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$689,000
1 Beds 2 Baths 618777 MLS
Home Sweet Home. Tucked beneath a canopy of tropical trees in the quiet Key Largo community of Pirates Cove, this charming island cottage is a place to slow down, create, and reconnect with nature. Set on an expansive 15,890-square-foot property, the home feels like a private botanical garden, where winding pathways, native plantings, and secluded outdoor spaces invite peaceful mornings and unhurried afternoons. Less than 500 feet from the salt waters of Florida Bay, the private community beach offers a place to swim, launch a kayak or paddleboard, and end the day with breathtaking Florida Keys sunsets. It is a neighborhood where life naturally unfolds outdoors. Inside, vaulted ceiling, impact windows and doors. The inviting island-inspired interior and bedroom that opens to its own garden patio create a comfortable and intimate living space. The screened porch, open courtyard, fire pit, and multiple outdoor gathering areas offer endless places to read, paint, write, entertain friends, or simply listen to the breeze through the palms. The oversized property provides room to dream, with space for a pool, artist's studio, guest cottage, garage, boat storage, or future expansion. Brick paver walkways, an outdoor shower, storage, and a dedicated laundry room add convenience while preserving the home's relaxed character. Pirates Cove is one of Key Largo's hidden gems, offering a voluntary neighborhood boat ramp and easy access to Florida Bay for boating, fishing, and exploring the backcountry waters, all while being just minutes from local restaurants, shops, and everyday conveniences. Whether you are an artist seeking inspiration, a nature lover searching for tranquility, or simply someone who appreciates the charm of a smaller home with an extraordinary sense of place, 13 Pirates Drive offers a rare opportunity to embrace the authentic, laid-back spirit of the Florida Keys.

13 Pirates Dr, Key Largo

$685,000
3 Beds 2 Baths 620336 MLS
Affordable Florida Keys Living with Weekly Rental Potential in the Heart of Marathon Whether you're searching for a full-time residence, a vacation retreat, or an income-producing investment property, this charming 3-bedroom, 2-bath Conch cottage offers exceptional value in today's market. This property blends classic Keys character with modern upgrades and desirable rental flexibility. Newly renovated the home is move-in ready and designed for easy island living. Interior features include quartz countertops, stainless steel appliances, impact-resistant windows, and energy-efficient mini-split A/C systems that help keep utility costs low. The low-maintenance lot provides ample parking and storage, making it ideal as a primary residence, second home, or vacation rental. Situated in a weekly rental area, this property offers excellent income potential while allowing owners to enjoy their own slice of paradise. Conveniently located just minutes from world-class boating, fishing, waterfront dining, shopping, and all the attractions that make the Florida Keys such a coveted destination, this Little Venice gem combines affordability, convenience, and investment opportunity. Don't miss this rare opportunity to own an affordable piece of the Florida Keys with the flexibility to enjoy it, rent it, or both. Schedule your private showing today!

11554 5th Ave, Marathon

$685,000
3 Beds 2 Baths 619422 MLS
Eden Pines Gem: Fully updated, low assumable flood Modern Island Living: Updated Stilted Retreat in Golf-Cart Friendly Eden Pines! Welcome to 29175 Violet Drive, a fully updated 3-bedroom, 2-bathroom stilted sanctuary in the heart of Big Pine Key. This home is tucked into the vibrant, family-oriented community of Eden Pines Colony-a neighborhood where neighbors are friends and the island lifestyle is at its best. Boating: The boat ramp is just around the corner and there is plenty of room to park your toys including a one car garage! EXPANSIVE STORAGE BELOW, fully enclosed. Designer Bathrooms: Both the primary and main bathrooms feature beautifully updated showers. Flooring runs through the entire interior and flows seamlessly onto the porch for a high-end, unified look. Updated with newer stainless-steel appliances and an open-concept layout flooded with natural light. Total Comfort: (2019) central AC system replaced. Curated Outdoor Living & Durability: Fresh & Low Maintenance: The home shines with a freshly painted exterior and vinyl hand and porch rails -no rust, no rot, just island beauty. Private Side Yard Oasis: Discover a stunning side yard retreat featuring authentic Key West bricks set against a lush, towering wall of tropical plants. Clean Curb Appeal: An expansive concrete driveway provides plenty of room for multiple vehicles, boat trailers, or RV parking. Upgraded Porch: Expand your living area to the porch! The perfect vantage point for watching the local Key Deer wander and enjoying unbeatable sunrises. Unbeatable Protection & Savings: Current owners receive all mitigation discounts on wind insurance. Fully protected with impact shutters and a durable metal roof (completed in 2019), offering maximum safety and substantial insurance discounts.

