A Local Expert’s Guide

Cape Cod has long been a dream destination for second-home buyers. With its charming coastal towns, rich history, and year-round appeal, it’s no wonder that families, retirees, and investors alike are drawn to this unique slice of Massachusetts. But when is the best time to buy a second home on Cape Cod?

As a licensed real estate agent in New Jersey, New York, and Cape Cod—and someone who personally owns a second home on the Cape—I’ve had the privilege of experiencing the joys of Cape living firsthand. At The Lisella Property Group, we bring over 50 years of combined experience to help buyers navigate this competitive and rewarding market. In this guide, I’ll share insider insights, market trends, and seasonal strategies to help you make the most informed decision possible.

Why Cape Cod Is the Ideal Location for a Second Home

Cape Cod offers a rare combination of natural beauty, lifestyle perks, and investment potential. Whether you’re looking for a summer retreat, a future retirement home, or a rental property, the Cape delivers.

Lifestyle Appeal

From beach days in July to cozy fireside evenings in December, Cape Cod is a year-round destination. Towns like Chatham, Falmouth, and Provincetown offer vibrant communities, excellent dining, and cultural events that make every season special [1].

Investment Potential

Cape Cod’s real estate market has shown consistent appreciation over the years. Limited inventory and high demand—especially for waterfront and amenity-rich properties—mean your investment is likely to grow in value [2].

Rental Income Opportunities

The short-term rental market is thriving. Websites like Airbnb and VRBO report strong occupancy rates even in the off-season, making Cape Cod a lucrative location for vacation rentals [3].

Understanding the Cape Cod Real Estate Market in 2025

The Cape Cod market remains strong in 2025, but it’s evolving. Here’s what you need to know:

Stable Prices with Slower Growth

The median sale price in Barnstable County is hovering around $727,000, with a modest 0.2% year-over-year increase [2]. While prices are still high, the pace of growth has slowed, offering buyers more negotiating power.

Longer Days on Market

Homes are staying on the market longer—26 days on average compared to 15 days last year [2]. This shift indicates a more balanced market, giving buyers time to make thoughtful decisions.

Inventory Challenges

Inventory remains tight, especially in desirable towns like Chatham and Orleans. Working with a knowledgeable agent is crucial to finding the right property before it’s snapped up [2].

Seasonal Trends: When to Buy for the Best Value

Timing is everything in real estate. Here’s a breakdown of seasonal buying advantages:

Spring (March–May)

Spring marks the beginning of the listing season. Sellers are motivated, and inventory starts to rise. However, competition can be fierce, especially for homes near beaches and golf courses.

Pros: Fresh inventory, motivated sellers
Cons: Higher competition, rising prices

Summer (June–August)

Summer is peak season for Cape Cod. While it’s a great time to experience the lifestyle, prices tend to be at their highest, and inventory moves quickly.

Pros: Ideal for experiencing the area
Cons: Premium pricing, limited availability

Fall (September–November)

Fall is arguably the best time to buy a second home on Cape Cod. The crowds thin out, sellers become more flexible, and you can enjoy the Cape’s quieter charm.

Pros: Lower prices, less competition, beautiful scenery
Cons: Fewer listings than spring

Winter (December–February)

Winter offers the best deals for savvy buyers. Sellers who list during this time are often highly motivated, and you may find hidden gems at reduced prices.

Pros: Deep discounts, motivated sellers
Cons: Limited inventory, weather-related challenges

Personal Insight: Why I Chose Cape Cod

Years ago, my family and I made the decision to purchase a second home on Cape Cod. It wasn’t just a financial investment—it was a lifestyle choice. Each year, I’ve enjoyed unforgettable moments with family and friends, from relaxing on the beach in the summer to enjoying our community’s annual holiday events in the winter.

This personal experience has given me a unique perspective. I understand the emotional and practical aspects of buying a second home here, and I use that insight to guide my clients through every step of the process.

Tips for Buying a Second Home on Cape Cod

1. Define Your Goals

Are you buying for personal use, rental income, or future retirement? Your goals will shape your search and financing strategy.

2. Choose the Right Town

Each Cape Cod town has its own vibe. Chatham offers upscale charm, while Eastham is perfect for nature lovers. Consider proximity to beaches, dining, and year-round amenities [1].

3. Understand Local Regulations

Short-term rentals are popular, but each town has its own rules. Make sure you understand zoning laws, rental permits, and HOA restrictions.

4. Work with a Local Expert

Cape Cod’s market is nuanced. Partnering with a local agent—like myself—ensures you get insider access to off-market listings, negotiation strategies, and trusted vendors.

5. Plan for Maintenance

Second homes require upkeep. Budget for landscaping, winterization, and property management services if you won’t be there year-round.

Financing Your Cape Cod Dream

Mortgage Rates

Rates are expected to stabilize in the mid-6% range in 2025 [2]. While not as low as previous years, they’re still manageable—especially if you lock in early.

Tax Benefits

Second homeowners may qualify for deductions on mortgage interest, property taxes, and rental-related expenses. Consult a tax advisor to maximize your benefits [3].

Cash Buyers

Many second-home buyers on the Cape pay in cash, especially for high-end properties. This can give you a competitive edge in a bidding war [1].

Rental Market Insights for 2025

Vacation rental bookings are up 14% compared to 2024 [4]. However, prices are stabilizing, with modest increases of 2–4%. The most popular rental weeks are late July and early August, but savvy buyers can capitalize on discounted rates during early summer and late August [4].

Why Work With The Lisella Property Group

At The Lisella Property Group, we combine decades of experience with a deep understanding of Cape Cod’s unique market. Our team is committed to helping you find the perfect second home—whether it’s a beachfront cottage, a luxury estate, or a cozy retreat.

As someone who’s walked this path personally, I bring empathy, expertise, and enthusiasm to every client interaction. Let’s make your Cape Cod dream a reality.

Final Thoughts: Is Now the Right Time to Buy?

If you’re considering buying a second home on Cape Cod, fall and winter offer the best opportunities for value and flexibility. With stable prices, motivated sellers, and a thriving rental market, 2025 is shaping up to be a great year for buyers.

Whether you’re looking for a peaceful escape, a smart investment, or a future retirement haven, Cape Cod has it all. And with the right guidance, you can find a property that brings joy for years to come.

Ready to explore Cape Cod real estate?
Let’s connect. I’d love to share my experience, answer your questions, and help you find your perfect second home.

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