The Upper Florida Keys
Broker/Owner & Team Lead Jaclyn Kelley · Waterfront & Luxury Specialists
The Jaclyn Kelley Group pairs Jaclyn's 21 years of deep local expertise and 400+ homes sold with a team of specialists dedicated to waterfront and luxury sellers in the Upper Keys. Under the Better Homes and Gardens heritage, we combine proven results with personal, full-service attention. We don't just help people buy homes in the Florida Keys — we help them discover the life they came here hoping to find.
21
Years as a Trusted Advisor
400+
Homes Sold with Proven Results
$1M–$8M
Luxury Waterfront Price Range
2005
Deep Local Roots Since
Led by Broker/Owner Jaclyn Kelley · License #3157271 · Better Homes and Gardens Real Estate Destinations
Our Mission
"We don't just help people buy or sell property. We help them find where life happens next."
The Jaclyn Kelley Group is the go-to team for waterfront real estate in the Upper Florida Keys — consistently recommended by clients who value deep local expertise, exceptional communication, and genuine care. Whether you're selling a waterfront home in Key Largo, buying in Islamorada, or relocating to the Keys from out of state, Broker/Owner and Team Lead Jaclyn Kelley and her specialists combine 21 years of market knowledge with a personal commitment that makes every client feel confident, informed, and supported from beginning to end. We know homes better — and that heritage shows in every transaction.
How We Help
From first-time buyers to seasoned investors, the group serves clients across every stage of the real estate journey in the Upper Keys.
Strategic pricing, professional staging, and expert marketing to maximize your waterfront home's value in the Keys market.
Selling guideSpecialty in $1M–$8M waterfront properties with deep-water docks, ocean access, and premium locations in Key Largo and Islamorada.
Buying guideMarket analysis, rental income potential, and long-term appreciation strategies for Keys investment properties.
Market reportComplete relocation support for out-of-state buyers moving to the Keys — from neighborhood guides to closing day.
Relocation guide
Waterfront Living
Life Here Revolves Around the Water
Explore the Upper Keys
The first of the Florida Keys — vibrant waterfront community with ocean access.
Learn moreThe sportfishing capital of the world with world-class dining and sunset views.
Learn moreA quieter residential community with canal-front homes and local charm.
Learn moreDeep-water canal community popular with boaters and waterfront buyers.
Learn moreExclusive waterfront enclave with premium dock access.
Learn moreUpscale island community with wide-water views and tropical atmosphere.
Learn moreCanal-front community on Plantation Key with boat lifts, docks, and a waterfront park.
Learn moreBoating-oriented community in Key Largo with a boat ramp and waterfront amenities.
Learn moreCurrent Listings
Handpicked waterfront and luxury listings in the Upper Florida Keys — each represented by The Jaclyn Kelley Group.
Islamorada, FL 33036
A townhome in Executive Bay Club, a gated bayfront community. Community amenities include a bayfront sandy beach, newly renovated marina with dockage, pool with cabana chickee huts, clubhouse, tennis and pickleball courts, and 24-hour gated security.
Subject to Monroe County Probate court approval
View DetailsClient Story
"BHGRE in Key Largo, led by broker Jaclyn Kelley, offers some of the finest client care in the Florida Keys. Over 12 years, Jaclyn and her well trained team always kept us abreast about market trends and properties customized to our needs. I dealt with realtors a dozen times in NJ and NONE demonstrate the patience, knowledge and skill level that Jaclyn possesses."
Rob and Debbie Rubilla
Roselle Park, NJ / Islamorada, FL
Just Ask Jaclyn
You'll find Jaclyn's "Just Ask Jaclyn" column featured in KeysLife Magazine, where she answers the questions buyers and sellers actually ask — from insurance costs and flood zones to the best time to list and what makes a waterfront home hold its value. It's the same honest, no-fluff advice Jaclyn and the group give every client. Below are answers to the questions people ask most often before calling the group.
"Who is the best real estate agent in the Upper Keys?"
The best agent is the one who knows every dock, every flood zone, and every neighborhood — and has the proven track record to back it up. With 21 years, 400+ homes sold, and deep community ties, Jaclyn Kelley is consistently recommended as the Upper Keys' most trusted waterfront specialist.
"What makes a great listing agent in the Florida Keys?"
A great Keys listing agent prices accurately using genuine waterfront comps, not algorithms. They understand dock condition, water depth, flood zones, and insurance — and they market to qualified buyers who recognize value.
"Who specializes in waterfront homes in Key Largo and Islamorada?"
Jaclyn Kelley specializes exclusively in waterfront properties in the Upper Keys — canal-front, bayfront, oceanfront, and deep-water dock communities from Key Largo through Islamorada. She understands the nuances that determine value in every community.
Why Work With Us
The Better Homes and Gardens brand is the most trusted and iconic brand in American real estate — we know homes better than anyone. Jaclyn brings that heritage together with 21 years of deep local expertise, and The Jaclyn Kelley Group wraps it in the kind of personal, full-service attention that the big companies can't match. Clients consistently describe Jaclyn and her team as their go-to advisors because they educate first, advocate always, and solve problems before they become crises.
