Monroe, FL Homes

• 

  

  

  /33

  $725,000 Sold Feb 21, 2025

  • 1,431 Sq Ft
  • $507/SF
  • 175 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  This beautifully maintained 3 bedroom, 2 bathroom home built in 2016 sits on a 7,500 square foot lot in highly sought after Cudjoe Key. Large open floorplan with dedicated dining area, well-appointed kitchen with granite countertops, stainless steel appliances and large center island offering plenty of space for family and friends to gather. Great insurance rates with metal roof, impact

  Pamela Stangler Expert Realty LLC

  22918 Cudjoe Dr, Cudjoe Key, FL 33042
• 

  

  /2

  Est $865,568 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  22974 John Avery Ln, Summerland Key, FL 33042

  22974 John Avery Ln, Summerland Key, FL 33042
• 

  

  

  /53

  $659,999

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

  Welcome to a stunning brand-new construction in the sought-after Venture Out community on Cudjoe Key. This turnkey investment property is designed for comfort and style offering high-quality upgrades and modern features. Built on 9-foot concrete columns with hardy board siding, metal roof and concrete stairs/decking, all meeting 2023 installation standards. Features open concept floor plan with

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
• 

  

  

  /20

  $250,000 Sold Feb 21, 2025

  • Land

  • 167 Days On Market

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  NIGHTLY RENTALS ALLOWED! Or build your Florida Keys dream home.Come on down to the ultimate RV paradise at this picture perfect lot in Venture Out! 35' x 69' of pure potential for your dream RV setup! Feel the good vibes as you park your rig and let the adventures begin! Dive into the laid-back lifestyle of Venture Out and make memories that will last a lifetime! Build your home here in the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
• 

  

  

  /19

  Est $881,731 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  221 Cutthroat Dr, Summerland Key, FL 33042

  221 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /46

  $599,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  Beautifully renovated 2 bedroom, 2 bathroom canal front home in a gated community with TRANSIENT RENTALS PERMITTED! Well appointed eat-in kitchen and open concept living with family room that opens onto your spacious outdoor porch overlooking the clear boating canal. 35-foot concrete seawall with quick boating access to the Gulf of Mexico and Atlantic Ocean. Home comes fully furnished and has

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
• 

  

  /40

  $550,000 Sold Feb 19, 2025

  • 816 Sq Ft
  • $674/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  Waterfront Paradise Awaits!This charming two-bedroom, two-bath mobile home offers a truly unique waterfront living experience. Enjoy breathtaking views and direct access to the sparkling waters of Cudjoe Key.Key Features:* Prime Waterfront Location: Situated directly on the water with a 35-foot concrete seawall, providing deep water access for boating enthusiasts.* Large windows for amazing views

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
• 

  

  /61

  Est $1,941,219 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  17153 Buttonwood Dr W, Summerland Key, FL 33042
• 

  

  /58

  $2,499,000

  • 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

  Team Spottswood/Vazquez Truman & Co. (KW)

  17210 Angelfish Ln, Summerland Key, FL 33042
• 

  

  /74

  $3,300,000 Sold Feb 18, 2025

  • 3,225 Sq Ft
  • $1023/SF
  • 313 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1963

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  A luxury waterfront estate with panoramic ocean views, this walled and gated masterpiece surrounded by gorgeous landscaping provides utmost privacy and the perfect Keys lifestyle and comes completely furnished. The unique 6-bedroom, 4-bathroom layout offers ample space for family and guests with breathtaking ocean vistas from almost every room. A secluded backyard oasis features a private beach,

  Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

  22572 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /39

  Est $1,377,978 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  17056 Wahoo Ln, Summerland Key, FL 33042

  17056 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /53

  $2,499,000

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft

  23086 Snapper Ln, Summerland Key, FL 33042

  Luxury Waterfront Fortress with Breathtaking Atlantic Ocean Views. Experience unparalleled coastal living with stunning, unobstructed views of the Atlantic Ocean and Kemp Channel from this oversized 12,000 sq. ft. corner lot. This one-of-a-kind CBS home is built for strength and style, offering the ultimate in durability and design. Featuring 4 bedrooms, 3 baths, and a spacious two-car garage,

  Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
• 

  

  /45

  $1,700,000 Sold Feb 13, 2025

  • 2,772 Sq Ft
  • $613/SF
  • 42 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1994

  20942 6th Ave W, Summerland Key, FL 33042

  Stunning canal front home in desirable Cudjoe Gardens, with Southern Exposure, massive 15,600 Sq. Ft. double lot, and deep-water access to Open Ocean and backcountry! Expertly outfitted with 125' of concrete seawall with running water, fillet station, swim ladders, 15K boat lift, davits, and turning basin! Situated on a clean flow-through canal, excellent for swimming and capable of accommodating

