Sweet Spots

Jeff Andrews wanted to live on South Wentworth Avenue. He wanted it bad. Strolling the streets of Bay View, the South Side slice of city known for its artsy vibe, clapboard bungalows and lakefront access, he sized up the streets where he could get the most bang for his first-time-buyer’s bucks. South Shore Drive? The most lust-worthy Bay View address because the houses overlook Lake Michigan. No way. Too expensive. And the homes never went on the market, but were always sold directly to family members and friends. But Wentworth – two blocks west of South Shore, lined with pretty…

Jeff Andrews wanted to live on South Wentworth Avenue. He wanted it bad.

Strolling the streets of Bay View, the South Side slice of city known for its artsy vibe, clapboard bungalows and lakefront access, he sized up the streets where he could get the most bang for his first-time-buyer’s bucks.

South Shore Drive? The most lust-worthy Bay View address because the houses overlook Lake Michigan. No way. Too expensive. And the homes never went on the market, but were always sold directly to family members and friends. But Wentworth – two blocks west of South Shore, lined with pretty houses and close enough for Andrews to walk his dog by the lake – Wentworth was affordable. But even its homes often got grabbed up the moment they listed, if not before.

Short on connections, Andrews tapped into the neighborhood network through real estate agent Julie Luettgen of Bay View Homes. For months they lay in wait, and Luettgen let potential sellers know she had a buyer.

When word came that a Wentworth Avenue house would soon be on the market, Andrews couldn’t wait. He and his fiancée were the first to see the house: “We loved it; made an offer that day and they accepted it,” he says.

The couple paid $200,000. “It was worth waiting for,” says Andrews, who moved into the house in May 2008.

Throughout metro Milwaukee, there are sweet spots – special places where the view, the style of homes, the trees, the nearby parkland, the unusual location, or some serendipitous intersection of aesthetics and accessibility creates a cozy niche where everyone seems to want to live. Places like Lone Tree Road in Elm Grove or Caples’ Park in the city of Waukesha or South Shore Drive in Bay View, where Lori Phillips grew up and still lives. “You’re sitting out in the yard and people will just randomly ask about buying the house,” says Phillips. “The house to the north has switched hands three times in the last 10 years, and a sign didn’t even go in the ground.”

But these days, with real estate prices stalling and sales slack, the situation has changed, say local agents. Even houses with destination addresses are lingering on the market. So if you’ve always lusted after a particular house, or longed for any house within a particular block or neighborhood, this year might be your best opportunity ever.

Longtime brokers with far-flung connections are usually the first to hear when a rising executive is about to be transferred. They’re also the ones who know when Grandma’s bungalow is becoming too much house for her.

Beth Jaworski, a Shorewest broker who lives in suburban west Wauwatosa, says that generational turnover accounts for houses selling regardless of market conditions. Seniors trading down to condos or assisted living, along with estate sales, force houses onto the market. It can take months for families to sort through the process, which opens a window for “whisper marketing,” whereby family and friends put the word out about the home.

In the current economy, the whispers of such marketing have gotten louder. Veteran Wauwatosa resident Jim Prindl, for instance, wants to sell his Ernest Flagg-designed home. It’s no secret: The sign outside his house at 7707 Stickney Ave. says so.

Prindl bought his first house in this sweet spot of the Lowell Damon Woods neighborhood directly from a friend. When the Flagg house popped up on the market 15 years ago, he captured it and moved down the block. But Prindl figures in today’s market, he can’t expect such instant action, even for a trophy house. So he’s priming the pump through the sign and fliers.

Five potential buyers have already put themselves on Prindl’s call-first list. Whoever gets his French country-style house may be guaranteed a hefty helping of envy along with the massive stone fireplace, recessed entrance and pitched roof. And of course, in the years to come, there’ll be passersby stopping to ask if the home is ever likely to be sold.

To find such sweet spots and pocket neighborhoods, we interviewed dozens of real estate agents, appraisers, assessors, neighborhood association leaders and home inspectors. Of course, most of the addresses actually on Lake Michigan are de facto prime property. In Milwaukee and the North Shore suburbs, most of those houses are huge, many are historic, and the million-dollar views will probably cost you at least a million dollars. But beyond this, there are many other coveted streets and subdivisions throughout the metro area.


