Summerland Key, FL Homes for Sale

/54
$799,000
- 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
/61
$1,699,000 Open House 3/28
- 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
/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
/125
$10,700,000
- 6 Beds
- 8 Baths
- 4,894 Sq Ft
1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress-- built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set on

Lisa Swanson The Agency Florida Keys

1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
/10
$450,000
- Land
30324 Frigate Ln, Big Pine Key, FL 33043

CLEARED WATERFRONT CORNER LOT IN TROPICAL BAY with active building permit! Build your dream CBS home in a wonderful subdivision. Building permit is good till 2028! Large dock already in place. 20' on short side and 55 feet on the long side. Seller financing possible.

Derrick Johnson Coco Plum Real Estate

30324 Frigate Ln, Big Pine Key, FL 33043
/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
/61
$1,149,000 Open House 3/28
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
417 Pirates Rd, Summerland Key, FL 33042

Welcome to this beautifully updated canal-front home in the highly desirable Jolly Roger Estates on Little Torch Key! Offering 3 bedrooms, 2 baths, 1,170 sq ft of living space plus a 110 sq ft flex/office area, this meticulously maintained waterfront home features a desirable split floor plan with an open layout, remodeled kitchen with quartz countertops and LG ThinQ smart refrigerator and range,

Maggie Beall Lokation Real Estate

417 Pirates Rd, Summerland Key, FL 33042
/75
$915,000
- 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
/42
$650,000
- Land
22948 Drake Ln, Summerland Key, FL 33042

Boater/Angler special: 70-foot concrete seawall features hard-to-find boat slip/basin, plus 10,000-pound boat lift . This canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water. Perfect location for new build. Previous house removed and lot is ready for your vision. Electric was in place, buyer to verify FKAA

Barbara Bowers Preferred Properties (KW)

22948 Drake Ln, Summerland Key, FL 33042
/30
$989,000
- 3 Beds
- 3 Baths
- 1,314 Sq Ft
3633 Blue Lagoon St, Big Pine Key, FL 33043

This meticulously maintained 3-bedroom, 3-bath home in Big Pine Key offers exceptional privacy with state owned non-buildable land on both sides of this tranquil property. With 1,314 square feet of living space, it features an open floor plan, strand woven bamboo floors, two en-suite bedrooms and a nice sized third bedroom.The kitchen includes custom granite countertops, soft close cabinets,

David Kaufmann Century 21 Circle

3633 Blue Lagoon St, Big Pine Key, FL 33043
/3
$120,000
- Land
19617 Date Palm Dr, Sugarloaf Key, FL 33042

Now only $120,000. Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 Tier III platted lot (infill lot located in a developed subdivision with adequate infrastructure). With its prime location and desirable features, this property is a rare find in today's market. Convenient to the community boat ramp

Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

19617 Date Palm Dr, Sugarloaf 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
/4
$100,000
- Land
- 1.01 Acres
- $99,010 per Acre
0 Acosta Rd, Summerland Key, FL 33042

Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

0 Acosta Rd, Summerland Key, FL 33042
/32
$785,000
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
29850 Journeys End Rd, Big Pine Key, FL 33043

Nestled among lush tropical foliage, this inviting 3-bedroom, 2-bath home offers privacy, comfort, and that classic Big Pine Key island vibe. Situated on a dry, double lot, the property provides extra space to relax, garden, or park your boat -- all within a fully fenced yard surrounded by nature and the occasional friendly Key deer 🦌.Step inside to an open, airy living space that flows

Karen Haack Coldwell Banker Schmitt RE Co.

