If You Lived Here … You’d Never Want To Leave

A real estate connoisseur’s guide to the Hub’s 65 absolute best streets.

What makes a street a great street? Is it leafy verdure, or honking-big houses? Proximity to lip-smacking vittles? Or bragging rights over the next neighborhood’s schools? Well…yes, yes, yes, and yes.

To determine which roads, lanes, avenues, drives, circles, and courts best fulfill those qualifications and rank as the area’s most desired addresses, we started by polling hundreds of Hub real estate brokers. (Thanks to the Massachusetts Association of Realtors for distributing our survey to its members.) Working from their nominations, our judge then logged 1,200 miles on Greater Boston asphalt to check out the candidates, tease out subtle distinctions, and make some hard choices. Streets were graded on six criteria—aesthetics, environment, amenities, public services, affordability, and access to transit—and when a town or neighborhood had more than one high-ranking thoroughfare, we chose only the top scorer. In some cases, a street had a certain extra something—an “X-factor,” in our system—that helped bump it up in the standings.

Three months and one “check engine” light later, we have our winners. Oh, and by the way: Professional ethics precluded us from including streets currently inhabited by our editorial staffers. But if any readers want to express gratitude for a spike in their property values, they should feel free to send checks to the author, care of Boston magazine.

The City
1. Waltham Street, South End
Aesthetics, Amenities, Transit
The South End’s seemingly endless supply of historic row houses, replete with rounded bay windows and wrought-iron railings, is the pride of the area’s blithely trendy residents. At a slight discount from those on idyllic Union Park and West Canton, homes on Waltham—around $600,000 for a two-bedroom condo, and $1 million for a townhouse—come with a vest-pocket park and are a five-minute walk from the Back Bay T stop. The block between Tremont and Shawmut, in particular, is a foodie haven, anchored by Barbara Lynch’s B&G Oysters and the Butcher Shop on one end and gourmet stinky-cheese shop South End Formaggio on the other. Parking on this one-way street tends to be tight, but that only leads to another bonus: less traffic.
X-factor: Lynch’s Plum Produce, a bodega at 106 Waltham that happens to sell $5 heirloom tomatoes.

2. Mount Vernon Street, West Roxbury
Aesthetics, Amenities, Transit, Environment
The part of West Roxbury known as “the Highlands” is full of leafy, suburban-style streets with big Blue Hills views. But the neighborhood is also in close proximity to the local commuter rail stop and a nucleus of Asian restaurants, pizza joints, and new boutiques like women’s clothing shop Talula Gray. The residences on Mount Vernon and neighboring Montview are a mix of big brick mansions and painted-lady Victorians. “Inside, they have, like, 13 or 14 rooms with pocket doors, fireplaces, and slate roofs,” says longtime Realtor Joe Bellanti, co-owner of Bostonia Properties. “They are really elegant…and expensive.” But they’re not as expensive as you might think, with prices ranging from a relatively reasonable $600,000 to a still-under-a-million $850,000.
X-factor: Millennium Park’s five new playing fields, built from Big Dig fill on a former garbage dump, just a two-minute drive away.

3.Waverly Street, Brookline
Amenities, Public Services, Transit
Waverly puts the “village” in Brookline Village, wrapping around secluded Emerson Garden’s pirate-themed playground and oft-used community bulletin boards. Many of its multi-million-dollar Crayola-bright Victorian Queen Annes are painted distinctly improper shades of mint, lilac, and yellow (and, in line with the neighborhood’s left-leaning spirit, many exhibit peace flags and antiwar signs). The 20 or so houses between Davis and Cypress are spitting distance from the antiques stores and restaurants of laid-back Harvard Street. Plus, notes neighborhood real estate guru Chobee Hoy, as if prospective buyers needed any further reminding: “They’ve got the Brookline public school system.”

