Summerland Key, FL Homes for Sale

/5
$139,000
- Land
Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
/51
$1,420,000
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
30890 Granada Ave, Big Pine Key, FL 33043

Welcome to your tropical oasis--where the true spirit of the Florida Keys comes to life. This spacious 3-bedroom waterfront home blends casual island style with relaxed coastal living, offering 1,764 square feet designed for comfort and ease. High ceilings lined with tongue-and-groove wood immediately set the island tone as you enter the open living space. The kitchen flows seamlessly into the

Sunnie San Lorenzo KeyIsle Realty

30890 Granada Ave, Big Pine Key, FL 33043
/21
$920,000
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
27360 Saint Croix Ln, Summerland Key, FL 33042

Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

Terry Bush Bluescape Real Estate

27360 Saint Croix Ln, Summerland Key, FL 33042
/33
$399,950
- 1 Bed
- 1 Bath
- 528 Sq Ft
30170 Linda St, Big Pine Key, FL 33043

Welcome to your charming new home! This delightful concrete 1-bedroom, 1-bathroom residence features a sturdy metal roof and is nestled on a generously sized, fully fenced lot, offering both comfort and privacy.Step inside to discover energy-efficient LED lighting throughout, complemented by an energy-efficient A/C system to keep you cool. The kitchen features a gas range, perfect for cooking

Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

30170 Linda St, Big Pine Key, FL 33043
/57
$1,650,000
- 2 Beds
- 2 Baths
- 1,392 Sq Ft
25368 2nd St, Summerland Key, FL 33042

Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

Ally Kelley Ocean Sotheby's International

25368 2nd St, Summerland Key, FL 33042
/9
$3,500,000
- Land
19657 Seminole St, Sugarloaf Key, FL 33042

Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

Derek Epperly Keys Atlantic Realty

19657 Seminole St, Sugarloaf Key, FL 33042
/33
$525,000
- 3 Beds
- 2 Baths
- 1,278 Sq Ft
31525 Avenue A, Big Pine Key, FL 33043

$525K Opportunity with so much potential. Privacy fence with 2 big double gates with access from both streets and no neighbor across the street. Unique CBS 3bd/2bth ground level home. Central AC, Tile Floors, Double corner lot. 100 X 100. Lots of parking, if you have work vehicles or an RV has rv elect, hook. Room for pool and entertaining. Patio deck area. Close to community park, public boat

Rose Dell Keller Williams Key West Compass Realty

31525 Avenue A, Big Pine Key, FL 33043
/60
$2,700,000
- 3 Beds
- 3 Baths
- 2,167 Sq Ft
556 Caribbean Dr E, Summerland Key, FL 33042

The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the

Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

556 Caribbean Dr E, Summerland Key, FL 33042
/24
$875,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
853 Indies Rd, Summerland Key, FL 33042

Move right into this well-maintained 3-bedroom, 2-bath canal front home, built in 2006 and cared for with pride. The bright, open layout features a split floor plan that offers comfortable space for everyday living and entertaining.The primary bedroom includes an en-suite bath and a versatile bonus room -- ideal for a home office, nursery, or cozy retreat. Step outside to enjoy peaceful canal

Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

853 Indies Rd, Summerland Key, FL 33042
/53
$1,799,000
- 4 Beds
- 2 Baths
- 2,605 Sq Ft
1481 Sugarloaf Blvd, Summerland Key, FL 33042

Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

Jenna Stauffer Ocean Sotheby's International Realty

1481 Sugarloaf Blvd, Summerland Key, FL 33042
/25
$745,000
- Land
28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

Barbara Eads Barbara Eads Realty

28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042
/49
$329,000 Open House 1/03
- 2 Beds
- 1 Bath
- 738 Sq Ft
701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

Jan Fritz Coldwell Banker Schmitt RE Co.

701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
/43
$925,000
- 2 Beds
- 2 Baths
- 1,292 Sq Ft
3686 Gulfstream St, Big Pine Key, FL 33043

Key Deer, Quick Access to Pine Channel, Canal Views & Updated Island Living: Your Florida Keys Dream Awaits!Imagine: breathtaking sunsets painting the sky, the gentle presence of Key Deer just outside your fence, and the tranquility of canal-front living in the heart of the National Key Deer Refuge. This charming 2-bedroom, 2-bathroom home offers a rare opportunity to live in harmony with nature

Gidget Jackson RE/MAX Realty Group

3686 Gulfstream St, Big Pine Key, FL 33043
/15
$644,500
- Land
132 Sugarloaf Dr, Summerland Key, FL 33042

Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

Heather Mason Coastal Collection Real Estate Inc.

