Newest Homes for Sale in Cudjoe Key, FL

/30
$485,000
- 2 Beds
- 1.5 Baths
- 604 Sq Ft
701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
/47
$649,000 New Construction
- 2 Beds
- 2 Baths
- 840 Sq Ft
701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

Ian Calderwood

Bluescape Real Estate

(786) 613-4104

701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
/64
$2,875,000
- 4 Beds
- 3 Baths
- 2,951 Sq Ft
20844 4th Ave W, Summerland Key, FL 33042

SOLD TURNKEY! INCLUDES FURNISHINGS, 2006 PONTOON BOAT & 2021 JET SKI! DEEP WATER! A remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

20844 4th Ave W, Summerland Key, FL 33042
/6
$225,000
- Land
124 Cutthroat Dr, Cudjoe Key, FL 33042

Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

Jimmy Lane Island Life Realty Experts

124 Cutthroat Dr, Cudjoe Key, FL 33042
/44
$1,150,000
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21855 Spain Blvd, Summerland Key, FL 33042

Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

Matthew Sheehan

Ocean Sotheby's International Realty

(786) 882-7957

21855 Spain Blvd, Summerland Key, FL 33042
/6
$400,000
- Land
21865 Spain Blvd, Summerland Key, FL 33042

Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

Matthew Sheehan

Ocean Sotheby's International Realty

(305) 614-8634

21865 Spain Blvd, Summerland Key, FL 33042
/49
$1,145,000
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
22737 Blackbeard Ln, Cudjoe Key, FL 33042

Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

Terry Garcia

Keller Williams Key West Compass Realty

(786) 321-8407

22737 Blackbeard Ln, Cudjoe Key, FL 33042
/3
$60,000
- Land
Lot 10 Rainbow Beach, Big Torch Key, FL 33042

Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

Shanti Cope Coldwell Banker Schmitt Key Largo

Lot 10 Rainbow Beach, Big Torch Key, FL 33042
/4
$285,000
- Land
Unlisted Address

Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

Coby Taylor

Taylor & Assoc. RE, Inc.

(786) 876-6382

Unlisted Address
/39
$640,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Main Dr in Cudjoe Key, FL. This beautiful property offers 2 bedrooms and 2 bathrooms within its 816 sq.ft. of finished living space. The home sits on a 2,568 sq.ft. lot, providing ample outdoor space for relaxing and entertaining. The property features a bright and airy interior with an open floor plan,

Randal Longo Keys Realty Redefined LLC

701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
/47
$569,900
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

Ian Calderwood

Bluescape Real Estate

(786) 686-7983

701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
/65
$1,099,000
- 4 Beds
- 3 Baths
- 2,448 Sq Ft
165 Cutlass Ln, Summerland Key, FL 33042

Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

Justyn Ewald Expert Realty LLC (HQ)

165 Cutlass Ln, Summerland Key, FL 33042
/43
$1,799,999
- 4 Beds
- 2 Baths
- 2,074 Sq Ft
22562 Jolly Roger Dr, Summerland Key, FL 33042

Jolly Roger Drive on Cudjoe Key, where custom design meets open water views. This 4-bedroom, 2-bathroom residence showcases a designer kitchen with Viking appliances and high-end finishes, perfect for entertaining. The first floor offers two guest bedrooms, an office, and a full bath, while the second floor features a spacious guest room and the primary suite with a private balcony, ensuite bath,

Krystal Thomas eXp Realty LLC

22562 Jolly Roger Dr, Summerland Key, FL 33042
/53
$985,000
- 2 Beds
- 2 Baths
- 888 Sq Ft
701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
/23
$3,750,000
- 4 Beds
- 4.5 Baths
- 3,228 Sq Ft
22815 Port Royal Ln, Summerland Key, FL 33042

DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

Rhonda Gailey Gailey Enterprises Real Estate

22815 Port Royal Ln, Summerland Key, FL 33042
/37
$999,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
22954 Buccaneer Ln, Summerland Key, FL 33042

Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(645) 230-1509

22954 Buccaneer Ln, Summerland Key, FL 33042
/55
$1,500,000
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21865 Spain Blvd, Summerland Key, FL 33042

Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

Matthew Sheehan

Ocean Sotheby's International Realty

(645) 215-8837

21865 Spain Blvd, Summerland Key, FL 33042
/49
$329,000
- 2 Beds
- 1 Bath
- 738 Sq Ft
701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

Jan Fritz Coldwell Banker Schmitt RE Co.

