Broker owners of Winslow Homes. 17+ years together, more than 3,000 homes sold, and the mortgage handled by the same team.
Ryan and Megan Winslow are the broker owners of Winslow Homes and work with buyers and sellers in Key Biscayne, Florida, and across Miami-Dade County, Florida. An island village across the Rickenbacker Causeway, with oceanfront condos, Crandon Park and Bill Baggs Cape Florida State Park.
Today, the typical Key Biscayne home is worth about $1,708,000 (+6.5% in a year); 15,111 people live here; 141 homes are for sale right now with a median list price of $2,400,000.
You get both of them on your sale or purchase: pricing from closed sales, professional photos and video, negotiation, and the loan through their work as Mortgage Bankers with The Federal Savings Bank.
Search every Key Biscayne listing with map, price and waterfront filters, then tour with Ryan and Megan.
Key Biscayne right now: 141 homes for sale, median list price $2,400,000, $1,158 per square foot, median 113 days on the market. 4 came on the market in the last 7 days; 30 are under contract; 77 are waterfront.
Mix: 97 condos, 36 single family homes, 8 townhouses. From the MLS feed, updated October 28, 2026 at 2:22 PM Eastern.
485 W Matheson Dr, Key Biscayne, FL
Single family home, 5 beds, 8 baths, 11,528 square feet
Listing courtesy of Coldwell Banker Realty
241 Cape Florida Dr, Key Biscayne, FL
Single family home, 8 beds, 8.5 baths, 9,159 square feet
Listing courtesy of Cervera Real Estate Inc.
100 Cape Florida Dr, Key Biscayne, FL
Single family home, 4 beds, 7 baths, 8,240 square feet
Listing courtesy of One Sotheby's International Realty
550 Harbor Dr, Key Biscayne, FL
Single family home, 7 beds, 7.5 baths, 6,497 square feet
Listing courtesy of Three Bridges Realty, LLC
120 Knollwood Dr, Key Biscayne, FL
Single family home, 6 beds, 6.5 baths, 6,208 square feet
Listing courtesy of Cervera Real Estate Inc.
445 Grand Bay Drive # 1A, Key Biscayne, FL
Condo, 5 beds, 5.5 baths, 8,435 square feet
Listing courtesy of One Sotheby's International Realty
799 Crandon Blvd # 8, Key Biscayne, FL
Condo, 5 beds, 5.5 baths, 4,566 square feet
Listing courtesy of Coldwell Banker Realty
520 S Mashta Dr, Key Biscayne, FL
Single family home, 5 beds, 4 baths, 3,085 square feet
Listing courtesy of Coldwell Banker Realty
631 N Mashta Drive, Key Biscayne, FL
Single family home, 4 beds, 4.5 baths, 2,255 square feet
Listing courtesy of Coldwell Banker
350 Ocean Dr, Key Biscayne, FL
Condo, 5 beds, 5.5 baths, 4,764 square feet
Listing courtesy of BHHS EWM Realty
640 S Mashta Dr, Key Biscayne, FL
Single family home, 4 beds, 4 baths, 3,620 square feet
Listing courtesy of DLS International Realty
131 Cape Florida Dr, Key Biscayne, FL
Single family home, 6 beds, 6.5 baths, 7,103 square feet
Listing courtesy of Vantage Real Estate LLC
201 Galen Dr # 110, Key Biscayne, FL
Condo, 2 beds
Listing courtesy of NEXXOS REALTY LLC
201 E Enid Dr # 31, Key Biscayne, FL
Condo, 2 beds
Listing courtesy of Florida Capital Realty
177 Ocean Lane Dr # 501, Key Biscayne, FL
Condo, 3 beds
Listing courtesy of BHHS EWM Realty
141 Crandon Blvd # 329, Key Biscayne, FL
Condo, 2 beds
Listing courtesy of Cervera Real Estate Inc.
77 Crandon Blvd # 3C, Key Biscayne, FL
Condo, 2 beds
Listing courtesy of E Realty International, Inc.
360 Harbor Ln, Key Biscayne, FL
Single family home, 6 beds
Listing courtesy of Coldwell Banker Realty
Miami MLS. Listings courtesy of MIAMI REALTORS® MLS (SEFMLS). The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of MIAMI REALTORS® (Southeast Florida Multiple Listing Service, SEFMLS). Real estate listings held by brokerage firms other than Winslow Homes LLC are marked with the name of the listing brokerage. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS, and all information should be independently verified. Based on information from the Southeast Florida Multiple Listing Service (SEFMLS) as of October 28, 2026 at 2:20 PM Eastern.
