Key West Homes with Fruit Trees Exterior features

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.

1028 Flagler Ave, Key West

$2,895,000

3 Beds ⋅ 4 Baths ⋅ 621305 MLS

Some homes in Key West give you a view. This one gives you an entire private world. Tucked behind its own gates on a lush 12,000-square-foot lot, 3615 Eagle Avenue is a custom-built retreat where a botanical garden isn't a backyard feature -- it's the whole point. Mature native palms, flowering tropical plants, and a resident population of birds and butterflies surround the home on every side, and nearly every room has been designed to keep that view in constant reach, with walls of impact-rated glass doors blurring the line between inside and out. Inside, cathedral ceilings and wide-plank tile floors set a calm, airy tone across sweeping one-level living space. The kitchen is built for people who actually cook and entertain -- Sub-Zero refrigeration, a gas range, dual dishwashers, a wine cooler, and an ice machine, all within reach of the garden views. The primary suite sits privately at the front of the home, paired with a fully renovated spa-style bath. A flexible office/den off the main living space easily converts to a fourth bedroom for guests, in-laws, or a work-from-home setup. Step outside to a covered pavilion overlooking a heated 33-foot pool and spa, connected by a sand pathway that winds through the garden -- an entertaining space that feels more resort than residential. A generator, oversized double-car garage with built-in storage, and covered parking for three additional vehicles round out the practical side of island living. Property includes 2 Rogos on Double Lot, allowing for a second structure to be built. This is a rare offering: real privacy, real green space, and real craftsmanship, minutes from everything that makes Key West Key West.

3615 Eagle Ave, Key West

$999,000

3 Beds ⋅ 2 Baths ⋅ 620987 MLS

Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

506 Grinnell St, Key West

$1,800,000

3 Beds ⋅ 1 Baths ⋅ 620880 MLS

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

511 Tabby Ln, Key West

$1,575,000

3 Beds ⋅ 2 Baths ⋅ 620577 MLS

A private pool, two off-street parking spaces, and single-level living--all in the heart of Old Town Key West. This beautifully updated 3-bedroom, 2-bath home brings together Key West charm and everyday comfort, with hardwood floors, tall ceilings, French doors, and a bright, open layout that makes gathering easy. The secluded backyard is an extension of the living space, surrounded by lush tropical landscaping with room to lounge, dine outdoors, and unwind. A saltwater pool with both a heater and chiller keeps swimming comfortable throughout the seasons, while an outdoor shower adds a classic island touch. Offered fully furnished and turnkey, the home is ready for your next chapter, whether that means settling into island life, enjoying a seasonal escape, or continuing its established use as a monthly vacation rental. Updates include the HVAC system, saltwater pool equipment, and furnishings. Neighborhood cafés, restaurants, and shopping are close at hand, with Duval Street, the Historic Seaport, and Higgs Beach within easy reach. Enjoy a morning out exploring Old Town, an afternoon by your own pool, and dinner at a favorite local spot. Part of a two-unit condominium association with no shared common elements, this property offers the privacy and feel of a single-family home with a setting that makes Key West living easy

1005 Watson St Unit 1, Key West

$799,000

2 Beds ⋅ 2 Baths ⋅ 620402 MLS

Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the thoughtful floor plan provides comfortable areas for both everyday living and entertaining. The well-appointed kitchen offers ample cabinetry, generous counter space and bar seating that creates a natural gathering place for family and guests. A dedicated laundry area adds every day convenience, while the home's open and functional layout enhances its comfortable coastal appeal. An inviting Florida Room extends the living area and serves as the perfect connection to the private backyard retreat. Step outside to discover your own massive fenced-in backyard designed for relaxation, featuring lush landscaping, a hot tub and plenty of entertaining space. Centrally located in New Town, you'll enjoy easy access to beaches, shopping, restaurants, schools, and all the attractions that make island living so desirable. Whether you're looking for a full-time residence, seasonal escape, or island investment, this Key West home offers comfort, character and an exceptional location.

3715 Flagler Ave, Key West

$895,000

4 Beds ⋅ 2 Baths ⋅ 620315 MLS

This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

3746 Paula Ave, Key West

$1,250,000

2 Beds ⋅ 2 Baths ⋅ 620075 MLS

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West

$1,250,000

2 Beds ⋅ 2 Baths ⋅ 619758 MLS

With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West

$899,000

3 Beds ⋅ 2 Baths ⋅ 619102 MLS

Welcome to 3011 Riviera Drive, nestled in the sought-after Riviera Shores neighborhood of Key West! This delightful 3-bedroom, 2-bathroom home boasts versatility and space, featuring a spacious bonus room--ideal for guests or an in-law suite. The property sits on a generous 6,000 sq ft lot with a large fenced backyard, perfect for adding a pool. Relish in the tranquility of mature banana and mango trees, complemented by tall Christmas palms enhancing the front yard's allure. Enjoy off-street parking, a concrete driveway, and the nearby public boat ramp for aquatic adventures. The home includes nice comforts such as a durable metal roof, sound proof windows and doors, storm shutters, and a privacy fence. Relax on the covered back patio, and appreciate the proximity to Key West's Old Town, beaches, schools, shopping, and businesses--truly an inviting retreat!

3011 Riviera Dr, Key West

$1,285,000

3 Beds ⋅ 2 Baths ⋅ 618990 MLS

Updated home with a bright floor plan featuring quartz counter tops, stainless steel appliances, luxury vinyl flooring, and wraparound windows with remote control blinds. Spacious primary suite with walk-in closet, ductless zoned A/C, and French doors to wraparound screened patio that's 612 sq. ft. Heated 13x7 swim spa with outdoor seating. Concrete, elevated for lower insurance, insulated windows, central A/C and heat, backup generator, security system, central vacuum, retractable awning, extra storage, and a one car garage. Move in ready/

1613 Trinidad Dr, Key West

$2,549,000

3 Beds ⋅ 4 Baths ⋅ 618952 MLS

**Seller Financing Considered** 2924 Riviera Dr is a Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room & kitchen gives you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was stripped to the concrete block walls and rebuilt (with permits) with all new materials. New impact windows & doors, roof (with straps), ductless AC ( 2 compressors, 6 heads), electrical - 200 Amp service, water supply lines, manifold style on demand water heater, Turkish Marble floors throughout (no ceramic tile), drywall on walls & ceiling, kitchen cabinets & counter tops, appliances, bathroom fixtures, and much, much more. Even has interior laundry & utility room. Expansive primary bedroom with walk thru closet and spacious ensuite bath, plus pool & canal views. Enjoy the convenience of living in Key West and having your boat in your back yard. Concrete seawall (59Ft) with newer 12,000 Ibs boat lift and inground pool (with newer pump / filter) compliment the canal-front back yard. Lot is 7,670 sq ft. Located close to schools, professional offices, shopping, airport & beaches. Just a short ride to Duval St and the all the Old Town KW attractions. House is turn-key. Simply unpack your swimsuit and start enjoying the Keys lifestyle. **Seller is open to financing the Buyer**

2924 Riviera Dr, Key West

Key West Homes with Fruit Trees Exterior features

Newest Key West Homes with Fruit Trees Exterior features

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