Summerland Key, FL Homes for Sale

/61
$975,000
- 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
/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
/62
$1,075,000
- 3 Beds
- 2 Baths
- 1,377 Sq Ft
231 W Indies Dr, Summerland Key, FL 33042

Welcome to your open-water paradise! This 3-bedroom, 2-bath home is all about embracing the Florida lifestyle. Wake up to breathtaking open-water sunrises while you sip coffee on your private balcony, then spend your afternoons lounging by the sparkling pool. The main level offers two comfortable bedrooms and a full bath -- perfect for family or guests -- while the entire second floor is your

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

231 W Indies Dr, Summerland Key, FL 33042
/49
$910,000
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
813 Hawksbill Ln, Summerland Key, FL 33042

Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board siding and a metal roof, this three-story retreat of island living. with GENERAC Generator. Inside, you'll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly

Miguel Solis Douglas Elliman Florida, LLC - Sunset Drive

813 Hawksbill Ln, Summerland Key, FL 33042
/6
$550,000 Open Sun 1PM - 3PM
- Land
21865 Spain Blvd, Summerland Key, FL 33042

Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

Matthew Sheehan Ocean Sotheby's International Realty

21865 Spain Blvd, Summerland Key, FL 33042
/43
$1,165,000
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
22737 Blackbeard Ln, Cudjoe Key, FL 33042

Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

Terry Garcia Keller Williams Key West Compass Realty

22737 Blackbeard Ln, Cudjoe Key, FL 33042
/49
$938,000 Open Sun 9AM - 11AM
- 2 Beds
- 2 Baths
- 1,124 Sq Ft
3667 S Seas St, Big Pine Key, FL 33043

***Open House Sunday October 5th 9a - 11a*** Discover your dream waterfront residence in the Florida Keys! Constructed with superior CBS building methods, featuring concrete floors, beams, and decorative railings, this home promises enduring quality. A full concrete seawall and robust 10k lb. boatlift offer convenient access to local sandbars, snorkeling spots, dining venues, and exceptional

Scott Brisson KeyIsle Realty

3667 S Seas St, Big Pine Key, FL 33043
/18
$849,000
- 4 Beds
- 2.5 Baths
- 1,924 Sq Ft
1433 Sunset Rd, Big Pine Key, FL 33043

Great income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogie Channel. Large lot with full seawall. Interior is cute and tidy and would be easy to rent or live in one side and generate extra income. Fully furnished.

Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

1433 Sunset Rd, Big Pine Key, FL 33043
/3
$60,000
- Land
Lot 10 Rainbow Beach, Big Torch Key, FL 33042

Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

Shanti Cope Coldwell Banker Schmitt Key Largo

Lot 10 Rainbow Beach, Big Torch Key, FL 33042
/2
$57,000
- Land
Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

This is a 2 point lot to be used toward a building permit in Monroe County. Add to your current ROGO application or use it when submitting a new ROGO application to Monroe County. Contact Monroe County Planning Department for specific details on how and when these points can be used.

Pamela Stangler Expert Realty LLC

Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
/2
$57,000
- Land
Lot 16 Treasure Chest Dr, Cudjoe Key, FL 33042

This is a 2 point lot to be used toward a building permit in Monroe County. Add to your current ROGO application or use it when submitting a new ROGO application to Monroe County. Contact Monroe County Planning Department for specific details on how and when these points can be used.

Pamela Stangler Expert Realty LLC

Lot 16 Treasure Chest Dr, Cudjoe Key, FL 33042
/17
$249,000
- Land
29859 Overseas Hwy Unit A-19, Big Pine Key, FL 33043

Your Florida Keys getaway and make some money too. RV lot and RV is staying. Owner has had it on Airbnb and HomeAway with good reviews. At current income/expense it can pay for itself in 8 years. Brings in $40K+ numbers work unlike most in the Keys. Net approximately $31K + per year. Breezy Pines is a RV park located in Big Pine Key with club house, kitchen, laundry facilities, bathrooms with

Rose Dell Keller Williams Key West Compass Realty

29859 Overseas Hwy Unit A-19, Big Pine Key, FL 33043
/60
$1,089,000
- 3 Beds
- 2 Baths
- 1,346 Sq Ft
29490 Ranger Ave, Big Pine Key, FL 33043

Location, Location, Location is the Key to this 2018 canal front coastal property featuring open concept living with 3 bdrms, 2 full baths in Pine Channel Estates. A sought-after lower keys waterfront community. Master bdrm with en suite bath features dual shower heads and vanities plus a private screened in porch overlooking the canal. Buyers will relish the integrated design of the Connell

Jennifer Sylvia Keller Williams Key West Compass Realty

29490 Ranger Ave, Big Pine Key, FL 33043
/39
$650,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Main Dr in Cudjoe Key, FL. This beautiful property offers 2 bedrooms and 2 bathrooms within its 816 sq.ft. of finished living space. The home sits on a 2,568 sq.ft. lot, providing ample outdoor space for relaxing and entertaining. The property features a bright and airy interior with an open floor plan,

Randal Longo Keys Realty Redefined LLC

701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
/53
$949,000
- 2 Beds
- 2 Baths
- 1,620 Sq Ft
22852 John Silver Ln, Summerland Key, FL 33042

Paradise Awaits on Cudjoe KeyDiscover 22852 John Silver Lane, a rare A-frame waterfront retreat in the peaceful Cutthroat Harbor Estates. This two-bedroom, two-bath home embodies the perfect balance of Keys character and modern comfort, wrapped in lush palms and native landscaping that create a true island sanctuary.Inside, soaring vaulted ceilings and impact-rated windows and doors fill the

Matthew Sheehan Ocean Sotheby's International Realty

22852 John Silver Ln, Summerland Key, FL 33042
/27
$987,500
- 4 Beds
- 2 Baths
- 1,536 Sq Ft
3962 No Name Rd, Big Pine Key, FL 33043

Investment Opportunity! Waterfront duplex with 2BD|1BA on each side. Property features concrete block construction, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry room on each side, 2 central AC units and 2 electric meters. New Metal Roof within 2 years. Fenced yard with room to park your boat trailer. Excellent boating access

Stacy Shahan Island Real Estate Company Florida Keys

3962 No Name Rd, Big Pine Key, FL 33043
/47
$589,900
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

Ian Calderwood Bluescape Real Estate

701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
/18
$299,999
- 3 Beds
- 2 Baths
- 984 Sq Ft
31036 Avenue H, Big Pine Key, FL 33043

ROGO EXEMPT WITH SELLER FINANCING OPPORTUNITY!Nestled on a lush lot, this move-in ready 3-bedroom, 2 bath home is perfect for nature lovers, investors, or anyone seeking a tranquil Keys lifestyle. The open-concept kitchen and living area create a bright, welcoming space for gatherings, while recent renovations to the kitchen and bathrooms add modern comfort and style. Step outside and enjoy

Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

31036 Avenue H, Big Pine Key, FL 33043
/44
$4,449,000
- 7 Beds
- 7 Baths
- 4,100 Sq Ft
1557 Long Beach Dr, Big Pine Key, FL 33043

1557 Long Beach Dr in Big Pine Key is more than a home, it's an opportunity to own one of the most unique properties in the Lower Keys. Set on a prime lot in the coveted Long Beach Estates, this CBS home has been upgraded with impact windows, a new metal roof, and a completely renovated kitchen. The property delivers what everyone wants but few can find: direct oceanfront with your own sandy

Guillermo Fernandez Pini Real Estate

1557 Long Beach Dr, Big Pine Key, FL 33043
/65
$1,175,000
- 4 Beds
- 3 Baths
- 2,448 Sq Ft
165 Cutlass Ln, Summerland Key, FL 33042

Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

Justyn Ewald Expert Realty LLC (HQ)

165 Cutlass Ln, Summerland Key, FL 33042
/39
$750,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
74 Pelican Ln, Big Pine Key, FL 33043

Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all close.And it also has a completely habitable game room with independent entrance.

Yunior Molina My Realty Group, LLC.