Bay View: South Shore Drive

Possibly the toughest city street to buy on, with vintage homes north and south of a narrow park with glorious views of Lake Michigan and the Downtown skyline. Turnover is rare and rarely public. $300,000-$500,000

Cherokee Point

It’s on South Cherokee Way, at South 41st Street and West Howard Avenue, and sandwiched between stretches of generic duplexes and cookie-cutter ranches. The brand-new subdivision of neo-Arts and Crafts homes gets it right with proportion, porches and pillars. Sure, the houses are close together, but where else in the city can you get a nearly new house with a whiff of historic authenticity, plus a three-car garage? $300,000-$350,000

East Side: Wahl Avenue

About as high and mighty as Milwaukee gets. The homes are high on a bluff overlooking Lake Michigan. People here don’t just live large; they feel rich, surrounded by ornament, woodwork and architectural flourishes befitting the industrial titans who built these trophy houses a century ago. Plus, they’re within walking distance of Whole Foods, Beans & Barley and the Farwell Avenue/North Avenue dining district. $500,000-plus

Jackson Park

This South Side, suburban-like enclave of brick ranches and Georgians adjoining the county park is much-loved by police and other city of Milwaukee employees, with its winding roads and relatively spacious lots. $150,000-$225,000


Adjacent to Wauwatosa, this area of tidy, well-kept postwar brick homes on suburban-sized lots is popular with city of Milwaukee employees who crave convenience. Mount Mary College is at 2900 N. Menomonee River Pkwy., and the neighborhood takes in about a four-block radius from West Concordia Avenue on the north to Cooper Park on the east and West Center Street to the south. $150,000-$250,000


Near West Center Street and North 47th Street is a classic “pocket neighborhood” of tidy brick bungalows whose historic details are cherished by longtime owners. Real estate agents say that this bit of Sherman Park is better-kept and more prestigious than surrounding blocks. $150,000-$225,000

Story Hill

Overlooking Miller Park, Story Hill was developed in one fell swoop 80 years ago by a local builder with a sense of whimsy. It looks like a subdivision built by famed children’s book illustrator Tasha Tudor. $200,000-$350,000


If it’s Arts and Crafts you crave, this far-West Side neighborhood is for you. It’s populated with so many bungalows, four-squares and storybook-style houses built in the first two decades of the 20th century that two streets – West Washington Boulevard and North Hi-Mount Boulevard – are nationally designated historic districts and the area’s sweet spot. $150,000-$350,000



Villageof BrownDeer

West of Green Bay Road is a vintage island in a sea of suburban sameness. Bounded by West River Lane on the north, Ruth Place on the south and 43rd Street on the west, this oasis is the original nucleus of the town. Many of the bungalows and Victorians are still occupied by the same families that built them some 90 years ago. “It’s completely different from what you expect to find in Brown Deer,” says village planning specialist Nate Piotrowski. $160,000-$175,000


Dexter Avenueand Bethmaur Lane

With its many midsized and smaller ranch houses, Glendale is often considered the North Shore’s starter community. The sweeter spots are Dexter Avenue and Bethmaur Lane. It’s a flashback to the 1940s, when WW II vets came home to tiny ranches and capes. And with several
small, new parks wedged in among the older houses, it’s easy for busy parents to rendezvous while their toddlers play. $130,000-$200,000


Larkin Street: 4000-4200 blocks

The most-desired entry point into this highly desirable North Shore village. “A small-town atmosphere, mostly bungalows, with affordability a key factor in an upscale community,” says Desty Lorino, a broker with Coldwell Banker. $350,000

North Wildwood Avenue: 4300-4400 blocks

Baby Tudors and brick Colonials are bigger than they look because families tend to stay and add on to the rear of the houses. $500,000-plus

North Wilshire Road: 4700 block

Paging Henry VIII. Castle-sized Tudors, leaded-glass windows and fortress-like façades make this block a Renaissance fair. $500,000-plus


Berkeley Boulevard

A streetscape of mid-1960s white-sided Colonials, this is where captains of industry live when they are lieutenants. $350,000-$500,000

