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426 Calle Limon, Marathon
$1,599,000
5 Beds ⋅ 5 Baths ⋅ 618246 MLS
High-performing vacation rental located in the highly sought-after Sombrero Beach neighborhood, just a short walk to the beach. This fully furnished, turnkey property offers immediate income potential while also delivering an exceptional Keys lifestyle — truly a home that checks every box. Featuring 5 bedrooms and 5 bathrooms, the residence is thoughtfully designed for both guests and owners, including a legal bedroom and bath on the first floor. All living areas are above flood, offering peace of mind along with functionality. The home has been extremely well maintained and continues to perform strongly as a vacation rental. The main living level showcases a bright open-concept floor plan with high ceilings, modern finishes, and abundant natural light. The spacious kitchen includes sleek cabinetry, stone countertops, stainless steel appliances, and a large breakfast bar, seamlessly connecting to the dining and living areas. Sliding doors open to a balcony ideal for outdoor dining and enjoying island breezes. The primary suite serves as a private retreat with generous proportions, a walk-in closet, and a spa-inspired bathroom featuring a soaking tub and separate glass-enclosed shower. Each additional bedroom includes its own private bath, enhancing comfort and privacy for guests. A ground-level bedroom with direct access to the pool area adds flexibility for multigenerational living or guest convenience. Outdoor living is a true highlight, featuring a resort-style pool, covered entertaining areas, and a fully equipped outdoor kitchen with BBQ, perfect for hosting and relaxation. Additional features include a metal roof, ample parking, and space for two 20' boats on trailers. While boating is a major draw, this location also appeals to those who enjoy kayaking from Sombrero, beach days, and nearby parks. Whether as an investment, second home, or primary residence, this property checks all the boxes in one of Marathon's most desirable neighborhoods

426 Calle Limon, Marathon

19617 Date Palm Dr, Sugarloaf
$85,000
618502 MLS
PRICED TO SELL. Now only $85k and the least expensive southernmost lot for sale in The Florida Keys! Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 Tier III platted lot (infill lot located in a developed subdivision with adequate infrastructure). With its prime location and desirable features, this property is a rare find in today's market. Convenient to the community boat ramp and near the Sugarloaf School for elementary through middle school grades, and the associated recreation venues. Building plans are not available, but at this low price, you may create your perfect home. Before making an offer, buyers are encouraged to verify their intent for the purchase with the Monroe County Building Dept., referencing Parcel ID: 00171770-000100. Don't miss this chance to invest in a lifestyle of comfort and adventure.

19617 Date Palm Dr, Sugarloaf

3424 N Roosevelt Blvd, Key West
$5,200,000
3 Baths ⋅ 617330 MLS
Prime Commercial Property in Iconic Key West - High Visibility & Versatility! This property offers a rare opportunity to own a substantial commercial footprint in one of Florida's most iconic destinations. Whether you're expanding a brand, launching a new concept, or investing in Key West's vibrant market, 3424 N Roosevelt Blvd is a strategic asset with flexible potential. Location Highlights include: • Strategic Location - Located on Key West's main commercial corridor • Proximity - 7 minutes (2.5 miles) to Key West International Airport • Exceptional Visibility - High traffic exposure from both locals and tourists • Surrounded by Amenities -Including hotels, restaurants, banks, shops, fitness centers, and grocery stores. Property Details • Building Square Footage: 3,420 sq ft • Building w/ Tiki: 7,491 sq ft • Lot Square Footage: 36,002 sq ft • Frontage: 155 feet Current Use • Vehicle - Rentals Currently operates as a successful vehicle rental business. • Service Department - Features a care center with six service bays. Business Opportunity sold separately, inquire with agent.

3424 N Roosevelt Blvd, Key West

31243 E Ave, Big Pine
$615,000
3 Beds ⋅ 2 Baths ⋅ 615736 MLS
**Price Improvement** Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebuyers seeking the quintessential Florida Keys lifestyle. Step inside to discover a comfortable and inviting living space, perfect for creating lasting memories. Outside, a small, fenced area provides a safe and convenient space for your furry friends to play. Enjoy the convenience of being just a short stroll from Big Pine Community Park - perfect for recreation and relaxation. For the outdoor enthusiast, boat ramps are easily accessible, offering endless opportunities to explore the crystal-clear waters of the Keys. Indulge in the vibrant local scene with a variety of restaurants and retail stores just minutes away. Beyond the immediate conveniences, this home boasts incredible access to the natural wonders that Big Pine Key is renowned for. Explore the unique flora and fauna, enjoy world-class fishing, or simply soak in the breathtaking beauty of the surrounding nature. An added bonus: this property currently has a VA loan, which may be assumable, offering a potentially significant financial advantage for qualified buyers. Don't miss your chance to own a piece of the Florida Keys dream! Very affordable insurances and flood transfers! Roof new in 2018.

