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 Cutler Bay, Florida, and across Miami-Dade County, Florida. Single family homes and townhomes south of Palmetto Bay, with Lakes by the Bay and access to Biscayne Bay.
Today, the typical Cutler Bay home is worth about $563,000 (+0.3% in a year); 45,833 people live here; 260 homes are for sale right now with a median list price of $599,000.
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 Cutler Bay listing with map, price and waterfront filters, then tour with Ryan and Megan.
Cutler Bay right now: 260 homes for sale, median list price $599,000, $324 per square foot, median 64 days on the market. 11 came on the market in the last 7 days; 62 are under contract; 29 are waterfront.
Mix: 167 single family homes, 52 condos, 36 townhouses, 4 land listings. From the MLS feed, updated October 28, 2026 at 2:21 PM Eastern.
8470 SW 184th St, Cutler Bay, FL
Single family home, 4 beds, 5 baths
Listing courtesy of Stefano Realty, LLC.
8000 SW 184th St, Cutler Bay, FL
Single family home, 3 beds, 1.5 baths, 1,709 square feet
Listing courtesy of Keller Williams Capital Realty
19209 SW 80th Ct, Cutler Bay, FL
Single family home, 5 beds, 4.5 baths, 4,894 square feet
Listing courtesy of Urban Key Realty Corp
19310 SW 88th Ct, Cutler Bay, FL
Single family home, 4 beds, 3 baths, 3,151 square feet
Listing courtesy of Beycome of Florida LLC
8095 SW 187th St, Cutler Bay, FL
Single family home, 4 beds, 4 baths, 3,651 square feet
Listing courtesy of Lapeyre Realty Inc
18490 SW 83rd Pl, Cutler Bay, FL
Single family home, 6 beds, 4 baths, 3,402 square feet
Listing courtesy of EXP Realty, LLC
18555 SW 83rd Pl, Cutler Bay, FL
Single family home, 5 beds, 3 baths, 2,347 square feet
Listing courtesy of Xcellence
19363 SW 79th Ave, Cutler Bay, FL
Single family home, 5 beds, 4 baths, 4,717 square feet
Listing courtesy of Genstone Realty
7876 SW 194th St, Cutler Bay, FL
Single family home, 5 beds, 4 baths, 4,717 square feet
Listing courtesy of Coldwell Banker Realty
19529 SW 80th Ct, Cutler Bay, FL
Single family home, 6 beds, 5 baths, 4,717 square feet
Listing courtesy of Elite Sales Group
7956 SW 195th St, Cutler Bay, FL
Single family home, 5 beds, 4.5 baths, 3,399 square feet
Listing courtesy of Charles Rutenberg Realty FTL
19508 SW 79th Ct, Cutler Bay, FL
Single family home, 5 beds, 4 baths, 4,717 square feet
Listing courtesy of Elite Sales Group
10340 SW 208th Ln, Cutler Bay, FL
Single family home, 3 beds
Listing courtesy of EXP Realty, LLC
11060 SW 196th St # 609, Cutler Bay, FL
Condo, 2 beds
Listing courtesy of Miami Properties Int'l Corp
8440 SW 202nd St, Cutler Bay, FL
Single family home, 4 beds
Listing courtesy of Luxury Level Realty Group, LLC.
11050 SW 196th St # 408, Cutler Bay, FL
Condo, 2 beds
Listing courtesy of Miami Properties Int'l Corp
20759 SW 80th Pl, Cutler Bay, FL
Townhouse, 3 beds
Listing courtesy of Cityside Realty Group
18520 SW 88th Rd, Cutler Bay, FL
Single family home, 3 beds
Listing courtesy of Real Estate Sales Force
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 Cutler Bay sales, not an online guess.
260 homes were listed for sale in Cutler Bay on October 28, 2026, with a median list price of $599,000. Another 62 were under contract.
Homes for sale in Cutler Bay have been on the market a median of 64 days, and 11 new listings came on in the last week. The median asking price is $324 per square foot.
The best agent for you knows Cutler Bay 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 Cutler Bay 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 Cutler Bay right now have a median of 64 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 Cutler Bay home from closed sales, not a guess.
Yes. They list and sell homes, represent buyers, and help investors in Cutler Bay and nearby Miami, Miami Beach, Coral Gables, Pinecrest, Key Biscayne, Aventura. 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