132 Sugarloaf Dr, Summerland Key, FL 33042
/18
$600,000
- Land
701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

The Spottswood Team Truman & Co. (KW)

701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
/100
$9,950,000
- 6 Beds
- 5 Baths
- 5,208 Sq Ft
16750 Old State Road 4a, Summerland Key, FL 33042

Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

Lisa Swanson The Agency Florida Keys

16750 Old State Road 4a, Summerland Key, FL 33042
/16
$775,000
- Land
28597 Peg Leg Rd, Little Torch Key, FL 33042

Vacant Land on Canal waiting on permit 41.5 points today for a 3809 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom four-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house. Open Water View. House Permit SF-DUP-2025-0111, 41.5

Barbara Eads Barbara Eads Realty

28597 Peg Leg Rd, Little Torch Key, FL 33042
/19
$475,000
- Land
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

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
/43
$875,000
- 2 Beds
- 2 Baths
- 912 Sq Ft
681 W Indies Dr, Summerland Key, FL 33042

This charming 2-bedroom, 2-bath home is your slice of paradise in the Lower Keys. Nestled on the open water, the property offers ocean views that will take your breath away. Enjoy your morning coffee or evening cocktails on the screened-in porch, perfect for relaxing and soaking in the coastal breeze. With a swim dock right out back, you'll have easy access to the crystal-clear waters for a quick

Karen Haack Coldwell Banker Schmitt RE Co.

681 W Indies Dr, Summerland Key, FL 33042
/39
$999,000
- 2 Beds
- 3 Baths
- 1,120 Sq Ft
421 Ixora Dr, Big Pine Key, FL 33043

Beautifully maintained elevated Florida Keys home offering 2 bedrooms and 2 bathrooms upstairs plus a legal bathroom downstairs. This thoughtfully designed residence sits on a spacious 10,568 sq. ft. lot with ample parking for an RV and/or boat trailer and features quality construction throughout. Home was completely remodeled post Irma down to the studs. The interior showcases porcelain

Melissa Graham Bluescape Real Estate

421 Ixora Dr, Big Pine Key, FL 33043
/9
$849,000
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
22920 Privateer Dr, Summerland Key, FL 33042

Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

Robin Nilsson Keller Williams Key West Compass Realty

22920 Privateer Dr, Summerland Key, FL 33042
/96
$1,698,000
- 4 Beds
- 3 Baths
- 2,353 Sq Ft
17176 Bonita Ln W, Summerland Key, FL 33042

Experience island living in this 2,353 sq ft, 4-bed, 3-bath Sugarloaf Shores home on a 12,500 sq ft lot. The split-level design includes two ensuite bedrooms with balcony access, plus two guest rooms on the ground floor. Skylights brighten the open living areas, flowing seamlessly to a 44' screened balcony.Out back, enjoy a 22' x 10' pool, gazebo, private boat ramp, swim ladder, and dual lifts

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

17176 Bonita Ln W, Summerland Key, FL 33042
/64
$3,199,000
- 3 Beds
- 2 Baths
- 2,232 Sq Ft
23941 Henry St, Summerland Key, FL 33042

Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

Stacy Shahan Island Real Estate Company Florida Keys

23941 Henry St, Summerland Key, FL 33042
/19
$329,000
- 2 Beds
- 1 Bath
- 756 Sq Ft
701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042

NIGHTLY RENTALS ALLOWED! Welcome to this immaculate 2-bedroom, 1-bathroom vacation retreat nestled at the picturesque southern tip of Venture Out, where the land gracefully meets the sea. The attention to detail is evident with luxurious travertine flooring added to this home. Don't let the square footage fool you. This home offers an open floor plan with an open kitchen over looking the family

Susan Halligan Live Local Realty of the Florida Keys

701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042
/30
$485,000
- 2 Beds
- 1.5 Baths
- 604 Sq Ft
701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
/9
$199,500
- Land
Vacant Picard Ln, Cudjoe Key, FL 33042

Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open

Sunnie San Lorenzo KeyIsle Realty

Vacant Picard Ln, Cudjoe Key, FL 33042
/11
$650,000
- Land
775 Pirates Rd, Summerland Key, FL 33042

Rare opportunity in Jolly Roger Estates on Little Torch Key. This 6,000 sq. ft. cleared and build-ready lot comes with two ROGO exemptions, allowing for immediate construction. The property features 60 feet of east-facing waterfront with a concrete dock, step-down, and davits already in place. Central sewer is connected. Located on a clean, deep canal (approx. 3 ft. control depth) with quick open

Melissa Gibbins Expert Realty LLC (HQ)

775 Pirates Rd, Summerland Key, FL 33042
/39
$1,100,000
- 3 Beds
- 2 Baths
- 2,198 Sq Ft
21073 7th Ave, Summerland Key, FL 33042

Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

21073 7th Ave, Summerland Key, FL 33042
/41
$2,450,000
- 2 Beds
- 2 Baths
- 1,577 Sq Ft
1176 Thatch Ln, Summerland Key, FL 33042

Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

Jonathan Minerick Homecoin.com

1176 Thatch Ln, Summerland Key, FL 33042
/42
$2,200,000
- 5 Beds
- 3 Baths
- 1,978 Sq Ft
94 Sacarma Dr, Cudjoe Key, FL 33042

Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

Michelle Blades Realty Executives Florida Keys Old Town

94 Sacarma Dr, Cudjoe Key, FL 33042
/42
$1,299,000
- 3 Beds
- 2 Baths
- 2,081 Sq Ft
27038 Angelfish Rd, Summerland Key, FL 33042

Owner financing possible **Stunning 3-Bedroom, 2-Bath Home on 15,000 Sq Ft Lot with Resort-Style Pool and Spa**Welcome to your dream home! This spacious 3-bedroom, 2-bathroom property offers everything you need for comfortable living and entertaining. Nestled on a generous 15,000 sq ft lot, you'll enjoy plenty of space both indoors and outdoors. The centerpiece of this property is the luxurious

Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

27038 Angelfish Rd, Summerland Key, FL 33042
/24
$1,100,000
- Land
- 5 Acres
- $220,000 per Acre
2231 Middle Torch Rd, Summerland Key, FL 33042

Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential. The property currently features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each

Stephany Duvall Engel & Volkers Marathon

2231 Middle Torch Rd, Summerland Key, FL 33042
/37
$725,000
- 3 Beds
- 2 Baths
- 1,078 Sq Ft
27394 Saint Lucie Ln, Summerland Key, FL 33042

Welcome to a Florida Keys waterfront retreat! This well-maintained 3 bedroom, 2 bath, stilted canal-front home offers bright, open living with soaring ceilings, large closets, and abundant natural light. The spacious living room flows seamlessly into the dining area and kitchen, while double French doors lead to a large, screened-in balcony overlooking the quiet canal - perfect for relaxing and

Casey Arnold eXp Realty LLC

27394 Saint Lucie Ln, Summerland Key, FL 33042
/16
$250,000
- Land
LOT 12 Saint Lucie Ln, Ramrod Key, FL 33042

Canalfront lot on Ramrod Key located in a desirable waterfront community oceanside between Key West and Marathon, offering quick access to the Atlantic Ocean then onto Florida Bay. No building permit is currently in place; buyers may apply through ROGO or purchase a separate building right.

Karan Moeller Ocean Sotheby's International Realty

LOT 12 Saint Lucie Ln, Ramrod Key, FL 33042
/7
$4,325,000 New Construction
- 5 Beds
- 5.5 Baths
- 3,119 Sq Ft
231 E Shore Dr Unit 6, 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 6, Summerland Key, FL 33042
/45
$715,000
- 3 Beds
- 2 Baths
- 1,488 Sq Ft
27163 Mariposa Rd, Summerland Key, FL 33042

Welcome to your slice of paradise in Ramrod Key! This newer built (2018) beautifully maintained single-family home offers 1,488 square feet of comfortable living space, perfectly situated on a spacious 6,000 square foot lot. Featuring 3 bedrooms and 2 bathrooms, this property is ideal for full-time residents, vacationers, or investors seeking a rental opportunity in the Florida Keys.Special

Jessica Roden Ocean Sotheby's International Realty

27163 Mariposa Rd, Summerland Key, FL 33042
/55
$2,299,999
- 3 Beds
- 3 Baths
- 2,288 Sq Ft
17210 Angelfish Ln, Summerland Key, FL 33042

Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of modern coastal comfort. Situated on an expansive 16,445-square-foot lot, the property features a private seawall for direct boating access and a sparkling pool perfect for relaxing after a day on the

The Spottswood Team Truman & Co. (KW)

17210 Angelfish Ln, Summerland Key, FL 33042
/46
$695,000
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
29172 Rose Dr, Big Pine Key, FL 33043

Remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek

Deni Heintzelman KeyIsle Realty

29172 Rose Dr, Big Pine Key, FL 33043
/39
$995,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042

Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath oceanfront home combines sleek design with comfort and quality craftsmanship. Step inside to discover 9ft ceilings, leather-finish granite countertops, and high-end finishes throughout. The home comes

The Spottswood Team Truman & Co. (KW)

701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
/10
$725,000
- Land
17220 Angelfish Ln, Sugarloaf Shores, FL 33042

Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the

The Spottswood Team Truman & Co. (KW)

17220 Angelfish Ln, Sugarloaf Shores, FL 33042

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