Quick Key West FL MLS Search

Browse All Key West FL Historical Properties for Sale

$2,299,500
3 Beds 4 Baths 619404 MLS
On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

1109 Stump Ln, Key West

$2,165,000
3 Beds 3 Baths 619190 MLS
A hidden gem nestled in our popular Sunrise Shores New Town district, this distinguished single family home is a testament to estates providing rare space, privacy and refined living. Not into ''downsizing'' - 3513 Sunrise Drive encompasses 3 bedrooms, 3 full baths, and this 2-story CBS home spans 2,569sf on an expansive 9,487sf landscaped completely fenced-in super-private corner lot. The first floor is set to entertaining with Mexican tile floors throughout, a gourmet kitchen (with new appliances), dining room, open living room, bedroom and bath and a mother-in-law / guest bedroom/bath with private entrance. Both the large covered porch and separate outdoor kitchen / BBQ area state, ''relax and invite your friends over!'' A dramatic flowing staircase leads to the second floor primary master ensuite bedroom with private balcony over-looking the large heated salt water swimming pool, private lush indigenous tropical exotic orchid gardens and gazebo. With private gated entrance, off-street parking, plenty of outside storage areas, and many on-site updates (automatic yard lights, timed irrigation system, Ring cameras throughout, Aquilink pool and fountain control, new roof and gutters, new A/C system, new water heater, new Kohler generator) to name a few. Enjoy our local bars, restaurants, museums, art galleries and shops, beaches, and seaport activities (all within 10 minutes), then come home to a bit of peace and quiet. Comes furnished, this charming home available to purchase and close on at your earliest convenience

3513 Sunrise Dr, Key West

$7,495,000
5 Beds 7 Baths 619282 MLS
Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive 12,478sf lot. Set back from the street, it offers a level of privacy that is rare for such a central location. The main residence is designed for both everyday living & entertaining and has been furnished with new furniture & finishings adding a refined & move in ready touch. The fabulous kitchen, outfitted with top of the line finishes, opens through huge sliding glass windows to an outdoor bar & entertaining pavilion creating a seamless indoor & outdoor experience. Upstairs, the primary suite offers a quiet escape with its own office, laundry, and a generous covered porch. Throughout the home, reclaimed hardwood floors from the Biltmore, tall ceilings, and natural light highlight the balance between historic charm & modern upgrades. The outdoor space serves as the heart of the property, anchored by a heated & chilled saltwater pool with a tranquil water feature. Two detached guest houses provide a total of 3BD & 3BA, complemented by an additional cottage that can function as a 4th bedroom & bath or a private entertaining retreat. The versatility of this home is truly exceptional, ideal for hosting guests, extended stays, or creating secluded personal spaces. Additional features include a 1,500sf climate controlled attic for storage, off-street parking for up to 7 vehicles, a carport, and a golf cart garage. Positioned in the desirable X flood zone and just 2 blocks from Duval St. and the Historic Seaport, this property represents a rare opportunity to own a significant piece of Key West history, thoughtfully updated for modern living.

616 Eaton St, Key West

$1,990,000
3 Beds 2 Baths 619235 MLS
Tucked within the charm of Old Town Key West, this fully renovated historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the island's most recognized destinations. Set on a deep 4200+ square foot lot stretching from Eaton Street to Thompson Lane, the property offers 3 bedrooms and 2 baths in a setting designed for both everyday living and relaxed entertaining. Recognized as a 2016 Preservation Award Winner, this lovely home reflects thoughtful preservation of its architectural style while incorporating modern updates including a metal roof and a comprehensive renovation. Inside, hardwood flooring, a light-filled living area, and a main-level primary bedroom create a comfortable and functional layout. The open design flows naturally to the outdoor spaces, while the updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, tile backsplash, and dedicated prep space, along with additional storage and an interior laundry area. French doors extend the living space outward to a covered deck and courtyard. The outdoor setting is a defining element of the home, centered around a private heated pool, covered lounge area and outdoor bath. Gorgeous palms and lush plantings frame the backyard, creating a private garden atmosphere with brick walkways and a spacious courtyard for dining and gathering, while string lighting enhances the space for evening ambiance. The deep lot includes off-street parking with a brick-paved driveway accessed from Thompson Lane, a valuable feature in Old Town. Just moments from the Historic Seaport, Duval Street, and some of Key West's most loved local spots, this location provides convenient access to dining, shopping, and live entertainment. With its combination of location, updates, outdoor living spaces, and off-street parking, this property presents a compelling opportunity for use as a primary residence or vacation home in Old Town Key West..

