80

Recently Sold Cudjoe Key Homes

Section Image
  • 701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    /36

    $330,000 Sold Apr 17, 2025

    • 728 Sq Ft
    • $453/SF
    • 63 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1983

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

    Welcome to your slice of paradise! This beautifully updated home is on the quiet, serene southwest side of the highly sought-after Venture Out Resort. With no neighbors behind you, you can enjoy added privacy and tranquility. The home is conveniently located next to the bathhouse for added convenience. Featuring two bedrooms and one bathroom, there is plenty of space to spread out and relax. The

    Frank Griffiths Ocean Sotheby's International

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
  • 268 Spanish Main Dr, Summerland Key, FL 33042
    268 Spanish Main Dr, Summerland Key, FL 33042
    268 Spanish Main Dr, Summerland Key, FL 33042
    /44

    $650,000 Sold Apr 17, 2025

    • 1,056 Sq Ft
    • $616/SF
    • 86 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1979

    268 Spanish Main Dr, Summerland Key, FL 33042

    Charming fishing bungalow located on oceanside Cudjoe Key just waiting to be yours. This waterfront haven features two bedrooms, two bathrooms and just under 1,100 square feet inside plus a permitted downstairs enclosure with plumbing and electric. Enjoy room for all to entertain in the open concept living area that seamlessly leads into the kitchen and dining. Waterside screened porch allows for

    Ally Kelley Ocean Sotheby's International

    268 Spanish Main Dr, Summerland Key, FL 33042
  • 468 Sawyer Dr, Summerland Key, FL 33042
    468 Sawyer Dr, Summerland Key, FL 33042
    468 Sawyer Dr, Summerland Key, FL 33042
    /57

    $1,375,000 Sold Apr 17, 2025

    • 1,797 Sq Ft
    • $765/SF
    • 215 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1972

    468 Sawyer Dr, Summerland Key, FL 33042

    Discover a Rare Gem in Cudjoe Gardens: Double Waterfront Lot with Private Boat BasinNestled in the Cudjoe Gardens costal community, this unique canal-front home boasts 4 bedrooms and 4 bathrooms, with an expansive upper deck offering stunning waterway views and breathtaking sunsets. The main house is ground level CBS construction and features terrazzo flooring throughout, capturing the true

    Stacy Shahan Island Real Estate Company Florida Keys

    468 Sawyer Dr, Summerland Key, FL 33042
  • 20914 7th Ave W, Summerland Key, FL 33042
    20914 7th Ave W, Summerland Key, FL 33042
    20914 7th Ave W, Summerland Key, FL 33042
    /40

    $850,000 Sold Mar 31, 2025

    • 1,312 Sq Ft
    • $648/SF
    • 59 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1987

    20914 7th Ave W, Summerland Key, FL 33042

    Welcome to your perfect coastal retreat! This inviting 2-bedroom, 2-bath home plus office offers the ideal blend of comfort and convenience for boating enthusiasts. Nestled on the Oceanside with no bridges to navigate, it boasts a private 15,000 lb boatlift on 80 ft concrete dock a generous 4-ft draft making it a dream for those who love the water. Relax and unwind in the screened patio, perfect

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    20914 7th Ave W, Summerland Key, FL 33042
  • 271 W Indies Dr, Ramrod Key, FL 33042
    271 W Indies Dr, Ramrod Key, FL 33042
    271 W Indies Dr, Ramrod Key, FL 33042
    /46

    $1,900,000 Sold Mar 27, 2025

    • 2,358 Sq Ft
    • $806/SF
    • 342 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2023

    271 W Indies Dr, Ramrod Key, FL 33042

    Brand new construction in Breezeswept Beach Estates! This modern 2,358 sq. ft. pool home offers unbeatable Open Water Views and high-end finishes. The open-concept layout features a Chef's Kitchen with premium stainless steel appliances, quartz countertops, ample storage, and a large island. A separate bar with a wine cooler adds convenience. Impact sliding glass doors lead to a covered veranda

    Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    271 W Indies Dr, Ramrod Key, FL 33042
  • 701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
    /32

    $450,000 Sold Mar 19, 2025

    • Land
    • 256 Days On Market

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

    A Fisherman's Paradise for the Big Boaters! This 40' seawall RV site located in the coveted Venture Out community is the perfect vacation and or income producing property for nightly/weekly rentals. The 60' wide canal is one of the best in the park providing deep draft clear water with ample maneuverability for the big boats. The canal provides a straight shot out to Kemp Channel and the open

