Who hasnt fantasized about running away to a luxury home on a remote island? As tempting as that fantasy is, the reality of living on an island comes with some not-so-fantastic challenges.

For starters, buying a home on an island can be legally difficult. To buy a home in Virgin Gorda, part of the British Virgin Islands, people who are not from the BVI have to get a non-belongers landholding license, said Christopher Smith, an agent with Coldwell Banker BVI, and the process can take about six months. Building a home on an island is likely to take longer than on mainland, too. Construction schedules obviously depend on scale and permitting requirements, but a typical single-family villa takes an average of 14 to 18 months from conception to move-in, said Corby Parfitt, a St. Thomas-based real-estate agent with USVI Sothebys International Realty.

Then there is the cost of island living. On Vinalhaven off the coast of Maine, which has a year-round population of about 1,200, the grocery store receives a delivery from the mainland every day. But, you can expect to pay more for food because of the added costs of transportation and logistics, according to Kris Davidson of Davidson Realty, who is also a resident of the island. Island-dwellers also cant expect shipments at the drop of a hat. The biggest challenge, for some, is recalibrating expectations of time, said Mr. Parfitt. Things just take longer down here and the sooner you make peace with that reality, the healthier your experience, and its true for a week-long visit or a permanent relocation.

But, youre still on a beautiful island. I couldnt believe how unspoiled it was, and it still is, said Mr. Smith, who moved to the BVIs in 1992. I mean, it really is. And also how friendly the people are. Theyre very warm.

Vinalhaven, Maine // $4.5 Million

This approximately 200-acre farm is on the island of Vinalhaven, off the coast of Maine. The timber frame house is 2,640 square feet and has three bedrooms, three bathrooms and one half-bathroom. In the kitchen are cherry cabinets and soapstone countertops and the living room has a two-story fireplace with a wood-stove insert. The primary bedroom is on the first floor; an office and two ensuite guest bedrooms are on the second level. With 6,000 feet of waterfront on Long Cove, the property has outbuildings that include barns, including a two-level sheep barn that is partially heated, and chicken coops. Several Merino sheep and farm equipment, such as a John Deere Gator, are included with the sale of this property. The property is listed by Davidson Realty.

Blakely Island, Wash. // $10.3 Million

Blakely Island, part of the San Juan Islands, is where this 2.23-acre property is located. The main house is 1,833 square feet and has two bedrooms and three bathrooms. The 2,005-square-foot carriage house has two bedrooms, two bathrooms and a 2,500-bottle wine cellar.

There is also a separate 1,502-square-foot beach house on the property with one bedroom, one bathroom, NanaWall folding glass wall systems and a honey onyx bar. The property also features a hangar adjacent to a tarmac with three utility vehicles. The property is listed by Orcas Island Realty.

Virgin Gorda, British Virgin Islands // $9.5 Million

This approximately 2,723-square-foot villa is on the island of Virgin Gorda. The home has four bedrooms and four bathrooms. Each guest bedroom has an ensuite bathroom, patio and private entrance.

An infinity pool overlooks the Caribbean Sea and there is an outdoor grilling and dining area. The property is listed by Coldwell Banker BVI.

More: A Waterfront Home in a Historic Section of Fort Myers, Florida, With a 75,000-Gallon Pool and a Hot Tub for 16

Water Island, St. Thomas, U.S. Virgin Islands // $6.899 Million

Water Island is 491.5 acres and a 10-minute ferry ride away from St. Thomas. The house is 4,600 square feet with four bedrooms, five bathrooms and one half-bathroom. It has outdoor dining and sitting areas as well as a pool, hot tub and a pool pavilion. One of the guest bedrooms features custom-made bunk beds.

There are billiards and ping-pong tables and a home theater. The house has imported structural beams and solar panels with Tesla Powerwall battery units. The property is listed by USVI Sothebys International Realty.

Middle Cay, Bahamas // $12 Million

Middle Cay is a 2-acre private island off Eleuthera in the Bahamas. On the island is a main house that is about 2,800 square feet with four bedrooms, three bathrooms and one half-bathroom as well as an aproximately 2,700-square-foot guest cottage with three bedrooms and 2 1/2 bathrooms.

The main home has a kitchen with granite countertops and stainless steel appliances and the living room opens to a patio with a heated pool and outdoor shower. The property is listed by Coldwell Banker Lightbourn Realty.

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Living on an Island Isnt Always a Breeze - Mansion Global