HOME PORTRAIT
Building Dreams
The Inspiring Journey of Islander Manny DeOliveira and Southwest Construction
By Diane Alter
Manny DeOliveira stepped onto Martha’s Vineyard at the tender age of 21, clutching little more than a plane ticket gifted by his mother and a modest foundation in the construction business. It was the early 2000s, an era of simpler dreams, and though he carried the grit of a tradesman, he could scarcely have foreseen that two decades later, he’d stand as the owner and president of Southwest Construction, Inc.–a thriving company woven into the Island’s fabric.
His path was no neatly paved road.
Like many newcomers to this windswept isle, Manny began humbly, scrubbing dishes at Espresso Love for a fleeting couple of months before the call of hammer and nail drew him back to construction.
With each project, Manny absorbed the rhythms of the trade, mastering the intricate dance of building and renovating homes amid the Vineyard’s salty air and shifting sands.
Over time, without fanfare or a grand blueprint, he found himself at the helm of his own enterprise.
Southwest Construction is more than a name etched on a worksite sign–it’s a promise of excellence. The company marries fine craftsmanship with a deep-rooted commitment to the client’s vision, ensuring every nail driven and beam raised reflects both expertise and care. Manny’s team–each member a steward of this ethos–prioritizes high-quality work, Island-savvy solutions, and clear, dependable communication.
Collaborating closely with architects and interior designers, they transform blueprints into living dreams, whether it’s a cozy cottage or a sprawling estate.
Choosing the right construction company is no trivial matter; it’s the linchpin that determines a project’s quality, timeline, and budget. Southwest Construction, now boasting a tight-knit crew of ten, operates year-round, deftly navigating the quirks of Island life.
“The logistics of getting materials can be brutal,” Manny admits, his voice tinged with the pragmatism of experience. “We’re at the mercy of the ferries. A storm rolls in, a shipment’s delayed, and the whole schedule teeters.”
The Vineyard’s isolation does indeed amplify every challenge.
Winter gales can snarl ferry schedules, stalling deliveries of lumber or concrete, while summer’s tourist throngs choke roads and docks, slowing the movement of equipment and crews. Fog or rain, frequent Island visitors, might delay a concrete pour, leaving workers idle and timelines stretched–a frustration well-documented in local lore.
Yet Manny thrives in this crucible, where building demands not just skill but resilience against high costs, scarce land, Byzantine regulations, fragile ecosystems, labor shortages, logistical tangles, community resistance, and creaky infrastructure.
Even a modest 2,000-square-foot home here can command a staggering $1 million and 18 to 24 months to complete–assuming no tempests or red tape intervene. Larger or commercial projects? They’re a high-stakes gamble, requiring deep resources, unwavering patience, and a native’s know-how.
Each of the Vineyard’s six towns—Aquinnah, Chilmark, Edgartown, Oak Bluffs, Tisbury, and West Tisbury–wields its own zoning codes, historic district edicts, and conservation mandates, all overseen by the exacting Martha’s Vineyard Commission.
A project might stall for months awaiting wastewater approvals (thanks to the island’s septic reliance), coastal compliance under the Wetlands Protection Act, or aesthetic blessings in Edgartown’s storied lanes. Permitting alone can drain tens of thousands in fees and consultant hours.
The Island’s delicate ecosystem—think coastal dunes, shimmering wetlands, and habitats for endangered species—adds another layer of complexity. Over 30% of the land is environmentally sensitive, and prime coastal lots, coveted for their vistas, trigger a gauntlet of state and local green laws. Erosion, rising seas, and stormwater woes loom large. In Chilmark, a builder might pour thousands into elevated foundations or intricate drainage to shield a nearby pond, all while the clock ticks.
Labor, too, is a scarce commodity.
The Vineyard’s year-round population hovers at 20,000, ballooning to over 200,000 in summer, yet skilled tradespeople–carpenters, electricians, plumbers–are elusive. With median home prices hitting $1.3 million (2023 figures), housing shortages drive workers off-island. Manny often leans on mainland commuters, ferried in at added cost and risk–weather or a missed boat can unravel a day’s plan.
Then there’s the community. In affluent pockets like Aquinnah or rural Chilmark, “not in my backyard” fervor runs deep. Residents, guarding the Island’s rustic charm, rally against new builds, sparking hearings, lawsuits, or permit denials. A 2022 affordable housing bid in West Tisbury withered under traffic and environmental gripes–a familiar Vineyard tale.
Infrastructure groans under the strain. Aging roads, a patchy power grid, and lean water supplies buckle as development creeps forward. New homes might fund transformer upgrades or road fixes, ballooning budgets. Up-island, well water and septic limits squeeze lot potential, demanding costly fixes to appease health codes.
Looming tariffs from the Trump administration, set to hit March 2025, threaten fresh chaos. With 25% levies on Canadian lumber and Mexican goods, and 20% on Chinese HVAC systems, costs could spike as America’s top trade partners vow some sort of retaliation. Evolving codes and affordability pressures only deepen the stakes.
Yet Manny endures, forging a loyal team despite seasonal flux and housing woes. Southwest Construction even offers employee housing–a rare lifeline ensuring skilled hands stay rooted.
“Manny’s detail-obsessed,” says Alisun Armstrong, the company’s self-effacing “gal Friday.” “He delivers early, not just on time–a unicorn in this business.”
Sustainability is Southwest’s hallmark, echoing the Vineyard’s green soul.
Partnerships with the Island Housing Trust yield affordable homes, senior living, and gems like the historic Aquinnah Church parsonage renovation. “We’re proud of this work,” Alisun beams. “It’s our Island, too.”
Their portfolio dazzles: an 8,000-square-foot West Chop overhaul, where dining room windows frame ferries gliding across Vineyard Sound; a sleek, minimalist Edgartown retreat, defying cedar-shingle norms; a cunning Oak Bluffs jewel, squeezing brilliance from a postage-stamp lot. Projects like Tashmoo House (2,200 square feet, Vineyard Haven), Hammett Lane House, State Road WT and Vineyard Haven Houses, and Sweet Water House showcase their versatility–all born from client dreams and Island ingenuity.
Active in the Martha’s Vineyard Builders Association, Southwest Construction stands as a pillar of standards and community. Twenty-one years after landing here, Manny calls the Vineyard home a place transformed, as has he, by shifting rules, design tides, and the relentless churn of a seasonal island. Through it all, his dedication–to craft, crew, and community–burns as bright as a lighthouse in a nor’easter.
To find out more about Southwest Construction, Inc. located at 90 Summer Street, in Vineyard Haven
Office: 508.274.7448, E-mail: info@southwestmv.com. To view a complete portfolio, visit southwestmv.com.