4. Chestnut Street, Beacon Hill
Aesthetics, Transit, Amenities
Sure, its steep incline turns a leisurely stroll into a Stair-Master workout, but Chestnut also claims black-shuttered brick townhouses, vintage gas lamps, and the prestige of a blueblood Beacon Hill address. Unlike some of its tonier neighbors, however, the street still has one-bedroom condos available for less than $500,000—though of course, at that price point, what you’re really getting is a glorified closet. No matter how much square footage you claim as your own, nearby Charles Street’s shops and lively cafés, including the always-packed ’hood hangout Panificio, provide plenty of reasons to get out and about. Another boon: Chestnut is less than a mile from Red, Green, and Blue Line stops.

5. Wellesley Park, Dorchester
Aesthetics, Environment, Affordability, Transit
Double takes are unavoidable for many who stumble onto Wellesley Park—this is Dorchester? The inner-city oasis’s 26 Queen Annes, all built in the late 1890s, are dressed up with turrets, column-lined porches, and period details like spindle-work entryways and built-in china cabinets. Most have been meticulously restored by current residents, an ethnically diverse group of families and straight and gay couples. Those lucky enough to snag one of these properties pay between $400,000 and $700,000 for a two-to-six-bedroom single-family home; for everyone else, until this year there was the annual Codman Square House Tour (now on hiatus), which let the curious peek inside. x-factor: The park in the center of the street, an oval of grass studded with fountains, beech trees, and century-old gaslights.

6. Abbottsford Road, Brookline
Aesthetics, Public Services, Amenities, Transit
Some Brookline residents never venture into Boston. Why bother, they ask, when Coolidge Corner has its own downtown-worthy amenities? Brookline Booksmith is one of the city’s best bookstores, the Coolidge Corner Theatre is a movie house par excellence, and new restaurants like Jeremy Sewall’s Lineage keep the dining scene fresh. A few blocks away, a grid of streets made up of Fuller, Naples, Osborne, and Abbottsford hosts a collection of delicate 19th-century houses. Abbottsford has the most curbside appeal, with one multimillion-dollar gingerbread home after another poking its gabled roof through the foliage.
X-factor: JFK’s birthplace on nearby 83 Beals Street gives history buffs something to boast about.

7. Commonwealth Avenue, Back Bay
Transit, Aesthetics, Amenities
Marlborough may be quainter and Newbury more fabulous, but no street in the Back Bay matches the architectural majesty of Comm. Ave. between Arlington and Hereford. Designed in the 1850s as a Champs-Élysées-style boulevard, it features grand homes and four stately rows of elms, all close to Newbury Street shopping and Green Line stops at Arlington, Copley, and Hynes. Condos start at around $500,000 for a one-bedroom and climb well into the seven figures for the larger units.
X-factor: The thousands of tiny white lights that appear each holiday season, which—though some uppity residents grumble about the glare—lend the mall a wonderland air.

8. Maple Avenue, Cambridge
Amenities, Aesthetics, Transit, Environment
Equidistant from Harvard Square’s bustle, Inman Square’s cuisine, and Central Square’s rock clubs, this strip in the heart of Cambridge is a showcase of 19th-century residential design: Queen Annes, stick styles, Italianates, and Second Empires line the blocks, along with a generous selection of subdivided triple-deckers. Single-family homes fetch upward of $1 million; condos start at $350,000. “It’s one of the most sought-after streets in Cambridge,” says Hammond Real Estate vice president Myra von Turkovich. “It has T access and unique architectural renovations.”
X-factor: The new funky, giant-Lego-like toddler park on the corner of Maple and Marie.

9. Hull Street, North End
Amenities, Environment
North Enders are forever battling tourists for sidewalk space. Except on Hull, which sits up the hill from the Old North Church and borders the southwest side of Copp’s Hill Burying Ground, a swatch of green far above the trattoria crowds. Condos in the street’s renovated tenement buildings run between $300,000 and $400,000, and reach upward of $500,000 for top-floor units with views of the U.S.S. Constitution and the Charlestown harbor. Many of the apartments are large enough for families, with anywhere from two to six bedrooms.
X-factor: The parking garage—one of the few in the neighborhood—located at the street’s end.