31243 E Ave, Big Pine

74560 Overseas Hwy, Islamorada
$3,100,000
3 Beds ⋅ 3 Baths ⋅ 618699 MLS
74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

74560 Overseas Hwy, Islamorada

100636 Overseas Hwy, Key Largo
$1,790,000
3 Beds ⋅ 3 Baths ⋅ 617751 MLS
Live your best life in the heart of Key Largo! This unique mixed-use property offers a beautifully renovated 3BD/3BA residence upstairs with your own rooftop hangout, sunny patio, and private yard space — a true tropical retreat right above the action. Downstairs sits a versatile commercial space with unbeatable visibility on US-1, perfect for a live-work setup, creative studio, boutique, or simply added flexibility. The solid concrete building stands approx. 15 ft above sea level and features impact windows with shutters, giving you peace of mind during storm season. Enjoy 5 private parking spots plus 5 additional leased spaces, so there's room for guests, toys, or tenants. You're centrally located near restaurants, cafés, marinas, and everything that makes Key Largo so special. An existing commercial operation currently occupies the first floor; optional details are available separately. A rare opportunity to live, create, and thrive right in the Florida Keys all from one amazing property! THIS IS A DUPLICATE LISTING

100636 Overseas Hwy, Key Largo

30 Cannon Royal Dr, Shark Key
$5,750,000
4 Beds ⋅ 5 Baths ⋅ 612702 MLS
Located in the prestigious gated community of Shark Key, 30 Cannon Royal Drive is a distinctive waterfront residence inspired by classic Mediterranean design. Architectural details such as soft arches, warm finishes, and elegant lines create a sense of timeless character rarely found in the Lower Keys. Thoughtfully designed to embrace indoor-outdoor living, the home offers spacious interiors filled with natural light and serene water views throughout. Two expansive porches overlook breathtaking sunset vistas, perfectly positioned on a generous 20,438 sq ft lot. The outdoor living experience is equally compelling, featuring a dedicated entertainment area complete with an outdoor fireplace and a private beach--ideal for both relaxed evenings and elevated gatherings. Additional highlights include two garages, an integrated indoor/outdoor speaker system throughout the home, and a dedicated space for a future elevator--offering both comfort and long-term flexibility. Whether enjoyed in its current form or reimagined to reflect a more modern vision, the property presents a rare opportunity to own a home with architectural presence and creative potential just minutes from Key West. Sold furnished with exclusions.

30 Cannon Royal Dr, Shark Key

308 Sabal St, Duck Key
$7,199,000
7 Beds ⋅ 6 Baths ⋅ 616613 MLS
Experience refined oceanfront living on sought-after Duck Key. This double lot estate offers 138 feet of protected deepwater dockage, complete with a solid concrete seawall designed to accommodate a sportfishing yacht, multiple center consoles, and all of your waterfront lifestyle needs. A true boater's paradise, this property offers both privacy and exceptional access to the Atlantic Ocean. The fully remodeled residence is constructed of concrete with a new roof. Inside, seven spacious bedrooms and six bathrooms provide ample accommodations for family and guests. Coastal-inspired interiors feature wood-look tile flooring throughout, woven statement light fixtures, and soaring ceilings with exposed beams and pecky cypress accents. Expansive impact windows and doors frame sweeping ocean views, bringing natural light into nearly every room. The gourmet kitchen anchors the main living space as the heart of the home, with a striking 12' island that creates the perfect setting for gatherings. Outfitted with top-of-the-line appliances, this space is equally suited for everyday living with family or hosting unforgettable evenings of entertaining. Spa-like marble bathrooms further elevate the home, blending comfort with luxury. Designed for both style and function, the property also offers a rare 4+ car garage and abundant storage. Outdoors, a sparkling pool invites afternoons in the sun, while the expansive double lot offers unmatched opportunities for expansion. Whether envisioning a private guest house, a tennis or pickleball court, or exploring the option to build and sell, this rare property provides endless possibilities for both personal enjoyment and investment potential—an uncommon luxury in the Florida Keys. Balancing modern sophistication with coastal simplicity, this sanctuary captures the essence of waterfront living from sunrise over the Atlantic to evenings by the water, in one of the most desirable neighborhoods in the Florida Keys.

