35

Summerland Key, FL Homes for Sale under $500,000

Section Image Section Image
  • /10

    $474,000

    $25K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $1,394,118 per Acre

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit and DEP and Army Corp mitigation fees paid on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • /23

    $459,000

    • Land
    • 1,742 Sq Ft
    • $11,475,000 per Acre

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

    Canal-front Paradise Awaits! Incredible view from your seawall!RV Lot 609 in Venture Out.Experience the epitome of waterfront Florida Keys living on this Canal Front RV Lot with 40' Seawallnestled within an exclusive gated community.This beautiful canal front property boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 40 ft seawall.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
  • /5

    $285,000

    • Land
    • 1.01 Acres
    • $282,178 per Acre

    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

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    Unlisted Address
  • /39

    $485,000

    $10K PRICE DROP
    • 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 withFlorida 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.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • /3

    $375,000

    • Land
    • 6,000 Sq Ft
    • $2,722,500 per Acre

    27378 Jamaica Ln, Summerland Key, FL 33042

    Vacant lot with active building permit. Permit and plans include a fully designed green home with full concrete construction and concrete roof for 3 bedroom 2.5 bathrooms, large porch, storage and guest space, downstairs storm rated impact windows and doors, solar panel, gray water reclaim system plus rainwater system for irrigation and boat washing fish at Dawn cook your cat by dusk near Loki

    Agent Photo

    Natallie Liz

    Expert Realty LLC

    27378 Jamaica Ln, Summerland Key, FL 33042
  • /17

    $255,000

    $10K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /58

    $267,000

    $28K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

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

    $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
  • /14

    $395,000

    • Land
    • 6,098 Sq Ft
    • $2,821,429 per Acre

    24285 Caribbean Dr, Summerland Key, FL 33042

    Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has

    Donna Pezzi Keller Williams Key West Compass Realty

    24285 Caribbean Dr, Summerland Key, FL 33042
  • /2

    $235,000

    $20K PRICE DROP
    • Land
    • 7.09 Acres
    • $33,145 per Acre

    Lot 7 Parcel 10, Cudjoe Key, FL 33042

    This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

    Pamela Stangler Expert Realty LLC

    Lot 7 Parcel 10, Cudjoe Key, FL 33042
  • /24

    $259,000

    $6K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,180,000 per Acre

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared 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 are always

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /51

    $425,000

    • 2 Beds
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

    Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

    Justyn Ewald Expert Realty LLC

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
  • /27

    $320,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

    Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
  • /47

    $445,000

    $10K PRICE DROP
    • Land
    • 2,078 Sq Ft
    • $9,328,296 per Acre

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

    ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
  • /19

    $425,000

    $50K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $8,500,000 per Acre

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

    Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • /13

    $450,000

    $92K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $2,812,500 per Acre

    1147 Basque Ln, Cudjoe Key, FL 33042

    BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water

    Brad Baker Key to the Keys Real Estate, Inc

    1147 Basque Ln, Cudjoe Key, FL 33042
  • /4

    $350,000

    • Land
    • 8,276 Sq Ft
    • $1,842,105 per Acre

    22776 Overseas, Cudjoe Key, FL 33042

    Prime Cudjoe Key Commercial Opportunity! Cleared Suburban Commercial parcel offering outstanding highway frontage and excellent visibility on the Overseas Highway. Zoning SC allows for a variety of uses flood zone AE 9 tier 3 lot. For investment or owner-use. Owner financing may be available to qualified buyers. Bring your vision and capitalize on one of the Lower Keys' high-exposure commercial

    Rose Dell Keller Williams Key West Compass Realty

    22776 Overseas, Cudjoe Key, FL 33042
  • /3

    $215,000

    • Land
    • 7,840 Sq Ft
    • $1,194,444 per Acre

    27334 Saint Lucie Ln, Big Pine, FL 33042

    Rare opportunity to own a piece of paradise in the heart of the Florida Keys. Located in the desirable Breezeswept Beach Estates community on Ramrod Key, this canal-front homesite offers the perfect blend of tranquility, natural beauty, and island living. The property benefits from a recorded Lot Line Adjustment that established the current buildable lot configuration, creating an excellent

