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Real estate in Boston’s Oak Square neighborhood.

Compare top Oak Square real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 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

Jul 1, 2026 - Sep 30, 2026

Median sale price
$1.1M
+49% from Q2 '26
Median list price
$1M
-0% from Q2 '26
Active listings
76
-21% from Q2 '26
Homes sold
32
+23% from Q2 '26
New pendings
17
-55% from Q2 '26
New listings
36
-36% from Q2 '26

Quarterly Pricing Trends for Oak Square

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Oak Square Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $933K Median sale price in Jan 2022 - Mar 2022: $940K Median sale price in Apr 2022 - Jun 2022: $625K Median sale price in Jul 2022 - Sep 2022: $739K Median sale price in Oct 2022 - Dec 2022: $655K Median sale price in Jan 2023 - Mar 2023: $773K Median sale price in Apr 2023 - Jun 2023: $988K Median sale price in Jul 2023 - Sep 2023: $767K Median sale price in Oct 2023 - Dec 2023: $650K Median sale price in Jan 2024 - Mar 2024: $1M Median sale price in Apr 2024 - Jun 2024: $1.1M Median sale price in Jul 2024 - Sep 2024: $615K Median sale price in Oct 2024 - Dec 2024: $933K Median sale price in Jan 2025 - Mar 2025: $950K Median sale price in Apr 2025 - Jun 2025: $906K Median sale price in Jul 2025 - Sep 2025: $843K Median sale price in Oct 2025 - Dec 2025: $798K Median sale price in Jan 2026 - Mar 2026: $844K Median sale price in Apr 2026 - Jun 2026: $770K Median sale price in Jul 2026 - Sep 2026: $1.1M Median list price in Oct 2021 - Dec 2021: $799K Median list price in Jan 2022 - Mar 2022: $754K Median list price in Apr 2022 - Jun 2022: $790K Median list price in Jul 2022 - Sep 2022: $650K Median list price in Oct 2022 - Dec 2022: $793K Median list price in Jan 2023 - Mar 2023: $940K Median list price in Apr 2023 - Jun 2023: $799K Median list price in Jul 2023 - Sep 2023: $869K Median list price in Oct 2023 - Dec 2023: $775K Median list price in Jan 2024 - Mar 2024: $1.1M Median list price in Apr 2024 - Jun 2024: $863K Median list price in Jul 2024 - Sep 2024: $739K Median list price in Oct 2024 - Dec 2024: $995K Median list price in Jan 2025 - Mar 2025: $899K Median list price in Apr 2025 - Jun 2025: $829K Median list price in Jul 2025 - Sep 2025: $889K Median list price in Oct 2025 - Dec 2025: $1.1M Median list price in Jan 2026 - Mar 2026: $850K Median list price in Apr 2026 - Jun 2026: $1M Median list price in Jul 2026 - Sep 2026: $1M Oct 2021 - Dec 2021 Median sale price $933K Median list price $799K Jan 2022 - Mar 2022 Median sale price $940K Median list price $754K Apr 2022 - Jun 2022 Median sale price $625K Median list price $790K Jul 2022 - Sep 2022 Median sale price $739K Median list price $650K Oct 2022 - Dec 2022 Median sale price $655K Median list price $793K Jan 2023 - Mar 2023 Median sale price $773K Median list price $940K Apr 2023 - Jun 2023 Median sale price $988K Median list price $799K Jul 2023 - Sep 2023 Median sale price $767K Median list price $869K Oct 2023 - Dec 2023 Median sale price $650K Median list price $775K Jan 2024 - Mar 2024 Median sale price $1M Median list price $1.1M Apr 2024 - Jun 2024 Median sale price $1.1M Median list price $863K Jul 2024 - Sep 2024 Median sale price $615K Median list price $739K Oct 2024 - Dec 2024 Median sale price $933K Median list price $995K Jan 2025 - Mar 2025 Median sale price $950K Median list price $899K Apr 2025 - Jun 2025 Median sale price $906K Median list price $829K Jul 2025 - Sep 2025 Median sale price $843K Median list price $889K Oct 2025 - Dec 2025 Median sale price $798K Median list price $1.1M Jan 2026 - Mar 2026 Median sale price $844K Median list price $850K Apr 2026 - Jun 2026 Median sale price $770K Median list price $1M Jul 2026 - Sep 2026 Median sale price $1.1M Median list price $1M
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
45
Neutral Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).

