Cudjoe Key, FL Homes

/46
$998,000 Sold Sep 09, 2025
- 1,318 Sq Ft
- $757/SF
- 16 Days On Market
- 3 Beds
- 2 Baths
- Built 2013
1117 Basque Ln, Cudjoe Key, FL 33042

Tropical Oasis And Butterfly Haven With Absolutely Adorable Home on a canal with easy access to both the Ocean and Back Country. Large additional garden enhanced lot that would be a great location for a pool, and designed for the resident's privacy. The 3 bedroom 2 bath home has been updated with beautifully finished Custom Florida Cypress cabinets and Cambria Quartz center island in the

Lynn Goodwin Coldwell Banker Schmitt Real Estate Co.

1117 Basque Ln, Cudjoe Key, FL 33042

/2
Est $801,670 Not Listed For Sale
- Studio
20874 4th Ave, Cudjoe Key, FL 33042

20874 4th Ave, Cudjoe Key, FL 33042

/12
$299,000 Under Contract
- Land
20822 1st Ave, Cudjoe Key, FL 33042

Located in the prestigious waterfront community of Cudjoe Gardens, this cleared and buildable 10,000 sq. ft. canal front lot offers an exceptional opportunity to create your dream home in the Lower Keys. With deep water, quick ocean access and no bridges, this property is perfect for boating enthusiasts and water lovers alike.Situated on a wide, clean canal just moments from the open ocean, the

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 713-1031

20822 1st Ave, Cudjoe Key, FL 33042
/39
$705,000 Sold Sep 08, 2025
- 1,090 Sq Ft
- $647/SF
- 7 Days On Market
- 2 Beds
- 2 Baths
- Built 1985
181 Doubloon Ln, Summerland Key, FL 33042

This super cute 2 Bedroom 2 Bath home in Cutthroat Harbor Estates on Cudjoe Key offers easy ocean access with no bridges from the 60' long concrete dock. The open concept floorpan features a remodeled kitchen with center island, new cabinetry, stainless appliances and granite countertops. The enclosed Florida Room and adjacent outdoor Porch both overlook the water and are the perfect places to

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

181 Doubloon Ln, Summerland Key, FL 33042

/2
Est $1,069,585 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
21034 Overseas Hwy, Cudjoe Key, FL 33042

21034 Overseas Hwy, Cudjoe Key, FL 33042

/57
$2,999,000 Under Contract
- 3 Beds
- 4 Baths
- 3,747 Sq Ft
22967 Redfish Ln, Cudjoe Key, FL 33042

Custom Luxury Meets Waterfront Living on Cudjoe Key. Welcome to 22967 Redfish Lane -- a one-of-a-kind luxury home crafted by one of the Keys' most respected builders as his personal residence. This 3,747 sq ft coastal estate offers 3 bedrooms, 3.5 baths, and high-end custom finishes throughout.Step inside to find black walnut hardwood flooring, soaring tongue-and-groove ceilings, and a true

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(645) 900-8075

22967 Redfish Ln, Cudjoe Key, FL 33042
/114
$1,477,000 Sold Sep 02, 2025
- 1,560 Sq Ft
- $947/SF
- 49 Days On Market
- 3 Beds
- 2 Baths
- Built 2018
153 Galleon Ln, Summerland Key, FL 33042

Welcome home to this beautifully maintained waterfront retreat in the heart of the Florida Keys! Located on the highly sought-after Cudjoe Key, this spacious & elegant home blends casual island living with refined comfort, all custom-designed & cared for with exceptional pride & attention to detail.From the moment you arrive, you'll notice the peaceful, private setting of this stunning tropical

Lindsay Ryan EXP Realty LLC

153 Galleon Ln, Summerland Key, FL 33042

/2
Not Listed For Sale
- 7,000 Sq Ft
1138 Basque Ln, Summerland Key, FL 33042

1138 Basque Ln, Summerland Key, FL 33042

/48
$319,000
- 2 Beds
- 1 Bath
- 720 Sq Ft
701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

Income-Producing Gem in Venture Out! Affordable 2BR/1BA Getaway with Resort Amenities.Discover an incredible opportunity to own a piece of the highly sought-after, gated community of Venture Out. This charming 2-bedroom, 1-bathroom home is one of the community's most affordable properties, offering a perfect blend of cozy comfort and exceptional investment potential.Ready for you to move in

Ian Calderwood

Bluescape Real Estate

(305) 570-4554

701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
/71
$3,150,000 Sold Aug 28, 2025
- 4,976 Sq Ft
- $633/SF
- 118 Days On Market
- 6 Beds
- 7 Baths
- Built 2010
225 Colson Dr, Summerland Key, FL 33042