29175 Violet Dr, Big Pine

$685,000
3 Beds 2 Baths 617211 MLS
Well maintained stilt family home with three bedrooms on the same floor. Open kitchen with beautiful white marble counter tops and white cabinets for the chef. Vaulted ceilings with plenty of windows allowing the natural light inside. Tile floors throughout this well-kept home. Metal roof for your security and plenty of outdoor space to enjoy the privacy. Room for a pool also. Lots of parking at this great location. Microwave is a convection and air fryer, all stainless-steel kitchen appliances. Washer and dryer stackable included. Newer sliding glass shower enclosure in primary bathroom. Move in condition and immaculate interior. Extra yard for your parking and entertaining needs. Storage shed in the private carport for extra storage. Open front porch to enjoy your morning coffee and afternoon tea time.

150 Peace Ave, Tavernier

$685,000
3 Beds 2 Baths 616942 MLS
Nestled in one of Key Largo's most desirable and friendliest neighborhoods, just across the street from multi-million dollar waterfront homes, sits this charming concrete Conch-style beauty which offers true island living. Featuring 3 bedrooms and 2 bathrooms, a concrete roof, lush tropical landscaping, a carport, sliding gate, large storage shed, fully fenced yard, and the coziest front porch perfect for relaxing. Inside, you'll find a spacious kitchen, beautiful wood ceilings, a Jacuzzi tub and separate shower in the primary suite, and two additional roomy bedrooms. Neighborhood Club is available for $250 a year for private access which includes a park with beach access, a boat ramp with easy access to ocean or bay, a club house with charcoal grill, two restrooms, an outdoor shower, basketball courts and swing sets.

13 Bass Ave, Key Largo

$685,000
2 Beds 2 Baths 618758 MLS
This top-floor 2-bedroom, 2-bath condo at Ocean Pointe generated an impressive rental income in 2025 -- all while allowing 12 weeks of owner use. A rare combination of strong income potential and personal enjoyment. Located in Building 4, this unit offers stunning ocean views and has been tastefully updated throughout. The kitchen features rich wood cabinetry, granite countertops, and an open layout perfect for entertaining. Both bathrooms have been beautifully updated, and the condo includes impact oceanfront sliders and front doors, along with attractive tiled flooring throughout. Ocean Pointe's resort-style amenities set it apart: -Direct ocean access marina -Double-wide boat ramp -Dry boat storage -Jr. Olympic-size heated pool -14-person hottub spa -Pool bar & oceanfront café -Lighted pickleball & tennis courts -Private beach area Located just minutes from Harry Harris Park for even more outdoor activities. Whether you're looking for an income-producing investment, a vacation getaway, or both -- this property delivers the full Florida Keys lifestyle.

500 Burton Dr Unit # 4415, Tavernier

$684,000
2 Beds 3 Baths 619770 MLS
Perfectly positioned just steps from the pristine shores of Sombrero Beach, premier shopping, and vibrant nightlife, Lemon Cove stands in a class entirely its own. No other condominium residence in the area offers such a rare combination of generous private parking, breathtaking canal frontage, impeccably manicured grounds, and a resort-style pool -- all seamlessly curated for the discerning buyer. This exceptional 2-bedroom, 2.5-bathroom canal-front residence commands sweeping views of both the sparkling pool and tranquil canal, framed by generously proportioned living spaces and refined, upscale finishes throughout. Every detail has been thoughtfully considered, offering an effortless lifestyle where luxury and low-maintenance living exist in perfect harmony. For those who have envisioned waking each morning to the serene beauty of waterfront living -- without compromise -- this is your moment to live near the beach!