    Paul Rogers Coldwell Banker Schmitt RE Co. Lower Keys Office

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
    /47

    $312,500 Sold Mar 17, 2025

    • 520 Sq Ft
    • $601/SF
    • 194 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2000

    701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

    OPEN WATER VIEWS with TRANSIENT RENTAL. This home is well cared for with newer construction (2000) offers a inviting opportunity to soak up Florida Keys sunshine with amenities readily available. Turnkey features allow you to move right in or get immediately into the rental market. Upgraded vinyl plank flooring, newly added stackable washer and dryer, all new drywall, accordion hurricane

    Anne Press Lokation Real Estate

    701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
    /14

    $225,000 Sold Mar 07, 2025

    • Land
    • 246 Days On Market

    701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

    Transient RV/Buildable lot in the much sought after Venture Out at Cudjoe Key. This is your chance to own a piece of paradise at an affordable price! The Venture Out Community is located only 19 miles from Key West, but with all of the amenities here you may never want to leave! There is a heated pool, hot tub, fuel docks, boat ramps, fish cleaning stations, bocce ball and tennis courts, pickle

    Mary Conklin Action Keys Realty FL Keys Inc

    701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
  • 184 Cutthroat Dr, Summerland Key, FL 33042
    184 Cutthroat Dr, Summerland Key, FL 33042
    184 Cutthroat Dr, Summerland Key, FL 33042
    /48

    $940,000 Sold Feb 28, 2025

    • 2,320 Sq Ft
    • $405/SF
    • 184 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1963

    184 Cutthroat Dr, Summerland Key, FL 33042

    Welcome to 184 Cutthroat Drive, a wonderful income producing waterfront home on the peaceful Cudjoe Key. This home is being sold fully furnished and with kayaks! Has a spacious open floor plan with lots of natural light.Main Level (Upstairs):4 bedrooms, split for plenty of privacy2 full bathroomsLarge living, dining area, and kitchen with an open layout and tons of counter space and cabinets, and

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    184 Cutthroat Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
    /29

    $800,000 Sold Feb 27, 2025

    • 828 Sq Ft
    • $966/SF
    • 14 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2001

    701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

    Beautiful open water home with direct ocean access. Completely furnished, ready to rent, future bookings in place. 52 foot concrete seawall with dock posts. Downstairs locked storage for all your fishing gear and what not, open deck for sunning, covered area for grilling and entertaining, fishing off the seawall. Gorgeous sunrise and sunsets. Community offers full service marina, convenience

    Susan Rich Select Properties of NWFL

    701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
  • 8 Calico Jack Circle Cir, Verifying, FL 33042
    8 Calico Jack Circle Cir, Verifying, FL 33042
    8 Calico Jack Circle Cir, Verifying, FL 33042
    /15

    $165,000 Sold Feb 24, 2025

    • Land
    • 18 Days On Market

    8 Calico Jack Circle Cir, Verifying, FL 33042

    Great Cudjoe Key Location with good boating access and sunset skies views down the canal. This lot can be purchased with house next door 22837 Calico Jack Circle. Picture a pool, tiki hut, family fun with beautiful Florida Keys waters... See lot survey in documents tab. Property outline in pictures is approximate. There is a possibility of change to AE zone. Reach out for further information.

    Beata Sharpe COLDWELL BANKER VANGUARD REALTY

    8 Calico Jack Circle Cir, Verifying, FL 33042
  • 8 Calico Jack Cir, Cudjoe Key, FL 33042
    8 Calico Jack Cir, Cudjoe Key, FL 33042
    8 Calico Jack Cir, Cudjoe Key, FL 33042
    /16

    $165,000 Sold Feb 24, 2025

    • Land
    • 212 Days On Market

    8 Calico Jack Cir, Cudjoe Key, FL 33042

    Great Cudjoe Key Location with good boating access and sunset skies views down the canal. This lot can be purchased with house next door 22837 Calico Jack Circle. Picture a pool, tiki hut, family fun with beautiful Florida Keys waters... See lot survey in documents tab. Property outline in pictures is approximate. There is a possibility of change to AE zone. Reach out for further information.