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20942 6th Ave W, Summerland Key, FL 33042
• 

  /2

  Est $1,175,798 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,274 Sq Ft

  21082 6th Ave, Summerland Key, FL 33042

  21082 6th Ave, Summerland Key, FL 33042
• 

  

  /39

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  164 Tortuga Ln, Summerland Key, FL 33042

  Welcome to 164 Tortuga Lane, a solid concrete stilted home perfectly positioned on a wide canal with quick access to open water. This move-in-ready property features 3 bedrooms, 2 bathrooms, 1,400 sq ft of living space, and a 6,000 sq ft lot.Highlights include: Private in-ground pool Metal roof (2018) with peel & stick underlayment Full hurricane protection with accordion shutters 10,000 lb boat

  Kathryn Baldwin Berkshire Hathaway HomeServices Knight & Gardner Realty

  164 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /46

  $1,750,000 Sold Feb 13, 2025

  • 2,073 Sq Ft
  • $844/SF
  • 150 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2011

  17194 Kingfish Ln W, Summerland Key, FL 33042

  This stunning 4-bedroom, 2-bathroom home offers the perfect balance of relaxation and entertainment. Enjoy your perfect lounge pool, designed with two removable lounge chairs for soaking in the sun while staying cool. Unwind in the jacuzzi or take advantage of the outdoor relaxation areas, including a covered space with a TV, hammock, fire pit, and a screened-in porch. Situated at the end of a

  Samantha Barrabeitg Expert Realty LLC (HQ)

  17194 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /81

  Est $1,504,674 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  23041 Snapper Ln, Summerland Key, FL 33042

  23041 Snapper Ln, Summerland 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

  $690,000 Sold Feb 11, 2025

  • Land

  • 8 Days On Market

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  Discover the perfect canvas for your dream home on this extraordinary canal-front lot located on Keystone Road, one of the most coveted streets in Sugarloaf Shores. This 20,000+ sq. ft. waterfront property is nestled on the no-bridge side of Sugarloaf Key, offering unparalleled privacy, tranquility, and easy access to open ocean waters via Tarpon Creek.The planned 1,404 sq. ft. home will meet

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  17295 Keystone Rd, Sugarloaf Shores, FL 33042
• 

  

  /19

  Est $831,464 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22910 Privateer Dr, Summerland Key, FL 33042

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /26

  $850,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  17245 Jamaica Ln, Summerland Key, FL 33042

  Welcome to 17245 Jamaica Lane, a waterfront 3-bedroom, 2-bathroom home in the desirable Sugarloaf Shores. This elevated residence offers 1,248 square feet of comfortable living space with beautiful canalfront views and direct canal access for boating and fishing enthusiasts. This home offers distinct living, dining, and kitchen areas, creating a natural flow. The kitchen includes granite

  Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /21

  $642,500 Sold Feb 10, 2025

  • 1,143 Sq Ft
  • $562/SF
  • 159 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  19518 Caloosa St, Summerland Key, FL 33042

  Elevated, 3BD/2BA, nestled in the highly desirable Indian Mound Estates neighborhood. located on Upper Sugarloaf Key. Home sits high & dry with covered parking & storage underneath, 10,000 square-foot lot with plenty of room to park the RV, Boat or other toys. This charming home features master bedroom on-suite walk-in closet, two guest bedrooms, with additional full bath, living room, eat-in

  Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty

  19518 Caloosa St, Summerland Key, FL 33042
• 

  

  /17

  Est $763,341 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  19481 Canal Dr, Summerland Key, FL 33042

  19481 Canal Dr, Summerland Key, FL 33042
• 

  

  /20

  $229,999

  • Land

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
• 

  

  /41

  $2,075,000 Sold Feb 03, 2025

  • 3,056 Sq Ft
  • $679/SF
  • 19 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2004

  20864 4th Ave W, Summerland Key, FL 33042

  This elegantly designed custom built ground level home was created by local architect Glenn Gray. Boasting a spacious open floor plan @ 3,056 sq ft. Two master bedrooms with ensuite baths, third bedroom, full bath and a half, and office all on first floor. Up the flight of stairs leads to a huge open loft space for a fourth bedroom/bunk room, theater room, art room or whatever your needs.

