24

Summerland Key, FL Homes for Sale under $300,000

Section Image Section Image
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /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

    Agent Photo

    Coby Taylor

    Taylor & Assoc. RE, Inc.

    (786) 876-6382

    Unlisted Address
  • 701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    /20

    $214,500

    • 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 418-4615

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    /48

    $299,000

    • 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (305) 570-4554

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 761-5180

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    /37

    $275,000

    • Land

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

    Buildable RV Lot. Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Located in a serene, well-maintained gated community at Mile Marker 23. This RV/Buildable lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with landscaping, pea rock, storage box and concrete parking pad. Lot is equipped with full hookups

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    /17

    $265,000

    • Land

    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
  • 701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    /49

    $280,000

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    Welcome to your slice of Paradise in the florida Keys! This cozy one bed/one bath mobile home is located in the highly desirable Venture Out gated community on Cudjoe Key. Thoughtfully designed and fully furnished, this home comfortably sleeps four and is in move-in ready. Enjoy the bright and inviting Florida room featuring durable Hardie board siding, along with a covered tile patio outback,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
  • 231 Pelican Ln, Big Pine Key, FL 33043
    231 Pelican Ln, Big Pine Key, FL 33043
    231 Pelican Ln, Big Pine Key, FL 33043
    /11

    $249,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    231 Pelican Ln, Big Pine Key, FL 33043

    The price is for the lot AND permit. Pre-construction showing a picture of the modular that is permitted. Make your changes now before price increases with work conducted OR purchase the property with the permit and finish it on your own. *Approved ROGO Allocation and Active Building Permit as of February 25, 2025. Building permit is ready to be picked up. Permit number: SFDUP-2023-0113 is

    Donna Pezzi Keller Williams Key West Compass Realty

    231 Pelican Ln, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
    /24

    $265,000

    • Land

    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
  • 27426 Martinique Ln, Summerland Key, FL 33042
    27426 Martinique Ln, Summerland Key, FL 33042
    27426 Martinique Ln, Summerland Key, FL 33042
    /4

    $300,000

    • Land

    27426 Martinique Ln, Summerland Key, FL 33042

    Vacant 6,000 SF lot in desirable Ramrod Key, ideally positioned near the world-class Looe Key Reef and just a five-minute boat ride to Picnic Island. This property offers an exceptional opportunity to build in one of the Lower Keys' most sought-after lifestyle locations. Walking distance to local favorites including The Tiki Bar and Boondocks Grille & Draft House. Buyer to obtain building permit

    Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27426 Martinique Ln, Summerland Key, FL 33042
  • 29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
    /17

    $219,900

    • 2 Beds
    • 1 Bath
    • 300 Sq Ft

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043

    Live affordably or invest wisely in this 8 year old tiny home located on its own private lot in Big Pine Key, Lower Keys. This 24 ft Cornerstone model with two lofts is in perfect condition, thoughtfully maintained, and completely move in ready. The exterior has been newly repainted, and the interior is impeccably kept, showing pride of ownership throughout. The open living space includes a

    Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    /33

    $268,500

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

    Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • 0 Candice Ave, Little Torch Key, FL 33042
    0 Candice Ave, Little Torch Key, FL 33042
    0 Candice Ave, Little Torch Key, FL 33042
    /3

    $300,000

    • Land

    0 Candice Ave, Little Torch Key, FL 33042

    Rare opportunity to acquire a 6-parcel assemblage totaling approx. 13.67 acres on Little Torch Key. Includes five 6,000 sq. ft. Mates Beach lots on Candice Avenue (two Tier 3 Infill) and a 12.97+/- acre tract with 2.61 acres upland and 10.36 acres environmentally sensitive land. Perfect for agricultural or beekeeping use, conservation project, or long-term investment. Located in a desirable Lower

    Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

    0 Candice Ave, Little Torch Key, FL 33042
  • 29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043
    /24

    $274,999 New Construction

    • 1 Bed
    • 1 Bath
    • 312 Sq Ft

    29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043

    Welcome to easy island living in this 2021 Skyline Park Model Home located in the desirable Breeze Pines RV Estate. Thoughtfully designed, this 1-bedroom, 1-bath residence with a loft offers comfort, style, and functionality in a welcoming community setting. The home comes fully furnished and features a cozy fireplace, three mini-split A/C units for efficient climate control, and a well-equipped

    Halley Haack Coldwell Banker Schmitt RE Co.