Experience the epitome of island luxury in this custom built 5,000 sq. ft. ICF (super energy efficient insulated concrete forms) constructed estate, where masterful design, refined finishes, and breathtaking ocean views come together in perfect harmony. Situated on over an acre of prime oceanfront land, this gated and walled compound offers the ultimate in privacy, serenity, and sophisticated

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

225 Colson Dr, Summerland Key, FL 33042

/61
Est $2,642,359 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,042 Sq Ft
20886 4th Ave W, Summerland Key, FL 33042

20886 4th Ave W, Summerland Key, FL 33042

/66
$539,000
- 2 Beds
- 2 Baths
- 836 Sq Ft
701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

Ian Calderwood

Bluescape Real Estate

(786) 882-1915

701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
/32
$450,000 Sold Aug 20, 2025
- 814 Sq Ft
- $553/SF
- 283 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

Charming Florida Keys Retreat at Venture Out on Cudjoe Key: Your Slice of Paradise Awaits! Welcome to your dream getaway nestled in the vibrant Venture Out community! This beautifully designed 2 BR, 2 BA home, built in 2016, is perfect for those seeking a blend of relaxation and adventure. Fully furnished and ready for you to move in or rent out nightly, this property is a true gem in the heart

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

/39
Not Listed For Sale
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

/48
$1,998,000
- 4 Beds
- 3 Baths
- 2,440 Sq Ft
22542 Jolly Roger Dr, Summerland Key, FL 33042

SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation . Offering Four generous size bedrooms with Three full

Emily Lombard

Ocean Sotheby's International Realty

(786) 788-8217

22542 Jolly Roger Dr, Summerland Key, FL 33042
/41
$1,350,000 Sold Aug 18, 2025
- 1,582 Sq Ft
- $853/SF
- 16 Days On Market
- 3 Beds
- 2 Baths
- Built 1985
20735 5th Ave W, Summerland Key, FL 33042

This beautifully renovated 3 Bedroom 2 Bathroom home is located in Cudjoe Gardens, a premiere boating community offering wide crystal clear deep draft canals, quick ocean access, neighborhood restaurant and a full service marina with fuel, bait, ice, refreshments and boat ramp. As you enter into this lovely and impeccably kept home a bright and sunny Great Room greets you highlighted with a

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

20735 5th Ave W, Summerland Key, FL 33042

/43
Not Listed For Sale
- 1 Bed
- 1 Bath
- 408 Sq Ft
701 Spanish Main Dr Unit 256, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 256, Cudjoe Key, FL 33042

/6
$499,000
- Land
22552 Jolly Roger Dr, Cudjoe Key, FL 33042

7049 sf Oceanfront Lot with beautiful views of Cudjoe Bay ! Build your dream home in Cudjoe Key ! Don't miss out on this great opportunity to build and live in one of the most desirable neighborhoods in the Keys !

Emily Lombard

Ocean Sotheby's International Realty

(786) 659-1030

22552 Jolly Roger Dr, Cudjoe Key, FL 33042
/34
$1,300,000 Sold Aug 18, 2025
- 2,100 Sq Ft
- $619/SF
- 214 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
22822 John Silver Ln, Summerland Key, FL 33042

Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key

Karen Haack Coldwell Banker Schmitt RE Co.

22822 John Silver Ln, Summerland Key, FL 33042

/2
Est $382,500 Not Listed For Sale
- Studio
27328 St Vincent Ln, Ramrod Key, FL 33042

27328 St Vincent Ln, Ramrod Key, FL 33042

/6
$550,000
- 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
/33
$665,000 Sold Aug 14, 2025
- 855 Sq Ft
- $778/SF
- 74 Days On Market
- 2 Beds
- 2 Baths
- Built 1975
21161 Old State Road 4a, Summerland Key, FL 33042

Island life awaits! Beautiful, elevated home boasts 2 spacious bedrooms and 2 recently renovated baths. Fenced yard with ample parking. Just off famous US1 this property is sited on a spacious lot with plenty of versatility! Zoning is Suburban Commercial (SC) which may allow for a Special Vacation Rental Permit. Perfect property for an owner occupier or investor. Wraparound porch offers sunrise

Bascom Grooms Bascom Grooms Real Estate (KW)

21161 Old State Road 4a, Summerland Key, FL 33042

/49
Est $325,789 Not Listed For Sale
701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

/44
$1,250,000
- 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
/47
$350,000 Sold Aug 14, 2025
- 675 Sq Ft
- $519/SF
- 228 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1984
701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

Currently the LOWEST priced waterfront property in Venture Out! Seller says bring an offer! Welcome to a slice of paradise tucked away in the gated community of Venture Out on Cudjoe Key, where your dream of coastal living becomes a reality. This charming 2-bedroom, 1.5-bathroom home invites you to embrace the tropical lifestyle, offering the perfect blend of comfort and tranquility. The interior

