Summerland Key, FL Homes for Sale

/60
$2,499,000 Open Fri 11AM - 1PM
- 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
$849,000 Open Sat 11AM - 1PM
- 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
/35
$825,000
- 3 Beds
- 3 Baths
- 1,224 Sq Ft
3672 Fox St, Big Pine Key, FL 33043

Discover a peaceful Keys escape on a quiet canal in Big Pine Key. This attractive 3-bedroom, 3-bath home blends relaxed, nature-forward living with modern comforts.Bright, open living area with high ceilingsUpdated kitchen with stainless steel appliances, granite counters, and ample cabinetry. Private master suite with en-suite bath and direct balcony access.Two additional bedrooms ideal for

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

3672 Fox St, Big Pine Key, FL 33043
/53
$1,710,000
- 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
- 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
/31
$624,900
- 3 Beds
- 2 Baths
- 1,218 Sq Ft
30023 Pine Channel Rd, Big Pine Key, FL 33043

Discover tranquil Keys living at 30023 Pine Channel Rd, a charming 3-bedroom, 2-bathroom home offering peaceful seclusion with effortless access to the Overseas Highway. Set on a generous lot and surrounded by mature, beautifully established trees, this property delivers the perfect blend of privacy, nature, and convenience.Step inside to find 1,218 sq ft of comfortable living space. The

Sam Williams Coldwell Banker Schmitt Real Estate Co.

30023 Pine Channel Rd, Big Pine Key, FL 33043
/43
$880,000
- 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 Nicklaus Vance

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
/57
$959,000
- 2 Beds
- 2 Baths
- 1,185 Sq Ft
2123 Spanish Channel Dr, Big Pine Key, FL 33043

Ocean Views, Direct canal frontage , in the ocean water in 2 minutes. Concrete Dock, Solid pour concrete column house is ready for making your own . Beautiful trees, planted newly landscaped with custom design fencing. Wildlife is amazing, quiet location near end of the road. Grocery store 1 mile away close to Key West or Marathon Roof replaced in 2018 also all new hurricane window, doors,

Anne Press Lokation Real Estate

2123 Spanish Channel Dr, Big Pine Key, FL 33043
/41
$665,000
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
29313 Coconut Palm Dr, Big Pine Key, FL 33043

Welcome to this beautifully maintained home that offers comfort, convenience, and the quintessential Keys lifestyle. Equipped with impact windows and doors, a durable metal roof, plantation shutters, and low insurance rates, this home provides peace of mind and enduring value. The newly renovated kitchen is bathed in natural light and thoughtfully designed to cater to both everyday living and

Scott Brisson KeyIsle Realty

29313 Coconut Palm Dr, Big Pine Key, FL 33043
/19
$465,000
- 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
/45
$1,775,000
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
31253 Hibiscus Dr, Big Pine Key, FL 33043

Experience the quintessential Florida Keys waterfront lifestyle from this open-water, 3-bedroom, 2-bathroom concrete home nestled along Big Pine Key's scenic Bogie Channel. This property boasts exceptional boating amenities, including two dedicated boat lifts and a convenient boat basin, ensuring effortless access to your vessels. Enjoy swift journeys, reaching the Atlantic in just two minutes or

Lara Hanousek Platinum Purpose Real Estate, LLC

31253 Hibiscus Dr, Big Pine Key, FL 33043
/39
$975,000
- 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
/21
$475,000
- 1 Bed
- 1 Bath
- 668 Sq Ft
701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
/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
/23
$1,595,000
- 3 Beds
- 3 Baths
- 2,022 Sq Ft
887 Bay Dr, Summerland Key, FL 33042

This 3-bedroom, 3-bath concrete fortress on a deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quick access to both the Gulf and Atlantic--just a 15-minute boat ride to open ocean--this home is a true boater's paradise. Additionally, enjoy Airstrip rights as part of the Summerland Airport community. Set on a generous 75' x 100' corner lot, the property offers

Amy Hanson Realty Executives Florida Keys Summerland Branch

887 Bay 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
/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
$185,000
- 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
/23
$730,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
74 Pelican Ln, Big Pine Key, FL 33043

Completely remodeled property with a new roof installed in 2024, new flooring, termite treatment completed in 2025, fully furnished, and ideally located just 30 minutes from Key West. It's close to restaurants, schools, beaches, recreational facilities, and everything you need for a peaceful and enjoyable life. It also features an additional, fully finished game room with a separate entrance. The

Yunior Molina My Realty Group, LLC.

74 Pelican Ln, Big Pine Key, FL 33043
/71
$1,150,000
- 3 Beds
- 2 Baths
- 1,068 Sq Ft
19881 Date Palm Dr, Summerland Key, FL 33042

Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home is tucked away in a quiet, secluded location and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal!Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek

Jimmy Lane Island Life Realty Experts

19881 Date Palm Dr, Summerland Key, FL 33042
/39
$1,050,000
- 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
/30
$525,000
- 3 Beds
- 2 Baths
- 1,431 Sq Ft
30461 Poinciana Rd, Big Pine Key, FL 33043

Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 bath home, with an office, features vaulted ceiling, brand new mini split air condition units and plenty of windows and French doors that allow light to fill the home. The large primary bedroom has a screened in porch off the back perfect for relaxing. Also, in the rear of the home is an attached, private 1/1

Dorry Santiago Keller Williams Realty Profess

30461 Poinciana Rd, Big Pine Key, FL 33043
/24
$995,000
- Land
- 5 Acres
- $199,000 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
/42
$785,000 Open Sun 11AM - 1PM
- 3 Beds
- 1.5 Baths
- 1,008 Sq Ft
31033 Hibiscus Dr, Big Pine Key, FL 33043

Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized double lot with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Additional highlights include an on-demand hot water heater, a seawall, and

Karen Haack Coldwell Banker Schmitt RE Co.

31033 Hibiscus Dr, Big Pine Key, FL 33043
/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
$4,375,000 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
/18
$3,999,999
- 5 Beds
- 5 Baths
- 3,700 Sq Ft
17229 Oleander Ln, Summerland Key, FL 33042

Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home

Justyn Ewald Expert Realty LLC (HQ)

17229 Oleander Ln, 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
/14
$299,000
- Land
27398 Jamaica Ln, Ramrod Key, FL 33042

Great Location vacant lot with seawall and boat ramp. Minutes to Open Water. Just waiting for a perfect home. This is a great option to purchase 231 W. Indies Open Water Home and have great boating with this lot.Please look at MLS616482

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

27398 Jamaica Ln, Ramrod Key, FL 33042

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