    Gilberto Imery Gilvan Realty Corp

    27334 Saint Lucie Ln, Big Pine, FL 33042
  • /45

    $493,000

    $36K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

    MINI LOBSTER SEASON PRICE REDUCTION!!! Price DROPPED AGAIN below 500k! This is THE lowest 2BR/BA priced home in Venture Out on Cudjoe Key! MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • /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
  • /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
  • /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
  • /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
  • /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
  • /14

    $255,000

    $255K PRICE INCREASE
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042

    Welcome to island living at its best in the gated waterfront community of Venture Out on Cudjoe Key. Lot 399 is a desirable 35' x 69' corner RV lot offering ocean peeks, full hookups, and endless possibilities. Whether you're looking for a personal Florida Keys retreat, an income-producing investment, or the perfect spot to build your future island home, this ROGO-exempt property checks all the

    Monika Rydzak eXp Realty LLC KW Branch

    701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042
  • /53

    $449,999

    • 1 Bed
    • 1 Bath
    • 408 Sq Ft

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

    Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key.NIGHTLY RENTALS ALLOWEDEnjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home,

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
  • /5

    $249,000

    $26K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $1,556,250 per Acre

    1155 Thatch Ln, Cudjoe Key, FL 33042

    Build your Florida Keys dream in Cudjoe Key just 3 lots from open water. Dock has already been approved and house plans are ready to submit to the county to begin the ROGO process.

    Tommy Mack Coastal Collection Real Estate Inc.

    1155 Thatch Ln, Cudjoe Key, FL 33042
  • /15

    $209,900

    • Land
    • 871 Sq Ft
    • $10,495,000 per Acre

    29859 Overseas Hwy Unit 27, Big Pine Key, FL 33043

    Welcome to 'The Island Girl'! This RV lot is an excellent investment at a low price. It is being booked as a very successful short term vacation rental with high profits and little overhead. This property is a little slice of paradise, lined with fruit trees and other tropical plants providing privacy and that 'keys vibe'. Enjoy the space anytime you want and rent it out the rest of the time.

    Cheryl Billings Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    29859 Overseas Hwy Unit 27, Big Pine Key, FL 33043
  • /30

    $499,000

    $40K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,253 Sq Ft

    31541 Avenue A, Big Pine Key, FL 33043

    Welcome to this Key West-style home located on Big Pine Key! Situated on a generous 7500 square-foot fully fenced lot, this property offers ample space for parking and storage, making it a perfect island retreat for those looking to escape the hustle and bustle. As you step inside, you'll be greeted by the cozy charm of two bedrooms and a well-appointed bathroom, providing a comfortable living

    Melissa Graham Bluescape Real Estate

    31541 Avenue A, Big Pine Key, FL 33043
  • /52

    $487,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

    Seller is Motivated!Coastal Charm Meets Modern ComfortWelcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key.Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
  • /8

    $365,000

    • Land
    • 2,178 Sq Ft
    • $7,300,000 per Acre

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

    Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living.Located within the

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
  • /12

    $400,000

    $20K PRICE DROP
    • Land
    • 6,098 Sq Ft
    • $2,857,143 per Acre

    29517 Big Pine St, Big Pine Key, FL 33043

    Commercial waterfront lot at 29517 Big Pine St, Big Pine Key. Deep-water canal with quick access to both the Gulf of Mexico and the Atlantic Ocean, icommercial fishing, marine operations, boating, or waterfront business use. Located on a quiet cul-de-sac with exceptional privacy--no neighbors in front or on either side. Nearly surrounded by county-owned land that is not expected to be developed.

    Steven Koleno Beycome of Florida, LLC

    29517 Big Pine St, Big Pine Key, FL 33043
  • /27

    $350,000

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 726 Sq Ft

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

    Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

    Monika Rydzak EXP Realty LLC

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
  • /16

    $320,000

    $5K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $3,200,000 per Acre

    27935 Tarpon Terrace, Summerland Key, FL 33042

    Heather Mason Coastal Collection Real Estate Inc.

    27935 Tarpon Terrace, Summerland Key, FL 33042
  • /11

    $460,000

    $20K PRICE DROP
    • Land
    • 1,742 Sq Ft
    • $11,500,000 per Acre

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

    Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
  • /6

    $499,000

    • Land
    • 6,969 Sq Ft
    • $3,118,750 per Acre

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042

    Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

    Lauren Dunn Coldwell Banker Schmitt Islamorada

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,164,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$1,000,000
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$921
Number of Homes for Sale
52
Last 12 months Home Sales
111
Months of Supply
5.60
Median List Price
$1,269,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home