Cudjoe Key, FL Homes

/33
$249,000
- 1 Bed
- 1 Bath
- 368 Sq Ft
701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room.The property is currently occupied by a long-term

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
/58
$1,164,000

Sold Dec 12, 2025

164 Tortuga Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1990
Last Sold Summary
- 3% Below List Price
- $831/SF
- 27 Days On Market
Current Estimated Value $1,156,148

Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

164 Tortuga Ln, Summerland Key, FL 33042

/50
Est $1,753,686

Not Listed For Sale

21025 Hamilton Ave, Summerland Key, FL 33042
- 6 Beds
- 3.5 Baths
- 4,060 Sq Ft
- Built 1983
21025 Hamilton Ave, Summerland Key, FL 33042

Last Sold Summary
- 47 Days On Market
Last Listing Agent Mike Kane Internet Realty of the Florida Keys

/9
$514,900
- Land
- 2,613 Sq Ft
- $8,581,667 per Acre
701 Spanish Main Dr Unit LOT 266, Cudjoe Key, FL 33042

Premier Waterfront RV Lot in Venture Out | 35' Seawall, Ocean Views & Proven Rental Income!Whether you are looking for your own personal Florida Keys getaway or a high-performing investment property, this lot offers the perfect blend of luxury, location, and lucrative returns. Boasting a consistent rental history, this turn-key property is a proven income producer with established guest

Carmen Brake Waterfront Keys Realty Inc.

701 Spanish Main Dr Unit LOT 266, Cudjoe Key, FL 33042
/4
$700,000

Sold Apr 23, 2026

20963 7th Ave W, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,556 Sq Ft
- Built 1985
Last Sold Summary
- 3% Below List Price
- $450/SF
Current Estimated Value $862,829

Last Listing Agent Wyelda Bierman Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

20963 7th Ave W, Summerland Key, FL 33042

/31
Est $656,105

Not Listed For Sale

701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042
- 2 Beds
- Built 1991
701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

Last Sold Summary
- 15 Days On Market
Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

/15
$895,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
135 Tortuga Ln, Summerland Key, FL 33042

If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and

Kathleen Reed Bruno Realty Group, Inc

135 Tortuga Ln, Summerland Key, FL 33042
/39
$1,300,000

Sold Jun 05, 2026

20838 5th Ave W, Cudjoe Key, FL 33042
- 3 Beds
- 2 Baths
- 1,944 Sq Ft
- Built 1987
Last Sold Summary
- 19% Below List Price
- $669/SF
- 187 Days On Market
Current Estimated Value $1,363,565

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

20838 5th Ave W, Cudjoe Key, FL 33042

/56
Est $1,774,014

Not Listed For Sale

20966 8th Ave W, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 2,166 Sq Ft
- Built 1982
20966 8th Ave W, Summerland Key, FL 33042

Last Sold Summary
- 31 Days On Market
Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

/38
$1,270,000

$120K PRICE DROP
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
174 Tortuga Ln, Cudjoe Key, FL 33042

Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Built in 2020 for peace of mind and

Sarah Bixby eXp Realty LLC

174 Tortuga Ln, Cudjoe Key, FL 33042
/27
$853,000

Sold Jan 09, 2026

22922 Blackbeard Ln, Cudjoe Key, FL 33042
- 3 Beds
- 2 Baths
- 1,195 Sq Ft
- Built 2012
Last Sold Summary
- 14% Below List Price
- $714/SF
- 105 Days On Market
Current Estimated Value $865,966

Last Listing Agent Krystal Thomas eXp Realty LLC

22922 Blackbeard Ln, Cudjoe Key, FL 33042

/41
Est $1,079,769

Not Listed For Sale

366 Sawyer Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,390 Sq Ft
- Built 1988
366 Sawyer Dr, Summerland Key, FL 33042

Last Sold Summary
- 4 Days On Market
Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

/12
$460,000

$35K PRICE DROP
- Land
- 2,178 Sq Ft
- $9,200,000 per Acre
701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

Anay Ramos Miami New Realty

701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
/18
$415,000

Sold Jun 26, 2026

701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
- Land
- 2,178 Sq Ft
- $8,300,000 per Acre
Last Sold Summary
- 12% Below List Price
- 228 Days On Market
Current Estimated Value $436,063

Last Listing Agent Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

/44
Est $801,491

Not Listed For Sale

268 Spanish Main Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1979
268 Spanish Main Dr, Summerland Key, FL 33042

Last Sold Summary
- 86 Days On Market
Last Listing Agent Ally Kelley Ocean Sotheby's International

/59
$535,000

$14K PRICE DROP
- 2 Beds
- 2 Baths
- 860 Sq Ft
701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

Amanda Taylor Bluescape Real Estate

701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
/62
$1,185,000

Sold Oct 06, 2025

22915 Bluegill Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 2001
Last Sold Summary
- 6% Below List Price
- $882/SF
- 37 Days On Market
Current Estimated Value $1,184,534

Last Listing Agent Deni Heintzelman KeyIsle Realty

22915 Bluegill Ln, Summerland Key, FL 33042

/36
Est $988,789

Not Listed For Sale

21066 3rd Ave, Summerland Key, FL 33042
- 2 Beds
- 1 Bath
- 1,245 Sq Ft
- Built 1974
21066 3rd Ave, Summerland Key, FL 33042

Last Sold Summary
- 326 Days On Market
Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

/50
$289,000

Under Contract
- 1 Bed
- 1 Bath
- 340 Sq Ft
701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
/2
$55,000

