18

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

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  • /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
  • /19

    $215,000

    • 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
  • /6

    $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

    28177 Julia Ave, Little Torch Key, FL 33042
  • /58

    $295,000

    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

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

    INCOME PRODUCING POWERHOUSE! Welcome to 'Conch Hideaway' #423, a proven tropical retreat and turnkey business in the premier Venture Out community. This charming 1BD/1BA home is a high-performing vacation rental that grossed $30,705 in 2025! INVESTMENT HIGHLIGHTS: Already live with rentals for 2026, this property has 27 days currently booked with $2,085.05 in gross revenue transferring to the

    Kate Baldwin Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
  • /2

    $275,000

    • Land

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

    Builders and Developers 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 619097, Cudjoe Key, FL 33042
  • /14

    $258,000

    • Land

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

    Venture Out RV Lot - Prime Location Near the StoreOpportunity to own a spacious RV lot in the highly desirable Venture Out community in Cudjoe Key. This pie-shaped lot measures approximately 65' x 67' x 63', offering generous space for your RV, outdoor living area, and parking.Conveniently located just a short distance from the community store and amenities, this lot provides easy access to

    Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
  • /2

    $299,000

    • Land

    28168 Julia Ave, Little Torch Key, FL 33042

    ROGO EXEMPT LOT! Build Now, No Waiting, Water Meter On Site, 6000 SF, Boat Ramp Within Walking Distance, Live The Dream. Single family home next door going on the market soon, buy both!

    Doug Addeo Regional Trust Corporation

    28168 Julia Ave, Little Torch Key, FL 33042
  • /49

    $275,000

    • 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
  • /17

    $255,000

    • 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

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /18

    $255,000

    • 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,

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
  • /4

    $275,000

    • 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
  • /33

    $255,000

    • 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

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 533, Cudjoe 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
  • /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
  • /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
  • /24

    $259,000

    • 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

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /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
  • /24

    $269,999 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

Home Trends in Summerland Key, FL

Housing Trends

Median Sale Price
$1,150,000
Median Single Family Sale Price
$1,185,000
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$915
Number of Homes for Sale
69
Last 12 months Home Sales
111
Months of Supply
7.50
Median List Price
$1,312,500
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-2%
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