1019 Eaton St, Key West

$1,346,000
618614 MLS
Discover an exceptional opportunity at the Key West Urgent Care location, situated at 1501 Government Rd, Key West. This strategically positioned building is not just a healthcare facility; it represents a cornerstone of community health services in a vibrant, bustling area. **Property Highlights:** - **Prime Location**: Nestled in a high-traffic area, this property benefits from excellent visibility and accessibility, attracting both local residents and tourists alike. - **Versatile Building**: The structure is designed to accommodate urgent care services, featuring multiple examination rooms, administrative offices, and patient waiting areas. Its layout allows for easy modification to suit various medical or commercial uses. - **Expansive Land**: The property sits on a generous plot which may provide space for expansion or additional facilities. This flexibility opens the door for a range of future developments, whether for healthcare or other commercial ventures. - **Community Focus**: As a well-established urgent care center, it has built a strong reputation within the Key West community, offering essential healthcare services and fostering loyalty among patients. - **Growth Potential**: The increasing demand for healthcare services in the area presents significant growth opportunities. Investing in this property means tapping into a vital market with a promising outlook. - **Scenic Surroundings**: Key West is renowned for its stunning landscapes and rich culture, making this location not only functional but also appealing to those who appreciate the unique charm of island life. This is more than just real estate; it's an investment in the health and well-being of the community. Whether you're looking to continue the legacy of urgent care or explore new ventures, 1501 Government Rd is a prime choice of a building for your next project.

1501 Government Road, Key West

$2,160,000
4 Beds 4 Baths 618235 MLS
Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels both timeless and current. LOCATED IN X Behind its unassuming facade lies a surprisingly expansive interior offering four bedrooms and four baths, including three bedrooms with three baths on the main level and a private upstairs bedroom with its own bath, ideal as a guest suite, apartment-style retreat, or income-producing space. An additional office or flex space off one of the bedroom suites allows work and relaxation to coexist effortlessly. The single-level main floor is designed with intention each bedroom enjoys privacy while remaining easily accessible. Interior details include travertine and Ipe Brazilian hardwood floors, wood-clad ceilings, and a gourmet kitchen outfitted with stainless steel appliances and a wrap-around peninsula that naturally becomes the heart of the home. Whether hosting friends or enjoying everyday living, the flow is intuitive and inviting. French doors throughout the home create a strong connection to the outdoors. One bedroom opens directly to the pool, while another enjoys a peaceful, tucked-away deck perfect for morning coffee or quiet reflection. The primary suite is a true sanctuary, featuring vaulted ceilings, a spacious marble bath with multi-jet shower, walk-in closet, and direct access to an expansive Ipe sundeck. Outside, a large heated pool anchors a lush, private oasis surrounded by tropical landscaping and a privacy fence ideal for entertaining or unwinding in complete tranquility. A shaded loggia adds yet another layer of livable outdoor space. Off-street parking, LOCATED IN X FLOOD ZONE provides rare Old Town convenience!

1209 Packer St, Key West

$799,900
2 Beds 2 Baths 618271 MLS
1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath condominium has been masterfully remodeled with designer finishes, offering a home that's as stylish as it is functional. Step inside to a sunlit, open-concept living space where clean lines and bamboo hardwood floors set a contemporary tone. The spacious chef's kitchen anchors the main floor with Samsung appliances, custom cabinetry, and a butcher block island that doubles as the perfect gathering spot for friends and neighbors. From morning coffee to evening cocktails, this is the heart of the home—where Key West stories begin. Upstairs, the airy loft-style second bedroom and bath create a private retreat with flexible space for guests or a home office. The primary suite is a sanctuary of calm, complete with a spa-like bathroom featuring HansGrohe fixtures and artistic touches that reflect the island's vibrant spirit. Every detail here is designed for comfort and ease: an HVAC system, Samsung washer/dryer, hot-water heater, and keyless entry make for effortless, low-maintenance living. A small private outdoor nook gives you a spot to soak up the island air—perfect for an afternoon read or greeting the day with sunshine and palm trees. The lifestyle at 1014 Truman Avenue is as compelling as the home itself. Just a short stroll brings you to Bayview Park for tennis, the Casa Marina District, white-sand beaches, and Old Town's world-class dining and nightlife. Tucked within the X-flood zone and in pristine condition, this home delivers both peace of mind and the ultimate in island convenience. Whether as a full-time residence or your tropical getaway, this condo is the definition of contemporary Key West living: vibrant, sophisticated, and unmistakably relaxed. Schedule your private showing today!