701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
/24
$580,175
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

Sarah Dolson Keller Williams Key West Compass Realty

701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
/9
$185,000
- Land
Vacant Picard Ln, Cudjoe Key, FL 33042

Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open

Sunnie San Lorenzo KeyIsle Realty

Vacant Picard Ln, Cudjoe Key, FL 33042
/25
$569,700
- 2 Beds
- 1 Bath
- 718 Sq Ft
701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

Sarah Dolson Keller Williams Key West Compass Realty

701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
/52
$425,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
/59
$1,569,999 New Construction
- 4 Beds
- 3 Baths
- 2,136 Sq Ft
142 Peg Leg Ln, Cudjoe Key, FL 33042

Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

Alejandro Perez Amerifirst Realty

142 Peg Leg Ln, Cudjoe Key, FL 33042
/42
$2,200,000
- 5 Beds
- 3 Baths
- 1,978 Sq Ft
94 Sacarma Dr, Cudjoe Key, FL 33042

Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

Michelle Blades Realty Executives Florida Keys Old Town

94 Sacarma Dr, Cudjoe Key, FL 33042
/44
$949,000
- 2 Beds
- 2 Baths
- 779 Sq Ft
701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
/60
$529,000
- 2 Beds
- 1 Bath
- 667 Sq Ft
701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

Ian Calderwood

Bluescape Real Estate

(786) 981-9841

701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
/40
$300,000
- Land
701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with new landscaping, pea rock and concrete parking pad and is equipped with full hookups including water, sewer, and 30, and 50 amp electric

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
/49
$999,000
- 2 Beds
- 2 Baths
- 1,248 Sq Ft
701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042

Welcome to your piece of paradise! This stunning high-rise is the largest square footage home in the exclusive gated community of Venture Out on Cudjoe Key. This property embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a

Ian Calderwood

Bluescape Real Estate

(786) 891-5684

701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042
/19
$225,000
- Land
701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

Ian Calderwood

Bluescape Real Estate

(786) 761-5180

701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
/16
$989,999
- 3 Beds
- 3 Baths
- 960 Sq Ft
22961 John Avery Ln, Summerland Key, FL 33042

Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

Rayden Vega CASA MIAMI REAL ESTATE

22961 John Avery Ln, Summerland Key, FL 33042
/55
$374,000
- 2 Beds
- 1.5 Baths
- 748 Sq Ft
701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
/41
$2,450,000
- 2 Beds
- 2 Baths
- 1,577 Sq Ft
1176 Thatch Ln, Summerland Key, FL 33042

Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

Jonathan Minerick Homecoin.com

1176 Thatch Ln, Summerland Key, FL 33042
/2
$324,999
- 2 Beds
- 2 Baths
- 980 Sq Ft
37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

This sale is for one 6000 square foot lot with a home in need of repairs or replacement. The value of this property is in the ROGO EXEMPT status. All the utilities are there and I can give you clear title for this property upon closing. I have also determined that financing for this project is very difficult to obtain. A cash deal is the easiest way to make this deal work.

Joseph Ordini Keller Williams Key West Compass Realty

37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
/2
$65,000
- Land
248 Yardarm Rd, Cudjoe Key, FL 33042

This is a listing for two transferable lots. lots # 35 & 36 each lot is 6000 sq. ft.

Joseph Ordini Keller Williams Key West Compass Realty

248 Yardarm Rd, Cudjoe Key, FL 33042
/9
$849,000
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
22920 Privateer Dr, Summerland Key, FL 33042

Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

Robin Nilsson Keller Williams Key West Compass Realty

22920 Privateer Dr, Summerland Key, FL 33042
/20
$224,500
- Land
701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

Ian Calderwood

Bluescape Real Estate

(786) 418-4615

701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
/61
$595,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom home, built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
/30
$470,000
- 1 Bed
- 1 Bath
- 748 Sq Ft
701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
/39
$1,100,000 Open Sat 11AM - 1PM
- 3 Beds
- 2 Baths
- 2,198 Sq Ft
21073 7th Ave, Summerland Key, FL 33042

Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

Diane Corliss Coldwell Banker Schmitt RE Co.

21073 7th Ave, Summerland Key, FL 33042
/39
$495,000
- 1 Bed
- 1 Bath
- 754 Sq Ft
701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

Ian Calderwood

Bluescape Real Estate

(786) 551-4336

701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

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