308 Sabal St, Duck Key

171 10th St, Key Colony
$1,174,000
2 Beds ⋅ 2 Baths ⋅ 617571 MLS
Experience the best of Keys living in this immaculate 2-bedroom, 2-bath waterfront home in coveted Key Colony Beach. The inviting coastal layout opens to a very spacious 480 sq. ft. screened-in covered porch enhanced with newer high-end furniture providing a dining area and living area with 55'' TV creating the perfect venue for entertaining friends and family and hosting Sunday afternoon football. Step outside to your private saltwater pool, offering the perfect place to unwind after a day on the water. Boaters will appreciate the 37.5 feet of dockage, along with a new seawall installed in 2022 and a durable concrete seawall cap for long-lasting confidence and convenience. This property conveys with rare deeded bay bottom, giving you full ownership of the submerged land beneath your dock. This rare asset sets the home apart from typical canal front properties. Key Colony Beach hosts the perfect Keys lifestyle with scenic biking and walking, a 9-hole golf course, a marina, tennis courts, pickleball, and a beautiful Sunset Park just moments away. Whether you seek a serene personal retreat or a proven income-producing property, this home delivers the ideal blend of comfort, coastal charm, and true waterfront living. This is a perfect turnkey property.

171 10th St, Key Colony

63 Sugarloaf Dr, Sugarloaf
$499,000
617936 MLS
Welcome to the lowest priced waterfront lot with an active building permit and DEP and Army Corp mitigation fees paid on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq. ft., 4-bedroom, 3-bath coastal-style home -- with Army Corps dock approval already secured. Build today or customize plans to suit your vision. Sugarloaf Key is beloved for its larger lots, upscale homes, and stunning natural beauty. Enjoy crystal-clear water, endless mangrove creeks perfect for paddleboarding or kayaking, and the convenience of being just 15 minutes from Key West. The neighborhood is quiet, well-maintained, and filled with luxury homes offering the perfect setting for full-time living, a vacation retreat, or investment property. Opportunities like this are rare, a cleared path to build in the most coveted location in the Lower Keys. Create your ideal Florida Keys dream home now while you still can!

63 Sugarloaf Dr, Sugarloaf

3205 Pearl Ave, Key West
$599,000
2 Beds ⋅ 2 Baths ⋅ 617888 MLS
Located in one of Key West's most desirable townhome communities, this inviting residence offers comfort, flexibility, and value — all with no HOA and no monthly fees. The main level features a full bathroom with a shower, along with washer and dryer conveniently located on the outside porch. The living area flows seamlessly into a well-sized kitchen and dining space, creating an easy and functional layout for everyday living. Upstairs, you'll find two bedrooms, a full bath, and a private deck accessible from both bedrooms, offering a peaceful spot to enjoy the island breezes. This home presents wonderful potential and works beautifully as either a primary residence or an investment property. The property is fenced, private, and ideally located in New Town, Key West, close to shopping, dining, and everyday conveniences. A rare opportunity to own in a well-established Key West community — don't miss your chance to make it yours.

3205 Pearl Ave, Key West

140 Gumbo Limbo Dr, Key Largo
$440,000
1 Beds ⋅ 1 Baths ⋅ 617396 MLS
Rare Redevelopment Opportunity in Key Largo! Situated on two oversized corner lots totaling 10,500 square feet, this unique property offers exceptional flexibility for investors, builders, or anyone looking to create their dream Florida Keys retreat. Included is a ROGO-Exempt Letter, allowing you to bypass the lengthy ROGO allocation process and immediately replace the existing home with a new residence. Build your custom island home utilizing both lots for an expansive estate, or develop on one lot while preserving the second for additional outdoor living, future possibilities, or potential future development (buyer to verify with Monroe County). Tier III with 34 points and sewer vent installed. While planning your vision, enjoy the existing fully furnished vintage cottage filled with Keys character. This charming 1-bedroom, 1-bath bungalow features an indoor tiki bar, open kitchen with granite countertops and oak cabinetry, custom oak flooring in the bedroom, porcelain tile throughout the living areas, and seamless indoor-outdoor living. Outside, you'll find a private pea-rock courtyard shaded by mature tropical trees, an outdoor shower, storage shed, two separate driveway entrances, and ample parking for boats, trailers, RVs, and guests. Located less than one mile from John Pennekamp Coral Reef State Park, you'll have easy access to world-class diving, snorkeling, fishing, boating, beaches, and the best of the Upper Keys lifestyle. Enjoy nearby waterfront dining, shopping, Harry Harris Park, and an easy one-hour drive to Miami. Whether you're searching for an immediate weekend getaway, a rental investment, or one of the few opportunities to build without waiting through the ROGO process, this property offers outstanding value with endless potential.