591 Sombrero Beach Rd Unit APT 1B, Marathon

$680,000
2 Beds 2 Baths 617778 MLS
Hawks Cay Resort Villa - Luxury, Lifestyle & Investment Potential. NIGHTLY RENTALS ALLOWED. This beautiful 2-bedroom, 1.5-bathroom end-unit villa is your gateway to paradise in the highly desirable Hawks Cay Resort. Perfectly positioned for both personal enjoyment and income generation, this property offers the best of both worlds: a tropical retreat and a savvy investment. • Prime Location: End-unit villa in Hawks Cay Resort, one of the Florida Keys' most sought-after destinations. • Upgraded Features: Impact windows & doors, metal roof, tile throughout, stainless steel appliances, and granite countertops. • Turnkey Condition: ready for immediate income generation or personal enjoyment. • Proven Performance: Comes with an outstanding rental history, making it an ideal short-term rental investment. • Nightly Rentals Allowed: Flexibility to maximize occupancy and income potential. Tax Advantages;: Owning a short-term rental property has never been more financially attractive. The recently passed legislation provides powerful tax incentives for STR owners: • 100% Bonus Depreciation Restored: Investors can immediately expense qualifying assets like appliances, furnishings, and renovations—accelerating deductions and reducing taxable income. • Permanent 20% Qualified Business Income (QBI) Deduction: Structured as an LLC or S-Corp, owners can deduct up to 20% of qualified rental income annually, boosting long-term profitability. • 1031 Exchanges Protected: Investors can continue deferring capital gains when swapping properties, preserving portfolio flexibility. • Enhanced SALT Cap: Raised from $10,000 to $40,000, making high-tax states more attractive for STR investment. These provisions mean better cash flow, faster growth, and stronger ROI for savvy investors who act now. Imagine waking up to the serene beauty of the Florida Keys, enjoying resort amenities, and knowing villa is working for you even when you're away.

5110 Sunset Village Dr, Duck Key

$679,500
2 Beds 2 Baths 619544 MLS
Welcome to your slice of paradise in the highly sought-after Key Cove community in Key West, FL, where island living meets enjoyable comfort. This beautifully designed townhome offers the perfect blend of coastal charm and modern convenience. Featuring a bright, open-concept layout, the living and dining spaces flow seamlessly with the well appointed kitchen. Ideal for entertaining or unwinding after a long day. Enjoy outdoor living with the covered balcony off of the living room. The Living Room & Foyer has updated Engineered Hardwood - European French Oak Flooring in March 2023. Kitchen Tile updated in August 2025. The stairs and Hallway have Hardwood flooring as well updated in June 2021. New Hot Water Heater in August 2025 along with updated Kitchen Light and Faucet in March 2026. Most of the rooms in the home have been freshly repainted with Sherwin Williams Paint. Upstairs features two spacious bedrooms with high ceilings. A gorgeous bathroom with plenty of light. There's also a hall laundry room for easier lifestyle duties. This home features covered parking with a garage door. Plenty of space underneath for extra storage. Key Cove residents love the laid-back lifestyle. Convenient location for food shopping, dining and entertainment. Also, there's a Community Pool to hangout and enjoy your day. Whether you're searching for a full-time residence or a second home, this home delivers the Key West lifestyle you've been waiting for and more.

3029 N Roosevelt Blvd Unit APT 11, Key West

$679,000
620693 MLS
An exceptional opportunity to acquire two (2) Waterfront Transferable Development Rights (TDRs akaTBRs) for use within the Village of Islamorada. Offered together for $679,000, this represents an outstanding value at approximately $339,500 per TDR--well below the cost of purchasing comparable rights individually. These development rights may be transferred to an eligible receiver property within the Village, providing a rare opportunity for builders, developers, and property owners to secure valuable development potential at a discounted price. Buyer shall pay all closing costs associated with the transaction, including the Village transfer fee. A recent, successful transfer provides buyers with confidence in a proven Village transfer process. This sale does not include any real property.

