Monroe, FL Homes

/5
$285,000
- Land
21731 Asturias Rd, Summerland Key, FL 33042

Private Acre on Cudjoe Key - Lush, Tropical, and Near the WaterEscape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility.Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and watersports.

Coby Taylor

Expert Realty LLC (HQ)

(786) 398-5093

21731 Asturias Rd, Summerland Key, FL 33042
/34
$6,000 per month
- 3 Beds
- 3 Baths
- 1,380 Sq Ft
- Property for Rent
59 Palm Dr, Key West, FL 33040

Enjoy the Keys lifestyle in this stunning canal-front 3-bedroom, 3-bathroom elevated modular home, located in the desirable Bay Point neighborhood, just behind Baby's Coffee. Available for $5,900 per month, this 2015-built home offers modern amenities and a spacious layout perfect for comfortable living.The lower level features a bedroom with a full bath, 9-foot ceilings, and access to a covered

Dan Serban

Key West Luxury Real Estate Inc (KW)

(645) 205-0832

59 Palm Dr, Key West, FL 33040
/19
$505,000 Sold Jul 30, 2025
- 1,056 Sq Ft
- $478/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
134 Tortuga Ln, Summerland Key, FL 33042

Waterfront Fixer-Upper with Endless Potential on Cudjoe Key in the Magical Lower Keys!Embrace the opportunity to transform this waterfront gem into your Florida Keys dream retreat! Nestled in the desirable community behind the famous Square Grouper Restaurant this property offers direct boating access to the Atlantic Ocean--no bridges, no hassle, just open water in mere minutes.Situated on a

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

134 Tortuga Ln, Summerland Key, FL 33042

/26
Est $413,740 Not Listed For Sale
- 1 Bed
701 Spanish Main Dr Unit 229, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 229, Cudjoe Key, FL 33042

/50
$1,699,000
- 4 Beds
- 3 Baths
- 1,967 Sq Ft
1068 Buttonwood Dr E, Summerland Key, FL 33042

Tucked away in the prestigious Sugarloaf Shores neighborhood this exceptionally private canal front retreat sits high on the ground sprawling over 1/2 acre of lushly landscaped fenced and gated grounds. Step inside the Living Room where large impact windows greet you boasting picturesque pool and garden views while flooding the space with natural light, creating an airy, welcoming atmosphere.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 751-6658

1068 Buttonwood Dr E, Summerland Key, FL 33042
/5
$725,000 Sold Jul 30, 2025
- 1,394 Sq Ft
- $520/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 1990
19462 Canal Dr, Summerland Key, FL 33042

Discover peace and privacy in this charming, elevated home nestled on a generous 14,000 sq ft lot on Sugarloaf Key. With a massive covered deck perfect for relaxing or entertaining, this 2-story stilt home offers 3 bedrooms, 2 full bathrooms, plus a versatile bonus room ideal for a home office, guest space, or playroom.Enjoy the convenience of covered parking for multiple vehicles, ample storage

Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

19462 Canal Dr, Summerland Key, FL 33042

/63
Est $1,914,129 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,366 Sq Ft
17057 Bonita Ln W, Sugarloaf Key, FL 33042

17057 Bonita Ln W, Sugarloaf Key, FL 33042

/41
$1,172,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
22946 Bluegill Ln, Summerland Key, FL 33042

If you are looking for the ''Island Life'' with the best boating access in the Keys, this is the property for you. This beautifully updated tropical Keys home on a lushly landscaped spacious 10,200 square foot lot, is located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable for its premier boating access to world class fishing and diving in both

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(305) 787-3949

22946 Bluegill Ln, Summerland Key, FL 33042
/47
$1,075,000 Sold Jul 30, 2025
- 1,120 Sq Ft
- $960/SF
- 189 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
128 Le Grand Ln, Summerland Key, FL 33042

Welcome to your stunning 3-bedroom, 2-bathroom oasis, nestled at the end of a peaceful cul-de-sac on a double canal. Surrounded by lush fruit trees, this home offers the perfect blend of tranquility and luxury. Step inside to find a spacious open floor plan that creates a bright and airy atmosphere, ideal for entertaining. The chef-friendly kitchen is equipped with modern appliances, making it a

Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

128 Le Grand Ln, Summerland Key, FL 33042

/9
Not Listed For Sale
Lot 8 Overseas Hwy, Summerland Key, FL 33042

Lot 8 Overseas Hwy, Summerland Key, FL 33042

/77
$13,995,000
- 31 Beds
- 19 Baths
21470 Overseas Hwy, Cudjoe Key, FL 33042

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

Jennifer Weeks

Select Properties of NWFL

(786) 882-8127

21470 Overseas Hwy, Cudjoe Key, FL 33042
/33
$1,350,000 Sold Jul 24, 2025
- 2,524 Sq Ft
- $535/SF
- 215 Days On Market
- 3 Beds
- 3 Baths
- Built 2011
20883 4th Ave, Cudjoe Key, FL 33042

Tucked away in the boating community of Cudjoe Gardens, this spacious 3 Bedroom plus Loft canal front home boasts over 2,500 sq. ft. with soaring ceilings and a 2-car garage. Thoughtfully designed for both relaxation and functionality, the space is filled with natural light which flows seamlessly from room to room. The massive Kitchen is highly functional featuring lots of granite counter space

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

20883 4th Ave, Cudjoe Key, FL 33042

/2
Est $225,557 Not Listed For Sale
- Studio
701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

/41
$1,449,000 Under Contract
- 3 Beds
- 2 Baths
- 1,582 Sq Ft
20735 5th Ave W, Summerland Key, FL 33042

This beautifully renovated 3 Bedroom 2 Bathroom home is located in Cudjoe Gardens, a premiere boating community offering wide crystal clear deep draft canals, quick ocean access, neighborhood restaurant and a full service marina with fuel, bait, ice, refreshments and boat ramp. As you enter into this lovely and impeccably kept home a bright and sunny Great Room greets you highlighted with a

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(305) 930-6655

20735 5th Ave W, Summerland Key, FL 33042
/66
$910,000 Sold Jul 23, 2025
- 1,541 Sq Ft
- $591/SF
- 427 Days On Market
- 3 Beds
- 2 Baths
- Built 1990
246 Colson Dr, Summerland Key, FL 33042

SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet

Tracey Petrusha Venture Realty Group

246 Colson Dr, Summerland Key, FL 33042

/2
Est $292,239 Not Listed For Sale
- Studio
701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

/35
$599,000 Under Contract
- 2 Beds
- 2 Baths
- 1,129 Sq Ft
19616 Aztec St, Summerland Key, FL 33042

Nestled in a quiet and charming neighborhood on Sugarloaf Key, this beautifully remodeled 2-bedroom, 2-bathroom home offers a perfect blend of modern updates and coastal charm. With plenty of natural light throughout and crown molding accenting every room, this home feels both elegant and welcoming. The kitchen features newer, stainless steel appliances and stylish finishes, making it ideal for

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(844) 948-3208

19616 Aztec St, Summerland Key, FL 33042
/8
$199,000 Sold Jul 22, 2025
- Land
- 149 Days On Market
13 Beach Dr, Key West, FL 33040

Permit awarded! BUILD your county approved CBS 3BR 2BA 1300+ sq foot GREEN home on this cleared oversized corner lot.Not your average lot-- larger than most other vacant land in the area. Buy now before permits are picked up and save money and time! Submit a simple plan amendment review for a manufactured home or wood build on site if preferred. Gorgeous sunset views of the Atlantic AND Gulf and

Natallie Liz Expert Realty LLC (HQ)

13 Beach Dr, Key West, FL 33040

/2
Est $663,061 Not Listed For Sale
- Studio
17172 Marlin Dr, Sugarloaf Shores, FL 33042

17172 Marlin Dr, Sugarloaf Shores, FL 33042

/39
$699,000
- 2 Beds
- 2 Baths
- 1,090 Sq Ft
181 Doubloon Ln, Summerland Key, FL 33042

This super cute 2 Bedroom 2 Bath home in Cutthroat Harbor Estates on Cudjoe Key offers easy ocean access with no bridges from the 60' long concrete dock. The open concept floorpan features a remodeled kitchen with center island, new cabinetry, stainless appliances and granite countertops. The enclosed Florida Room and adjacent outdoor Porch both overlook the water and are the perfect places to

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 882-0498

181 Doubloon Ln, Summerland Key, FL 33042
/42
$630,000 Sold Jul 21, 2025
- 768 Sq Ft
- $820/SF
- 43 Days On Market
- 2 Beds
- 3 Baths
- Built 1980
92 Frazier Ln, Summerland Key, FL 33042