10. Mendum Street, Roslindale
Environment, Amenities, Transit
What makes this road spectacular is its location: A low stone wall separates the backyards of single-family homes from, well, 265 acres of more backyard, in the form of the Arnold Arboretum’s rolling hills. At the same time, it’s a five-minute downhill walk to the commuter train and Roslindale Village’s restaurants, including Sophia’s Grotto, which serves sangria al fresco on its patio during warmer months.

11. Brattle Street, Cambridge
Aesthetics, Amenities, Transit
Birthplace of Cambridge’s first $10 million asking price, old Tory Row is among the Hub’s most prestigious addresses.
X-factor: Past and present deep-thinking neighbors
Robert Reich, John Kenneth Galbraith, and John Malkovich.

12. Clinton Road, Brookline
Aesthetics, Public Services, Transit, Environment
Clinton’s Tudor homes are similar to nearby Fisher Hill’s gated estates, only slightly smaller and cheaper—comparable steals at around $1 million—and close to a playground and the Green Line.

13. Highland Avenue, Hyde Park
There’s a reason a lot of savvy business-people live in the Fairmount Hill section of Hyde Park. They know how to spot a real bargain, and Highland’s $400,000-to-$800,000 restored Victorians are too good to pass up.

14. Bay State Road, Fenway
Transit, Amenities
Occasional rowdiness from Boston University coeds is a small price to pay for one of the towering brownstones flanking the south bank of the Charles River. x-factor: Kenmore Square’s continuing transformation from student ghetto to high-end ’hood, which makes this spot one to watch (and to buy into early).

15. Orchard Street, Cambridge
Amenities, Transit
Not far from the Somerville border, Orchard offers proximity to offbeat Davis and workaday Porter squares, and has refurbished $750,000 Victorians on generously sized lots.

16. Ocean Street, Dorchester
Aesthetics, Affordability
There’s abundant room in the colossal homes atop Ashmont Hill. And at about $450,000 per house, buyers will have enough scratch left over to use the acclaimed Ashmont Grill as their personal cafeteria.
X-factor: The MBTA’s ongoing $44 million renovation of Ashmont Station, which promises to make it the pride of the Red Line.

17. Saint Germain Street, Back Bay
Aesthetics, Amenities, Transit
Though technically part of the Back Bay, verdant Saint Germain is more like a South End street in miniature. And Symphony Hall is near enough to hear James Levine’s baton taps.

18. Winthrop Street, Charlestown
Aesthetics, Amenities
The homes along Chucktown’s common are less expensive but no less impressive than those around the Bunker Hill Monument. And they’re closer to local haunts like Todd English’s Olives and Moroccan-themed Tangierino.

19. Eliot Street, Jamaica Plain
Amenities, Transit
No two houses are the same on the blocks sandwiched between the urban sanctuary of Jamaica Pond and the hipster Xanadu of Centre Street.
X-factor: The 320-year-old Eliot School, where residents can take classes in subjects like watercolor and woodworking.

20. Fort Avenue, Roxbury
Transit, Affordability
The townhouses surrounding Highland Park and its Disneyesque 120-foot-high Fort Hill tower cost half of what they would in the South End and boast sweeping views of Boston’s southern neighborhoods.

1. West Street, Braintree
Transit, Amenities, Affordability
Lovingly maintained Victorians and Dutch Colonials, many in the $500,000 neighborhood, pepper West Street on the hilltop between Washington and Granite streets. Despite a decidedly suburban feel, the avenue is close to the Red Line and is a two-minute drive from I-93 and the bustling South Shore Plaza shopping center. Thayer Academy’s pristine prep school campus and the Hollis Field baseball diamond are also nearby.
X-factor: The Blue Hills Reservation, which touches West Street’s northern side and offers another 7,000 acres of recreation possibilities.

2. Main Street, Hingham
Aesthetics, Public Services, Amenities
Eleanor Roosevelt once declared Hingham’s main strip the most beautiful street in America. Today it retains a collection of historic 17th-, 18th-, and 19th-century homes that is one of New England’s finest; the area north of Route 228 is especially photogenic. “The community is incredibly safe, and the schools are excellent,” says Commonwealth Realtors owner-broker Grace Ruth Hatch. Before the recent market correction, she adds, “it was terribly prohibitive in price, but now people are being more realistic.” Of course, on the buyer’s side, in this area “realistic” still means having more than $1 million to burn.
X-factor: Tosca, the Square Café, and the other first-rate eateries that make Hingham the South Shore’s restaurant mecca.