2x Waterfront Tdr For Sale, Not Provided

$679,000
2 Beds 2 Baths 620133 MLS
PRIVACY GALORE! For buyers who crave true seclusion and one level living, this rare gem delivers unmatched privacy with absolutely no stairs to climb. Soaring tall ceilings and dramatic walls of glass in the living room and kitchen frame a lush, private sanctuary of tropical foliage and towering trees -- nature's own privacy screen. Step onto the wrap-around screened balcony and let yourself be swept away by the symphony of birdsong surrounding you on all sides. This spacious two-bedroom, two-bath condo offers incredible flexibility, with the dining room easily convertible into a third bedroom -- giving you room to grow without ever sacrificing your privacy. Both bathrooms have been beautifully and thoughtfully updated. The kitchen shines with granite countertops and stainless steel appliances, all bathed in natural light from your very own private tropical backdrop. Your privacy extends beyond the unit itself -- a large, secured outdoor storage area on the first floor keeps your kayaks, bikes, and personal belongings safe and out of sight. And when you're ready to venture out, you're just a short walk from several restaurants and the world-famous Hawks Cay Resort Marina, where adventure awaits -- right before you retreat back to your own private paradise.

8301 Marina Villas Dr, Duck Key

$679,000
5 Beds 4 Baths 619887 MLS
A versatile multi-unit opportunity in the heart of Tavernier. Offering three separate residences with a combined total of 5 bedrooms and 4 bathrooms, this property is well-suited for extended family living, income-producing potential, or a combination of both. Recent updates include a metal roof, updated kitchens with new appliances, new flooring in the front building, and a gas stove in the rear unit. The property also features a mix of impact windows, an impact sliding door, and shutters. Ideally located near Harry Harris Park, you'll have convenient access to a boat ramp, beach, oceanfront park, restrooms, and ball fields - where boating, beach days, and outdoor living are part of your everyday routine.

235 Antigua Rd, Tavernier

$679,000
5 Beds 4 Baths 619453 MLS
A versatile multi-unit opportunity in the heart of Tavernier. Offering three separate residences with a combined total of 5 bedrooms and 4 bathrooms, this property is well-suited for extended family living, income-producing potential, or a combination of both. Recent updates include a metal roof, updated kitchens with new appliances, new flooring in the front building, and a gas stove in the rear unit. The property also features a mix of impact windows, an impact sliding door, and shutters. Ideally located near Harry Harris Park, you'll have convenient access to a boat ramp, beach, oceanfront park, restrooms, and ball fields - where boating, beach days, and outdoor living are part of your everyday routine.

235 Antigua Rd, Tavernier

$679,000
618347 MLS
Premium Waterfront Lot includes a building right/TBR - READY TO BUILD no waiting, INCLUDES 2 SETS OF HOUSE PLANS, The VACANT LAND PRICE is 679,000. Alternatively, you can choose to have the Seller coordinate the New Construction Project already planned to begin in 2026 at a completed price of 2,795,000. Breathtaking Views with Deep Water Protected 50 Ft Dockage! Discover your dream home in Marathon, Florida, offering 3,200 sq. ft. of luxurious living space. This 5-bedroom, 5-bathroom masterpiece features a private pool, elevator, and a stunning rooftop observation deck-perfect for enjoying epic sunsets over Boot Key Harbor. Work with Keys Dream Properties to customize your finishes, including interior and exterior colors, tile, quartz countertops, lighting, and plumbing fixtures. Tailor every detail to your taste and make this house truly your own. Located in the heart of Marathon, you'll enjoy easy access to endless shopping and dining options, from fine dining to casual eats. With a protected deep-water dock, you're minutes from both the Atlantic and Gulf, offering World-Class Fishing, Snorkeling-Diving, and Boating adventures. For those breezy days, Boot Key Harbor provides calm waters for social boating, complete with on-the-water dining and cocktails. Best of all, there are NO HOA FEES, and the property allows 7-day rentals, giving you the flexibility to offset your investment through vacation rentals in Marathon's thriving market. This home's combination of luxury, customization, and location offers the best of the Florida Keys Lifestyle. Construction scheduled to begin in 2026. Don't miss this rare opportunity to design and own your slice of paradise. Contact us today!