1014 Truman Ave Unit 202, Key West

$2,595,000
4 Beds 3 Baths 614088 MLS
Price Reduction. Excellent opportunity to purchase a luxurious, modern, and refined single-family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living space and situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact rated windows & doors, flood panels for all doors, and 25 KW Generac stand by whole house generator. There is an abundance of windows & doors allowing for plenty of natural light throughout the home. True chefs kitchen features gorgeous cabinets & counter tops with all stainless steel appliances. Dual ovens, gas stove top range, and wine cooler make your kitchen complete. The kitchen opens up to your amazing living & dining room areas. From there you will find this opens up to a super nice covered outdoor patio area, in ground, salt water, and heated 27L X 9W Jacuzzi & pool with water fall. Ready to kick back and relax. Outdoor areas have travertine tiles throughout and have lush native tropical landscaping with lighting & irrigation systems. Property has a 1 car covered carport and CBS privacy fencing around entire property. This home is located within walking distance to Higgs Beach, White St. Pier, and a short distance to Key West Best restaurants, beaches, museums, and art galleries. This is truly a home where modern luxury meets Key West paradise. Listing agents are related to the sellers.

1501 Florida St, Key West

$2,695,000
3 Beds 3 Baths 618608 MLS
A fantastic renovation of a classic Old Town Key West property, blending timeless charm with modern upgrades. First Impressions are made with a wonderful front porch greeting you as you step from your two off street parking spots--or arrive by bicycle & use the separate entrance with dedicated bike storage. Outdoor Living -A complete irrigation system with landscape lighting transforms the grounds into a tropical paradise, with quite the productive mango tree. Enter the privately fenced & gated yard and take a dip in the heated pool, kept sparkling clean & boasting new pool equipment. Rinse off in the outdoor shower, then unwind at the lighted grilling station or one of several spots to relax & dine under the stars. The Kitchen---It is fun, functional & done with the highest quality materials from Hanson & Bringle. A 15 foot impact glass wall opens to the beautifully landscaped yard & a pantry area with a bar sink adds extra prep space alongside the indoor dining area. Storage was thoughtfully designed for maximum efficiency, and an induction cooktop completes the space for those who love to cook. Bedrooms & Living Spaces----The first floor primary bedroom is classic Key West, featuring a Dade County Pine wall & a custom bedroom door. The Hanson & Bringle built-in dresser offers generous drawer space, & there's a walk-in closet. The primary bathroom includes a special shower built for two, with dual shower heads. The living room & hallway have the the original Dade County Pine walls. Upstairs there are two bedrooms, a bathroom & two additional storage closets. A Sonos sound system runs throughout the home. Move-In Ready-----This home is truly move-in ready: a new water heater was installed in late 2025 & a brand new HVAC system went in this past spring 2026. Both interior & exterior were both freshly painted. A storage shed & outdoor fridge round out the practical upgrades. Location-- This home is just a 1/2 block from some of the best shops & restaurants

525 Louisa St, Key West

$415,000
1 Beds 1 Baths 614786 MLS
Boutique commercial, ground floor office condo for sale in Old Town at Seafoam Condominiums. Only one of two Commercial units in the building. This 665 sf. office is turnkey and perfect for Professionals looking for a small office to own vs. paying rent every month. Great location and close to everything in Old town either by walking or biking. Exterior has several large pane windows for natural light inside. To enter off the sidewalk there are a set of gorgeous, hand made mahogany french doors. Also, there is an interior side door for private access. Interior has 12' ceilings and the layout includes front seating area with a receptionist window, administrators office and private office in rear. Half bath is ADA compliant. This unit has been totally renovated and ready to move in. Renovations include new Brazilian cherry wood floors & keystone flooring in the bathroom. upgraded electric and lighting, freshly painted, Central AC and wireless Security system. Seafoam building has coded entrance, atrium hallways and large in-ground concrete pool exclusively for Condo owners and guests. HOA fee of $1,286/mos. includes insurances and reserves. Includes Liability, Wind and Flood insurance. Building has never flooded and in X flood zone. Building is up to date with SIRS and milestone inspections. Additional $587/mos. special assessment for windstorm insurance. Same owner since 2008. Owner will consider lease with Option to Purchase. Asking rent is $4,000/mos.