Circle Drive

The quintessential address, and the first one mentioned by agents as the most prestigious street in Whitefish Bay. As Circle Drive loops west from Lake Drive and then back to it, each vintage house seems more picturesque than the last, with Juliet balconies, colonnaded porches and massive chimneys. And it’s near the main shopping strip. $600,000-plus


Links Way

Colonials, ranches and capes are settled on this pleasant diversion from Lake Drive. $400,000-$500,000

Bridge Lane

Go over – yes, the bridge – from Lake Drive down this leafy wormhole that twists past stone Colonials and New Englandy farmhouses back to Lake Drive. $400,000-plus


Lake Drive and its offshoots are studded with classically designed, often oversized Colonials, Tudors, Georgians and “traditional contemporaries” (big, new houses with stone façades, bay windows, front porches and other upscale finishes), most set on manicured lots, many on ravines or slopes. This and our two streets in Fox Point are the most desired in the area, say local realty agents.

East Dean Road

Follow the leafy tunnel east from Lake Drive to Doctors Park, a favorite haunt of bird-watchers. Not to mention kids, who flock to the playgrounds and tot lots. $300,000-plus


The names that built Milwaukee’s businesses – Allis, Ilsley, Bradley – made their own enclave in 1930 when they moved the Milwaukee Country Club here. They put more country around the club by incorporating the village and specifying a minimum lot size of 5 acres. The most exclusive estates are hidden by long drives and private roads that keep the riffraff out, especially on the banks of the Milwaukee River. There, you’ll find the toniest of streets, River Road, an address that by itself may add another $10,000 to a home’s value, says former village trustee Bob Chernow. Fairy Chasm Road – west of University School – and Dean Road are also lusted-after locales. $900,000-$5 million


West El Rancho Drive

Hipster alert: This dead-end street off North Port Washington Lane is lined with
classic midcentury ranches. And the price is right for a starter home in this area. $130,000-$200,000

North Wyngate Trace

Just east of I-43, the Wyngate Trace subdivision was built with an unusual amenity: a central parkway. The result: a hilly berm in the center of the street, so everybody gets a landscaped view. Not that looking at each other’s Colonials is that painful. $500,000-plus

Range Line Road

“Everybody would love to live on Range Line Road,” says Coldwell Banker broker Ken Read, referring to the stretch between Donges Bay Road and County Line Road. Not hard to see why: sprawling mansions, some with barns, coach-house-like garages and other outbuildings. $850,000-plus


Center Street, Madison Avenue and St. John Avenue

If you crave the ambiance of downtown Cedarburg, the Victorians and stone homes of these streets get you near – but not in – the action, says local real estate agent Patty Eubanks. $200,000-$300,000


Lake Shore Road

These oversized homes built in the 1960s and ’70s, are generally set back both from the street and the bluff that overlooks Lake Michigan. $500,000-plus


Montgomeryand Milwaukee streets

The reward for chugging up the steep hill rising from downtown Port Washington is the view: A handful of Victorians overlook the port and Lake Michigan. These stone and brick homes are the town’s traditional hot spot, reports Barbara Beattie of Schmit Realty Inc. $290,000-plus

Noridge Trail

With million-dollar sunrise views over Lake Michigan, this is part of Port’s prestige area known as “The Bluff.” Watching sailboats is a local pastime, and many of the homes – oversized contemporaries abound – have big yards for entertaining. $600,000-$800,000


SaukTrail Beach

Farmland gently rolls to the water in this unincorporated part of the town of Belgium in the far northeast corner of Ozaukee County. Apocryphal unfinished summer cabins right on the lake still exist on Sauk Trail Beach, side by side with enormous new trophy houses that are nearly at water level. That’s the good news. The bad: Your neighbors are likely to be Illinoisans. Guess which homes they own. $260,000-$750,000




Colonists had the right idea: When everyone faces a common, you can share responsibility for livestock and kids. Livestock’s not allowed anymore, not in well-behaved suburbs anyway, but there’s a bumper crop of families near Cudahy’s commons. Pulaski Park – two blocks long, one block wide – is framed by Hately and Swift avenues. In between are playgrounds and plenty of space to run. And with K-through-12 schools all within walking distance, this is a no-carpool zone popular with young families. $120,000-$180,000

South Lake Drive:
Sheridan Park

For the price, one of the best lakefront locations in the metro area. And every house is wide-eyed: Front windows from vintage Mediterranean to contemporary have been replaced with plate glass, so nothing comes between homeowners and their views. Located just south of the St. Francis border where Bottsford Avenue curves into Sheridan Drive. Bushes and trees render lake views seasonal for some homeowners, but a stroll to Sheridan Park reveals the Milwaukee skyline. $250,000-$350,000


Alphabet Streets

Historic sites aren’t usually as down-home as Greendale. “It’s Mayberry U.S.A.,” says Coldwell Banker’s Cathy Cooley.

