Are you considering a two-home retirement lifestyle? The ultimate retirement dream is having a perfect snowbird balance, escaping to a warmer climate during the winter months and having a second home close to family in New England, with a more temperate climate during the summer and close proximity to the airport. When choosing a location, consider your lifestyle preferences. Do you prefer a coastal setting or a desert environment? Are you looking for a bustling city or a quiet retreat? What price range options does the location you are considering offer? Do you need indoor parking for your car while you are away? There are many factors to consider.
This guide will walk you through some of the best places to have two homes, along with the pros and cons of each area, so you can make an informed decision. Finding the ideal winter and summer homes involves careful planning and consideration. We’ll explore what you should think about when searching for your two perfect havens.
1. Choosing the Right Location for each property

Winter Retreat
The first step in finding the perfect dual living situation is deciding where you want to spend your winters. Popular snowbird destinations include Florida, Arizona, Texas, and Southern California. Direct flights between homes and proximity to the airport are key factors to consider. Each of these locations offers unique benefits:
Florida: Known for its sunny weather and beautiful beaches, Florida is a top choice for snowbirds. Cities like Naples, Sarasota, and Orlando offer vibrant communities and a range of recreational activities. There are direct flights from Boston to Miami, Fort Myers, Fort Lauderdale, Tampa, Jacksonville, Orlando, Sarasota, Key West, and Palm Beach.
Arizona: With its warm, dry climate and stunning desert landscapes, Arizona is another favorite winter escape. Places like Scottsdale and Tucson provide a mix of outdoor activities and cultural experiences. Boston offers direct flights to Phoenix.
Texas: Mild winters, affordability, plentiful outdoor activities, sandy beaches, beautiful scenery make Texas a great option for snowbirds. There are daily direct flights from Boston to Dallas, Houston, Austin, and San Antonio.
Southern California: Offering both beachside and inland options, Southern California is perfect for those who enjoy a mix of sun and surf. Cities like San Diego and Palm Springs are popular among snowbirds. Direct flights from Boston to California include San Diego, Los Angeles, Sacramento, San Francisco, and San Jose.
Coastal Summer Retreat
Whether you're seeking a more temperate climate during the summer or an investment opportunity, New England offers a variety of charming locales that cater to different needs and preferences and convenient proximity to Logan International Airport. Each of these locations offers unique benefits:
Salem, Massachusetts: Nestled on the scenic North Shore of Massachusetts, Salem offers a unique blend of historic charm and modern convenience. Known for its rich history, the city boasts well-preserved colonial architecture, fascinating museums, and vibrant cultural events. Residents enjoy a strong sense of community, with bustling farmers’ markets, local festivals, and an array of dining and shopping options. With its picturesque waterfront, Salem combines the allure of historic New England with the benefits of contemporary living. Distance to Logan International Airport, 40 minutes. Visit RIVERWALKSALEM.COM to learn more about the newest in waterfront luxury single-level living in Salem, Massachusetts!
Rockport, Massachusetts: This seaside town boasts a vibrant arts scene, stunning coastal views, and a charming, small-town feel. It’s perfect for those who enjoy artistic culture and beautiful landscapes. Distance to Logan International Airport, 1 hour.
Marblehead, Massachusetts: With its historic homes, harbor views, and quaint downtown area, Marblehead is ideal for those who appreciate history and maritime heritage. Distance to Logan International Airport, 30 minutes.
Scituate, Massachusetts: Known for its lovely beaches and charming downtown, Scituate offers a more laid-back vibe with convenient access to Boston. Distance to Logan International Airport, 1 hour.
Duxbury, Massachusetts: Featuring expansive beaches and historic homes, Duxbury is great for those seeking a peaceful and upscale summer retreat. Distance to Logan International Airport, 1 hour.