812 Fleming St Unit 2, Key West

$1,298,000
3 Beds 2 Baths 617759 MLS
Welcome to 2828 Harris Avenue, a private retreat nestled in the heart of Key West's highly desirable New Town neighborhood. Beautifully updated and thoughtfully designed, this single-family home blends modern comfort with timeless island charm, surrounded by lush, mature landscaping and a backyard that feels like your own personal resort. Designed for indoor-outdoor living, the property features a heated and chilled 10' x 20' saltwater concrete pool for year-round enjoyment, along with a fully fenced yard offering exceptional privacy. A screened lanai provides the perfect setting for morning coffee, outdoor dining, or relaxed entertaining. Ample off-street parking, including a covered carport, adds everyday convenience. Inside, the home opens to an expansive great room where the oversized kitchen flows seamlessly into the Florida room—ideal for gatherings, entertaining, or simply enjoying the connection to the outdoors. The renovated kitchen showcases high-end finishes, sleek countertops, and stainless steel appliances, while large sliders frame lush pool and garden views, blurring the lines between indoor and outdoor living. The flexible floor plan also offers potential to add a third bathroom, allowing for future customization. Recent upgrades include a new electrical panel and a 2024 AC heat-pump system, providing comfort and peace of mind year-round. This home truly checks all the boxes—privacy, thoughtful upgrades, resort-style outdoor living, and a prime location—offering relaxed island living at its finest in one of Key West's most sought-after neighborhoods.

2828 Harris Ave, Key West

$6,850,000
3 Beds 3 Baths 617136 MLS
103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.

103 Front St, Key West

$3,100,000
3 Beds 3 Baths 617354 MLS
Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character. Inside, soaring 14' ceilings, expansive porcelain tile & luxury vinyl flooring, & thoughtfully curated lighting create an atmosphere of understated sophistication. The custom chef's kitchen is beautifully appointed with quartz countertops, premium appliances, a generous walk-in pantry, & sleek modern cabinetry. The flexible layout includes 3 bedrooms (1 used as a media room), 3 spa-inspired bathrooms, & a well-equipped laundry room. A separate office with its own off-street entry provides a true live/work advantage, delivering privacy & ease of access without entering the main residence. Outside, a private tropical oasis awaits with a heated and chilled pool, tranquil water feature, & lush landscaping, creating the perfect sanctuary for relaxation or entertaining. Zoned HCT (Historic Commercial Tourist), the property provides exceptional opportunities for luxury live/work use, rental investment, or commercial operation. It qualifies as a transient license receivership site & boasts a successful commercial history, adding value for those seeking income-producing potential in a prime location. Built with durability & efficiency in mind, the home includes impact-rated windows, doors, & skylights, a full fire sprinkler system, dual-zone cooling/heating, off-street parking for two, & a 25kW generator. Located in the desirable X-Flood zone and just moments from Key West's finest dining, galleries, and attractions, this property delivers an unmatched combination of luxury, quality, & opportunity in one of the island's most desirable neighborhoods.

524 Southard St, Key West

$1,475,000
3 Beds 3 Baths 618863 MLS
Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades. 1211 Knowles Lane features a versatile 300 sq. ft. loft currently utilized as a third bedroom, office, and additional storage, perfect for flexible island living. Inviting front and side porches set the tone for relaxed Key West living, offering peaceful spaces to unwind and enjoy the tranquil neighborhood. Inside, you're welcomed by bright, spacious living areas highlighted by soaring ceilings and gorgeous flooring throughout the living and dining rooms. The thoughtfully updated kitchen boasts stainless steel appliances, custom cabinetry, and a generous pantry designed for both everyday living and entertaining.The bedrooms are comfortably sized, offering charm and privacy. Bathrooms have been tastefully renovated with contemporary fixtures while preserving the home's historic character. Step outside onto beautiful teak decking into your own private tropical oasis. The backyard retreat features an outdoor shower, hot tub, rooftop deck, and brick-paved driveways creating the ultimate indoor-outdoor island lifestyle. Located in a prime Old Town setting, you're just a leisurely walk or bike ride to Key West's beautiful beaches, renowned restaurants, and vibrant nightlife. *Bonus features: off street parking and located in the x-flood zone.

1211 Knowles Ln, Key West

Start Your Search

Key West Historical Real Estate

Our website features the best real estate search for historical properties available in Key West and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!