“Jill Fitzpatrick went above and beyond in every way. Saying we were lucky to have her as our real estate agent is an understatement. Working with her was 10/10 in every category! Highly, highly recommend.”
Century 21 C21 North East
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for June 2026. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
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Oak Square real estate Market Report.
Information and statistics on the latest trends in the Oak Square real estate market. *
Latest Rolling 3-Month Snapshot
Feb 1, 2026 - Apr 30, 2026
Median sale price
$787K
-6.7%
from
Q1 '26
Median list price
$793K
-6.7%
from
Q1 '26
Active listings
79
+32%
from
Q1 '26
Homes sold
19
+5.6%
from
Q1 '26
New pendings
33
+38%
from
Q1 '26
New listings
55
+28%
from
Q1 '26
Quarterly Pricing Trends for Oak Square
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Oak Square
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Oak Square
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Oak Square
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Oak Square
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Oak Square
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
24
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Feb 2026 - Apr 2026).
Oak Square is currently tilted toward sellers, with the local gauge reading a seller’s market despite signs of cooling. Over the latest rolling three-month period ending in April 2026, there are about 7.6 months of supply, up sharply from a year ago and higher than Boston’s 6.4 months. Home values have moved lower year over year, with the typical home value down noticeably compared to the same period last year.
Inventory has expanded while demand has softened, helping explain this shift. Active listings are up strongly from a year ago, and new listings have climbed more than 30 percent year over year, giving buyers more options than in recent springs. At the same time, homes are taking much longer to sell, with median days on market up significantly compared to a year earlier, signaling less urgency. Even with this slowdown, about 39 percent of recent sales still closed above list price, and the average sale-to-list ratio is holding near 99 percent.
Compared with the broader Boston market, Oak Square’s prices are slightly lower and its supply is somewhat higher, suggesting conditions may feel more negotiable for buyers than in some nearby areas. Buyers can use the increased inventory and longer marketing times to be more selective and deliberate, while sellers still benefit from a market that leans in their favor when homes are priced well. To navigate these mixed signals and recent shifts, both buyers and sellers can turn to Agent Pronto to connect with a local agent who understands Oak Square’s current dynamics.
Learn more about what Oak Square has to offer.
Oak Square offers residents a tight-knit, walkable neighborhood with accessible parks, convenient local shops and dining, dependable transit options, and a balanced mix of housing that supports a vibrant, connected community.
Oak Square offers a distinctly neighborhood feel compared with busier nearby areas of Boston like Allston and Brighton Center. Centered around a classic New England rotary, Oak Square blends triple-decker homes, modest condo buildings, and side streets lined with trees, giving residents a quieter base with quick access to downtown.
Locals rely on the 57 bus line and nearby Green Line B branch stops, making commutes into Back Bay or the Financial District straightforward. Proximity to Massachusetts Turnpike entrance points is a plus for drivers. Oak Square is also close to the Charles River, where the Herter Park and Charles River Reservation paths draw runners, cyclists, and dog walkers.
Daily life centers on small businesses, with casual restaurants, corner markets, and coffee spots that give the area a familiar, lived‑in character. Families appreciate access to neighborhood schools and the broader educational resources of Boston, as well as nearby institutions in Brookline and along the Longwood Medical and Academic Area.
Whether you are weighing a condo purchase near the square or considering listing a long‑held multifamily, timing and preparation are key in Oak Square’s competitive market. Agent Pronto can connect you with a knowledgeable local agent who understands current pricing, buyer demand, and how to position your move, helping both buyers and sellers make the most of their next step.
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“Sarah Rodewald was excellent, especially with being a first time home buyer. She was friendly and responsive when I had questions or concerns. Sarah was a strong advocate for me during negotiations to secure a fair price and credits towards closing. I would highly recommend Sarah for anyone looking for a dedicated expert agent.”
SR Realty
“I can't thank John Dean enough for handing the sale of my home. John's knowledge of the industry and the area was exceptional. He kept me informed of all the issues and guided me with decisions that had to be made. He offered to make several trips to the house to meet and coordinate the inspections and other people that assisted me with the move. Not being available to make it to the property for various reasons being the distance and caring for a disabled husband, John saved me from having to be there. John was there to manage everything for me. If you need a professional agent, look no further than John Dean.”
Engel & Völkers Engel & Volkers Boston
“I interviewed several Realtors, and none of them asked the thoughtful questions that Katherine did to better understand my needs. She also demonstrated a deep knowledge of the Boston program I was using for financing, and her years of experience working in and around Boston was key. But more than anything else, we got along really well in our initial meeting and she had my full trust almost as soon as the process began.”
LAER Realty Partners
“He was honest enough to direct us away from one of the homes that we looked at because of the horrible basement there. He also showed us at least 5+ homes before we settled on the one we're living in now.”
Elias Group Realty
“We were referred to Michelle by a friend. She knows Newton and the surrounding areas; she knows real estate; she knows everyone associated with real estate, including mortgage brokers, inspectors, and insurance agents. Michelle is very professional but also personable. She has a knack for explaining markets trends and is skilled at reading the psychological aspects of an offer/counter-offer. She was extremely responsive and helped us buy an incredible house in a great location - in the hottest market in history! In short, I recommend Michelle with great enthusiasm. She is the absolute best.”
Michelle Lane Real Estate
“I was recommended by a friend to call Kerry Lapiana with Prestige Homes. I am so glad I did. Kerry went up and beyond from the beginning until the end. She was always available with any questions I had and she made the offer process so easy. It didn't end there. She even took time after I closed to ask me how it was going if I needed anything additional. She went up and beyond every step of the way. I would highly recommend Kerry Lapiana and Prestige Homes to friends, family and colleagues.”
Diamond Key Real Estate
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”
William Raveis Residential
“Scott was excellent and I highly recommend him. As a first time buyer, I had many questions and concerns, and he answered and alleviated all of them. We were on the same page from the start regarding strategy, and he deftly navigated through a couple unexpected and complicated situations after the initial offer had been accepted. I definitely plan on using Scott for any future real estate needs.”
Engel & Völkers
“Kyle moore and kim arsenalt saved my llife. I Just had a son. Lost my mom. My paperwork wasnt great. these 2 put things together that i couldnt have emagined.hear i am now in a multi. Tenants ask how i want the rent paid. I look at them like they're crazy for 2 seconds and say "check or M.O.".IF YOU Feel like me. Those are the ones you want on your team. Then grab KATHY as the lawyer. Shes the best too”
Zander Realty Group
Frequently Asked Questions
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There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Oak Square. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Oak Square Realtor® or real estate agent today.
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