3. Gay Street, Westwood
Public Services, Environment
Zigzagging through the heart of Westwood, Gay Street connects the town’s shops and restaurants with the Islington neighborhood’s commuter rail stop. Along the way, it’s lined by rambling farmhouses and Colonials on ample lots surrounded by stone walls and woodlands. Often lumped in with the other “W”s—Wellesley, Weston, Winchester—Westwood has a comparably superb school system, but offers more-for-your-money housing: Prices start at $400,000 for a 1,100-square-foot house, and go to $1.7 million for a 3,500-square-foot spread on 5 acres.
X-factor: Vello’s at the intersection of Gay and High, where the clam chowder is the tastiest south of Boston.

4. Grand View Avenue, Quincy
Transit, Amenities
Grand View’s summit on Wollaston Hill lends its residents a panorama of the Harbor Islands and the Blue Hills. The scenery is further enhanced by the architecture: Dozens of gingerbread Queen Annes and Second Empires, ranging from $400,000 to $800,000, dot the avenue. A mix of pizza shops and bakeries and the Wollaston T stop are found down the slope in Quincy’s commercial district.
X-factor: The Furnace Brook links, a nine-hole golf course on the hill’s south side.

5. Powder Point Avenue, Duxbury
Aesthetics, Environment, Public Services
Original shipwrights’ homes are responsible for only half the beauty of this ultraposh avenue jutting into Duxbury Bay. The rest comes from the interplay of light and water on the surrounding salt marshes. Powder Point’s half-mile-long wooden bridge leads to Duxbury Beach, one of the state’s prettiest stretches of sand. Not surprisingly, you’ll pay handsomely for the privilege of living amid this serene splendor—almost all of the houses here carry seven-figure price tags.

6. Summit Avenue, Hull
Environment, Transit
Summit has Cohasset scenery without Cohasset prices, as well as a future Greenbush Line rail station. Its oversize beach cottages range from $300,000 to several million dollars.
X-factor: The street’s sandbox-size Crescent Beach, used almost exclusively by residents.

7. Warren Avenue, Plymouth
Environment, Amenities
Tree-studded fields stretch to the ocean along the section of Warren wedged between Plymouth Long Beach, Plimoth Plantation, and Plymouth’s bustling downtown (home of the rock). The avenue’s estates run from $500,000 to well over $1 million.

8. Jerusalem Road, Cohasset
Aesthetics, Environment, Public Services
A string of multimillion-dollar mansions graces the landscaped bluffs along this seaside road, making it look more Malibu than Massachusetts.

9. Village Avenue, Dedham
Transit, Aesthetics, Amenities
Taylor Real Estate proprietor Jonathan Taylor, a 60-year-resident of Dedham, describes this area as a mix of “large old antique homes and a few churches.” Route 1’s nearby commercial strip takes care of all shopping needs; for a jolt of culture, there are regular art-house screenings at the community theater in Dedham’s blue-collar downtown.

10. River Street, Norwell
Public Services, Environment
Dense forest cloaks the twisting curves of this country byway between Routes 3 and 123. Eighteenth-century Colonials and Greek Revival farmhouses line the lane, which spills into the Norman Rockwell–worthy Norwell Center.

11. Prospect Hill Drive, Weymouth
Environment, Affordability
Some of the South Shore’s cheapest water views can be had on this street on Weymouth Neck, a peninsula full of $300,000-to-$500,000 Cape cottages and bungalows on Hingham Bay. The working-class neighborhood is packed with cavorting kids and “Slow, Children” signs.

12. Pilgrim Road, Marshfield
About $800,000 will get you one of the eclectic houses along this street on Marshfield’s Snake Hill, which overlooks acres of tidal flats that unfurl toward the sea and give a good sense of how the town got its name.