Master-planned in 1936 as a Depression-busting public works project, Greendale’s two-block downtown is flanked by parks and ringed with modest concrete-block houses. While many of the small houses and duplexes have been renovated, they’re still a collective period piece. The “alphabet” streets starting with A through E are the most desirable (Apple Court, Bentwood Lane, Crocus Court, Daffodil Lane and Euston Street, to name a few). Houses that back up to the parkways command a premium. Others, such as Arrowwood Street, offer rows of pastel-painted cottages evoking an English village. $170,000-$200,000



Kids, take a clue: If your parents start haunting this subdivision, directly across from Franklin High School on South 51st Street, you’re probably not getting your own car. In an area where three-car garages are the standard, River Park garages are built for two. Practical parents move here when their kids enter high school to minimize chauffeuring. And with Franklin cops frequenting the high school environs, River Park is burglar-free. $250,000-$350,000

Prairie Grass Preserve

Located off Highway 100, this is a commuting sweet spot: 15 minutes to Downtown Milwaukee and 10 minutes to the airport, but without the congestion of either. That makes it attractive to middle managers with heavy travel schedules. Though building lots are still available, several existing houses recently sold, even in the doldrums of 2008. $300,000-$450,000


Lake Drive: Grant Park

It’s called Lake Drive, but at this point, it faces the forest of Grant Park. The park sprawls with tennis courts and a golf course, not to mention lake views from its bluff. Houses on Oak Street and Sycamore and Elm avenues are closest to the park’s northern entrance, which makes them the wished-for addresses here, says Peter M. Stefaniak, a broker with Milwaukee’s Stefaniak Group. $200,000-$300,000

Lake Shore Boulevardand Montana Avenue

The motley assortment of houses on these two blocks aren’t quite sure what to do with their blufftop views of Lake Michigan – which starts beyond the municipal water filtration plant. But if you’re after a bargain view, it’s worth tracking this stretch – plus Third Avenue, which stutters along the lakefront – for a modest house with immodest views. $250,000-$300,000


West Rita Drive

The Kinnickinnic River meanders through this little corner of West Allis, giving residents on Rita Drive and Kinnickinnic River Parkway views of a lush greenway. Brick capes and split-levels deliver the same space as more prestigious western suburbs for a better price. On the south side of the river, Milwaukee residents get corollary benefits on West Jackson Park Drive. $250,000-$350,000


Foxwood Crossing

Just north of West Layton Avenue, sales are consistently strong in this newer subdivision, thanks to the reputation of Whitnall School District. $300,000-$400,000


South Whitnall Wayand Whitnall Court

In walking distance of Boerner Botanical Gardens and sheltered from commotion by the forested west side of Whitnall Park, these streets have been newly redeveloped with oversized houses rarely found in older suburbs. $600,000



Pasadena Boulevard

Champagne taste, beer budget? Here’s the street for you. Baby castles and understated Tudors are evenly spaced, with none of the dreaded intrusions by new, aesthetically out-of-step infill building. $250,000

Olde Hillcrest: 68th to 76th streets from Lloyd Street to Milwaukee Avenue

If it’s instant friendship you want, buy here and join the neighborhood wine club, the restoration club or the group hosting the annual Christmas party. $250,000-plus

Jackson Park Boulevard, Stickney Avenue and Underwood Avenue

Traffic flows around, but not through, these three streets just west of busy Wauwatosa Avenue, reports Jim Gehrke, president of the Lowell Damon Woods Neighborhood Association. That makes this a destination for families with young children. Plus, residents get to have parties at the historic Lowell Damon House. $250,000-plus


