The Most Expensive Streets in Braintree, MA — What 3,100 Home Sales Actually Show

Ask ten people in Braintree which street is the priciest and you'll get ten answers, most of them some version of "up by the Hills" or "over near Cochato." Nobody actually knows, because nobody has sat down and run the numbers.

So we did. Every single-family home sale recorded in Braintree from January 2015 through August 2026 — 3,100 transactions, $1.87 billion in volume, spread across 493 streets.

The short answer: Messina Woods Drive, where homes have sold at a median of 94% above whatever the town median was that year. Cedar St carries the highest raw price tag at $1.1 million, but it isn't the biggest premium once you account for when those sales happened.

There's a second answer too. Measure by price per square foot instead and you get a completely different top ten that shares no streets with the first — including one that's genuinely among the more affordable roads in town. That divergence is the most useful thing in this article, and we'll get to why.

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First, what Braintree did as a whole

Before you can say a street is expensive, you need to know what normal looks like — and normal kept moving. Here's the town-wide median for single-family homes, year by year:

A few things worth pulling out of that table.

Price per square foot is up 69% since 2015. The median sale price is up 85%. The gap between those two numbers means buyers aren't just paying more — they're buying bigger, too.

Volume has fallen off a cliff. Braintree did around 300 single-family sales a year from 2015 through 2021. Since 2023 it's been closer to 200. That's not a demand problem; it's an inventory problem, and anyone who's tried to buy here in the last three years already knows it.

2020 to 2021 was the jump. Median price per square foot went from $318 to $348 in a single year — a 9.4% move, the largest in the dataset. Median price went up $65,000.

This is the yardstick. When we say a street sells at a premium below, we mean against the town median for the same year the house actually sold — a 2016 sale gets measured against 2016, a 2025 sale against 2025. Otherwise you're just measuring which streets happened to have houses trade recently, which tells you nothing.

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The most expensive streets in Braintree

Here's the ranking that matters. Every sale measured against what the median Braintree house sold for that same year, then taken to the median per street. A 2016 sale is judged against 2016; a 2025 sale against 2025.

Minimum six sales since 2015, or one renovated outlier swings a whole street.

Messina Woods Drive is the most expensive street in Braintree — homes there have sold at a median of 94% above whatever the town was doing that year. Nearly double.

Notice something the raw prices hide. Cedar St has the highest median sale price on the list at $1.1 million, but ranks fifth. That's the year-normalization doing its job: Cedar St's sales cluster in later years when the whole town was more expensive, so its raw number flatters it. Once each sale is compared to its own year, four streets sit above it.

All ten, street by street

Messina Woods Dr (+94%) is a 2000s subdivision — the nine recorded sales are homes built between 2001 and 2015, running 2,900 to 4,456 square feet. The street's own record tells the story cleanly: 31 Messina Woods Drive sold for $1,030,000 in October 2019, then again for $1,380,000 in June 2022 — the identical 4,456-square-foot house, up 34% in under three years. One caveat worth naming: the most recent recorded sale here is 2022, so this is a street that established its premium and then stopped trading.

Canavan Dr (+80%) is older stock — mostly 1985 to 1997 — but very large, up to 7,362 square feet. It has the widest spread of any street in the top ten, from $740,000 in 2018 to $1,600,000 in March 2026. That March sale is one of the strongest recent numbers anywhere in town.

Albee Dr (+78%) has the biggest houses of any ranked street, a median of 4,300 square feet on late-1980s builds. It also produced 8 Albee Drive in May 2025 — a 2024 new build that hit $519 per square foot, the highest figure among Braintree's eight largest sales.

Cochato Rd (+72%) is the interesting one, and the only pre-war street near the top. The houses date from 1900 to 1951 — but look closer and you find 68 Cochato Road built in 2020 and 50 Cochato Road built in 2021, selling for $1,200,068 and $1,155,000. New construction is being dropped into a century-old street, and the established homes are keeping pace: 52 Cochato Rd went $1,250,000 in August 2022 and $1,450,000 in September 2025, while 49 Cochato Rd hit $1,550,000 in August 2026 — the most recent sale in this entire analysis.

Cedar St (+67%) carries the highest median price in town at $1.1 million across seven sales, in houses around 3,372 square feet dating to roughly 1911. Its top sale, 179 Cedar St in August 2024, brought $1,770,000.

Teaberry Ln (+66%) is the most uniform street in the top ten — seven sales, and every house built within two years of each other, 1997 to 1999. A late-90s cul-de-sac development that has held its premium without much drama: $900,000 in 2015, $1,140,000 in July 2026. One house, 75 Teaberry Lane, sold twice — $850,000 in September 2019, then $1,130,000 in May 2023, a 33% gain on the same 2,790 square feet.

