80

Summerland Key, FL Homes for Sale with Pool

Section Image
  • 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

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
    /45

    $529,000

    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

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

    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 access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • 1733 Sunrise Dr, Big Pine Key, FL 33043
    1733 Sunrise Dr, Big Pine Key, FL 33043
    1733 Sunrise Dr, Big Pine Key, FL 33043
    /71

    $2,069,000

    • 3 Beds
    • 2 Baths
    • 1,849 Sq Ft

    1733 Sunrise Dr, Big Pine Key, FL 33043

    Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

    Norman De la Cruz Florida Realty of Miami Corp

    1733 Sunrise Dr, Big Pine Key, FL 33043
  • 231 E Shore Dr Unit 4, Summerland Key, FL 33042
    231 E Shore Dr Unit 4, Summerland Key, FL 33042
    231 E Shore Dr Unit 4, Summerland Key, FL 33042
    /7

    $4,375,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft

    231 E Shore Dr Unit 4, Summerland Key, FL 33042

    Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

    Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 4, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
    /61

    $595,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

    Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom home, built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 604, Cudjoe 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
  • 701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    /28

    $495,000

    • Land

    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
  • 701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
    /37

    $879,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

    VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT.Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental

    Jamie Caudill Lokation Real Estate

    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
  • 31473 Warner St, Big Pine Key, FL 33043
    31473 Warner St, Big Pine Key, FL 33043
    31473 Warner St, Big Pine Key, FL 33043
    /49

    $2,550,000

    • 3 Beds
    • 4 Baths
    • 2,087 Sq Ft

    31473 Warner St, Big Pine Key, FL 33043

    Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and

    Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    31473 Warner St, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    /59

    $549,000

    • 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
  • 701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    /18

    $445,000

    • Land

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

    Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
  • 3742 Seagrape St, Big Pine Key, FL 33043
    3742 Seagrape St, Big Pine Key, FL 33043
    3742 Seagrape St, Big Pine Key, FL 33043
    /47

    $5,390,000

    • 3 Beds
    • 3 Baths
    • 4,687 Sq Ft

    3742 Seagrape St, Big Pine Key, FL 33043

    Escape to “The Castle”, a luxurious gated Gulf-front estate spanning 1.14 acres on Big Pine Key. Built in 2014 with poured concrete, impact windows/doors, elevator, and generator, this 4,600+ sq. ft. masterpiece offers 3 bedrooms, 3 baths, and breathtaking Gulf views. Boaters enjoy 235’ of dockage: 140’ protected canal dock with lift, ramp, and slip, plus 95’ open-water pier dock with lift and

    Jo Ann Cook Ocean Sotheby's International

    3742 Seagrape St, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    /55

    $374,000

    • 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

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
  • 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 97, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    /54

    $839,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

    Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
  • 1163 de Lussan Ln, Summerland Key, FL 33042
    1163 de Lussan Ln, Summerland Key, FL 33042
    1163 de Lussan Ln, Summerland Key, FL 33042
    /61

    $1,699,000 Open Sun 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    1163 de Lussan Ln, Summerland Key, FL 33042

    Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift

    Jan Fritz Coldwell Banker Schmitt RE Co.

    1163 de Lussan Ln, Summerland Key, FL 33042
  • 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,

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
  • 27332 St Martin Ln, Ramrod Key, FL 33042
    27332 St Martin Ln, Ramrod Key, FL 33042
    27332 St Martin Ln, Ramrod Key, FL 33042
    /61

    $869,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    27332 St Martin Ln, Ramrod Key, FL 33042

    Welcome to Breezeswept Beach Estates-- In the heart of the Florida Keys! Here, boating, diving, and fishing are a way of life. This waterfront concrete block (CBS) 3-bed, 2-bath home sits on a deep, ocean-side canal just minutes to open water; Looe Key's clear blue reef is about a 15-minute boat ride away, and Key West is roughly 30 minutes by car. Thoughtfully updated for low-maintenance Keys

    Mark Gable Engel & Volkers Marathon

    27332 St Martin Ln, Ramrod Key, FL 33042
  • 701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
    /75

    $939,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

    This is the house for your boat!ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront residence. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water & an unmatched

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    /46

    $419,000

    • 2 Beds
    • 1 Bath
    • 833 Sq Ft

    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

    This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
  • 231 E Shore Dr Unit 2, Summerland Key, FL 33042
    231 E Shore Dr Unit 2, Summerland Key, FL 33042
    231 E Shore Dr Unit 2, Summerland Key, FL 33042
    /7

    $4,150,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft

    231 E Shore Dr Unit 2, Summerland Key, FL 33042

    Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

    Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 2, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
    /77

    $450,000

    • Land

    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

    Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and walkway,

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
  • 2211 San Sebastian Dr, Big Pine Key, FL 33043
    2211 San Sebastian Dr, Big Pine Key, FL 33043
    /2

    $1,700,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft

    2211 San Sebastian Dr, Big Pine Key, FL 33043

    Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled

    Greg MacLaren Internet Realty of the Florida Keys

    2211 San Sebastian Dr, 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
    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
  • 231 E Shore Dr Unit 5, Summerland Key, FL 33042
    231 E Shore Dr Unit 5, Summerland Key, FL 33042
    231 E Shore Dr Unit 5, Summerland Key, FL 33042
    /7