Melissa Graham Bluescape Real Estate

701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

/8
Est $579,753 Not Listed For Sale
17256 Keystone Rd, Sugarloaf Key, FL 33042

17256 Keystone Rd, Sugarloaf 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
/19
$505,000 Sold Jul 30, 2025
- 1,056 Sq Ft
- $478/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
134 Tortuga Ln, Summerland Key, FL 33042

Waterfront Fixer-Upper with Endless Potential on Cudjoe Key in the Magical Lower Keys!Embrace the opportunity to transform this waterfront gem into your Florida Keys dream retreat! Nestled in the desirable community behind the famous Square Grouper Restaurant this property offers direct boating access to the Atlantic Ocean--no bridges, no hassle, just open water in mere minutes.Situated on a

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

134 Tortuga Ln, Summerland Key, FL 33042

/2
Not Listed For Sale
23008 Overseas Hwy, Cudjoe Key, FL 33042

23008 Overseas Hwy, Cudjoe Key, FL 33042

/53
$949,000
- 2 Beds
- 2 Baths
- 1,620 Sq Ft
22852 John Silver Ln, Summerland Key, FL 33042

Paradise Awaits on Cudjoe KeyDiscover 22852 John Silver Lane, a rare A-frame waterfront retreat in the peaceful Cutthroat Harbor Estates. This two-bedroom, two-bath home embodies the perfect balance of Keys character and modern comfort, wrapped in lush palms and native landscaping that create a true island sanctuary.Inside, soaring vaulted ceilings and impact-rated windows and doors fill the

Matthew Sheehan

Ocean Sotheby's International Realty

(786) 981-3309

22852 John Silver Ln, Summerland Key, FL 33042
/47
$1,075,000 Sold Jul 30, 2025
- 1,120 Sq Ft
- $960/SF
- 189 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
128 Le Grand Ln, Summerland Key, FL 33042

Welcome to your stunning 3-bedroom, 2-bathroom oasis, nestled at the end of a peaceful cul-de-sac on a double canal. Surrounded by lush fruit trees, this home offers the perfect blend of tranquility and luxury. Step inside to find a spacious open floor plan that creates a bright and airy atmosphere, ideal for entertaining. The chef-friendly kitchen is equipped with modern appliances, making it a

Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

128 Le Grand Ln, Summerland Key, FL 33042

/14
Est $492,661 Not Listed For Sale
- 1 Bed
701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

/47
$589,900
- 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
/33
$1,350,000 Sold Jul 24, 2025
- 2,524 Sq Ft
- $535/SF
- 215 Days On Market
- 3 Beds
- 3 Baths
- Built 2011
20883 4th Ave, Cudjoe Key, FL 33042

Tucked away in the boating community of Cudjoe Gardens, this spacious 3 Bedroom plus Loft canal front home boasts over 2,500 sq. ft. with soaring ceilings and a 2-car garage. Thoughtfully designed for both relaxation and functionality, the space is filled with natural light which flows seamlessly from room to room. The massive Kitchen is highly functional featuring lots of granite counter space

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

20883 4th Ave, Cudjoe Key, FL 33042

/2
Est $828,543 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
53 Gold Boullion Rd, Cudjoe Key, FL 33042

53 Gold Boullion Rd, Cudjoe 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
/66
$910,000 Sold Jul 23, 2025
- 1,541 Sq Ft
- $591/SF
- 427 Days On Market
- 3 Beds
- 2 Baths
- Built 1990
246 Colson Dr, Summerland Key, FL 33042

SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet

Tracey Petrusha Venture Realty Group

246 Colson Dr, Summerland Key, FL 33042

/69
Not Listed For Sale
- 1 Bed
- 1 Bath
- 420 Sq Ft
701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 554, 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
/55
$1,800,000 Sold Jul 18, 2025
- 2,638 Sq Ft
- $682/SF
- 164 Days On Market
- 4 Beds
- 4 Baths
- Built 1993
22925 John Avery Ln, Summerland Key, FL 33042

Welcome to your forever island home! Fully furnished and turnkey! One of a kind, solid, custom-built (no modular here) coastal home with magnificent sunset, ocean and bay views from your wrap around porches and balconies. Located on crystal-clear waters filled with tropical fish, a boat ramp for beach launching kayaks or small boats and 60ft of waterfront with dock that can accommodate a 36ft

Jonathan Minerick Homecoin.com

22925 John Avery Ln, Summerland Key, FL 33042

Showing Results 41 - 80, Page 2 of 18

Florida Monroe County Cudjoe Key

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Monroe County Homes

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage