72 Winstead Road
Brewster, MA · $1,675,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

72 Winstead Road

Brewster, MA 02631
$1,675,000
1 days on market · Listed Apr 29, 2026
Data refreshed Apr 30, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
4
Baths
3.5
Sq Ft
3,021
Acres
2.32
Year Built
2010
$ / Sq Ft
$554
Days on Market
1

Investment Snapshot

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Occupancy
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STR Range (P50)
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Location & Nearby

Map of 72 Winstead Road, Brewster MA with nearby beaches and points of interest
HThis property
  • A
    🐟 Long Pond Brewster Beach
    0.14 mi
  • B
    🐟 Seymour Pond
    0.45 mi
  • C
    🐟 Long Pond
    0.45 mi
  • D
    🚤 Fisherman's Landing
    0.50 mi
  • E
    🐟 Sheep Pond
    0.52 mi
  • F
    🐟 Seymour Pond
    0.95 mi
  • G
    🐕 Brewster Dog Park
    1.49 mi
  • H
    🚴 CCRT Headwaters Drive Trailhead
    1.80 mi

About this property

A masterfully crafted custom residence, impeccably maintained with many updates. This exceptional home is set on an expansive, private lot just steps from Long Pond beach and boat ramp, within the prestigious Pond Oaks Estates. Designed with both elegance & comfort in mind, the sun-drenched interior features soaring cathedral ceilings, dramatic walls of glass, & rich hardwood floors, creating a seamless, light-filled living experience. With over 3,000 square feet of living space, the home offers a luxurious first-floor primary suite complete with a spa-caliber bath, as well as a chef's kitchen designed for entertaining, showcasing hi-end cabinetry, premium finishes, & meticulous attention to detail.Gracious living spaces include an intimate breakfast nook and a beautifully appointed living room with fireplace--perfect for both relaxed living & elegant gatherings. Expansive sliders open to a generous deck, while a front patio captures serene views of Long Pond, framed by exquisitely landscaped grounds & beautiful gardens. Ideally situated near the bike trail & beach, this rare offering is for the discriminating buyer seeking to live the Cape Life Style at it's Best .

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📋 Brewster Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Brewster
Listed by Alberti Team, Gibson Sotheby's International Realty