140 Gumbo Limbo Dr, Key Largo

617 Front Unit B41 Week 1, Not Provided
$42,000
2 Beds ⋅ 2 Baths ⋅ 618085 MLS
Views of the famous Key West Sunset, Ocean, and Pool await you when you arrive at this 4th-floor end unit. Enjoy the sounds of the live music from your balcony as it saunters your way from the Tiki Bar. This highly desirable week offers ideal winter weather, a peaceful post-holiday atmosphere, and all the magic of Key West. Enjoy beaches, world-class dining, boating, and vibrant local culture--an exceptional way to start the year. There are elevators, and one unassigned parking space. There is a sauna & exercise room, and also on the premises is the Pirates Cove cafe, all located inside a gated community. This view unit is located just two blocks from the World Famous Duval Street, and steps away from the marina and Key West's Historic Seaside Village, where you can walk to have a sumptuous dinner or pop down for Happy Hour. Enjoy the smoked fish dip of the day and Key Lime Margarita, Yum Yum. Charter a boat to the sandbar, rent jet skis, or do some fishing; it is all within steps of this unit. There are gas grills situated on the Marina side of the Galleon that provide space for you to grill today's catch and partake at the dedicated outdoor dining tables. This is mid-season at the Resort, so it's not so busy. Choose to stay a week or join RCI/Interval International and trade or rent out the unit. The Galleon features an on-site concierge to greet you upon arrival and assist with your needs. Additionally, the Galleon may help you with renting out your unit for the week. This 2-bedroom, 2-bath unit on the 4th floor will rent for approximately $5,705 to $7,875 per week. Brand-new interior furnishings installed March 2026. The primary suite features a luxurious en-suite with a 5-piece master bath, a walk-in shower, and a jetted soaking tub. The other bedroom features two twin beds that can be combined. The updated kitchen is fully equipped, and the unit features a washer/dryer. Sleeps 6. Rooftop deck in building C with great views!

617 Front Unit B41 Week 1, Not Provided

81906 Overseas Hwy Unit 2, Islamorada
$2,495,000
3 Beds ⋅ 4 Baths ⋅ 617838 MLS
Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy, while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000 lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Ideal for a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

81906 Overseas Hwy Unit 2, Islamorada

200 Harborview Dr Unit 101, Tavernier
$640,000
2 Beds ⋅ 3 Baths ⋅ 618028 MLS
NEW LOWER PRICE!! This beautiful 2-bedroom, 2.5-bathroom condo offers everything you need for an stress-free retreat or your full-time piece of paradise. Step inside to a light and bright interior filled with upgrades and thoughtful finishing touches. Two screened lanais provide the perfect spot to relax, unwind, and soak in the stunning views of the lush tropical landscaping, sparkling pool, BBQ tiki hut, and the breathtaking Florida Bay sunsets. This condo comes with assigned parking, dockage and ground-level storage, ideal for keeping your fishing and diving gear just steps from your boat, making your water adventures effortless. Located in a prime spot, it's an easy commute to Miami for a quick weekend getaway or an extended stay in paradise. You'll also be close to the best shopping, dining, and nightlife the Florida Keys have to offer. BONUS: Enjoy peace of mind with the state-mandated engineering inspection complete and all restorative work finished. This is a rare opportunity to own a worry-free slice of paradise! Don't wait—schedule your private showing today and experience the best of bayfront living in the Florida Keys!

200 Harborview Dr Unit 101, Tavernier

1115 Fleming St, Key West
$1,775,000
4 Beds ⋅ 2 Baths ⋅ 618211 MLS
This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The nearly 5,000-square-foot lot stretches from Fleming Street to Stickeny Lane, offering ample off-street parking and a golden opportunity to expand your tropical living dreams. Nestled in the heart of Old Town, 1115 is just blocks from the historic Seaport and a stone's throw from the city's famous restaurants and nightlife. Early 1900s Sanborn maps even hint at an additional house on the property that may be rebuilt with city permissions (buyers to verify). The home still contains generous pockets of its original Dade County pine, along with historic windows and double balconies that invite sea breezes and sunset cocktails. Currently a legal duplex, each side offers 2 bedrooms and 1 bath. You can keep the duplex as-is, or transform it into a stunning single-family residence in the most sought-after neighborhood in all of Key West.

1115 Fleming St, Key West

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