    Beata Sharpe Coldwell Banker Vanguard Realty

    8 Calico Jack Cir, Cudjoe Key, FL 33042
  • 22918 Cudjoe Dr, Cudjoe Key, FL 33042
    22918 Cudjoe Dr, Cudjoe Key, FL 33042
    22918 Cudjoe Dr, Cudjoe Key, FL 33042
    /33

    $725,000 Sold Feb 21, 2025

    • 1,431 Sq Ft
    • $507/SF
    • 175 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2016

    22918 Cudjoe Dr, Cudjoe Key, FL 33042

    This beautifully maintained 3 bedroom, 2 bathroom home built in 2016 sits on a 7,500 square foot lot in highly sought after Cudjoe Key. Large open floorplan with dedicated dining area, well-appointed kitchen with granite countertops, stainless steel appliances and large center island offering plenty of space for family and friends to gather. Great insurance rates with metal roof, impact

    Pamela Stangler Expert Realty LLC

    22918 Cudjoe Dr, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
    /20

    $250,000 Sold Feb 21, 2025

    • Land
    • 167 Days On Market

    701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

    NIGHTLY RENTALS ALLOWED! Or build your Florida Keys dream home.Come on down to the ultimate RV paradise at this picture perfect lot in Venture Out! 35' x 69' of pure potential for your dream RV setup! Feel the good vibes as you park your rig and let the adventures begin! Dive into the laid-back lifestyle of Venture Out and make memories that will last a lifetime! Build your home here in the

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
    /40

    $550,000 Sold Feb 19, 2025

    • 816 Sq Ft
    • $674/SF
    • 22 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1996

    701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

    Waterfront Paradise Awaits!This charming two-bedroom, two-bath mobile home offers a truly unique waterfront living experience. Enjoy breathtaking views and direct access to the sparkling waters of Cudjoe Key.Key Features:* Prime Waterfront Location: Situated directly on the water with a 35-foot concrete seawall, providing deep water access for boating enthusiasts.* Large windows for amazing views

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
  • 22572 Jolly Roger Dr, Summerland Key, FL 33042
    22572 Jolly Roger Dr, Summerland Key, FL 33042
    22572 Jolly Roger Dr, Summerland Key, FL 33042
    /74

    $3,300,000 Sold Feb 18, 2025

    • 3,225 Sq Ft
    • $1023/SF
    • 313 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1963

    22572 Jolly Roger Dr, Summerland Key, FL 33042

    A luxury waterfront estate with panoramic ocean views, this walled and gated masterpiece surrounded by gorgeous landscaping provides utmost privacy and the perfect Keys lifestyle and comes completely furnished. The unique 6-bedroom, 4-bathroom layout offers ample space for family and guests with breathtaking ocean vistas from almost every room. A secluded backyard oasis features a private beach,

    Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

    22572 Jolly Roger Dr, Summerland Key, FL 33042
  • 20942 6th Ave W, Summerland Key, FL 33042
    20942 6th Ave W, Summerland Key, FL 33042
    20942 6th Ave W, Summerland Key, FL 33042
    /45

    $1,700,000 Sold Feb 13, 2025

    • 2,772 Sq Ft
    • $613/SF
    • 42 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1994

    20942 6th Ave W, Summerland Key, FL 33042

    Stunning canal front home in desirable Cudjoe Gardens, with Southern Exposure, massive 15,600 Sq. Ft. double lot, and deep-water access to Open Ocean and backcountry! Expertly outfitted with 125' of concrete seawall with running water, fillet station, swim ladders, 15K boat lift, davits, and turning basin! Situated on a clean flow-through canal, excellent for swimming and capable of accommodating

    Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    20942 6th Ave W, Summerland Key, FL 33042
  • 20864 4th Ave W, Summerland Key, FL 33042
    20864 4th Ave W, Summerland Key, FL 33042
    20864 4th Ave W, Summerland Key, FL 33042
    /41

    $2,075,000 Sold Feb 03, 2025

    • 3,056 Sq Ft
    • $679/SF
    • 19 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 2004

    20864 4th Ave W, Summerland Key, FL 33042

    This elegantly designed custom built ground level home was created by local architect Glenn Gray. Boasting a spacious open floor plan @ 3,056 sq ft. Two master bedrooms with ensuite baths, third bedroom, full bath and a half, and office all on first floor. Up the flight of stairs leads to a huge open loft space for a fourth bedroom/bunk room, theater room, art room or whatever your needs.

    Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

    20864 4th Ave W, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
    /35

    $217,000 Sold Jan 31, 2025

    • Land
    • 22 Days On Market

    701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

    TRANSIENT RENTALS ALLOWED!!Live the Island Life in Your Own Slice of Paradise! Ahoy, fellow adventurers! Set your sails for this dreamy RV lot nestled in the vibrant Venture Out Community, just a breezy 19 miles from the heart of Key West. This spacious 35' x 69' lot is ready to welcome even the biggest rigs, so bring your home on wheels and let the good times roll! With lush landscaping already

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
  • 22727 Jolly Roger Dr, Cudjoe Key, FL 33042
    22727 Jolly Roger Dr, Cudjoe Key, FL 33042
    22727 Jolly Roger Dr, Cudjoe Key, FL 33042
    /31

    $800,000 Sold Jan 31, 2025

    • 1,008 Sq Ft
    • $794/SF
    • 146 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2001

    22727 Jolly Roger Dr, Cudjoe Key, FL 33042

    Idyllic Canal-Front Cudjoe Key retreat on a generous fenced-in lot in a prime location! This bright and spacious Cutthroat Harbor Estates home boasts an open concept main living space and three generous bedrooms! Coming soon, the seller is replacing the existing roof with a new metal roof. Upon entry, this turnkey home is tailor-made for entertaining. The living room flows seamlessly with a

    Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    22727 Jolly Roger Dr, Cudjoe Key, FL 33042
  • 622 Sawyer Dr, Summerland Key, FL 33042
    622 Sawyer Dr, Summerland Key, FL 33042
    622 Sawyer Dr, Summerland Key, FL 33042
    /43

    $2,520,000 Sold Jan 31, 2025

    • 2,156 Sq Ft
    • $1169/SF
    • 165 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1986

    622 Sawyer Dr, Summerland Key, FL 33042

    Indulge in the epitome of Keys living with this delightful turnkey 3-bedroom, 3 1/2 bathroom stilt home on 1 1/2 lots. Embracing the coastal allure, this residence features serene blue to aqua tones indoors, complemented by elegant white plantation shutters that evoke a sense of timeless charm. Step onto the expansive covered patio, where panoramic views of the pool and a long canal stretch

    Laura Derrickson Keller Williams Coastal Partners

    622 Sawyer Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
    /27

    $240,000 Sold Jan 28, 2025

    • Land
    • 210 Days On Market

    701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

    Escape to your own piece of paradise in the Venture Out community, where the amenities are as plentiful as the margaritas at a Jimmy Buffett tribute. Picture yourself lounging by the heated pool overlooking the sparkling ocean. Serve up some friendly competition on the tennis courts or Pickleball courts, or head over to the marina to gas up for a day out on your boat. This is not just a property

    Katrina Vanek Bluescape Real Estate

    701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
  • 124 Yardarm Rd, Cudjoe Key, FL 33042
    124 Yardarm Rd, Cudjoe Key, FL 33042
    124 Yardarm Rd, Cudjoe Key, FL 33042
    /30

    $740,000 Sold Jan 21, 2025

    • 1,064 Sq Ft
    • $695/SF
    • 22 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2023

    124 Yardarm Rd, Cudjoe Key, FL 33042

    Welcome to this brand-new 3BD/2BA stilted modular home on the Gulfside of Cudjoe Key, just 20 minutes from Key West! Situated on a spacious 6,000 sq. ft. lot, this never-lived-in gem offers an inviting 1,064 sq. ft. open-concept design with soaring ceilings and sunlit interiors from large windows that bring the Florida sunshine indoors.**Enjoy the sleek tile flooring, a modern kitchen with

    Team Spottswood/Vazquez Truman & Co. (KW)

    124 Yardarm Rd, Cudjoe Key, FL 33042
  • 22940 Gasparilla Ln, Summerland Key, FL 33042
    22940 Gasparilla Ln, Summerland Key, FL 33042
    22940 Gasparilla Ln, Summerland Key, FL 33042
    /48

    $975,000 Sold Jan 21, 2025

    • 1,465 Sq Ft
    • $666/SF
    • 50 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1986