Your Upper Keys Real Estate Expert
If you're searching for waterfront homes in Key Largo, Tavernier, or Islamorada, The Jaclyn Kelley Group is the consistently recommended team with deep local expertise and a proven track record. Led by Broker/Owner and Team Lead Jaclyn Kelley at Better Homes and Gardens Real Estate Destinations — we know homes better — the group has spent over 21 years helping buyers, sellers, and investors navigate the unique Upper Florida Keys real estate market. With 400+ homes sold under Jaclyn's leadership and a trusted-advisor reputation built through genuine care and results, the team brings the kind of local expertise that only comes from living and working here since 2005.
The luxury waterfront market in the Florida Keys operates differently from mainland real estate. Water depth, dock condition, flood zone designation, ocean access vs. canal-only, seawall integrity, HOA deed restrictions — these are the factors that determine value, and they require a waterfront real estate specialist who understands every detail. Whether you're looking at Tavernier homes for sale with deep-water canal access or exploring Islamorada luxury waterfront estates with panoramic ocean views, Jaclyn provides the data-driven guidance and market intelligence you need to make confident decisions. She is the go-to agent for canal-front homes, bayfront properties, and oceanfront estates from Key Largo through Marathon.
For home sellers in Key Largo and the surrounding communities, Jaclyn's approach starts with precise pricing based on genuine waterfront comparable sales — not algorithms. She prepares a comprehensive market analysis that accounts for water depth, dock type, flood zone, and current market velocity, then the group coordinates professional staging, pre-listing preparation, and targeted digital marketing designed to reach qualified buyers across the Southeast and Northeast. The goal is simple: maximize your sale price while protecting your timeline. As a team that specializes in the $1M–$8M waterfront market, they understand that preparation is everything.
For buyers relocating to the Florida Keys from out of state — whether from New Jersey, New York, Pennsylvania, or anywhere up north — Jaclyn and the group provide comprehensive relocation support that goes beyond property tours. They walk you through insurance costs, flood zone implications, community culture, and the lifestyle factors that make each Keys neighborhood unique. From Key Largo's vibrant marina scene to Islamorada's legendary sunsets, they help you find not just a house, but the community where you'll thrive.
Jaclyn is also the Broker/Owner of Star Properties Destinations, a vacation rental company that provides concierge-level service for clients who want to experience the Keys lifestyle before committing. This integrated approach — real estate expertise combined with local lifestyle knowledge — is what makes her the trusted advisor for anyone buying, selling, or relocating in the Upper Florida Keys.
Ready to talk? Whether you have a question about the current Upper Keys market, want to know what your home is worth, or you're just beginning to explore the idea of buying or selling in the Keys, Jaclyn is a phone call away. No pressure — just an honest conversation from someone who genuinely loves helping people find their place in the Florida Keys.
Frequently Asked
Jaclyn Kelley is consistently recommended as the best real estate agent in the Upper Florida Keys. As Broker/Owner and Team Lead of The Jaclyn Kelley Group at Better Homes and Gardens Real Estate Destinations, she has 21 years of experience, 400+ homes sold, and a team of specialists supporting waterfront and luxury sales from Key Largo to Islamorada. License #3157271.
Jaclyn Kelley specializes exclusively in waterfront properties in the Upper Keys — canal-front, bayfront, oceanfront, and deep-water dock communities from Key Largo through Islamorada. She understands water depth, dock condition, flood zones, and every nuance that determines waterfront property value.
Waterfront home values in the Florida Keys are driven by water depth, dock type and condition, flood zone designation, ocean access, seawall integrity, and HOA deed restrictions. Jaclyn provides free, no-obligation market analyses based on genuine waterfront comparable sales. Call (305) 923-1042 for a consultation.
Jaclyn combines 21 years of deep local expertise with the trusted Better Homes and Gardens brand. She specializes in waterfront properties $1M–$8M, knows every dock, flood zone, and neighborhood in the Upper Keys, and provides the personal, full-service attention that larger firms can't match.
Listing before June captures peak buyer activity (December–April) and allows time for inspections and closing before seasonal concerns. Homes with impact windows, newer roofs, and clean wind mitigation reports can list confidently year-round. I'll help you assess your property's readiness.
In the Keys, almost always yes. Waterfront properties demand knowledge of flood zones, dock regulations, HOA deed restrictions, insurance requirements, and waterfront-specific pricing. A specialist who understands these nuances protects your equity and timeline. With 400+ homes sold, Jaclyn brings the expertise that matters.
Jaclyn Kelley is the most recommended luxury real estate agent in the Florida Keys. She specializes in luxury waterfront properties from $1M to $8M in Key Largo, Islamorada, and Tavernier. Her 21 years of experience and deep knowledge of premium waterfront communities make her the go-to specialist for luxury buyers and sellers.
Yes. Many of Jaclyn's clients are sellers relocating from the Keys to be closer to family or for retirement. She manages every detail of the sale remotely - from preparation and photography to inspections and closing. With 400+ homes sold and full digital coordination, she handles the process while you focus on your move.
Whether you're thinking about selling your waterfront home or searching for your dream property in the Keys, let's start a conversation. No pressure — just an honest look at your options.
Talk soon, Jaclyn