Oak Square currently reflects a neutral market, with conditions balanced between buyers and sellers. Months of supply has risen to 4.1, up sharply from a year ago, which eases some of the pressure on buyers. At the same time, homes still command strong prices, keeping sellers engaged.

A rolling three-month look shows typical home values around $1.15 million, up more than 30 percent from a year earlier, signaling substantial price growth. Year over year, inventory has increased, with active listings up while homes sold have dipped, and pending sales are down more than a third, suggesting some buyers are pausing or taking longer to commit.

Homes are taking slightly longer to sell than last year, with a median of 22 days on market, yet nearly 30 percent still go off the market within two weeks. About one-third of sales close above list price, and the average sale-to-list ratio is just under 100 percent, indicating sellers who price correctly can still achieve near-asking offers. Compared with the broader Boston market, Oak Square shows stronger price gains and somewhat leaner supply. In this nuanced environment, both buyers and sellers can benefit from Agent Pronto’s help connecting with an agent who understands these local trends.



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.

Find your Oak Square real estate agent today →


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“I can't thank Emiel enough for helping me purchase not only my first home, but also my first investment property! From our very first phone call, he helped ease my nerves about the overwhelming homebuying process. He was knowledgeable, patient, responsive, and kept me informed every step of the way. Beyond helping me find my home, he took the time to educate me on becoming a landlord and connected me with valuable resources. He also coordinated so much of the behind-the-scenes work, making the entire experience much less stressful. I'm so glad I put my trust in Emiel! Thank you so much for helping me become a homeowner and take the first step toward building generational wealth. I couldn't have asked for a better realtor!!! I highly recommend him to anyone looking to buy a home or invest in real estate, and I look forward to working with him again in the future!”

fabedme ·

Photo of Emiel Barbosa
Vicente Realty LLC
“I genuinely could not have had a better house buying experience than I did working with Kaitlin. She went above and beyond across the board. She was extremely responsive and was more than happy to truly understand my situation and goals, as well as to explore locations that may have been a bit further from her normal ones. She approached each visit and listing with enthusiasm and offered helpful advice along the way. I never once thought she was simply telling me what I wanted to hear - she was honest, forthcoming, and always available to talk through all my questions or concerns (or even nerves) as a first time buyer. From when my offer was accepted to the final closing date, there were a lot of hurdles, delays, and winding roads due to other external factors. Kaitlin was able to navigate those with the utmost professionalism to make the process a success, even when it seemed like the cards were really stacked against us. I simply would not have been able to close on this house without her. She was an absolute rockstar the entire time and she always had my back and helped me truly understand all the inner workings while not overwhelming me with too many details. I am so impressed, and am extremely grateful that I worked with her, as well as the wonderful contacts she recommended for other aspects of the close. She was supportive and extremely knowledgeable, and was always able to exude confidence and poise throughout the entire process. She truly cares about her work, her clients, and their wants / needs. I always knew she was in my corner. This post does not come close to doing her justice, but I could not give her a higher recommendation. Whenever I am back in the market, she will be the first person I reach out to. Thank you Kaitlin for all you do - anyone is lucky to work with you!”