All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright ©2026 BeachesMLS, Inc.
Properties displayed may be listed or sold by various participants in the MLS.
Zillow Home Value Index and Redfin data by ZIP code.
We interviewed several top agents in the New Smyrna Beach area, and Winslow Homes distinguished themselves immediately with their strategic insight and professionalism. Living out of state, we relied heavily on Ryan and Megan to manage the process, and they exceeded expectations at every stage. They oversaw all property preparation, including flooring, repairs, painting, and cleaning, and executed a highly effective marketing strategy. During the inspection phase, Ryan efficiently coordinated all necessary repairs within a very tight timeframe, utilizing a trusted network of professionals. He also maintained close oversight of the property, ensuring it was well cared for throughout the process. His attention to detail, responsiveness, and commitment to delivering results made a difficult situation significantly easier for our family. We highly recommend Winslow Homes for anyone seeking a high-level, seamless real estate experience.
J DefinnisThey Fight for Their Clients whether Buying Or Selling!!!!!! Winslow Homes is a One stop Realtor. Buying, selling or Mortgage lender. They are very knowledgable & helpfull with all your real estate needs. Together They are the Best in The Business & Made our real estate experience A Pleasure.. Thank You
K Helcok, Vilken PropertiesThe process was so easy, and they are just amazing. I would definitely recommend them and use them again.
EmilyShe was knowledgeable, professional, and always available to answer my questions whenever I needed to reach her. Her attention to detail, honest advice, and excellent communication made the entire refinancing process a success. She kept faith, and never gave up on me during the whole process to help keep the home for my children. She went above and beyond to ensure we got the best possible outcome. I highly recommend Megan to anyone looking for a dedicated, trustworthy, and hardworking real estate professional. Thank you for making this such a positive experience! Words cannot express how grateful I am. We are very blessed.
C BenoitRyan and Megan send a value from closed Key Biscayne sales, not an online guess.
141 homes were listed for sale in Key Biscayne on October 28, 2026, with a median list price of $2,400,000. Another 30 were under contract.
Homes for sale in Key Biscayne have been on the market a median of 113 days, and 4 new listings came on in the last week. The median asking price is $1,158 per square foot.
The best agent for you knows Key Biscayne sales, explains the numbers in plain words and puts every fee in writing. Ryan and Megan Winslow of Winslow Homes have 17+ years together and more than 3,000 homes sold, and they handle the sale and the mortgage as one team. Call or text 386-690-5858 to interview them.
Commissions in Key Biscayne are set by agreement, not by law. Since the 2024 NAR settlement, buyers sign a written agreement that states what their agent is paid, and sellers decide what, if anything, they offer a buyer's agent. Ryan and Megan put both in writing before you start.
Homes listed in Key Biscayne right now have a median of 113 days on the market. Pricing from recent sales nearby, strong photos and a clear plan for the first two weeks on the market matter most. Ryan and Megan price every Key Biscayne home from closed sales, not a guess.
Yes. They list and sell homes, represent buyers, and help investors in Key Biscayne and nearby Miami, Miami Beach, Coral Gables, Pinecrest, Aventura, Bal Harbour. They also handle relocation for buyers moving from another state.
Yes. Ryan and Megan are Mortgage Bankers with The Federal Savings Bank, so your pre-approval, loan and purchase run through one team. Apply at winslowloan.com or call 386-690-5858.
Ryan and Megan Winslow list, sell and finance homes in these towns.
New Smyrna Beach · Daytona Beach · Ormond Beach · Port Orange · Ponce Inlet · Edgewater · DeLand
Orlando · Winter Park · Windermere · Winter Garden · Celebration · Reunion
Miami · Miami Beach · Coral Gables · Pinecrest · Key Biscayne · Aventura · Bal Harbour · Sunny Isles Beach · Surfside · Doral · Palmetto Bay · South Miami · Miami Shores · Cutler Bay · Homestead · Brickell · Coconut Grove
Fort Lauderdale · Las Olas · Weston · Davie · Plantation · Coral Springs · Parkland · Pembroke Pines · Miramar · Hollywood · Hallandale Beach · Pompano Beach · Lighthouse Point · Lauderdale-By-The-Sea · Wilton Manors · Sunrise · Cooper City · Southwest Ranches · Deerfield Beach
