366 Winslow Gray Road
Yarmouth, MA · $525,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

366 Winslow Gray Road

Yarmouth, MA 02673
$525,000
12 days on market · Listed Apr 1, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
3
Baths
2
Sq Ft
1,155
Acres
0.23
Year Built
1800
$ / Sq Ft
$455
Days on Market
12

Investment Snapshot

🟡 MEDIUM RISK
Monthly Carrying
$2,962
Cash Flow / yr
$20,184
Cash-on-Cash
13.7%
Cash Required
$147,000
Projected Revenue / yr
$74,290
Avg Daily Rate
$399
Occupancy
51%
STR Range (P50)
$55,146
🟡 MEDIUM RISK — Current bylaw expires November 2026. Registration required.
STR revenue range: $37,431$75,652

Location & Nearby

Map of 366 Winslow Gray Road, Yarmouth MA with nearby beaches and points of interest
HThis property
  • A
    🌲 Swan Pond Boardwalk
    0.44 mi
  • B
    🚤 Parker's River Boat Ramp
    0.48 mi
  • C
    🚴 CCRT Peter Homer Park Trailhead
    0.56 mi
  • D
    🛝 Peter Homer Park Playground
    0.67 mi
  • E
    🛒 Stop & Shop - Yarmouth
    0.70 mi
  • F
    🐕 Yarmouth Dog Park
    0.72 mi
  • G
    🐟 Long Pond
    0.73 mi
  • H
    🍽️ F and L Pizza Cafe 2
    0.79 mi

About this property

Charming 1790s Antique Cape. This 3bedroom, 2bath Antique Cape was moved to its current location in the mid 1990s and set on a new, full foundation--offering the best of historic character with modern stability. The spacious living room welcomes you with extra-wide pine plank flooring, exposed beams, a pine paneled fireplace wall, chair rail detailing, and classic 12 over 12 windows that fill the space with natural light. A dining room (or den) features built-ins, exposed beams, and matching wide plank floors, creating a warm and flexible gathering space. The kitchen, rich with character thanks to exposed brick and beams, wide plank flooring, skylight, dedicated pantry, copper lantern fixtures, built-ins, fabulous soapstone sink, and a charming alcove perfect for a breakfast nook or cozy reading corner. A hallway with multiple closets and a full bath--complete with clawfoot tub and wide plank floors--round out the first floor. Upstairs, you'll find three inviting bedrooms, all with wide plank flooring, built-ins, knee wall storage, and surprisingly ample closets, not often found in antique homes and second full bath. A large, sun-drenched sunporch offers the perfect spot to unwind on summer evenings, surrounded by windows and overlooking a natural landscape filled with flowering trees, perennials, brick walkways, and stone paths. The property includes a large newer shed with loft (approx. 10' x 12'), a smaller potting shed, and an outdoor shower. With a bit of TLC, this lovely Antique home can be restored to its full historic glory. Its solid full basement, abundant character, and generous living and storage space make it a rare opportunity for antique home enthusiasts

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📋 Yarmouth Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Yarmouth
Listed by Cape Cod Retirement Group, Kinlin Grover Compass