It’s no secret that the Florida Keys are home to some of the most spectacular waterfront properties in all of South Florida.
Here are the top ten most expensive homes currently on the market in the Upper Keys. Not surprisingly, these homes boast impressive open water views and and represent truly luxurious island living.
Go on . . , dream a little!
The link will take you to the properties, where you can read more about them and see additional photos of the homes.
When comparing January 2019 to January 2020, it shows that the real estate market in the Upper Keys remains stable. There were both gains and losses in average sales price across the various categories.
More residential properties were sold in 2020 than in 2019, and the average sales prices remained consistent. The area with the biggest change is condos, townhomes and condo-tels – with more units sold in 2020, and a noticeable drop in sales price from 2019 to 2020 for units have water views.
Click on the graphic to the side to see more details.
This island home features two large bedrooms and shared bath on the main living level, and two bedrooms and two baths in the downstairs enclosure. Located on one and a half lots in a great neighborhood – Bay Harbor – this home has access to a private homeowners park with boat ramp, dockage and sandy beach, just down the street, making it a perfect weekend retreat or full-time residence. All cedar plank siding, freshly painted, metal roof, and fenced yard with access from 2 streets.
Located halfway between Key Largo and Islamorada, this home is centrally located close to schools, shopping and everything the Upper Keys has to offer.
Offered unfurnished at $465,000, with a motivated seller.
Click here for more information and additional photos.
It’s no secret that the Florida Keys is an expensive place to live. But there are still places you can find under the $250,000 price range.
It may be a small condo, or a small home, and it may or may not be in need repairs and remodeling. In some cases, the homes are un-inhabitable, but since there is already a structure on the land, you can get a permit to build a new home much quicker than if it was just a vacant parcel of land.
From Key West to Key Largo, here is what is on the market under $250,000.
Vacation Rentals. We know they are a popular choice among travelers, or sites like VRBO, HomeAway and AirBnB would not exist.
The Florida Keys are no exception. Many an owner has offered their condo or home for vacation rentals to earn income that can offset the cost of owning and maintaining a home in the Keys.
But before you start welcoming guests into your home away from home, it’s important to know if it is legal to do so. Almost every condo association and single family home owner associations have rules and regulations regarding vacation rentals. In some cases, even in when the association allows rentals, Monroe County may not.
Almost all single family home neighborhoods have restrictions in place that do not allow rentals under 28 days. That’s straight forward enough. Some condos have restrictions allow rentals of one month or longer, while some others allow weekly rentals.
But lately, Monroe County has been taking aim at condo associations, and hitting owners that do short term rentals that the county deems “illegal” with hefty fines.
The county requires two things for each vacation rental: an annual permit and a property manager licensed with Monroe County to manage the rental. Learn more about the two requirements by clicking here. Not having both a permit and a licensed manager will result in a violation. Unless you file for and get an exemption.
There are exceptions that could get you an exemption. A vacation rental permit is not required for the following: (1) A vacation rental of a dwelling unit located within a controlled access, gated community with a homeowner’s or property owner’s association that expressly regulates or manages vacation rental uses; or (2) A vacation rental of a dwelling unit within a multifamily building located within a multifamily district, which has 24 hour on-site management or 24 hour on-site supervision. To meet these on-site management or supervision requirements, a designated individual must be physically located within the building or within 300 feet of the subject building and must be available at all times to respond to tenants’ and neighbors’ complaints. You can learn more about the exceptions by clicking here.
To make matters more complicated, incorporated cities within the Monroe County, such as Islamorada and Marathon, have their own set of rules and regulations regarding rentals that must also be adhered to in addition to Monroe County rules.
For instance, there are condos in the Islamorada area that, according to their condo docs, allow short term vacation rentals. However, the Village of Islamorada has a financial threshold that a property must pass before it would even be considered for a vacation rental permit, much less approved. Even though the condo docs allow rentals, units that aren’t assessed high enough for tax purposes do not qualify for a permit to do anything less than 28 days.
Once you’ve done the background research to see if a property qualifies, you will still need to apply for the proper licenses (not permits) from Monroe County and the State of Florida to remit the collected sales tax each month. It is required to collect and remit 12.5% sales tax on all rentals under 6 months. The State of Florida gets 7.5% and Monroe County takes 5%.
There are still plenty of opportunities to own a vacation rental in Monroe County, just as long as you do your research and follow the proper guidelines. When in doubt, check with your real estate professional or speak directly to officials at Monroe County.
The 2018 real estate market was a fairly brisk market, especially considering that much of the Keys was still recovering from Hurricane Irma in September of 2017. While it’s true that many “investors” flooded the Keys, hoping to buy damaged properties from desperate sellers at bargain prices, many of the homes in the Upper Keys suffered little to minor damage during the storm. Still, many long-time residents chose to leave the Keys permanently.
So far, 2019 has not been as intense as 2018. Investors looking for deals have left to look in other storm damaged areas, such as the Florida Panhandle after Hurricane Michael struck. Open water home and canal front homes saw a slight reduction in prices, particularly open water homes.