River Place

Not all subdivisions are plain vanilla. River Place has more character than most, tends to be in more demand and holds its value better than most. Built in the late 1990s, the subdivision slopes down to the Fox River, overlooks a wetland and affords residents treetop views. Every house has an old-fashioned lamp post, creating pretty strings of light that trace the curved streets – instant heritage. $225,000-$350,000

Caples’ Park

High on a hill south of Waukesha’s historic district – with its numerous coffee houses and antique stores – Caples’ Park takes a not-so-academic interest in nearby Carroll University: A good portion of its staff and professors live here. East Newhall Avenue, South Hartwell Avenue, Windsor Drive, Oxford Road and South East Avenue are the approximate boundaries for this national historic district. Styles range from baby Tudors to full-grown Tudors, three-story brick Federalists and occasional midcentury ranches thrown in for variety. $275,000-$400,000


Rolling Meadows

Brady Bunch alert! You expect to see Mike and Carol playing ball with the kids in front of one of the sharp-angled contemporaries that jut from the slopes of the Rolling Meadows subdivision on Gebhardt Road. In a suburb so well-planned that it’s short on funky niches or best-kept secrets, this may be the star area. A few brand-new upstarts notwithstanding, the oversized split-levels in Rolling Meadows mostly celebrate the casual chic of 1960s and 1970s home design. $280,000-$300,000


Lone Tree Road

You only arrive at Lone Tree Road if you intend to. It’s sequestered on the far western border of Elm Grove. The gentle swells and sloping woods of this secluded part of town shelter spacious capes and Colonials that settle self-confidently into the landscape. This is what McMansions want to be like when they grow up. $350,000-plus

Indian Hills

North of Juneau Boulevard, east of Highland Drive and west of the train tracks rises Indian Hills. Wooded ravines and sharp hills give nearly every house a lofty outlook. They’re all big, but even so, teardowns are clearing the way for even bigger spreads. (Honestly, who really needs a six-car garage?) Home inspector Kent Baumgardt says homes here don’t get their feet wet: They’re well above Elm Grove’s notorious flood plain. $400,000-plus



Golf course developments are relative novelties in the southwestern suburban fringe. Champions Village works it, naming streets after golf legends. It’s built around the sixth and seventh holes of the Muskego Lakes Country Club golf course. And there are water hazards: wetlands protected by the Department of Natural Resources. $300,000-$400,000


The Conservancy

This new subdivision on West Janesville Road continues to sell strongly, not because of its pleasantly generic farmhouses and bland Tudors, but because of what’s beneath them. City water and sewer services are big selling points. The Conservancy has them, while well- and septic-dependent subdivisions elsewhere in town languish. $300,000 -$350,000


Merchant’s Plat

Residents can walk to downtown Oconomowoc for lunch or a gelato. But why leave, especially if you live on Glenview Avenue, whose vintage homes back up to Lac La Belle. Colonials, Arts and Crafts houses and capes exude small-town friendliness. $250,000



Somebody took the maxim “a man’s home is his castle” literally in this rising-manager subdivision just south of I-94. Neo-Tudors line streets named “Kings Way” and “Castle Combe.” Many overlook the subdivision’s own Sherwood – a pond stocked with fish and flanked by picnic tables and weeping willows. $400,000


Capitol Drive

The prettiest stretch of vintage Hartland is east of downtown on Capitol Drive. The blocks between downtown and Merton Avenue capture the country Victorian ambiance that many people associate with old-fashioned small-town living. Prices vary widely.

Four Winds

Those looking for a subdivision that’s not at all cookie-cutter
gravitate to Four Winds on the north side of Hartland. But these farmhouses-on-steroids are pricey. $500,000-plus


Rocky Point Road

PewaukeeLake’s Rocky Point peninsula glitters with richly appointed mansions featuring sunset views from lawns that slope gently to the water. $450,000-$1.5 million


An expanding downtown
complements turn-of-the-century farmhouses tucked into the streets adjoining Ten Chimneys, the house/museum listed on the National Register of Historic Places. Live where the Lunts – legendary midcentury Broadway stars – once did. $200,000


In addition to Pewaukee Lake, plenty of other bodies of water dot Waukesha County’s Lake Country. Here, more than anywhere, primo properties sell by word of mouth – the ultimate whisper sales made to insiders and family members who’ve often waited years to buy. Until the sales slump, you couldn’t get onto some of these lakes for less than $1 million. But in 2008, only three homes sold for more than $2 million, says one broker. Here are the primo waterfront addresses in Lake Country. $275,000-$4.5 million


The town of Oconomowoc’s nearly secret lake. North-shore homes occupy spreads of at least 4 acres with 200 feet of frontage on a crystal clear spring-fed fisherman’s paradise.