zuser20150325072453169 ·

“Thanks to Chris Johnson and the YPC Team I would like to extend my deepest gratitude to Chris Johnson and his incredible team at YPC for helping my father and me navigate what could have been an overwhelming process during a difficult time. Our families have shared a longstanding connection over the years, which made this experience even more meaningful. However, it was Chris’s professionalism, direct communication, dedication, and swift action that truly made the difference in bringing our homeownership journey to life. My father, a proud veteran and I had spent approximately 6–12 months struggling to secure the appropriate pre-approval needed to purchase our family home. After experiencing delays and a lack of clear, personalized communication throughout the process, we were understandably discouraged. That all changed when Chris and his team stepped in. From the moment we connected in mid-September, Chris moved with an impressive sense of urgency and purpose. Through his network and coordination with a connected lender and the VA, we secured a pre-approval that exceeded our expectations. What once felt like a distant possibility quickly became a reality. From submitting our offer to closing on our fully renovated, four-bedroom, two-bathroom single-family home in Brockton, Massachusetts, the entire process was completed in just 24 days! I would be remiss if I did not acknowledge that the experience came with some stress, as any major life decision can. However, Chris and his team remained responsive, answered my questions in real time, and clearly communicated what was needed at each stage to keep everything moving forward. Knowing what to expect and having a team that was willing to guide us through every step made all the difference. Hearing those words, _“clear to close,”_ was truly a moment we will never forget\! Mr. Johnson, thank you for your outstanding work, your commitment, and your ability to turn a challenging situation into such a positive outcome for our family. You and your entire team and professional network are truly exceptional. Your work speaks volumes about your talent, dedication, and understanding of what it takes to get the job done. You have always had my trust, the gratitude, and my highest recommendation. YPC will forever be my first choice when referring friends, family, and colleagues. Experiences like ours are a powerful reminder that having the right professionals in your corner can make all the difference in the world. Thank you for helping make this milestone possible for my father and our family. This is more than a home purchase; it is a meaningful accomplishment for our family, and a memory we will cherish for years to come. May God continue to bless you, your team, and the work you do for others. You undoubtedly have a gift, Chris, and I hope you continue to use it to make a difference in the lives of many more families. With heartfelt appreciation and gratitude, The Williams Family”

williams ca7178 ·

Photo of YPC Real Estate
YPC Real Estate LLC
“Tyler is a real estate professional, he is very responsive and thoughtful. He showed us many properties and was patient with our search process. Most importantly, he brought to our attention the property we did eventually purchas, because he understood our new home criteria and style.”

Edward Malouf ·

Photo of The EverHome Group
Coldwell Banker
“I very highly recommend Zack Harwood! Zack was incredibly helpful, patient, and supportive throughout the entire process. Buying a first home was overwhelming, but he made the process so much easier by guiding me every step of the way, answering all my questions, being extremely thorough and very responsive. Zack’s professionalism, knowledge and genuine care made such a difference. I am so grateful and I could not have asked for a better realtor! Thank you so much for making my first and forever dream condo a reality! Kari Grossman”

Kari Grossman ·

Photo of Zack Harwood
Berkshire Hathaway Warren Residential
“Excellent!”

Matt Ruggiero · Boston, MA

Photo of Matt Ruggiero
Stuart St James
“Phil was a huge help during my selling and purchasing of property last year. I knew nothing of the process and he was patient, informative and answered all my questions quickly. He was quick to get me into properties at a moments notice and was encouraging even when my open houses were not. I would highly recommend Philip Elias and if I ever have to move again I will call him.”

chefchristine99 ·

Photo of Philip Elias
Elias Group Realty
“Amanda was more than helpful with my search for a new home we talked about my family’s needs and completely understood what I was looking for and the few non exempt things that where a must like the one and only must be able to have my dog wherever we would call home I didn’t have a lot of money to spend and she found me a nice one bedroom condo with a fair price decent amenities and best of all my pet was welcome with open arms I was told I was a piece of cake to deal with glad she thought so I would say I was a basket case thru out the process I have at 57 years old never owned a house but this amazing agent put up my crazy question and did my family right I would recommend her to anyone anytime I am so happy i got meet a wonderful careing person to find my forever home thanks again and anyone reading this trust me use Amanda she’s great answers even the dumb question anytime day or night or weekends always keeps you informed”

Jay Rams ·

Photo of Amanda & Gerard George
Lamacchia Realty
“Andre helped me get my house listed and sold quickly and was very responsive. He is great to interact with and I would highly recommend him. He was able to explain the process thoroughly whenever I had questions and I did not feel pressured at all during our interactions. I had already left the state for closing and Andre had no issues with covering everything no questions asked.”