Click to enlarge – Properties MM 70 to MM106
Non-waterfront single family homes is currently one of the most active segments of the market. Often, non-waterfront homes are in neighborhoods with a community boat ramp, making access to boating right from your own neighborhood easy and convenient.
Click to enlarge – Properties MM 70 to MM106
Condominiums have also seen an increase in interest from buyers. Condos appeal to many buyers because they have everything a buyer is looking for – pool, tennis, security, etc. They are also easier to use as a vacation rental unit than a single family home, since most neighborhoods of single family homes restrict the minimum length of legal rentals to be 28 days or longer. But many condos can offer weekly or even daily rentals, making for more potential rental income.
What will the next quarter of 2019 look like compared to 2018. Time will tell, but I believe the market will do fine.
** The data here is for properties located in the Upper Florida Keys – from Mile Marker 70 to Mile Marker 106 – and is an average of all sales. Each group encompasses a variety of homes, from luxury homes to basic construction. Properties sold both above and below the averages sales prices shown here.
With the ever rising popularity of smart devices such as Amazon’s Echo and Alexa, in addition to in-home video surveillance systems, owners of homes on the market may be able to listen in, or even watch, while you tour their home.
Sellers could be listening or watching to see what your reactions and comments are about their home. Even remarks that you may think are harmless can be used against you.
For instance, if you gush about how much you love the house and can’t wait to buy it, that seller will most likely be less inclined to negotiate the price with you, since they know you love it and have to have it.
But what about privacy?
In many ways, when you open your private home to the public, it can be similar to a shopping mall, restaurant, sports arena or any other public space. Allowing the public in can change the dynamics in terms of strength and amount of rights you may or may not have.
Many agents argue that homes that have such devices installed should include a notice or sign indicating that there are recording devices present. Currently, there are no laws that require such notice.
In the meantime, use caution when viewing homes. Sure, you can discuss things with your agent, but be sure to keep them neutral. Leave the serious talk about writing offers or how much you’re willing to pay until you are in a place where you know the seller won’t be listening.
Buyers looking for an affordable way to purchase a home often consider buying one that needs updating or possibly even a complete remodel. Before you make that leap into the work of remodeling a home, consider these 3 points.
1 ~ Know the Local Zoning and Building Regulations. That charming Conch cottage built back in the 40’s certainly carries a lot of nostalgia and Keys history, but your dream of expanding it and turning it into a spacious new home won’t be easy. Many of the ground level cottages built in the 40’s, 50’s and even 60’s are built below base flood plain elevation. That will make it difficult, if not totally impossible to add on to it, since you will not be given permits to expand the home at its current elevation. It may also cost more to insure with flood insurance.
2 ~ Price Building Supplies and Contractors You Will Need Locally. There’s a saying that Paradise isn’t cheap. The cost of building supplies and even labor can be quite different than what you may be used to paying back home. The Keys don’t have but two Home Depots that serve the entire island chain from Key Largo to Key West. Many areas of the Florida Keys are still completing repairs from Hurricane Irma, and finding contractors can be challenging and expensive.
3 ~ Don’t Skip Inspections Because You’ll Be Remodeling Anyway. It may be tempting to skip the inspection period, especially if you’re planning on tearing out a kitchen or bathroom. But having an inspection may bring to light issues in areas of the home you weren’t planning on changing. You don’t want to start taking out a kitchen or bath only to find that the plumbing or electrical systems are inadequate. Having an inspection will look at the whole house, and can help you decide if you plans will even work once you’ve purchased.
Finding an older home and making it your dream home is possible, but be sure to keep an open mind and work on the project knowing the facts before you purchase.
Not all condos in the Keys are created alike . . .
One of the biggest downside I hear from condo buyers is that many units feel like a box, with limited floorplans.
Not so at Ocean Harbour. These units have unique floorplans, and are some of the most spacious units in the Upper Keys. With two bedroom, three bedroom and even four bedroom units, these units break the norm and feel like a luxury home.
But it’s not just the units that are so attractive. The grounds are immaculate. The grounds consist of beautiful, lush green spaces, a large free-form swimming pool, a marina and boat ramp, an oceanfront clubhouse, a private gym, large oceanfront tiki with BBQ area and covered parking.
Tucked away in a private and gated community off The Old Road, these units all have endless Ocean views and views of the grounds. They feature large kitchens and master bedrooms with ocean views, a private master bath and a dressing are with walk-in closet.
Located in Islamorada, Ocean Harbour is close to everything you’ll need in terms of restaurants, shopping, medical needs, etc.
The Florida Keys have long been known as an ideal destination in South Florida, either as a place to vacation or a place to live full-time.
The perception is that most places to live in the Keys are out of reach for many buyers. While it is true that the Keys are home to some of the most expensive real estate in South Florida, there are also places you can find for under $250,000.
Here is a list of all the properties in the Keys, from Key West to Key Largo. Many of them are condos, but there are also some single family homes.
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It’s no secret that the Florida Keys are home to some of the most spectacular waterfront properties in all of South Florida. 