    $4,400,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft

    231 E Shore Dr Unit 5, Summerland Key, FL 33042

    Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

    Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 5, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    /56

    $579,900

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

    Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
  • 3746 Park Ave, Big Pine Key, FL 33043
    3746 Park Ave, Big Pine Key, FL 33043
    3746 Park Ave, Big Pine Key, FL 33043
    /52

    $1,700,000

    • 2 Beds
    • 2 Baths
    • 1,312 Sq Ft

    3746 Park Ave, Big Pine Key, FL 33043

    Welcome to your private paradise in the Lower Keys! This beautifully updated 2 bed, 2 bath two-story home offers complete privacy with no direct neighbors on all sides, making it a peaceful escape surrounded by nature and the charm of the Key Deer.Step outside to your tropical oasis featuring a brand-new concrete heated pool, concrete dock with a boat lift and jet ski lift, plus an elevated

    Kelsey Caputo Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    3746 Park Ave, Big Pine Key, FL 33043
  • 1631 Sunrise Dr, Big Pine Key, FL 33043
    1631 Sunrise Dr, Big Pine Key, FL 33043
    1631 Sunrise Dr, Big Pine Key, FL 33043
    /56

    $2,099,000 New Construction

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft

    1631 Sunrise Dr, Big Pine Key, FL 33043

    Seller motivated and furnishings can convey. This 2023 new construction waterfront home in Tropical Bay Estates offers luxury coastal living with stunning sunrise and water views from nearly every room. Built with full CBS construction on 10-foot stilts, it features 10-foot ceilings, 8-foot doors, impact windows, and a metal roof for durability and storm protection. The 2,000+ sq ft open floor

    Hector Vazquez Premium Properties Real Estate

    1631 Sunrise Dr, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    /49

    $669,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

    OCEANFRONT TRANSIENT RENTAL IN VENTURE OUT - CUDJOE KEYAmazing open water views of the sparkling Atlantic set the tone the moment you arrive. From this premier waterfront location, you'll enjoy sweeping vistas of the marina, lagoon, Tiki hut, and the iconic Bird Point sanctuary. Sunrise glows over endless blue water, creating a peaceful and ever-changing coastal backdrop.Positioned on a 35-foot

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    /30

    $460,000

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

    Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    /46

    $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 Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
  • 231 E Shore Dr Unit 1, Summerland Key, FL 33042
    231 E Shore Dr Unit 1, Summerland Key, FL 33042
    231 E Shore Dr Unit 1, Summerland Key, FL 33042
    /7

    $3,995,900 New Construction

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft

    231 E Shore Dr Unit 1, Summerland Key, FL 33042

    Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

    Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 1, Summerland Key, FL 33042
  • 27433 Antigua Rd, Summerland Key, FL 33042
    27433 Antigua Rd, Summerland Key, FL 33042
    27433 Antigua Rd, Summerland Key, FL 33042
    /60

    $175,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    27433 Antigua Rd, Summerland Key, FL 33042

    NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • 27426 Martinique Ln, Summerland Key, FL 33042
    27426 Martinique Ln, Summerland Key, FL 33042
    27426 Martinique Ln, Summerland Key, FL 33042
    /44

    $1,174,000

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft

    27426 Martinique Ln, Summerland Key, FL 33042

    Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

    Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27426 Martinique Ln, Summerland Key, FL 33042
  • 22815 Port Royal Ln, Summerland Key, FL 33042
    22815 Port Royal Ln, Summerland Key, FL 33042
    22815 Port Royal Ln, Summerland Key, FL 33042
    /23

    $3,600,000

    • 4 Beds
    • 4.5 Baths
    • 3,228 Sq Ft

    22815 Port Royal Ln, Summerland Key, FL 33042

    DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND w/room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

    Rhonda Gailey Gailey Enterprises Real Estate

    22815 Port Royal Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    /21

    $575,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

    Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and

    Mary Conklin Action Keys Realty of the Lower FL Keys LLC

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
  • 231 E Shore Dr Unit 3, Summerland Key, FL 33042
    231 E Shore Dr Unit 3, Summerland Key, FL 33042
    231 E Shore Dr Unit 3, Summerland Key, FL 33042
    /7

    $4,375,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft

    231 E Shore Dr Unit 3, Summerland Key, FL 33042

    Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10'

    Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 3, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    /11

    $480,000

    • Land

    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
  • 29558 Ranger Ave, Big Pine Key, FL 33043
    29558 Ranger Ave, Big Pine Key, FL 33043
    29558 Ranger Ave, Big Pine Key, FL 33043
    /19

    $1,750,000 New Construction

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft

    29558 Ranger Ave, Big Pine Key, FL 33043

    Experience the Ultimate Keys Lifestyle - New Construction with 75' of Waterfront on a Wide Boating CanalComing Fall 2025 - Nestled on a spacious 7,500 sqft lot (75x100) along a deep, wide boating canal, this brand new 1,500 sqft home offers the perfect blend of modern coastal living and exceptional boating access. With quick entry to Pine Channel, you're just minutes from both the Atlantic Ocean

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    29558 Ranger Ave, Big Pine Key, FL 33043
  • 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

Showing Results 41 - 80, Page 2 of 2

Florida Monroe County Summerland Key

Homes for Sale with Pool in Summerland Key, FL

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

In Summerland Key, there are currently 80 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Summerland Key, FL and discover your ideal residence.

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