    22940 Gasparilla Ln, Summerland Key, FL 33042

    Stunning 2-Bedroom, 2-Bath Waterfront Home with Ocean Access! Discover your dream home in the heart of the Florida Keys! This beautifully renovated 2-bedroom, 2-bathroom waterfront home offers everything you need for a perfect island lifestyle. Enjoy direct boating access to the Atlantic Ocean from your private 60' dock and take in the spectacular ocean views from your spacious open floor

    Bobby Krug Ocean Sotheby's International Realty

    22940 Gasparilla Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
    /27

    $225,000 Sold Jan 13, 2025

    • Land
    • 161 Days On Market

    701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

    Oversized RV Lot for big RVs or Build your home here in the private, gated community of Venture Out on Cudjoe Key. Cleared and paved lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
    /30

    $649,000 Sold Jan 08, 2025

    • 864 Sq Ft
    • $751/SF
    • 176 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1999

    701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

    Welcome to your slice of paradise located in the gated Venture Out community! This stunning 2 bedroom, 2 bathroom home offers unparalleled views of the open water from the living room, kitchen, and outdoor entertaining areas. Step inside to discover a beautifully appointed interior that exudes both comfort and style. The spacious living room is the perfect spot to relax and unwind, while the

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
    /51

    $777,000 Sold Dec 23, 2024

    • 864 Sq Ft
    • $899/SF
    • 27 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2006

    701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

    Island Oasis Awaits! Welcome to your dream retreat in the heart of paradise! This turn-key 2 bedroom, 2 bath canal front home offers an idyllic escape with stunning open water views. Picture yourself waking up to the gentle sounds of the waves and enjoying your morning coffee while soaking in the tropical sunshine. Nestled within the secure, gated community of Venture Out on Cudjoe Key, this

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
  • 21024 2nd Ave, Summerland Key, FL 33042
    21024 2nd Ave, Summerland Key, FL 33042
    21024 2nd Ave, Summerland Key, FL 33042
    /35

    $1,025,000 Sold Dec 16, 2024

    • 1,313 Sq Ft
    • $781/SF
    • 196 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2005

    21024 2nd Ave, Summerland Key, FL 33042

    Presenting a stunning waterfront residence in the prestigious Cudjoe Gardens of Cudjoe Key, Florida. This exquisitely designed 2-bedroom, 2-bath home offers an abundance of natural light through its expansive windows and seamless indoor-outdoor flow via sliding glass doors, ideal for hosting and entertaining. The property features modern, upgraded appliances and is offered fully furnished with

    Britannie Wesley Bascom Grooms Real Estate (KW)

    21024 2nd Ave, Summerland Key, FL 33042
  • 0 La Fitte Dr, Cudjoe Key, FL 33042
    0 La Fitte Dr, Cudjoe Key, FL 33042
    0 La Fitte Dr, Cudjoe Key, FL 33042
    /14

    $385,000 Sold Dec 11, 2024

    • Land
    • 183 Days On Market

    0 La Fitte Dr, Cudjoe Key, FL 33042

    2 Tier III Highly visible Commercial Lots on US 1. These lots are located between Cudjoe Sales and The Square Grouper for maximum exposure. Access from LaFitte Dr and US 1 make it super accessible. Zoned SC

    Greg MacLaren Internet Realty of the Florida Keys

    0 La Fitte Dr, Cudjoe Key, FL 33042
  • 22903 Jolly Roger Dr, Summerland Key, FL 33042
    22903 Jolly Roger Dr, Summerland Key, FL 33042
    22903 Jolly Roger Dr, Summerland Key, FL 33042
    /44

    $685,000 Sold Nov 27, 2024

    • 1,152 Sq Ft
    • $595/SF
    • 108 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    22903 Jolly Roger Dr, Summerland Key, FL 33042

    Assumable VA mortgage at 2.2% Waterfront home with quick and easy access to open water and 135 feet of concrete seawall. Home is solid CBS construction with three bedrooms and one and a half bathrooms. Home has many updates, including new impact windows, fresh paint, light fixtures and roof coating. Large attached screeded in patio and laundry room are an extra bonus spaces. There is an

    Monique Thiel Sunshine State Realty Services

    22903 Jolly Roger Dr, Summerland Key, FL 33042
  • 320 Spanish Main Dr, Summerland Key, FL 33042
    320 Spanish Main Dr, Summerland Key, FL 33042
    320 Spanish Main Dr, Summerland Key, FL 33042
    /34

