# 1028 Flagler Avenue, Key West, FL 33040 > **TL;DR:** 4bd/4ba single family, $4,650,000 ($1296/sqft), built 1958, 3,589 sqft. > Pool, View, A/C. Est. $24,869/mo. Listed 13 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $4,650,000 | | Price/sqft | $1296 | | Bedrooms | 4 | | Bathrooms | 3 full, 2 half | | Square Feet | 3,589 | | Year Built | 1958 | | Lot Size | 11,587 sqft (0.27 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 13 | ## Why This Home Stands Out - **Pool** - Porch - **Views** - Water ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $23,513 | | Estimated Insurance | $1,356 | | **Total** | **$24,869** | ## Key Amenities - Pool - View - A/C ## Property Highlights - Built in 1958 - 0.27 acre lot - Private pool ## Description ### Agent Description A CASA MARINA ORIGINAL. Some houses capture a moment in time. Others seem to have understood, from the beginning, what makes Key West such an extraordinary place to live. Built in 1958, 1028 Flagler Avenue is a striking example of tropical mid-century modern architecture, set within a private three-building compound on 11,586 square feet in Casa Marina, one of the island's most distinguished neighborhoods. Behind substantial privacy walls lies a world of its own. Winding pathways lead through lush native and tropical gardens that seem borrowed from a movie, connecting the main residence, separate two-bedroom guest quarters, and detached garage/workshop. Mature palms, flowering gardens, shaded terraces, and a custom swimming pool create an extraordinary sense of seclusion. Inside, clean architectural lines, high ceilings, and generous proportions celebrate indoor-outdoor living. Expansive living and dining areas, a library, and a separate study offer room to gather or retreat. Impact-rated windows and doors provide modern peace of mind without sacrificing the home's character. The guest quarters include their own living area and kitchen, ideal for family and visitors. Together, the three buildings offer 3,589 square feet of combined enclosed space: 3,173 square feet of living area plus a 416-square-foot garage/workshop. Covered outdoor dining, an outdoor kitchen, and abundant off-street parking make this compound as practical as it is beautiful. Just two blocks from Higgs Beach and the Atlantic Ocean, with White Street Pier, waterfront parks, tennis, pickleball, and some of Key West's best-loved restaurants close at hand. Old Town is minutes away, yet the privacy and tranquility of Casa Marina remain entirely your own. ## Location - **Address:** 1028 Flagler Avenue, Key West, FL 33040 - **County:** Monroe - **Neighborhood:** Martello Towers (1.0) - **Coordinates:** 24.549546, -81.788204 - **Google Maps:** https://www.google.com/maps?q=24.549546,-81.788204 ## Virtual Tour & Media - **Video Tour:** https://my.matterport.com/show/?m=dLvow5iZFt8 ## Listing Agent - **Name:** Team Kaufelt - **Brokerage:** Truman & Co. Real Estate Services - **Broker Phone:** (305) 292-2244 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1028-Flagler-Ave_Key-West_FL_33040_M63448-89750?f=listhub&s=KWARFL&m=621710&c=propsimple) ## Photos ![1028 Flagler Avenue - Photo 1](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f4204960085r.jpg) ![1028 Flagler Avenue - Photo 2](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f62553424r.jpg) ![1028 Flagler Avenue - Photo 3](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f4017516426r.jpg) ![1028 Flagler Avenue - Photo 4](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3734282326r.jpg) ![1028 Flagler Avenue - Photo 5](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f4175014809r.jpg) ![1028 Flagler Avenue - Photo 6](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f1903719046r.jpg) ![1028 Flagler Avenue - Photo 7](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f4070670344r.jpg) ![1028 Flagler Avenue - Photo 8](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f2906421417r.jpg) ![1028 Flagler Avenue - Photo 9](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f1811131501r.jpg) ![1028 Flagler Avenue - Photo 10](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f404257801r.jpg) ![1028 Flagler Avenue - Photo 11](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f48687030r.jpg) ![1028 Flagler Avenue - Photo 12](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3174783151r.jpg) ![1028 Flagler Avenue - Photo 13](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f2714421001r.jpg) ![1028 Flagler Avenue - Photo 14](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f238367425r.jpg) ![1028 Flagler Avenue - Photo 15](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3396051263r.jpg) ![1028 Flagler Avenue - Photo 16](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f2937414273r.jpg) ![1028 Flagler Avenue - Photo 17](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f888021018r.jpg) ![1028 Flagler Avenue - Photo 18](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f26590865r.jpg) ![1028 Flagler Avenue - Photo 19](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3202306068r.jpg) ![1028 Flagler Avenue - Photo 20](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f1416650915r.jpg) ![1028 Flagler Avenue - Photo 21](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f205687813r.jpg) ![1028 Flagler Avenue - Photo 22](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f2429446793r.jpg) ![1028 Flagler Avenue - Photo 23](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f4112260946r.jpg) ![1028 Flagler Avenue - Photo 24](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3204609871r.jpg) ![1028 Flagler Avenue - Photo 25](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3486887497r.jpg) ![1028 Flagler Avenue - Photo 26](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f91047828r.jpg) ![1028 Flagler Avenue - Photo 27](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f1181700242r.jpg) ![1028 Flagler Avenue - Photo 28](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f1495113613r.jpg) ![1028 Flagler Avenue - Photo 29](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f2195596442r.jpg) ![1028 Flagler Avenue - Photo 30](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f1487605320r.jpg) ![1028 Flagler Avenue - Photo 31](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3352779975r.jpg) ![1028 Flagler Avenue - Photo 32](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f775700833r.jpg) ![1028 Flagler Avenue - Photo 33](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f249161996r.jpg) ![1028 Flagler Avenue - Photo 34](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f3654233428r.jpg) ![1028 Flagler Avenue - Photo 35](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f696215840r.jpg) ![1028 Flagler Avenue - Photo 36](http://lh.rdcpix.com/76dbbe1dadff8c99f0a81e4d998c922el-f61005384r.jpg) --- **MLS#:** 621710 | **Updated:** 2026-10-25 **Source:** listhub *Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/1028-flagler-avenue-key-west-fl-33040-47d42fa8631e4aaca09fa5a391a6ae12) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/1028-flagler-avenue-key-west-fl-33040-47d42fa8631e4aaca09fa5a391a6ae12#listing", "url": "https://www.propertysimple.ai/listing/1028-flagler-avenue-key-west-fl-33040-47d42fa8631e4aaca09fa5a391a6ae12", "name": "1028 Flagler Avenue, Key West, FL 33040", "description": "A CASA MARINA ORIGINAL. Some houses capture a moment in time. Others seem to have understood, from the beginning, what makes Key West such an extraordinary place to live. 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