29850 Journeys End Rd, Big Pine Key, FL 33043
/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 Marinucci Serhant Florida LLC - Delray Beach Office

231 E Shore Dr Unit 2, Summerland Key, FL 33042
/77
$440,000
- 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
/43
$1,121,665
- 3 Beds
- 3 Baths
- 1,591 Sq Ft
3759 Seagrape St, Big Pine Key, FL 33043

Wake up to endless water views and wind down with breathtaking Keys sunsets at this peaceful island retreat. Set on a quiet corner lot, this 3-bedroom, 3-bath home offers the perfect blend of privacy, comfort, and classic Keys charm. A wraparound screened in porch with six sets of sliding glass doors fills the home with natural light and cooling tropical breezes, while rich pecky cypress accents

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

3759 Seagrape St, Big Pine Key, FL 33043
/36
$675,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
31107 Avenue I, Big Pine Key, FL 33043

Discover the ultimate Florida Keys lifestyle in this meticulously maintained 3-bedroom, 2-bathroom home with 2-car garage and a fresh, bright interior with new paint, this residence is move-in ready and full of potential. Located just moments from the water, you'll enjoy a sense of space and privacy that is hard to find. Whether you’re looking for a peaceful primary residence or a high-potential

Maria Downing LoKation

31107 Avenue I, 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
/78
$2,900,000
- 3 Beds
- 4 Baths
- 1,700 Sq Ft
29581 Richard Rd, Big Pine Key, FL 33043

Spectacular Open-Water Retreat with Unmatched Sunset ViewThis exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve.The property features over 200 feet of concrete seawall, a 35' x 15' boat basin making it ideal for

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

29581 Richard Rd, Big Pine Key, FL 33043
/46
$1,080,000
- 3 Beds
- 2 Baths
- 1,539 Sq Ft
29523 Enterprise Ave, Big Pine Key, FL 33043

Welcome to effortless waterfront living in the heart of Big Pine Key. This updated canal-front retreat 3 bedrooms 2 baths delivers the true Florida Keys lifestyle with comfort, convenience, and outstanding boating access.Sitting on a fully fenced property--ideal for outdoor enjoyment--this home quick, direct access to both the Atlantic Ocean and Gulf of Mexico.Start your mornings with peaceful

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

29523 Enterprise Ave, Big Pine Key, FL 33043
/20
$950,000
- 3 Beds
- 2 Baths
- 1,565 Sq Ft
24840 Park Dr, Summerland Key, FL 33042

Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bedrooms 2 full baths and open living space. Summerland key cove is just 25 miles from Key West. Great place to raise a family or to retire. Be it you're a boater, pilot, fisherman or just want the open space to walk and enjoy privacy of the park. This quit Island neighborhood offers rare access to the

Thomas Murphy LAER Realty

24840 Park Dr, 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 Marinucci Serhant Florida LLC - Delray Beach Office

231 E Shore Dr Unit 5, Summerland 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
/50
$849,000
- 2 Beds
- 2 Baths
- 1,592 Sq Ft
27369 Saint Vincent Ln, Summerland Key, FL 33042

Easy to show on short notice, call listing agent. Rare opportunity to step into instant equity with this custom built home in the desirable Lower Keys boating community. Owner spared no expense hardening this waterfront home, hardie board siding (2015), impact windows & doors (2013), metal roof (2013). One of the higher elevated lots in the neighborhood. Major capital improvements already

Brian Kruszewski LoKation Real Estate

27369 Saint Vincent Ln, Summerland Key, FL 33042
/39
$799,000
- 2 Beds
- 2 Baths
- 984 Sq Ft
744 Blackbeard Rd, Summerland Key, FL 33042

Welcome to your piece of Keys living in this charming 2 bedroom, 2 bathroom home in Little Torch Key on the ocean side. Enjoy a lovely west-facing screen porch overlooking the canal for a quiet morning coffee or to view the colors of the evening sunset. This fully fenced stilted modular home offers direct boating access to Pine Channel and Newfound Harbour for some of the best boating in the

Debra Farrell Island Welcome Real Estate

744 Blackbeard Rd, Summerland Key, FL 33042
/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
/9
$2,400,000
- Land
- 0.55 Acre
- $4,356,000 per Acre
24356 Overseas Hwy, Summerland Key, FL 33042

Begin your Florida Keys venture at this exceptional waterfront Commercial property. The site consists of four lots measuring 60'x100' each, creating a 24,000-square-foot parcel with 240 feet of concrete seawall. The property comes equipped with water and electrical connections. Its strategic location offers excellent access to both the Atlantic and Gulf waters, including proximity to Looe Key

Scott Brisson KeyIsle Realty

24356 Overseas Hwy, Summerland Key, FL 33042
/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
/48
$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
/5
$319,999
- 2 Beds
- 2 Baths
- 980 Sq Ft
230 Yardarm Rd, Summerland Key, FL 33042

This property is above the flood zone so it can be rebuilt, with some restrictions. It does not fall into the Monroe County 50% rule.