    $910,000 Sold Nov 26, 2024

    • 1,056 Sq Ft
    • $862/SF
    • 18 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1989

    320 Spanish Main Dr, Summerland Key, FL 33042

    Beautifully remodeled open floor plan 2 bed, 2 bath waterfront oasis offering stunning canal and sunset views, a large screened porch, and a 10,000 lb. boat lift. Inside, enjoy a modern kitchen with granite countertops, updated bathrooms, and wood-look tile flooring. The den off the living room is perfect for a home office or potential small 3rd bedroom.. The lower level (permitted 634 sqft)

    Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

    320 Spanish Main Dr, Summerland Key, FL 33042
  • 22861 John Silver Ln, Cudjoe Key, FL 33042
    22861 John Silver Ln, Cudjoe Key, FL 33042
    /2

    $60,000 Sold Nov 19, 2024

    • Land
    • 255 Days On Market

    22861 John Silver Ln, Cudjoe Key, FL 33042

    Tier III canal front lot in Cudjoe Key!

    Tommy Mack Coastal Collection Real Estate Inc.

    22861 John Silver Ln, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
    /21

    $435,000 Sold Nov 18, 2024

    • 770 Sq Ft
    • $565/SF
    • 0 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1978

    701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

    This is your chance to own an income property or full-time retreat in the Florida Keys! Cuddie cottage is currently the most competitively priced ocean front single family unit in Venture Out on Cudjoe Key.Make this 2-bedroom, 1-bath island home yours. World class boating and fishing from your own concrete dock equipped with filet table and ladder for quick salt water dips. Following is a

    Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

    701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042
    /41

    $250,000 Sold Nov 15, 2024

    • 316 Sq Ft
    • $791/SF
    • 193 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1980

    701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042

    Possible Seller Financing, Motivated seller! Income producing property! Welcome to your tropical paradise retreat on Cudjoe Key! This charming mobile home, nestled within the Venture Out community, offers the perfect balance of comfort, convenience, and island living. As you step inside, you'll be greeted by a cozy yet efficiently designed living space, complete with dining area, living room,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042
  • 133 Galleon Ln, Summerland Key, FL 33042
    133 Galleon Ln, Summerland Key, FL 33042
    133 Galleon Ln, Summerland Key, FL 33042
    /47

    $1,120,000 Sold Nov 14, 2024

    • 1,780 Sq Ft
    • $629/SF
    • 128 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    133 Galleon Ln, Summerland Key, FL 33042

    CANAL-FRONT POOL HOME IN CUDJOE KEY - step inside and you'll be impressed by the soaring, tongue and groove ceilings and exposed cedar beams throughout this custom-built design. Just shy of 1800 sq. ft., the living area is light and airy, a brand-new kitchen offers abundant white cabinets and quartz counters; all floors are tile. Pocket sliders open onto porches on both levels allowing the

    Patti Nickless Coldwell Banker Schmitt Real E

    133 Galleon Ln, Summerland Key, FL 33042
  • 22766 Jolly Roger Dr, Summerland Key, FL 33042
    22766 Jolly Roger Dr, Summerland Key, FL 33042
    22766 Jolly Roger Dr, Summerland Key, FL 33042
    /49

    $1,800,000 Sold Nov 14, 2024

    • 1,884 Sq Ft
    • $955/SF
    • 80 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    22766 Jolly Roger Dr, Summerland Key, FL 33042

    COASTAL BEAUTY and MODERN COMFORT in the Fabulous Florida Keys. This fully remodeled Atlantic Oceanfront residence offers a seamless fusion of modern comforts and the natural beauty that surrounds it. A spacious front yard, professionally landscaped with native flora, welcomes you to the property. Each of the three oversized bedrooms accommodate king size beds and walk-in or double door

    Donna Pezzi Keller Williams Key West Compass Realty

    22766 Jolly Roger Dr, Summerland Key, FL 33042
  • 22532 Jolly Roger Dr, Cudjoe Key, FL 33042
    22532 Jolly Roger Dr, Cudjoe Key, FL 33042
    22532 Jolly Roger Dr, Cudjoe Key, FL 33042
    /34