13. Adley Drive, Abington
This quiet cul-de-sac in rural Abington has mammoth new homes with brick fronts, gables, and substantial front yards strewn with children’s toys; prices start at $400,000 for around 2,500 square feet of space. It’s a half-hour ride to Boston from the town’s rail station.

14. York Road, Mansfield
The Forest Park neighborhood is a Leave It to Beaver tableau of individually designed new homes with three-car garages and sculpted lawns. The I-95/495 interchange and concert hot spot the Tweeter Center are reachable by a quick drive.

15. Columbine Road, Milton
Transit, Public Services
Just across the Milton-Mattapan line and a short uphill walk from two Red Line stations, Columbine anchors a leafy neighborhood of large $700,000 neo-Colonials. While Milton is best known for its eponymous private academy, its public schools are also top-notch.

1. Hammond Street, Newton
Public Services, Transit, Aesthetics, Amenities
Few houses blend more harmoniously into their environment than those on the Newton side of Chestnut Hill. Hammond’s million-dollar-plus brick mansions and smaller, 19th-century homes mix effortlessly with the neighborhood’s copper beech groves, rhododendron gardens, and rocky outcroppings—and at the end of the street, all that natural beauty leads to the consumerist bounty of the Chestnut Hill and Atrium malls. Plus, living on Hammond (like everywhere else in Newton) gets you low crime rates and stellar schools.
X-factor: Hammond Pond Reservation, with its quaking bog and tree-lined hiking trails.

2. Cottage Street, Wellesley
Public Services, Transit, Amenities
Many of the residences along this street near Wellesley College sport plaques from the local historical commission. Constructed in the mid-to-late 1800s, they form a group of congruent Greek Revivals priced between $700,000 and $1.5 million apiece. (The homes were built by the owner of a shoe factory to house his workers, notes Mary Jean Fitzpatrick, a Re/Max Landmark Realtor.) Cottage is bisected by the trilling Fuller Brook and its bankside trails, and is five minutes from Wellesley Center and the commuter rail stop. Test scores at area schools are off the charts.
X-factor: Ming Tsai’s Blue Ginger—the gourmet stalwart is just steps away.

3. Meriam Street, Lexington
Aesthetics, Amenities, Public Services
In 1775, Sam Adams witnessed the Battle of Lexington, with its “shot heard round the world,” from his perch atop Meriam Hill. The neighborhood has come a long way since that bloody melee: Breathtaking three-story Victorians now soar where Adams once stood, affording their well-heeled residents great vistas of the surrounding hills. The million-dollar-plus homes are a short stroll from Lexington Center’s restaurants (South Indian spot Khushboo and Rancatore’s ice cream parlor are standouts) and second-to-none schools.
X-factor: The chance to watch battle reenactments from your bedroom window on Patriots’ Day.

4. Main Street, Concord
Aesthetics, Amenities, Transit
A commercial strip in the midst of Thoreau country, Concord’s Main Street lets its local businesses prosper by shunning big-name chains—here you’ll find the Toy Shop of Concord, the oldest specialty toy store in America, and the Concord Bookshop, offering an incomparable staff and selection. The street is also chock-a-block with immaculate Colonials that cost between $1 million and $3 million; some have been subdivided into more-affordable $300,000 condos. Aside from providing quick access to Route 2, Main runs between the Concord and West Concord train stops.

5. Salem End Road, Framingham
Aesthetics, Amenities, Public Services
Colonials from the 1700s share Salem End with everything from raised ranches to sleek contemporary boxes, providing diversi
ty in both housing stock and neighbors. Prices, too, are all over the map, with some lots selling for less than $400,000. “It has an unusual mix of old and new, big and small houses,” says Realtor Lisa Zemack. She adds the street is “a commuter’s dream,” thanks to its proximity to Routes 9 and 126, I-95, and the Pike, as well as to the shopping on the Framingham/Natick Golden Mile.

