact of the new transparency and fairness regulations seem to be overshadowed by doom or gloom here.

This market segment really reminds me of the recession. I can’t tell you as a buyer, seller, or renter there will be less risk by making moves now. But what I can say is that historically, in several years many will look back at this time period and wish they had or were at least able to make a purchase or sale position to bolster their portfolios.


Do you know what I’m really high on right now? The Patriots. I had them at an improved 7-9 wins this year and they appear to be blowing by those expectations. Really, I was just hoping for more than the paltry 4 wins from 2024, and a much improved Drake Maye. In reality, we have a quarterback that has not only exceeded expectations for a 2nd year starter, but has surpassed many of his quarterback peers, landing him in elite company with the leagues best. Anything can happen of course, and I can’t be too upset by a little heartbreak at the end of the season, however the last 5 games has shown consistency at quarterback on a level we haven’t seen since, bless his name, Tom Brady. On a side note, I peaked as a real estate professional when I was quoted in a Forbes article talking about his property a few years ago. Anyways, I’m excited for football again.


Because it is the final day of spooky season, and I haven’t really been able to do anything on theme, I’ll have you check out the Spooky Real Estate blog article I wrote in the past. Case law is fascinating, and real estate case law is My jam. Anyways, haunting are real according to courts and you should read to find out why.


Lastly, as we approach Thanksgiving and the season of giving back, I want to turn your attention to a great cause our team is supporting. As many of our clients know, we have hosted events at our office and handed out Thanksgiving Pies along with a cocktail party. Loads of fun and we hope to get back to that at some point. This year, however, we are partnering with an organization called Community Servings. We are selling pies with all proceeds going the toward providing scratch-made meals to individuals with chronic illness and their families who are facing food insecurity. With SNAP benefits being tabled for the month of November, our humble fundraiser has become much more important. Pies can be purchased from our Seller page for $35.00, and picked up on Tuesday, November 25th, 2025, between the ours of 12:00 PM and 6:00 PM at our office located at 130 Concord Ave, Belmont, MA 02478. We’d love to see you, and appreciate any effort put toward the cause.


This rambling, sorry excuse for a blog entry was proudly written by Mike DelRose Jr., and not ChatGPT, although it probably should have been. 

ApartmentsLegal July 2, 2025

Fairness, Transparency, and a Long Overdue Rental Reform In Massachusetts: The Potential Elimination of Tenant Broker Fees

July 2nd, 2025- By Mike DelRose Jr.-The Massachusetts Legislature just took a big step toward balancing the scales in our housing market. Included in the Fiscal Year 2026 budget is a provision that would ensure rental broker fees are only paid by the party who actually hires the broker. It’s a simple idea that mirrors how we already handle buyer and seller agency in real estate sales. And frankly, it’s long overdue.

As someone who has spent years working in both marketing and real estate, I see this proposal as a win for transparency and fairness. Too often, tenants are burdened with a financial load that goes far beyond their first month’s rent. They’re paying for the last month, a security deposit, and a broker fee—sometimes totaling four times the monthly rent. Even worse, those broker fees often pay for services that exclusively benefit the landlord: advertising, tenant screening, showings, and lease negotiations.

Governor Maura Healey’s budget originally proposed the complete elimination of tenant-paid broker fees. While this final version doesn’t go that far, it does make the responsibility clear. If a broker works for a landlord, the landlord pays. If a tenant hires a broker to represent them, then the tenant pays. It’s not complicated. It’s aligned with how agency works in most real estate transactions.

The disconnect has been especially glaring in Boston. With an annual flood of college students and limited housing near transit and universities, demand has driven up prices while quality lags far behind. In neighborhoods like Allston and Brighton, I’ve had contractors tell me they’re shocked by the conditions of some units. Yet every year, tenants are paying more for less and often feel like they’re being rushed into decisions with little support or advocacy.

An image of a reddit user commenting how terrible it is to rent in Boston, using an image from the hunger games to make their point

Boston Apartments-May The Odds Ever Be In Your Favor

There’s a reason tenants feel like the system is stacked against them. The structure incentivizes speed and volume over service and quality. I’ve had more than one client ask why there isn’t a review system for landlords and tenants—similar to what we see in short-term rentals. It’s a great question, and the answer likely lies in fragmented listing systems, data costs, and lack of industry-wide incentives to build something better.

That said, not every rental story is negative. In the suburbs surrounding Boston, many of the landlords I work with take a more measured and respectful approach. The pace is slower. The negotiations are thoughtful. And while the challenges aren’t absent, the experiences are generally more positive.

Ultimately, this reform is about correcting an imbalance. It brings the rental process more in line with the fairness we expect in real estate sales. While I understand that some agents and landlords may need to adjust their models, the broader goal of improving access to housing and removing financial barriers is one I fully support.

If I have one point I’d want considered in this provision, it would be appropriately addressing application fees. Currently, the law states a landlord cannot charge an application fee for an apartment, but it can be required by a brokerage. As it stands, a landlord or broker could be responsible for paying a third parties screen fee multiple by the number of tenant applicants. Whether that is paid by the broker or landlord, it could create an uncapped cost that could result in substantial higher rent prices. That increase in cost could theoretically be passed down to the tenant regardless. Some Agents I have spoken with about the proposal thinks this will happen regardless, which may be the case. Even so, an amortized cost-recuperation on behalf of the landlord would be much more affordable than charging exorbitant up front cost. If passed, it remains to be seen how the market will react. 

These views are my own and offered with respect to my peers in the real estate community. Many of us work hard to uphold ethical practices in every transaction. But if we’re honest, this change helps move the industry in the right direction. Governor Healey has until July 10 to sign the budget. If she does, this new rule goes into effect on August 1, 2025. I believe it will bring much-needed relief to renters while holding our industry to a higher standard of fairness and transparency.