74 Pelican Ln, Big Pine Key, FL 33043
/38
$779,000
- 2 Beds
- 2 Baths
- 860 Sq Ft
22464 La Fitte Dr, Summerland Key, FL 33042

Cudjoe Key Canal Front Living -- Newly renovated home with covered carport, custom master bath, real wood slim shaker cabinets, quartz countertops, and new appliances and A/C. Features impact doors/sliders, new floors, and fresh P-rock landscaping. Two open porches overlook a 60' canal for relaxing or entertaining. Permitted storage below is ideal for gear or tools. Yard is a blank slate--build

Steven Koleno Beycome of Florida, LLC

22464 La Fitte Dr, Summerland Key, FL 33042
/15
$315,000
- Land
27345 Guadaloupe Ln, Ramrod Key, FL 33042

Discover an exceptional canal-front lot that boasts direct bridge-free boating access, making it a fisherman's paradise and an ideal spot for your dream home. Nestled conveniently close to US 1 between Key West and Marathon, this location offers easy access to an array of restaurants, shopping, and mini golf--everything you need for the perfect Keys lifestyle. This Tier III lot is currently in

Scott Brisson KeyIsle Realty

27345 Guadaloupe Ln, Ramrod Key, FL 33042
/52
$700,000
- 3 Beds
- 2 Baths
- 1,076 Sq Ft
31240 Avenue H, Big Pine Key, FL 33043

Welcome to your slice of paradise in Big Pine Key! This beautifully updated 3-bedroom, 2-bath home offers move-in-ready comfort with thoughtful upgrades throughout. Step inside to a beautifully renovated kitchen complete with quartz countertops, soft-close cabinetry, and premium finishes. The home offers new luxury vinyl plank (LVP) flooring throughout, blending durability with coastal style. The

Charity Coffman Brightwild Real Estate

31240 Avenue H, Big Pine Key, FL 33043
/15
$999,965
- Land
701 Spanish Main Dr Unit 369, 370, Cudjoe Key, FL 33042

Boater's Paradise with Expansive Waterfront Views! Rare opportunity to own one of only three double lots in Venture Out on Cudjoe Key with unbeatable waterfront views and a newer 70-ft concrete seawall equipped with davits, bumpers, swim ladder, fish cleaning station, and upgraded dock posts and cleats--perfect for accommodating your large boats. Take advantage of the double buildable lot

Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

701 Spanish Main Dr Unit 369, 370, Cudjoe Key, FL 33042
/45
$7,000,000
- 3 Beds
- 4 Baths
- 2,851 Sq Ft
0 Melody Key Unit 616249, Summerland Key, FL 33042

An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

Scott Forman Royal Palms Realty (KW)

0 Melody Key Unit 616249, Summerland Key, FL 33042
/25
$349,000
- 2 Beds
- 1 Bath
- 756 Sq Ft
27944 Tarpon Terrace, Little Torch Key, FL 33042

Don't miss this amazing opportunity to own a great piece of waterfront property on a clean plugged canal. Excellent for swimming, kayaking, paddle boarding, fishing and snorkeling in your own backyard. This well maintained updated home has stainless steel appliances with an ample amount of cabinets in the kitchen and a nice bright open living room. Just a few steps down the hall, is your comfy

Tracy Shields KeyIsle Realty

27944 Tarpon Terrace, Little Torch 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
/35
$729,000
- 3 Beds
- 1.5 Baths
- 1,247 Sq Ft
29283 Coconut Palm Dr, Big Pine Key, FL 33043

Welcome to Coconut Palm Drive -- a hidden gem in one of Big Pine Key's peaceful residential neighborhoods. This 3-bedroom, 1.5-bath island home offers vaulted ceilings, crown molding, and an open-concept layout that brings in natural light and a spacious feel. The tropical backyard is fully fenced for privacy and features mature banana trees. A generous downstairs storage area offers endless

Stephany Duvall Engel & Volkers Marathon

29283 Coconut Palm Dr, Big Pine Key, FL 33043
/53
$985,000
- 2 Beds
- 2 Baths
- 888 Sq Ft
701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

Panoramic Ocean Views With Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
/47
$985,000
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
786 Jamaica Ln, Little Torch Key, FL 33042

ASSUMABLE MORTGAGE at 3.125% to qualified Buyers! Come enjoy coastal living blended with modern conveniences. Discover the perfect blend of comfort and convenience in this well-built 3-bedroom, 2-bath home. Easy to show. Within minutes you're out on the water with access to the Atlantic Ocean and Gulf. Located on a clear canal, this property offers the ideal setting for those seeking

Donna Pezzi Keller Williams Key West Compass Realty

786 Jamaica Ln, Little Torch Key, FL 33042
/23
$3,750,000
- 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 with 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
/4
$245,000
- Land
30921 Bailey Rd, Big Pine Key, FL 33043

Ready..Set.. Build!! Welcome to the future home site in the sought-after neighborhood of Big Pine Key! There are two ROGO-exempt vacant lots available for $245,000 each that offer a rare opportunity to build your dream home in paradise. No waiting for permit allocation!!