Sold Dec 04, 2025

Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
- Land
- 6,000 Sq Ft
- $399,300 per Acre
Last Sold Summary
- 90% Above List Price
- 73 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

/2
Est $1,334,360

Not Listed For Sale

23047 Bluegill Ln, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,440 Sq Ft
- Built 1991
23047 Bluegill Ln, Summerland Key, FL 33042

/52
$949,000

Pending
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
22811 Buccaneer Ln, Summerland Key, FL 33042

Looking for a move-in-ready waterfront home with concrete block construction and quick boating access? This beautifully updated Cudjoe Key retreat checks all the boxes! Tucked away on the south side of the neighborhood, you'll be just minutes from open water while enjoying a peaceful setting away from the noise of US-1. At the same time, you'll still be close to Lower Keys favorites like Square

Madeleine Young Island Welcome Real Estate LLC

22811 Buccaneer Ln, Summerland Key, FL 33042
/29
$235,000

Sold Oct 31, 2025

701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
- Land
- 2,078 Sq Ft
- $4,926,179 per Acre
Last Sold Summary
- 2% Below List Price
- 76 Days On Market
Current Estimated Value $252,576

Last Listing Agent Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

/49
Est $1,841,504

Not Listed For Sale

22766 Jolly Roger Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,884 Sq Ft
- Built 1989
22766 Jolly Roger Dr, Summerland Key, FL 33042

Last Sold Summary
- 80 Days On Market
Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

/3
$275,000
- Land
- 0 Sq Ft
0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042

Take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

Pamela Stangler Expert Realty LLC

0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042
/45
$1,300,000

Sold Mar 03, 2026

1185 Hakluyt Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1989
Last Sold Summary
- 7% Below List Price
- $1,128/SF
- 10 Days On Market
Current Estimated Value $1,282,207

Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

1185 Hakluyt Ln, Summerland Key, FL 33042

/29
Est $843,123

Not Listed For Sale

22774 Cudjoe Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,216 Sq Ft
- Built 1987
22774 Cudjoe Dr, Summerland Key, FL 33042

Last Sold Summary
- 44 Days On Market
Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

/45
$1,150,000

$100K PRICE DROP
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
20868 5th Ave W, Summerland Key, FL 33042

Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

Karen Haack Coldwell Banker Schmitt RE Co.

20868 5th Ave W, Summerland Key, FL 33042
/36
$685,000

Sold Oct 15, 2025

701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Built 2010
Last Sold Summary
- 16% Below List Price
- $793/SF
- 164 Days On Market
Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

/64
Est $1,169,433

Not Listed For Sale

184 Cutthroat Dr, Summerland Key, FL 33042
- 4 Beds
- 2 Baths
- 2,320 Sq Ft
- Built 1963
184 Cutthroat Dr, Summerland Key, FL 33042

Last Sold Summary
- 151 Days On Market
Last Listing Agent Beata Sharpe Coldwell Banker Schmitt Real Estate Co.

/55
$329,000

$98K PRICE DROP
- 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 as

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
/12
$269,000

Sold Sep 29, 2025

20822 1st Ave, Cudjoe Key, FL 33042
- Land
- 9,999 Sq Ft
- $1,171,764 per Acre
Last Sold Summary
- 10% Below List Price
- 18 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

20822 1st Ave, Cudjoe Key, FL 33042

/58
Est $1,652,364

Not Listed For Sale

22440 Jolly Roger Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,292 Sq Ft
- Built 1988
22440 Jolly Roger Dr, Summerland Key, FL 33042

Last Sold Summary
- 85 Days On Market
Last Listing Agent Sandra Tuttle Island Welcome Real Estate

/32
$339,000

$210K PRICE DROP
- 2 Beds
- 1 Bath
- 728 Sq Ft
701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

Melissa Graham Bluescape Real Estate

701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
/39
$900,000

Sold Jul 02, 2026

21073 7th Ave, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 2,198 Sq Ft
- Built 1975
Last Sold Summary
- $409/SF
- 0 Days On Market
Current Estimated Value $1,295,547

Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

21073 7th Ave, Summerland Key, FL 33042

/45
Est $1,178,267

Not Listed For Sale

23058 Sailfish Ln, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,280 Sq Ft
- Built 1980
23058 Sailfish Ln, Summerland Key, FL 33042

Last Sold Summary
- 145 Days On Market
Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

/42
$1,299,000

$26K PRICE DROP
- 3 Beds
- 2 Baths
- 1,741 Sq Ft
21025 3rd Ave, Summerland Key, FL 33042

Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

Diane Corliss Coldwell Banker Schmitt RE Co.

21025 3rd Ave, Summerland Key, FL 33042
/66
$775,000

Sold Aug 03, 2026

701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 842 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $920/SF
- 231 Days On Market
Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

/16
Est $1,927,453

Not Listed For Sale

23076 Tarpon Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
- Built 1975
23076 Tarpon Ln, Summerland Key, FL 33042

Last Sold Summary
- 82 Days On Market
Last Listing Agent Lisa Lennon Berkshire Hathaway HomeServices Knight & Gardner Realty

/16
$895,900

$94K PRICE DROP
- 2 Beds
- 2 Baths
- 960 Sq Ft
22961 John Avery Ln, Summerland Key, FL 33042

Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million!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

Rayden Vega Casa Miami Real Estate

22961 John Avery Ln, Summerland Key, FL 33042

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Cudjoe Key, FL Homes

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