6. Pelham Island Road, Wayland
Environment, Public Services
Encircled by a wildlife refuge, Pelham Island is the closest most people will get to living in a national park. The strip between the Sudbury River and Heard Pond has a mix of postwar homes and modern pads priced from $500,000 to $1 million.

7. Clifton Street, Belmont
Aesthetics, Environment, Public Services, Transit
Behind Route 2’s gleaming Mormon temple lies Clifton Street, where gigantic brick homes—some topping 5,000 square feet—sit back on lush lawns. Belmont Center’s crush of boutiques is a two-minute drive away.

8. Fair Oaks Park, Needham
Aesthetics, Amenities, Public Services, Transit
Close by the Needham Center commuter station, grand Colonial Revivals line both sides of Fair Oaks’ verdant center median.

9. Pleasant Street, Arlington
Aesthetics, Amenities, Transit
On one end of Pleasant is Route 2; on the other, Arlington Center. In between are $700,000 single-family homes blessed with views of Spy Pond.

10. Hillside Road, Franklin
Aesthetics, Public Services, Affordability
Situated along I-495 and the commuter rail, Franklin has emerged as an affordable bedroom community. Its Hillside Road has both Victorians and smaller, modern homes under $400,000, and is within hoofing distance of the Dean College campus.

11. Pope Road, Acton
Environment, Public Services, Transit
“Slow down, this is not a f#$%* freeway,” reads a sign in a Pope Road driveway. Not that the stretch could ever be mistaken for an autobahn: Large 20th-century residences, at $500,000 to $2 million apiece, are nestled among its palette of oak forest and horse farms.

12. Cedarwood Avenue, Waltham
Transit, Affordability
On the edge of Brandeis University, Cedarwood is stocked with professor-friendly Capes and English cottage–style homes that cost less than $400,000, and are near I-95 and a two-minute drive from Moody Street’s restaurant row.

13. Prospect Street, Winchester
Aesthetics, Amenities, Public Services, Transit
Climbing precipitously up Winchester’s Mount Pleasant, Prospect plays host to a parade of million–dollar romantic gabled Victorians. All are close to the commuter rail station and several of the town’s well-performing schools.

14. Stoneleigh Road, Watertown
Aesthetics, Amenities, Transit
Roomy $600,000 brick Colonial Revivals sit high on Stoneleigh, with the Oakley Country Club as a manicured backdrop. Bustling Watertown Square and the Arsenal Mall are just down the hill.

15. Prospect Hill Road, Harvard
Aesthetics, Environment, Public Services
Prospect Hill includes the loftiest point between Boston and the Berkshires. “The views are magnificent, looking over three states, and Wachusett Mountain, Mount Monadnock, and Mount Washington,” says Harvard Realty president Rhonda Sprague. The assorted homes cost between half a million and 1.4 million bucks each.

1. Burrill Street, Swampscott
Public Services, Amenities, Affordability

Rare is the town common as scenic as Swampscott’s Linscott Park, and the Victorians that line Burrill, on the park’s western side, are an out-and-out bargain at about $350,000 each. Just a brief amble away, Humphrey Street’s oceanfront promenade has shops and seafood restaurants, while farther up Burrill is the commuter rail (North Station is a 25-minute ride south). And the first-rate public schools routinely post rock-solid SAT scores.

2. Bellevue Avenue, Melrose
Aesthetics, Amenities, Transit
When the railroad arrived in Melrose in 1845, wealthy urban businessmen followed, moving to this burg 7 miles outside Boston in pursuit of a pastoral lifestyle. Their legacy includes the best-preserved collection of Victorians in the area. At its epicenter is Bellevue, which is now home to young professionals who’ve scooped up turreted, mansard-roofed homes for little more than the price of a condo in Boston (costs average about $500,000). Lot sizes are on the small side, but the neighboring 2,500-acre Middlesex Fells Reservation has hiking, boating, and mountain biking galore.
X-factor: Downtown Melrose and its quintessentially pre-Wal-Mart Main Street.