    $1,600,000 Sold Nov 14, 2024

    • 1,288 Sq Ft
    • $1242/SF
    • 157 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2019

    22532 Jolly Roger Dr, Cudjoe Key, FL 33042

    Welcome 22532 Jolly Roger Dr. This impressive open water 3/2 home was built in 2020. The home is finished with all impact rated doors and windows, plank tile flooring, stone countertops, metal roof, Hardie board siding, waterfront balcony and a spacious and inviting open floor plan. The lower level area is finished with street facing garage doors for privacy and security, seamlessly pavered

    Lynn Lucas Berkshire Hathaway HomeServices Keys Real Estate

    22532 Jolly Roger Dr, Cudjoe Key, FL 33042
  • Lot 7 Blk 14, Cudjoe Key, FL 33042
    Lot 7 Blk 14, Cudjoe Key, FL 33042
    /2

    $42,500 Sold Oct 31, 2024

    • Land
    • 94 Days On Market

    Lot 7 Blk 14, Cudjoe Key, FL 33042

    ROGO Lot for dedication purposes. Buyer to confirm points & process with Monroe County Dept. of Planning.

    Paul Rogers Coldwell Banker Schmitt RE Co. Lower Keys Office

    Lot 7 Blk 14, Cudjoe Key, FL 33042
  • 1106 Thatch Ln, Summerland Key, FL 33042
    1106 Thatch Ln, Summerland Key, FL 33042
    1106 Thatch Ln, Summerland Key, FL 33042
    /58

    $1,675,000 Sold Oct 23, 2024

    • 2,548 Sq Ft
    • $657/SF
    • 50 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2016

    1106 Thatch Ln, Summerland Key, FL 33042

    Fall in love with this fully furnished 4-bed, 3.5-bath oceanfront canal CBS home, offering 2,548 sq ft of luxury living and 1,370 sq ft of balcony space. Built in 2016, recent upgrades include a new pool and dock for the perfect Florida Keys lifestyle. The second floor has 3 bedrooms, 2 baths, a laundry room, a second living area, and a large balcony. The third floor boasts an open-concept living

    Aryl and Pati Robison RE/MAX All Keys Real Estate

    1106 Thatch Ln, Summerland Key, FL 33042
  • 1135 Hakluyt Ln, Cudjoe Key, FL 33042
    1135 Hakluyt Ln, Cudjoe Key, FL 33042
    1135 Hakluyt Ln, Cudjoe Key, FL 33042
    /8

    $200,000 Sold Sep 30, 2024

    • Land
    • 7 Days On Market

    1135 Hakluyt Ln, Cudjoe Key, FL 33042

    Build this 2-story, 3 bedroom, 2 bath, elevated waterfront home with great water views and boating in the very desirable area of Cutthroat Harbor Estates on Cudjoe Key. Located oceanside with only a short drive to Key West. Plans have been submitted and are currently in ROGO waiting for its allocation. Plenty of time to change the plans should you desire.

    John Nazzaro Keller Williams Realty Premier Properties

    1135 Hakluyt Ln, Cudjoe Key, FL 33042

Showing Results 1 - 40, Page 1 of 2

Florida Cudjoe Key Cudjoe Key

Recently Sold Real Estate & Homes in Cudjoe Key, Cudjoe Key

Learn more about living in Cudjoe Key

Frequently Asked Questions

What is the average time to sell a house in Cudjoe Key, FL?
The houses for sale in Cudjoe Key, FL spend an average of 129 days on the market.
What is the number of active homes for sale in Cudjoe Key, FL?
There are 37 active homes for sale in Cudjoe Key, FL.

Home Trends in Cudjoe Key, FL

On average, homes in Cudjoe Key, FL sell after 129 days on the market compared to the national average of 47 days. The average sale price for homes in Cudjoe Key, FL over the last 12 months is $1,402,916, down 3% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$1,120,000
Median Single Family Price
$1,175,000
Median Townhouse Price
$2,300,000
Median 2 Bedroom Price
$820,000
Average Price Per Sq Ft
$831
Number of Homes for Sale
37
Last 12 months Home Sales
72
Months of Supply
6.20
Median List Price
$1,285,000
Median Discount From 1st List Price
3%
Median Home Sale Price YoY Change
-10%
How to Buy a Home How to Sell a Home How to Rent a Home

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

Copyright © 2025 CoStar Group