Beaumont Lane, Beaver Lake Road, Cindy Lane, Spence Road and Stevens Road.

Crooked Lake

Just about anywhere – few homes, and most are large estates.


A quiet cul-de-sac on the otherwise rambunctious party lake, Okauchee.

Lac La Belle

Besides Glenview Avenue and Merchant’s Plat, there’s Monastery Hill Drive, Beggs Isle Drive and Blackhawk Drive.

LowerNashotah Lake

DeKoven and Interlaken drives.

MiddleGenesee Lake

Hollyhock Woods Road.


The southeast corner of the lake offers sunset views and that rare commodity – elbow room between homes.


Hewitts Point Road, SouthBeach Road, Pabst Court, Lake Club Circle, North Sawyer Road,

Buchanan Roadand Petit Road.


South Bayview Road, Snyder Lane, Rolefson Road, and Roads O and M.


Highway 83, County Roads C and K, Brumder Drive, Maple Lane, Oakland Road, Pheasant Drive and Paulines Wood Drive.


Silver Cedar Lane.

UpperNemahbin Lake

Mill Road.

UpperNashotah Lake

Mission Road.



Highland View Drive

Every town has its Pill Hill, where its first generation of doctors and lawyers clustered in a well-read clique. In West Bend, the hill is west of the historic downtown, and Highland View Drive is one of its most prestigious streets. Brick Tudors and Georgians are settled on extra-big lots nicely set back from the streets. $200,000-$400,000

Lake District

Little Cedar, Big Cedar and Silver lakes cluster on West Bend’s southeast side, west of the big-box strip on Paradise Drive. If you want to walk straight out to the water, these are the lakes for you. Houses tightly hug the narrow shores with little room between, but you can walk from your door onto your pier without breaking stride. Houses are usually sold from owner to owner, says local real estate agent Cyndi Seefeldt of First Weber. “Kids grow up on the lake and buy from other neighbors,” she says. $400,000-$900,000


Tree Tops

Tree Tops hasn’t got many treetops, but it’s a top-of-the-line subdivision for Germantown. And, for time-pressed homeowners, it has a reputation for being well-run, right down to having its own parks and stormwater management. $350,000-$900,000


Tamarack Ridge

Here’s a serious subdivision: Tamarack Ridge, on the west side of Pilgrim Road at Stonewood Circle. It’s not for beginners, say brokers. With a wider variety of home styles – from yellow-sided farmhouses to shingle-sided neo-Arts and Crafts – the subdivision borders Tamarack Park, which provides a buffer of quiet. $320,000-$500,000



The popular Bugline bike trail runs through tiny Merton (from Menomonee Falls) and right to Bark River Crossing, a huge subdivision of huge houses on huge lots. Residents have a sprawling park with soccer fields. $500,000-plus

Joanne Cleaver is a Milwaukee-based freelancer. Write to her at letters@

How To Be First In Line

Tricks of the trade on buying that highly desirable home.

If you’re cultivating a relationship with a real estate agent in the hopes you’ll get first crack at a house, the agent will likely ask you to sign a single-party listing agreement. This agreement is between the agent and the seller, and authorizes the agent to present the seller’s home to an already-identified potential buyer, explains Kevin King, general counsel for the Wisconsin Realtors Association. Instead of a general listing, which covers all potential buyers, the single-party listing only covers the purchase between the seller and that buyer.

And if you’re cultivating a neighbor in hopes of snagging her house before she puts it on the market, make sure you are named as an exception to any contract she signs with an agent. This means that, because the seller was already discussing the possibility of selling the house to you, she can sell without having to pay a commission to the agent. Of course, if someone else buys the house, the seller will owe the commission, says King. To move fast with your offer on a desirable home, you’ll have to assemble cash or be preapproved for a mortgage, because chances are slim you can make an offer stick if it’s contingent on selling your current house. As the Boy Scouts would say, be prepared.