Colby Rd (+55%) shows the sharpest run in the top ten. It sat at $510,000 in 2015 and $670,000 in 2016, then produced back-to-back sales of $1,350,000 and $1,282,500 within eight weeks of each other in the autumn of 2022. The houses are 1930s and 1940s stock at around 3,200 square feet. 83 Colby Road is the cleanest illustration in the whole dataset: $670,000 in January 2016, $1,060,000 in June 2023 — same 3,191 square feet, up 58%.

Monatiquot Ave (+54%) has the deepest record of any top-ten street, with thirteen sales, and it is genuinely mixed: houses from 1882, 1895, 1900 and 1902 sitting alongside 2015 and 2016 new builds. It holds Braintree's fourth-largest sale on record — 56 Monatiquot Avenue at $1,650,000 in June 2021, a 5,200-square-foot 1930 home — and 67 Monatiquot at $1,600,000 in June 2026. That same 67 Monatiquot sold for $928,000 in July 2016 as a brand-new build, which is a 72% gain in a decade.

Summit Ridge Dr (+45%) is a late-1960s and 1970s subdivision, nine sales, and the steadiest climber on the list — $586,000 and $590,000 in 2015–2017, up to $1,085,000 in August 2024. No dramatic flips, no new construction, just consistent movement. If you want evidence that Braintree's established subdivisions have carried the market rather than lagged it, this is the street.

Mount Vernon Ave (+44%) is the oldest housing stock in the top ten — every recorded sale is a home built between 1892 and 1900. It also contains the tidiest repeat sale in the dataset: 72 Mount Vernon Avenue sold for $1,100,000 in August 2022 and $1,302,000 in November 2024, the same 3,161 square feet, up 18% in twenty-seven months. Three of its six sales came in 2022 alone.

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The other way to measure it: price per square foot

Rank the same data by price per square foot instead — again normalized to each sale's year — and you get a completely different list. Not one street appears on both.

Every street here has a median house under 1,750 square feet, most under 1,400, typically built between 1915 and 1955. These are not Braintree's expensive streets. They're the streets where small, mostly pre-war homes command an outsized price for the space they offer.

Hillcrest Rd is the clearest case. Nine sales since 2015, and the houses are genuinely small — 702, 792, 816, 1,080, 1,141 square feet. The most recent, 28 Hillcrest Rd in June 2026, went for $650,000 at $570 per square foot, 36% above what the town was doing that year. Meanwhile 54 Hillcrest Rd sold twice: $280,000 in January 2016, then $420,000 in September 2021, on 792 square feet.

There's also a fast turn in the record — 14 Hillcrest Road sold for $378,000 in October 2018 and again for $493,000 eight months later at the same 1,269 square feet. A 30% gain in under a year on an unchanged footprint is a renovation story, not a market story.

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Why the two lists disagree

This is worth understanding, because it changes how you read every "most expensive street" article you've ever seen — including the ones that rank by price per square foot without saying so.

Price per square foot systematically favors small houses. A lot in Braintree carries value of its own — the land, the location, the school assignment, the walk to the T. That value doesn't shrink because the house on it is small. So dividing sale price by living area, a modest 1,100-square-foot cape on a good street produces a higher number than a 4,000-square-foot colonial two streets over, even though the colonial sold for three times as much.

Hillcrest Rd tops the price-per-square-foot table at 32% above town. Its median sale price is $378,000 — half Braintree's 2026 median of $755,000. By any ordinary meaning of the word, it is one of the more affordable streets in town.

Albee Dr ranks third by price at $965,000. Its price per square foot is $247 — below the town median. The houses are simply enormous.

Both facts are true. The two measures answer different questions:

• Price against the town median answers "where are the expensive houses?" — the question almost everyone actually means. - Price per square foot answers "where does the market charge the biggest premium per foot?" — useful for spotting location value, misleading as a wealth ranking.

We lead with the first because it's the honest answer to the question in the title.

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The biggest sales on record

Eight sales in the dataset cleared $1.6 million:

47 Addison Street at $2.5 million is the highest single-family sale in Braintree in the last decade — 7,638 square feet, and interestingly, a 1955 build rather than new construction.

Note how many of these are recent builds. Whites Hill Drive shows up twice with 2023 and 2024 construction. 8 Albee Drive is a 2024 build that hit $519 per square foot — the highest figure in the entire top-eight list, and 24% above what the rest of Albee Dr commands. New construction is where Braintree's ceiling is being set right now.

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Where values grew fastest

Different question again: not which streets are expensive, but which ones moved the most. Here we compared each street's median price per square foot in 2015–2018 against 2023–2026, requiring at least four sales in each window.

Braintree as a whole grew 69% over that stretch. Elm St beat the town by 24 points. Howie Rd, Franklin St, Holmes St and Beechwood Rd all outran the market meaningfully.