🌴 Island Living at Its Sweetest - 92 Frazier Lane, Sugarloaf Key 🐚Tucked away at the end of a quiet lane in the heart of Sugarloaf Key, this adorable island cottage is brimming with charm, sunshine, and laid-back Keys vibes. Set on an expansive double lot (10,000 sq ft!), this beautifully renovated hideaway offers the perfect blend of privacy and paradise.Step inside and be

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

92 Frazier Ln, Summerland Key, FL 33042

/2
Not Listed For Sale
- 2 Beds
- 1 Bath
- 897 Sq Ft
701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

/38
$810,000
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
22957 Drake Ln, Cudjoe Key, FL 33042

Excellent boating and pretty open water views down the canal at this gorgeous Cudjoe Key retreat! Enjoy quick no-bridge access to Cudjoe Bay for frequent boating and fishing adventures with ease. Inside this well-maintained home, the main living area boasts high ceilings and an open concept. The well-equipped kitchen features stainless steel appliances, abundant storage, and a large center island

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 964-3201

22957 Drake Ln, Cudjoe Key, FL 33042
/55
$1,800,000 Sold Jul 18, 2025
- 2,638 Sq Ft
- $682/SF
- 164 Days On Market
- 4 Beds
- 4 Baths
- Built 1993
22925 John Avery Ln, Summerland Key, FL 33042

Welcome to your forever island home! Fully furnished and turnkey! One of a kind, solid, custom-built (no modular here) coastal home with magnificent sunset, ocean and bay views from your wrap around porches and balconies. Located on crystal-clear waters filled with tropical fish, a boat ramp for beach launching kayaks or small boats and 60ft of waterfront with dock that can accommodate a 36ft

Jonathan Minerick Homecoin.com

22925 John Avery Ln, Summerland Key, FL 33042

/2
Est $178,992 Not Listed For Sale
- Studio
825 Hawksbill Ln, Sugarloaf Key, FL 33042

825 Hawksbill Ln, Sugarloaf Key, FL 33042

/58
$2,599,000
- 4 Beds
- 3 Baths
- 2,886 Sq Ft
1260 Sugarloaf Blvd, Summerland Key, FL 33042

Fabulous Sunset Views over Sugarloaf Sound at this 4 Bedroom 3 Bath 2,886 sq. ft. open water concrete home in Sugarloaf Shores, an upscale coastal community of waterfront homes located just 15 minutes outside of Key West. Built by the current owner the home features a massive Great Room boasting stunning open water views from all angles and an open Kitchen highlighted by a center cooking island

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 855-6752

1260 Sugarloaf Blvd, Summerland Key, FL 33042
/50
$550,000 Sold Jul 14, 2025
- 864 Sq Ft
- $637/SF
- 245 Days On Market
- 2 Beds
- 2 Baths
- Built 2021
701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

MOTIVATED SELLER. BRING THE OFFERS! BEST VALUE IN VENTURE OUT! HUGE PRICE DROP! NEGOTIABLE.! 2-YEAR HOME WARRANTY. TOTAL ELEGANCE! Experience the pinnacle of stilt-home living in this stunning residence at Venture Out, built just 3.5 years ago and meticulously designed with premium upgrades throughout. This 2-bedroom, 2-bathroom manufactured gem is move-in ready and fully furnished, offering a

Joe Sappington Waterfront Keys Realty Inc.

701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

/2
Not Listed For Sale
0 E Circle Dr, Saddlebunch, FL 33040

0 E Circle Dr, Saddlebunch, FL 33040

/52
$1,999,000
- 4 Beds
- 4 Baths
- 2,400 Sq Ft
17077 Bonita Ln W, Summerland Key, FL 33042

Escape to the tranquil beauty of Sugarloaf Shores with this beautifully renovated 4 bedroom + bunk room, 3.5 bath CBS home, ideally positioned on a tropically landscaped 12,500 sq ft lot with stunning open water views of Sugarloaf Sound. Inside, you'll find a bright and spacious open-concept great room that effortlessly blends indoor and outdoor living, perfect for both relaxing and entertaining.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(305) 304-0656

17077 Bonita Ln W, Summerland Key, FL 33042
/54
$615,000 Sold Jul 11, 2025
- 864 Sq Ft
- $712/SF
- 194 Days On Market
- 2 Beds
- 2 Baths
- Built 1999
701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

Are you dreaming of owning a piece of paradise in the Fabulous Florida Keys? Look no further than this gorgeous 2 bedroom, 2 bath waterfront home in the highly desired Venture Out Park in Cudjoe Key. This clean and updated home features a 35' concrete dock with whips, heavy duty aluminum posts, and easy access to enjoy both the gulf and ocean for world-class fishing and diving adventures. Inside,

Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

/34
Not Listed For Sale
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

/42
$1,999,000
- 3 Beds
- 2 Baths
- 2,047 Sq Ft
20771 2nd Ave W, Summerland Key, FL 33042

Wonderful Cudjoe Gardens property! High quality concrete construction and custom metal roof. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool, tiki and firepit. Exceptional boating- the 100' concrete dock is set up for 2 boats- with a 20,000 lb lift and davits rated to 10,000 lbs. Enjoy easy boating access to world class fishing and diving

Sandra Tuttle

Island Welcome Real Estate

(786) 952-5792

20771 2nd Ave W, Summerland Key, FL 33042
/56
$1,725,000 Sold Jul 11, 2025
- 1,660 Sq Ft
- $1039/SF
- 258 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
17159 Amberjack Ln, Summerland Key, FL 33042

Discover the pinnacle of Florida Keys living in this charming waterfront home on prestigious Sugarloaf Key, just 20 minutes from Key West! This stunning 3-bedroom, 2-bath, 1,660 sq. ft. stilted home is set on a spacious 12,500 sq. ft. lot along a crystal-clear wide canal, complete with a brand new gorgeous pool with a heater and chiller, a 32ft Dock and 12,000 lb. boat lift. Step inside and fall

Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

17159 Amberjack Ln, Summerland Key, FL 33042

/2
Est $1,049,961 Not Listed For Sale
- 1 Bed
- 1 Bath
- 1,008 Sq Ft
18954 Acosta Trail, Summerland Key, FL 33042

18954 Acosta Trail, Summerland Key, FL 33042

/47
$1,499,000
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
17166 Wahoo Ln W, Summerland Key, FL 33042

This spacious 1,723 sq. ft. 3 Bedroom 2 Bath canal front Pool home is located in prestigious Sugarloaf Shores, an upscale community of waterfront homes just 15 miles from the magic of Key West. The resort-style home boasts a tropical waterfront pool with adjacent tiki bar to enjoy refreshments after a day out on the water. Boaters will appreciate the 100' of concrete dockage with davits on an

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 744-8525

17166 Wahoo Ln W, Summerland Key, FL 33042
/83
$3,300,000 Sold Jul 11, 2025
- 3,086 Sq Ft
- $1069/SF
- 299 Days On Market
- 3 Beds
- 2 Baths
- Built 2015
16705 Tamarind Rd, Summerland Key, FL 33042

Exquisite Open Water Estate on Prestigious Southpoint, Sugarloaf Key! Experience unparalleled luxury at this stunning solid concrete open water property, located just 20 minutes from the magic of Key West and Key West Airport. Situated on prestigious Southpoint, Sugarloaf Key, this magnificent estate offers breathtaking open water views and a lifestyle of elegance and comfort.Spanning 3,086

Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

16705 Tamarind Rd, Summerland Key, FL 33042

/2
Not Listed For Sale
Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

/5
$350,000
- Land
25091 Overseas Hwy, Summerland Key, FL 33042

Attention all Commercial Fisherman and Marine Mechanics! Fantastic canal front commercial fishing district lot on Summerland Keys boasting 60' of road frontage with excellent highway visibility. 60' Concrete dock. Allowed uses include commercial fishing operations, boat repair and mechanic business and other home businesses.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(855) 526-7517

25091 Overseas Hwy, Summerland Key, FL 33042
/45
$2,090,000 Sold Jul 07, 2025
- 1,938 Sq Ft
- $1078/SF
- 65 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2025
23066 Tarpon Ln, Summerland Key, FL 33042

''BRAND NEW' CBS Construction ready for occupancy!!! Amazing New Oceanside Home with 4 Bedrooms, 3.5 Baths, in Beautiful Cudjoe Ocean Shores, (Custom Built by Dream Builders of the Florida Keys). This home offers Open Water Views, Instant Deep Draft Boating for Big Boat Action, Protected Concrete step-down Dock, Open Floor plan, Dining Area, two Master Suites, High Ceilings, Chefs Kitchen with

Greg MacLaren Internet Realty of the Florida Keys

23066 Tarpon Ln, Summerland Key, FL 33042

/10
Not Listed For Sale
19 Palm Dr, Saddlebunch, FL 33040

19 Palm Dr, Saddlebunch, FL 33040

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