Joe Ordini Keller Williams Key West Compass Realty

230 Yardarm Rd, Summerland 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
/41
$864,000 Open Sat 2PM - 4PM
- 2 Beds
- 2 Baths
- 960 Sq Ft
154 Cutthroat Dr, Summerland Key, FL 33042

Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New fence with double gates and an entrance gate, gutters, landscaping, tile flooring, freshly painted

Pamela Stangler Expert Realty LLC

154 Cutthroat Dr, Summerland Key, FL 33042
/68
$1,890,000 Open Sat 1PM - 3PM
- 4 Beds
- 3.5 Baths
- 2,639 Sq Ft
30985 Watson Blvd, Big Pine Key, FL 33043

MODERN ISLAND RETREAT ON BOGIE CHANNEL - BIG PINE KEY, FLDiscover the epitome of Lower Keys living in this luxurious 4-bedroom, 3.5-bath CBS pool home, ideally positioned on Bogie Channel with direct BOATING access. Built in 2022 and offered furnished, this elevated residence combines modern design, coastal charm, and unmatched functionality. It's a rare find to own approximately .62 of an acre

Donna Pezzi Keller Williams Key West Compass Realty

30985 Watson Blvd, Big Pine Key, FL 33043
/36
$779,000 Open House 3/28
- 2 Beds
- 2 Baths
- 912 Sq Ft
1719 Narcissus Ave, Big Pine Key, FL 33043

Located in the peaceful National Key Deer Refuge, this charming 2BD/2BA canal front home in Eden Pines offers the perfect blend of tranquility and classic Florida Keys living. Enjoy frequent visits from the beloved Key Deer while relaxing on one of the screened porches. The property features a fenced yard, outdoor shower, garage, storage area, and rainwater collection system for easy landscape

Karen Haack Coldwell Banker Schmitt RE Co.

1719 Narcissus Ave, Big Pine Key, FL 33043
/28
$995,000
- 4 Beds
- 2 Baths
- 1,344 Sq Ft
27376 Tobago Ln, Summerland Key, FL 33042

Nestled in Breezeswept Beach Estates, this fully remodeled canal-front home is the perfect Keys getaway. This 4-bed, 2-bath house features an open floor plan, vaulted ceilings, and a modern kitchen with granite countertops, new cabinets, and stainless steel appliances. The master suite offers a walk-in closet and spa-style bathroom, while the additional bedrooms provide plenty of space for family

Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

27376 Tobago Ln, Summerland 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
/75
$3,500,000
- 4 Beds
- 3 Baths
- 2,812 Sq Ft
16805 Tamarind Rd, Summerland Key, FL 33042

OPEN WATER ELEGANCE on prestigious Southpoint, Sugarloaf Key. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breathtaking open water views from nearly every room and delivers the ultimate Florida Keys lifestyle.Positioned on a generous, beautifully landscaped lot with mature palms and established tropical greenery, the property welcomes you with a paved circular

Lisa Swanson The Agency Florida Keys

16805 Tamarind Rd, Summerland Key, FL 33042
/15
$1,495,000
- Land
- 2.29 Acres
- $652,838 per Acre
1261 Avenue A, Big Pine Key, FL 33043

NO WAIT TO BUILD!! ROGO Exempt 2.29 private and exclusive estate acreage with Bay Bottom on Bogie Channel with spectacular open water views. Property rests at the end of a quiet street and neighbors a park. USACE permitted a 412' dock before the pandemic that recently expired but is in discussion for renewal. Former home on property was damaged in Hurricane Irma and has since been demolished and

Sasha Naimi Charles Rutenberg Realty FTL

1261 Avenue A, Big Pine Key, FL 33043
/25
$569,700
- 2 Beds
- 1 Bath
- 718 Sq Ft
701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

Sarah Dolson Keller Williams Key West Compass Realty

701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

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