What these streets have in common is that they started cheap. Every one of them was under $290 per square foot in 2015–2018, most under $270. The streets that were already expensive in 2015 have mostly grown with the town, not ahead of it — which is what you'd expect. The catching-up happens at the bottom.

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The new-construction pockets

A handful of streets in Braintree are effectively new neighborhoods, and they price differently from anything around them:

Whites Hill Drive is in a category of its own — a median of $1,538,500, which is more than double Braintree's town median and 40% above Cedar St, the priciest established street. With only four recorded sales it's too thin to rank alongside the others, but it's the clearest signal in the data of where the top of this market is heading.

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Where the teardowns and gut jobs are happening

One more thing the data shows that a normal comp search never will. When the same address sells twice, you can see exactly what happened in between — and some of these are not appreciation.

Braintree grew 69% over this period. None of these are that. A 159% gain in 282 days on Livoli Ave isn't the market moving — it's a house that was bought, rebuilt or gutted, and resold. Same for 243 Common St at +149% in eighteen months, and 343 Franklin St at +149% in twenty months.

This is worth knowing for two reasons. If you're a seller with an older, tired house, these are the buyers who pay cash and move fast, and they're active across a wide range of Braintree streets — Inglewood, Davis, Elm Terrace, Livoli, River, Common, Franklin. If you're a buyer looking at a recently flipped property, the prior sale price is public record, and it tells you what the seller paid before the renovation.

It also explains part of the appreciation table above. Streets that show enormous growth are sometimes streets where several houses got rebuilt, not streets where the market independently decided to pay more.

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The busiest streets

Worth knowing if you're buying: some streets almost never trade, and some come up constantly.

Liberty St alone accounts for 139 sales — roughly one in every 22 single-family transactions in Braintree over the past decade. It's a long road, but that's still remarkable turnover.

If you want to live on Hillcrest Rd, you'll be waiting: nine sales in eleven and a half years works out to less than one a year.

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What this means if you're buying

If you want the best house per dollar, look at the streets that rank high on sale price but low on price per square foot — Albee Dr at $247/sqft, Canavan Dr at $273, Messina Woods Dr at $275. You're buying serious square footage at below-town rates per foot. The tradeoff is that these are mostly 1980s-and-later subdivisions rather than walkable older neighborhoods.

If you want the location premium, the price-per-square-foot table is your list — but understand you're paying up for the address, not the house. A 1,141-square-foot home on Hillcrest Rd is still a 1,141-square-foot home, whatever the premium per foot says.

If you're looking for appreciation, history suggests the streets that were cheap relative to the town have moved most. Elm St nearly doubled. That's not a prediction — past growth doesn't guarantee future growth, and the streets that grew fastest are no longer cheap.

What this means if you're selling

The single most useful thing here is the year-normalized comparison. If you're on Cochato Rd, your street has historically sold at 72% above the town median — and on Magnolia St, at 29% above the town median per square foot. Those are real, defensible numbers to bring into a pricing conversation — and it's the kind of thing that gets missed when an agent pulls three comps from the last six months and calls it a day.

If you're on a street that isn't in these tables, that's not bad news. Most of Braintree's 493 streets don't have enough transaction volume to rank, which means the comps that matter for your home are the ones nearby, not the ones on your road.

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How we did this, and what we left out

The data is every closed single-family transaction in Braintree recorded in MLS PIN from January 1, 2015 through August 21, 2026 — 3,100 sales after filtering.

What we filtered out and why:

• Condominiums (1,277 sales) — a different market with different dynamics. Worth its own article. - Multi-families, land, and commercial — same reasoning. - Sales under $100,000 — almost always family transfers or distressed situations, not market transactions. - Homes under 500 or over 10,000 square feet — a handful of records with data-entry issues.

A note on street names. MLS data is entered by hand, so Washington Street arrives as "Washington," "Washington St," "Washington St.," "Washington Street" and "Washington Street-" — five spellings, 72 sales that would otherwise have been split five ways and buried. We normalized suffixes to merge these. We deliberately did not merge across different suffixes: Walnut Ave and Walnut St are two different roads and are counted separately.

Why 2015 and not earlier. We'd have liked a longer run. Braintree's MLS records before 2015 are too sparse in this dataset to build a reliable year-by-year baseline from — a handful of sales in 2007, 2013 and 2014 total. Rather than pad the analysis with a decade of thin data, we started where the record becomes complete.

Minimum sample sizes. Street rankings require at least six sales; the growth table requires four in each period. One flip or one teardown can move a street's median dramatically, and streets with two sales tell you nothing reliable.

Medians, not averages, throughout. A single $2.5 million sale on a quiet street would drag an average into fantasy. Medians describe the typical house.

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Analysis by Justin Rollo, Signal Real Estate, Braintree MA. Data from MLS PIN, current through August 21, 2026. If you'd like to know what your specific street has actually done — including ones too small to appear here — get in touch and we'll run it.