Maryann Warren Coldwell Banker - Ft. Lauderdale

30921 Bailey Rd, Big Pine Key, FL 33043
/27
$309,900
- 2 Beds
- 1 Bath
- 672 Sq Ft
27983 Snapper Ln, Little Torch Key, FL 33042

Keys Living at a Great Price!This 2-bedroom, 1-bath mobile home offers an excellent opportunity to own in the Lower Florida Keys. Located on a quiet street on Little Torch Key, the home backs to a swimming canal -- a peaceful setting for relaxing, paddleboarding, or a refreshing dip.Inside, you'll find vaulted ceilings, an open-concept living and kitchen area, and a layout that maximizes space

Sandra Dolowy KeyIsle Realty

27983 Snapper Ln, Little Torch Key, FL 33042
/70
$1,975,000
- 3 Beds
- 3 Baths
- 2,295 Sq Ft
20889 7th Ave W, Summerland Key, FL 33042

Luxury Waterfront Living in Prestigious Cudjoe Gardens, ROOM FOR A POOL! Discover refined island living in the heart of one of the Florida Keys' most exclusive waterfront communities renowned for its deepwater access, upscale ambiance, and close proximity to Key West.This elegantly designed residence is positioned on an 8,000sf lot, offering exceptional canal frontage on a 50ft wide canal only 6

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

20889 7th Ave W, Summerland Key, FL 33042
/3
$300,000
- Land
0 Candice Ave, Little Torch Key, FL 33042

Rare opportunity to acquire a 6-parcel assemblage totaling approx. 13.67 acres on Little Torch Key. Includes five 6,000 sq. ft. Mates Beach lots on Candice Avenue (two Tier 3 Infill) and a 12.97+/- acre tract with 2.61 acres upland and 10.36 acres environmentally sensitive land. Perfect for agricultural or beekeeping use, conservation project, or long-term investment. Located in a desirable Lower

Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

0 Candice Ave, Little Torch Key, FL 33042
/45
$1,590,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
28538 John Silver Rd, Summerland Key, FL 33042

Experience the best of the Keys lifestyle in this beautifully appointed 3-bedroom, 2-bath home, ideally positioned on a premium corner lot with approximately 236 feet of waterfront along a wide canal. Offering direct and easy access to open water, this property is a dream for boaters and water lovers alike.Step inside to a bright, open layout where expansive windows frame stunning views of

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

28538 John Silver Rd, Summerland Key, FL 33042
/68
$998,755
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
460 Barry Ave, Summerland Key, FL 33042

Experience the Ultimate Florida Keys Lifestyle in This One-f-A-kind Coastal Retreat!Step onto Coastal elegance with this stunning 3-bedroom 2-bathroom home offering 1440 square feet of thoughtfully designed living space. The expansive great room showcases soaring 20-foot ceilings- a rare gem in the Keys- creating an airy, open feel.Stylish wide- plank luxury vinyl flooring runs throughout

Noel Betancourt Tropic Shores Realty LLC

460 Barry Ave, Summerland Key, FL 33042
/30
$375,000
- 3 Beds
- 1 Bath
- 1,044 Sq Ft
27960 Porgie Path, Little Torch Key, FL 33042

Canal Front Coral Shores Estates! This 3 Bedroom home with Open Water views of South Pine Channel has a wonderful Swimming Canal ,perfect for kayaking, SUP, and can be easily accessed from the beautiful large new deck- with ladder access to the water. The front of the yard has new fencing, and room to park several cars off street. The inside has 3 bedrooms and a bath, and 2 living room areas.

Elaine Coyle Keller Williams Key West Compass Realty

27960 Porgie Path, Little Torch Key, FL 33042
/55
$1,750,000 Open Sun 1PM - 3PM
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21865 Spain Blvd, Summerland Key, FL 33042

Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

Matthew Sheehan Ocean Sotheby's International Realty

21865 Spain Blvd, Summerland Key, FL 33042

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