Portsmouth, New Hampshire: Portsmouth boasts a rich history with its well-preserved colonial architecture and vibrant downtown area. Located on the Atlantic Coast, it offers scenic views and waterfront activities. New Hampshire has no state income tax, which is attractive for retirees and investors. Portsmouth does have a small airport that offers limited direct flights to Tampa, Orlando, and Punta Gorda and is 1-1.5 hours to Logan Airport in Boston.
Cape Cod, Massachusetts: Cape Cod is known for its charming towns, picturesque scenery, and relaxed atmosphere. From beaches to biking trails, there’s plenty to do. Distance to Boston Logan Airport 2 hours, distance to T.F. Green Providence Airport, 2 hours.
2. Assessing Property Types
Once you’ve chosen a location, it’s time to think about the type of property you want. Snowbirds have several options, including:
Single-Family Homes: Ideal for those who want more space and privacy, single-family homes offer a personal retreat with the option to entertain guests. This type of property also requires considerable maintenance and a care-taker while vacant.
Condos and Apartments: For a lower-maintenance option, consider a condo or apartment. These properties also include amenities like pools, gyms, and social events, making them a good choice for active adults and usually include a property management company for any maintenance issues. This option is great for anyone who wants to simply lock the door and leave for the season. Considering condo ownership? Visit RIVERWALKSALEM.COM to learn more about the newest in waterfront luxury single-level living in Salem, Massachusetts!
Retirement Communities: If you’re looking for a community with amenities tailored to seniors, retirement communities might be the way to go. They often offer a range of activities and social opportunities. The limitations to this option are a lack of diversity of fellow owners and a limited re-sale market.
3. Pros and Cons of Investing in Multiple Homes
Pros:
Rental Income: Renting out your property during the off-season can provide a steady income stream.
Tax Advantages: Some states offer tax benefits for property owners, which can be advantageous.
Property Appreciation: Over time, the value of your property may increase, providing a good return on investment.
Financial Security: Multiple properties can serve as a financial cushion. If the market for one property takes a hit, others might perform better.
Cons:
Maintenance Costs: Owning a second home comes with ongoing maintenance and management costs, especially if you’re not living there full-time. Consider a condominium to minimize liability and maintenance needs.
Vacancy Risks: If you’re not renting out the property, you might face periods where it sits vacant.
Market Fluctuations: Real estate markets can fluctuate, affecting the value of your investment.
4. Evaluating Costs and Financing
Budgeting for a second home involves more than just the purchase price. Consider the following costs:
Property Taxes: Different states and regions have varying property tax rates. Make sure you understand the tax implications in your chosen area.
Homeowners Association (HOA) Fees: If you’re considering a condo or a property within a community, be aware of HOA fees and what they cover.
Maintenance Costs: Factor in the cost of maintaining a second home, including landscaping, utilities, and any potential repairs.
Explore financing options and speak with a financial advisor to ensure you’re prepared for the financial aspects of owning a second home.
5. Understanding Local Regulations
Different states and municipalities have their own regulations regarding property ownership. Research local laws and regulations, including:
Short-Term Rental Restrictions: If you’re considering renting out your property when you’re not there, check for any restrictions or requirements.
Insurance Requirements: Make sure you understand the insurance requirements for your new property, especially if it’s in an area prone to natural disasters.
Residency Rules: Some states have specific rules about how long you can stay as a non-resident. Be sure to understand these rules to avoid any legal issues.
Final Thoughts
Finding the perfect primary and second homes as a snowbird requires careful consideration and planning. By choosing the right location, property type, and understanding the associated costs and regulations, you’ll be well on your way to enjoying dual home lifestyle. Whether you’re looking for a sunny beachside escape or a cozy desert hideaway, the right preparation will help ensure your second home is everything you’ve dreamed of and more.
Happy house hunting, and here’s to sunny winters, breezy seaside summers, and endless relaxation!
Considering Salem, Massachusetts on the North Shore of Boston? Visit RIVERWALKSALEM.COM to learn more about the newest in waterfront luxury single-level living in Salem, Massachusetts!
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