1021 27th St, Marathon

$675,000
4 Beds 3 Baths 620908 MLS
Discover the charm and comfort of this spacious ground-level home with an attached guest suite, perfect for extended family, visitors, or private rental income. Nestled in the desirable Crane Hammock Preserve, in this family-friendly neighborhood, residents enjoy access to both a private community beach and a boat ramp, offering endless opportunities for swimming, boating, and fishing just minutes from your doorstep. This corner lot is surrounded by native hammocks and mature foliage, creating a private, natural and protected sanctuary with plenty of room to relax. The property offers tremendous potential for customization, whether you envision updating to your own style, adding outdoor living spaces, or enhancing the guest suite, the opportunities are endless. With seller financing available, this home presents a rare chance to secure a piece of the Keys lifestyle with flexibility and ease.

5353 Dogwood Dell St, Marathon

$675,000
2 Beds 2 Baths 620881 MLS
ONE OF THE LOWEST PRICED HOMES IN THE VILLAGE OF ISLAMORADA! Charming Home in a desirable Plantation Key Subdivision! This well-maintained Sheffield Steel home offers excellent curb appeal with lush, tropical landscaping. Inside, enjoy an open-concept layout with two bedrooms and two bathrooms, highlighted by beautiful Dade County Pine ceilings and an abundance of natural lighting. Step out onto the open upstairs balcony--perfect for relaxing and soaking in the Florida Keys lifestyle. The spacious front yard provides ample parking, and the ground level features a large storage room. Whether you're looking for a full-time residence or a great investment opportunity, this property checks all the boxes. Conveniently located near top-rated schools, shopping, restaurants, and hospital.

115 Fontaine Dr, Tavernier

$675,000
2 Beds 2 Baths 620876 MLS
Newly updated waterfront half-duplex just a short walking distance to Sombrero Beach. This canal front property features brand-new vinyl plank flooring throughout, and an updated kitchen with Stainless appliances. Freshly painted inside and out, the home feels crisp, modern, and move-in ready. Outside, enjoy a new seawall, new 45-ft dock, and partial open-water views, perfect for boating and waterfront living. Whether you're looking for a strong rental income opportunity or a low-maintenance permanent waterfront home, this property checks all the boxes for Keys living. Priced BELOW appraised value! Bonus opportunity: the other half of the duplex is also available for purchase, see MLS # 618475 offering the rare chance to own the entire waterfront property.

18 Man-O-War Dr, Marathon

$675,000
2 Beds 2 Baths 620875 MLS
Newly updated waterfront half-duplex just a short distance to Sombrero Beach. This bright and inviting property features brand-new vinyl plank flooring throughout, a beautifully tiled shower, and an updated kitchen with newer appliances. Freshly painted inside and out, the home feels crisp, modern, and move-in ready. Outside, enjoy a new seawall, new 45-ft dock, and partial open-water views, perfect for boating and waterfront living. Whether you're looking for a strong rental income opportunity or a low-maintenance permanent waterfront home, this property checks all the boxes for Keys living. Priced BELOW appraised value! Bonus opportunity: the other half of the duplex is also available for purchase, see MLS # 618475 offering the rare chance to own the entire waterfront property.

17 Manowar Dr, Marathon

$675,000
2 Beds 3 Baths 620025 MLS
Located just 10 miles from Key West, this 2 story elevated home is the perfect space for full time living or a second home get away. This beautifully maintained 2 bedroom, 2.5 bath modular home offers the perfect blend of comfort, durability, and low-maintenance Florida Keys living. Situated on a fully fenced lot with artificial turf for year-round curb appeal and easy upkeep, the property is ideal as a full-time residence, vacation retreat, or second home investment. Built for peace of mind, the home features a metal roof along with all impact-rated windows and doors, helping keep insurance costs lower while providing excellent storm protection. The elevated design offers covered parking and storage space below, plus an exterior shed for all your tools, bikes, fishing gear, and island toys. Inside, you'll find a bright and inviting layout with spacious bedrooms, open living areas, and a functional floor plan designed for relaxed Keys living. Enjoy the convenience of being just minutes from Key West while still having the privacy and laid-back atmosphere of the Lower Keys. Whether you're looking for a low-maintenance primary home or the perfect island getaway, this property checks all the boxes.

