YOUR ISLAND RETREAT
A vacation home on Nantucket offers something rare: your own piece of one of America's most exclusive summer destinations. Generations of families have built traditions around their Nantucket retreats, returning season after season to the same cherished property.
This guide covers everything you need to know about buying a second home on the island, from seasonal considerations and rental potential to property management and the best neighborhoods for vacation living.
Whether you're seeking a simple beach cottage or a luxury estate, understanding the unique aspects of vacation home ownership will help you make the right decision.
TIMING MATTERS
Nantucket transforms throughout the year, and understanding these seasonal rhythms is essential for vacation homeowners. Your property experience varies dramatically depending on when you visit.
June - August
Maximum enjoyment of beaches, restaurants, and social scene. This is when most vacation homeowners visit. Plan arrivals/departures around busy travel times.
May, September - October
Quieter island with many amenities still available. Perfect weather for biking, walking, and exploring. Popular with experienced island owners.
November - April
Quiet, intimate island experience. Limited services but peaceful atmosphere. Essential for checking on property and handling maintenance.
INCOME OPPORTUNITY
Many vacation homeowners offset costs through summer rentals. Understanding the rental market helps you evaluate properties and set realistic expectations.
Summer rentals can cover significant portions of annual carrying costs including mortgage, taxes, and maintenance.
Rent during peak weeks you don't plan to use, then enjoy the property the rest of the season.
Regular renters and property managers help identify maintenance issues early.
Rental use accelerates wear on finishes, appliances, and furnishings. Budget for more frequent updates.
High-demand weeks (July 4th, August) generate the most income but are also when you may want to be there.
Either invest time in self-management or pay 20-35% of rental income to a property manager.
Entry-Level Cottage
$3,000 - $6,000/week
Mid-Range Home
$6,000 - $12,000/week
Premium Property
$12,000 - $25,000/week
Luxury Waterfront
$25,000 - $75,000+/week
REMOTE OWNERSHIP
Managing a vacation property from the mainland requires planning. Several options exist depending on your rental goals, desired involvement, and budget.
Comprehensive care including rental bookings, guest services, maintenance coordination, and property oversight year-round.
Property monitoring, seasonal prep, and basic maintenance without rental management involvement.
Handle all aspects of property care remotely with occasional on-island contractors as needed.
WHERE TO BUY
MAKE THE RIGHT CHOICE
Property used primarily for personal enjoyment with occasional rental income.
Renting a vacation property each year without ownership commitment.
FREQUENTLY ASKED QUESTIONS
Late fall through early spring often provides the best opportunities for vacation home buyers. Inventory increases as seasonal sellers list properties, and there's less competition from other buyers. However, quality properties sell year-round, so be prepared to act when the right opportunity arises.
Rental income varies significantly based on location, size, amenities, and condition. Entry-level homes might rent for $3,000-6,000 per week during summer, while premium properties command $12,000-25,000+ weekly. Most properties can book 8-12 peak weeks. A realistic analysis specific to your property type is essential before purchasing.
If you plan to rent, furnishing for rentals makes sense. Coastal-casual, durable furnishings that photograph well are recommended. Many owners invest $30,000-100,000+ in furnishings for rental-ready properties. Factor this into your budget if the home isn't already furnished.
Most out-of-town owners work with local property managers or caretakers. Full-service management handles everything from rentals to maintenance for 20-35% of rental income. Caretaker services provide property checks and maintenance coordination for a monthly fee. Choose based on your rental plans and desired involvement level.
Vacation homes have complex tax implications involving mortgage interest deductions, rental income reporting, and potential depreciation. If you rent more than 14 days annually, rental income is taxable. Consult with a tax professional familiar with vacation property ownership before purchasing.
Yes, but there are practical and tax considerations. Blocking weeks for personal use reduces rental income and may affect tax treatment. Most owners designate specific periods for personal use and rent the rest. Working with a good property manager helps balance personal enjoyment with rental revenue.
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Whether you're buying, selling, or exploring Nantucket real estate opportunities, we're here to help.