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  20864 4th Ave W, Summerland Key, FL 33042
• 

  /2

  Est $2,037,499 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /61

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom home, built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
• 

  

  /35

  $217,000 Sold Jan 31, 2025

  • Land

  • 22 Days On Market

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  TRANSIENT RENTALS ALLOWED!!Live the Island Life in Your Own Slice of Paradise! Ahoy, fellow adventurers! Set your sails for this dreamy RV lot nestled in the vibrant Venture Out Community, just a breezy 19 miles from the heart of Key West. This spacious 35' x 69' lot is ready to welcome even the biggest rigs, so bring your home on wheels and let the good times roll! With lush landscaping already

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
• 

  

  /41

  Est $438,027 Not Listed For Sale

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042
• 

  

  /42

  $1,175,000

  • 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 your very own

  Terry Garcia Keller Williams Key West Compass Realty

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /31

  $800,000 Sold Jan 31, 2025

  • 1,008 Sq Ft
  • $794/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  Idyllic Canal-Front Cudjoe Key retreat on a generous fenced-in lot in a prime location! This bright and spacious Cutthroat Harbor Estates home boasts an open concept main living space and three generous bedrooms! Coming soon, the seller is replacing the existing roof with a new metal roof. Upon entry, this turnkey home is tailor-made for entertaining. The living room flows seamlessly with a

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  /2

  Est $2,192,243 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,514 Sq Ft

  16725 Tamarind Rd, Summerland Key, FL 33042

  16725 Tamarind Rd, Summerland Key, FL 33042
• 

  

  /7

  $225,000

  • Land
  • 1.02 Acres
  • $220,589 per Acre

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042

  Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. It is a special lot that features mature trees. Near Sugarloaf School. 25 minutes to Key West.

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
• 

  

  /43

  $2,520,000 Sold Jan 31, 2025

  • 2,156 Sq Ft
  • $1169/SF
  • 165 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1986

  622 Sawyer Dr, Summerland Key, FL 33042

  Indulge in the epitome of Keys living with this delightful turnkey 3-bedroom, 3 1/2 bathroom stilt home on 1 1/2 lots. Embracing the coastal allure, this residence features serene blue to aqua tones indoors, complemented by elegant white plantation shutters that evoke a sense of timeless charm. Step onto the expansive covered patio, where panoramic views of the pool and a long canal stretch

  Laura Derrickson Keller Williams Coastal Partners

  622 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /27

  Est $1,707,884 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft

  22836 Port Royal Ln, Summerland Key, FL 33042

  22836 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /29

  $504,000

  • Land

  701 Spanish Main Dr Unit 240, Cudjoe Key, FL 33042

  BUILDABLE Waterfront RV Lot with Transient 1 day Rental Opportunity!! This RV site is perfect for your needs. Can accommodate a large RV, easy when parking and has room for storage shed and the rights to build a home in the future. The lot it is located in a private street, providing privacy and enjoyment. 24 hour Gated Security entry. Located near Key West (19 Miles) this property is perfect

  Howard & Lily Leitner Robert Slack LLC

  701 Spanish Main Dr Unit 240, Cudjoe Key, FL 33042
• 

  

  /34

  $775,000 Sold Jan 30, 2025

  • 1,340 Sq Ft
  • $578/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  191 Doubloon Ln, Summerland Key, FL 33042

  Located on a spacious corner lot of a quarter acre in the heart of Cudjoe Key, this home offers both peace and potential. The large, fenced-in yard provides endless opportunities for outdoor activities, with plenty of space for water toys, gardening, or just relaxing in a private, open space. The 25K boat lift makes it an ideal spot for those who love life on the water, while the expansive lot

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  191 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $1,043,193 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  17055 Kingfish Ln W, Summerland Key, FL 33042

  17055 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /13

  $495,000

  • Land

  1147 Basque Ln, Cudjoe Key, FL 33042

  PERMIT IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water Views all with a

  Brad Baker RE/MAX Keys To The Key

  1147 Basque Ln, Cudjoe Key, FL 33042
• 

  

  /18

  $1,520,000 Sold Jan 29, 2025

  • 3,538 Sq Ft
  • $430/SF
  • 0 Days On Market

  • 7 Beds
  • 4 Baths
  • Built 1982

  17042 Starfish Ln W, Summerland Key, FL 33042

  Woah! This is THE LOWEST price per sq foot figure for any waterfront single family home in The Florida Keys (according to the keywest MLS)! Over 3,500 interior sq ft in this elevated home on a double lot with 100 ft of canal frontage. Concrete seawall has davits & boat ramp. Currently configured as 7 bedrooms & 4 baths. Roof replaced in 2018 & windows (impact on upper level) replaced in 2019

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  17042 Starfish Ln W, Summerland Key, FL 33042

Showing Results 201 - 240, Page 6 of 18