    29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043
  • 30351 Flamingo Ln, Big Pine Key, FL 33043
    30351 Flamingo Ln, Big Pine Key, FL 33043
    30351 Flamingo Ln, Big Pine Key, FL 33043
    /10

    $279,999

    • Land

    30351 Flamingo Ln, Big Pine Key, FL 33043

    RemarksRemarks:Excellent neighborhood! Cleared land surrounding $800,000 homes plus range. In Rogo, Tier II . All homes are required to be CBS and no modular homes allowed. Plans for a 3 bedroom 2 bath home have been approved (county permits alterations to the house plans before you build, enabling you to design to your own specific needs). PERMIT Number is 16103833. Annual low association of

    Ana Tavel Paz Coldwell Banker - Pinecrest

    30351 Flamingo Ln, Big Pine Key, FL 33043
  • 29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
    /8

    $224,890

    • 2 Beds
    • 1.5 Baths
    • 780 Sq Ft

    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043

    Own a Piece of Paradise - A Renovator's Dream!Embrace the possibilities with this project home opportunity. Whether you're looking to renovate the existing structure or replace it with a modern stilt home, the choice is entirely yours.Property Highlights: Spacious Lot: Enjoy one of the larger lots in the area, offering plenty of room for creative outdoor designs.Home Features: A 2-bedroom,

    Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    /18

    $265,000

    • Land

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

    Welcome to RV Lot 642, located in the gated, waterfront community of Venture Out on Cudjoe Key. This well-positioned lot offers the perfect setup for your Florida Keys getaway, seasonal stay, or investment opportunity.Enjoy all the perks of a golf-cart-friendly community with resort-style amenities, including a large saltwater pool, marina with boat ramp, pickleball and tennis courts, bocce,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
  • 29859 Overseas Hwy Unit 23, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit 23, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit 23, Big Pine Key, FL 33043
    /15

    $200,000

    • 2 Beds
    • 1 Bath
    • 240 Sq Ft

    29859 Overseas Hwy Unit 23, Big Pine Key, FL 33043

    OPPORTUNITY AWAITS! INEXPENSIVE PLACE TO GET AWAY. Maybe do a Airbnb or rent out the lot space and bring your own RV when your in town. So you don't have to worry during hurricane season. Quiet RV park with common areas of outdoor tables and chairs, men and women bathrooms, laundry facilities. Pool 3-5 ft areas. Shuffle board. Community Kitchen and living area for gathering or hanging out.

    Rose Dell Keller Williams Key West Compass Realty

    29859 Overseas Hwy Unit 23, Big Pine Key, FL 33043
  • 28177 Julia Ave, Little Torch Key, FL 33042
    28177 Julia Ave, Little Torch Key, FL 33042
    28177 Julia Ave, Little Torch Key, FL 33042
    /5

    $240,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    28177 Julia Ave, Little Torch Key, FL 33042

    Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5

    Maria Acosta Keller Williams Capital Realty - Coral Gables

    28177 Julia Ave, Little Torch Key, FL 33042
  • 124 Cutthroat Dr, Cudjoe Key, FL 33042
    124 Cutthroat Dr, Cudjoe Key, FL 33042
    124 Cutthroat Dr, Cudjoe 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
  • 27057 Angelfish Rd, Ramrod Key, FL 33042
    27057 Angelfish Rd, Ramrod Key, FL 33042
    27057 Angelfish Rd, Ramrod Key, FL 33042
    /15

    $250,000

    • Land

    27057 Angelfish Rd, Ramrod Key, FL 33042

    6000 square foot lot with a building permit IN-PROCESS for a 3 bedroom / 2 bath stilted single family residence. 1320 square feet. The plans are for an Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment, great for your insurance rates.Located a bike ride away from Boondocks

    Donna Pezzi Keller Williams Key West Compass Realty

    27057 Angelfish Rd, Ramrod Key, FL 33042
  • 701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
    /26

    $259,000

    • 2 Beds
    • 1 Bath
    • 664 Sq Ft

    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042

    2 bedroom 1 bath mobile home located at 701 Spanish Main Dr Lot #457 Cudjoe Key FL in Venture Out, an individually owned residential condominium community with 24hr gated security located 20 miles from world famous Key West. This mobile home is on a non-waterfront lot w/ a peek-a-boo view of eastern facing canal. Other ideal use as a ROGO exempt buildable lot for a new elevated home. No age

    Deirdre Praught Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit 457, Cudjoe 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
    /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
  • 30921 Bailey Rd, Big Pine Key, FL 33043
    30921 Bailey Rd, Big Pine Key, FL 33043
    30921 Bailey Rd, Big Pine Key, FL 33043
    /4

    $245,000

    • Land

    30921 Bailey Rd, Big Pine Key, FL 33043

    Ready..Set.. Build!! Welcome to the future home site in the sought-after neighborhood of Big Pine Key! There are two ROGO-exempt vacant lots available for $245,000 each that offer a rare opportunity to build your dream home in paradise. No waiting for permit allocation!!

    Maryann Warren Coldwell Banker - Ft. Lauderdale

    30921 Bailey Rd, Big Pine Key, FL 33043
Florida Monroe County Summerland Key

Real Estate & Homes in Summerland Key, FL under $300,000

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

Browse a range of homes for sale under $300,000 in Summerland Key, offering accessible options for prospective buyers. With 24 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Summerland Key, FL.

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 © 2026 CoStar Group