3. Chestnut Street, Salem
Aesthetics, Amenities, Environment
Flush with wealth from the China Trade, 15 families of “new money” Federalists abandoned Salem Center around 1800 to build their own high-class enclave. Their massive homes are examples of Adams-esque Federal style, with imposing columned entryways, Palladian windows, and rooftop balustrades. Despite being a regular stop on the Salem tourist trail, Chestnut remains a tight-knit neighborhood of professionals who are religious about keeping up the street’s historic appeal.
X-factor: Number 18 was briefly home to Nathaniel Hawthorne.

4. Washington Street, Marblehead
Amenities, Aesthetics, Public Services
The wooden plaques on these houses brag of 18th-century origins, but thanks to meticulous renovations the buildings still look brand-new. The homes here aren’t the only things that recall an earlier era—Marblehead is still remarkably civic-minded, with a flurry of community clubs, neighborhood organizations, and spirited town meeting debates. Washington’s $700,000-and-up residences are interspersed with boutiques such as upscale children’s shop Lester Harry’s.
X-factor: Abbot Hall at 188 Washington, which houses the original The Spirit of ’76, Archibald Willard’s famous Revolutionary War painting.

5. Island Road, Essex
Environment, Aesthetics, Public Services
Skirting the edge of the windswept Stavros Reservation, Island Road looks like the Newfoundland coast, with gray clapboard houses that vanish into twisted trees and tidal flats. Few corners of the North Shore offer more seclusion, yet it’s only a five-minute drive to the fried clams and antiques shops of Essex. Homes here and on adjoining Hardy Lane sell for $300,000 to $800,000 (when they come on the market, which is rarely). As a bonus, Manchester Essex Regional High has one of the smallest student-teacher ratios around, and 99 percent of students go on to a four-year college.
X-factor: The Cape Ann Golf Course and the boat ramp leading to the Essex River sit at Island’s opposite ends.

6. Federal Street, Newburyport
Amenities, Aesthetics
Federal has impeccably restored early-19th-century homes, as well as easy access to the Tannery, an old mill turned shopping galleria.

7. Great Pond Road, North Andover
North Andover began offering boating permits on Lake Cochichewick in 2002, significantly upping housing values for those living along its shores. Homes here cost anywhere from $400,000 to $1.5 million.

8. Summer Avenue, Reading
Transit, Public Services
When school lets out in early afternoon, Summer is flooded with kids walking home to attractive $500,000-to-$700,000 Colonial Revivals.

9. Masconomo Street, Manchester-by-the-Sea
Aesthetics, Environment, Public Services
Masconomo proves the town could well be named Mansions-by-the-Sea. The street’s gargantuan villas are perched on the granite boulders above Belly Ache Cove.
X-factor: Picture-perfect Singing Beach, which is minutes away by foot.

10. Central Street, Andover
Aesthetics, Public Services, Amenities
The rows of million-dollar-plus traditional white Victorians lining Central are a stone’s throw from preppy clothing boutiques and the cultural offerings of Phillips Academy Andover.

11. Little Nahant Road, Nahant
Public Services, Environment
A postage stamp of a community between Lynn and Nahant proper, Little Nahant has ocean vistas and homes from $500,000 to $1.4 million—cheaper than those across the sound.

12. Rolfe’s Lane, Newbury
Environment, Public Services
Just off Newbury’s idyllic town green, Rolfe’s leads toward Plum Island and the vast expanse of the Parker River Wildlife Refuge. The lane’s homes cost anywhere from $400,000 to $1 million.

13. South Street, Rockport
This tree-lined boulevard leading into Rockport is not far from the waterfront’s restaurants and art galleries, but it escapes the latter’s tourist throng.
X-factor: The French toast at Flav’s Red Skiff. (Trust us.)

14. Durham Drive, Lynnfield
Public Services, Environment
Basketball nets and bicycles are legion on this curvy street full of $800,000 brick residences; the homes themselves are full of families taking advantage of the town’s strong school system.
X-factor: Three golf courses, all within a few miles.

15. Chestnut Street, Wakefield
Transit, Affordability
Wakefield owes its Pleasantville vibe to a healthy stock of $400,000
properties with barbecue–ready yards and a downtown packed with mom-and-pop stores.