AlecHeilmann ·

Photo of Andre Fuller
Coldwell Banker Back Bay Global Luxury
“Fantastic agent to work with in all categories. It was an absolute pleasure to work with John in both the purchase of our new house and sale of our old house. John is extremely knowledgeable about the entire process from start to finish and always has his finger on the pulse of the market. He routinely went out of his way to help us understand and navigate the complexities of the entire process. His communication was prompt, accurate, and honest. He went the extra mile to represent us professionally through what would have otherwise been a very difficult purchase. John was able to negotiate great deals for us on both our purchase and sale agreements amid a turbulent market. I would highly recommend anyone entering the real estate market to work with John. We couldn’t have been more thrilled!”

Sam Wiley ·

Photo of John Dean
Engel & Völkers Engel & Volkers Boston
“Daniela was truly incredible to work with! She is extremely knowledgeable, professional, responsive, and attentive. She consistently went above and beyond to make sure we found a place with everything we wanted and made sure we felt confident in every decision. Beyond being exceptional at what she does, she is also genuinely one of the kindest people. It was clear that she truly cared and wanted the very best for us. She took the time to call us and walk us through every aspect of the process, always giving honest and helpful advice. She brought important details to our attention that we would never have known to ask, or think about ourselves. We feel incredibly lucky to have worked with Daniela and look forward to working with her in the future. If you are looking for a realtor, we cannot recommend Daniela enough, she is absolutely the person you want by your side!”

Jessica Boulden ·

Photo of Daniela Cafaro
Compass MA LLC
“Excellent Realtor – Highly Recommended! We had a wonderful experience working with our realtor Josh Stiles while buying our apartment. From the very beginning, he was professional, knowledgeable, patient, and always available to answer our questions and guide us through every step of the process. Josh truly listened to what we were looking for and helped us find the right apartment. His expertise, attention to detail, and excellent communication made the entire buying process much easier and less stressful. We always felt that he had our best interests in mind and were working hard to help us make the right decision. We are very grateful for all their help and support and couldn't be happier with our new apartment. We highly recommend him to anyone looking to buy or sell a home. Thank you for making this such a positive and successful experience! Best regards”

LEONID FONAROV ·

Photo of Josh Stiles
Compass Real Estate
“We had an excellent experience working with Samson during the purchase of our new home. From the beginning of our home search all the way through closing, Samson was professional, knowledgeable, patient, and truly committed to helping us find the right home for our family. He took the time to understand exactly what we were looking for, answered our questions clearly, and guided us through every stage of the home-buying process. He was always responsive and available when we needed him, and his communication made what could have been a stressful process feel organized and manageable. What impressed us most was how genuinely Samson looked out for our best interests. We never felt pressured into making a decision. Instead, he gave us thoughtful advice, helped us evaluate our options, and made sure we were comfortable and informed before moving forward. Samson went above and beyond our expectations, and we are extremely grateful for the hard work, dedication, and professionalism he showed throughout our journey. Thanks to his guidance, we are now proud homeowners and very happy with our new home. We would confidently recommend Samson to anyone looking to buy or sell a home. If you want a realtor who is dependable, knowledgeable, hardworking, and truly cares about his clients, Samson is an excellent choice. Thank you, Samson, for helping our family find a place we can proudly call home!”

pgitaumburu ·

Photo of Samson Kimani
RE/MAX REMAX REAL ESTATE CENTER
“Nick is GREAT to work with. He’s extremely knowledgeable of Boston and the surrounding areas and makes the entire process easy from start to finish. I’ve worked with him a couple of times now, and most recently he helped me rent out my place within 2 weeks and for well above asking price. He always shares great advice along the way. I highly recommend him.”