59 Ed Swift Rd, Big Coppitt

$675,000
4 Beds 2 Baths 619277 MLS
This 4-bedroom, 2-bath, 1566 sq. ft. home has so much to offer for the price! A spacious living area separates the primary bedroom and ensuite bath from the remaining bedrooms and bath. Features include tile floors throughout, a separate laundry room, a big sundeck and a ground-level storage enclosure. Covered parking is conveniently accessed from either Avenue C or Sands Rd. The 5,000 sq. ft. lot is landscaped to provide a privacy buffer. If you're a lover of mangos, you're in luck since there are multiple mango trees! Local shops and amenities are nearby, with easy commutes to Marathon or Key West. The Big Pine Community Park is less than half a mile away, offering activities for all ages, including playground, skatepark, tennis, bocce, picnic areas, and more; leashed pets are allowed.

31011 Ave C, Big Pine

$675,000
3 Beds 3 Baths 618909 MLS
Two well kept condo units at Solana Village in Key West's New Town neighborhood represents a solid investment opportunity. Conveniently situated near local schools, government offices, retail centers, a movie theater, and marinas, the property offers both lifestyle and income potential. The second-floor unit (13) is a 2-bedroom, 2-bathroom with all-tile flooring and a private balcony currently rented for $2,975, while the first-floor unit (13A ) is a 1 bedroom, 1 bathroom both in move-in ready, rentable condition estimating $2,675 monthly rent. Investors can lease out both units for steady rental income, or choose to live in one while renting the other to help cover mortgage and ongoing expenses. Unit 13 is currently occupied by tenants, so a minimum of 24 hours' notice is required for showings.

3314 Northside Dr Unit 13 & 13A, Key West

$675,000
2 Beds 2 Baths 617613 MLS
Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water—just minutes to both the Gulf and the Atlantic. Situated on a spacious double lot, the property includes a 30 ft. Step down boat slip cut in, ideal for docking your boat and enjoying effortless days on the water. Designed for seamless indoor-outdoor living, the home features a bright, open layout and a well-appointed kitchen complete with granite countertops. A separate laundry area adds everyday practicality, while one of the bedrooms includes a private entrance, perfect for guests, in-laws, or a home office. The home is equipped with ductless A/C systems, providing customizable comfort and excellent energy efficiency. The second lot provides incredible flexibility—ideal for building a pool, creating additional parking, expanding the main home, or adding a stand-alone garage. Lush, mature landscaping surrounds the property, enhancing both beauty and privacy. Located on a quiet dead end street, free from light and air pollution, where the night stars are as clear as day. This location offers excellent water access and is just a short distance from local shopping, restaurants, and everything the area has to offer. Perfect for boating enthusiasts or anyone seeking a serene, island retreat.

30920 Baileys Ln, Big Pine

$670,000
2 Beds 2 Baths 620825 MLS
Let 101 Golf Club Drive be the key to your slice of paradise! This home is nestled mid-way in the Key West Golf Course Community which is gated with manicured lush vegetation, pools, fitness center, and a club house. From the home, the back faces unobstructed views of the 1st Fairway, while the front faces the quaint, white picket fence lined drive. Upstairs, each bedroom has its own bathroom and balcony, providing privacy to you and your family or guests. No need to make upgrades as new stainless steel appliances, hot water heater, flooring, & paint are throughout! The home has also been recently tented with warranty, giving an additional peace of mind your home is protected. Whether this is your full time home, vacation property, or investment, 101 Golf Club Dr is move in ready for you to start enjoying the Key West lifestyle!!

101 Golf Club Dr, Key West

$670,000
3 Beds 2 Baths 619890 MLS
Welcome to your dream island getaway in the highly sought-after Bluewaters community. Nestled at the south end of Key Largo, this 1974 doublewide manufactured home has been transformed into a delightful oasis. Upgraded with impact windows, wood plank tile throughout, newer kitchen with stainless appliances, quartz counters, tile backsplash, and a built-in banquette; both bathrooms have been fully updated with bright white tile and feature glass shower doors for a modern, clean look. An above-ground pool was an excellent addition to the backyard, offering a refreshing escape during the warm summer months. Outdoor aluminum pergola. For boating enthusiasts, the property includes 20 feet of dockage on a deepwater canal with direct ocean access.

212 Buttonwood Ln, Key Largo