Erik Lepke ·

Photo of Chris Vietor Homes
eXp Realty
“Working with Sarah was the easiest and most rewarding decision I've made. She came highly recommended by someone I trust in the industry, and she absolutely delivered. I owned my home in Somerville for 21 years, and when it was time to sell, it needed some attention. Sarah helped me prioritize where to invest and where to hold back so I got the most out of every dollar. She had wonderful contacts to get the work done, along with a genuine eye for design that guided the interior choices - and she came by herself to help with the final touches. She was thoughtful about timing, invested real care in the marketing and the open houses, and was patient with my endless questions from start to finish. Sarah held my hand through the whole process. I would work with her again in a heartbeat and recommend her to anyone.”

Lisa Colucci · Somerville, MA

Photo of Sarah Rodewald
SR Realty
“We truly could not recommend Brandon enough! As first-time homebuyers, the entire process was completely new to us, and Brandon made everything feel so much easier and less overwhelming. He was incredibly knowledgeable, responsive, patient, and always willing to answer our many questions along the way. From searching for the right home, to putting in our offer, navigating the inspection and negotiations, and finally making it all the way to closing, we always felt like Brandon genuinely had our best interests in mind. He was there for us every step of the way and made sure we understood what was happening throughout the entire process. We are so grateful for all of his help in getting us into our first home and couldn’t have asked for a better realtor to guide us through such a huge milestone. We would absolutely recommend Brandon to anyone looking to buy or sell a home. Thank you for everything, Brandon!!”

isabellashaw954 ·

Photo of Brandon Fisher
Coldwell Banker Realty
“We started working with Paige Shelton January 2025 when we called about a home for sale. It was already under contract but she met with us and got to know what we were looking for. She continued to send us listing and we saw many homes. She was always positive and available. June of 2026 we put in an offer and it was accepted. This was when we realized what a gem she is. She navigated us through an unfamiliar and scary process. She was knowledgeable and always got back to us promptly. She guided us every step of the way. Working with the sellers agent, the lawyer,lender,insurance agents,inspectors,city hall and more. Provided referrals to all the professionals needed in buying a home. She saved us many hours of work and stress. We are now looking forward to working with her again when we put our current home on the market.”

Jacquelyn Mackay ·

Photo of The Mark Lesses Group
Coldwell Banker Lexington
“As a first-time homebuyer, I couldn't have asked for a better experience with Hector. I have never met anyone who goes above and beyond the way he does to make the home-buying process smooth and stress-free. From the very beginning, Hector explained every step in detail and made sure I understood everything. He was always available to answer my questions and guided me through the entire process, coordinating with brokers, lenders, and town services to ensure everything stayed on track. His professionalism, knowledge, patience, and dedication made what could have been an overwhelming experience feel exciting and manageable. Thanks to Hector, I felt confident every step of the way. I highly recommend him to anyone looking to buy a home, especially first-time homebuyers. You won't find someone more committed to helping you achieve your dream of homeownership.”

olivoaude97 ·

Photo of Hector Cocar
Cameron Real Estate Group Inc
“Paul was fantastic to work with throughout our home search and purchase. He was knowledgeable, responsive, professional, and always had our best interests in mind. He made the process smooth and stress-free, and we truly appreciate all his help in finding our new home. Highly recommend Paul!”

Jahnavi And Karthik ·

Photo of Paul Sadatis III
Homie Realty Group
“Ashley was fabulous to work with from start to finish! She made sure to share new homes as soon as they came on the market, and welcomed feedback based on our wants and needs. Ashley went above and beyond when searching for our future home. She was a great communicator, and responded quickly to any texts we sent. When it came to putting in offers and closing, she provided guidance to help us make decisions that were right for us, and thoughtfully and clearly answered any questions we had. She made the entire home-buying process manageable and achievable. Absolutely recommend her to any future home-buyers!”

Sarah Runkle ·

Photo of Ashley Harwood
Keller Williams Chestnut Hill

Frequently Asked Questions

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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