Homes for Sale near Monroe County School District Virtual Instruction Program

• 

  

  

  /35

  $1,495,000

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040

  Charming Old Town Duplex located in the heart of old town. Ideally located on Simonton Street this charming duplex places you just steps from Duval Street, along with world-class dining, boutique shopping, beaches, and neighborhood parks.This versatile property is the perfect Key West residence, second home, or income-producing investment. Live in one side and rent the other, or maximize its

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040
• 

  

  

  /18

  $715,000

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  1119 Simonton St Unit A1, Key West, FL 33040

  Ideally located on Simonton Street in the heart of Old Town, this charming half-duplex is just steps from Duval Street and close to dining, shopping, beaches, and neighborhood parks.Perfect as a full-time island residence, second home, or investment property, this home offers the quintessential Key West lifestyle in one of the island's most desirable locations.The property features a welcoming

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A1, Key West, FL 33040
• 

  

  

  /31

  $1,560,000

  • 2 Beds
  • 4 Baths
  • 1,092 Sq Ft

  709 Olivia St, Key West, FL 33040

  Legal duplex in the heart of Old Town Key West offering flexibility for investors or owner-occupants alike. Each residence features a private entrance, in-unit laundry, electric meter, and thoughtful renovations that make the property truly turn-key.Classic Key West character shines throughout with vaulted ceilings, exposed beams, skylights, and beautiful wood floors creating a bright and airy

  Corey Breingan RE Florida Homes

  709 Olivia St, Key West, FL 33040
• 

  

  

  /36

  $799,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  616 Caroline St Unit 6, Key West, FL 33040

  Situated along one of Old Town's most storied corridors, residence #6 at 616 Caroline Street offers a refined Keys lifestyle just steps from the Historic Seaport, Duval Street dining, galleries, and marinas. Tucked within a boutique setting, this private upstairs home balances character and comfort with a bright, welcoming living area and an efficient layout that makes everyday living--and easy

  Jimmy Lane Island Life Realty Experts

  616 Caroline St Unit 6, Key West, FL 33040
• 

  

  

  /47

  $2,538,000

  • 10 Beds
  • 6 Baths
  • 3,876 Sq Ft

  912 Pohalski St, Key West, FL 33040

  Unlock the potential of this exceptional multifamily complex nestled in the heart of Old Town Key West. With a total of six units offering a diverse mix of layouts, including three 1-bedroom/1-bathroom units, two 2-bedroom/1-bathroom units, and one 3-bedroom/1-bathroom unit, this property presents an unparalleled investment opportunity in one of the most coveted destinations in the Florida Keys.

  Richard Haskins Buy The Keys

  912 Pohalski St, Key West, FL 33040
• 

  

  /18

  $499,000

  • 2 Beds
  • 2 Baths
  • 808 Sq Ft

  3930 S Roosevelt Blvd Unit 208N, Key West, FL 33040

  Welcome to Las Salinas --one of Key West's most desirable condominium communities. This beautifully maintained second-floor, 2-bedroom, 2-bath residence offers comfort, style, and the relaxed charm of island living. Filled with natural light, the condo features an open and airy layout designed for easy living. The kitchen is thoughtfully appointed with granite countertops and stainless steel

  Monika Rydzak eXp Realty LLC KW Branch

  3930 S Roosevelt Blvd Unit 208N, Key West, FL 33040
• 

  

  /17

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 958 Sq Ft

  1401 Simonton St Unit 11, Key West, FL 33040

  This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom

  Ralph Sanchez Century 21 All Keys Inc (KW)

  1401 Simonton St Unit 11, Key West, FL 33040
• 

  

  /22

  $439,900

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft

  3312 Northside Dr Unit 202, Key West, FL 33040

  Enjoy the largest floor plan in the Santa Clara building with this spacious 2-bedroom, 2-bath condo in the heart of New Town Key West!Welcome to easy island living in tropical Key West, FL! This spacious 2-bedroom, 2-bath condo features the largest floor plan in the building and is conveniently located on the second floor with elevator access. The residence offers tile and laminate flooring,

  DANICA WATKINS Keller Williams Key West Compass Realty

  3312 Northside Dr Unit 202, Key West, FL 33040
• 

  

  /20

  $3,395,000

  • Land

  6810 Front St Unit S-LL-1A,1B,1C,1D, Stock Island, FL 33040

  LARGE YACHT COUNTRY * Four Boat Slips - Perfect for large boats and wide beam catamarans. Rare opportunity to purchase four liveaboard boat slips side by side as a package at Safe Harbour Marina on Stock Island. Slip sizes: 1A 100' x 39', 1B 100' x 27', 1C 100' x 34' and 1D 100' x 25'.Each slip can accommodate up to 125' boat. (each slip has 20'' steel pylons approximately 60' from dock)The total

  Jerry Hughes Old Town Realty

  6810 Front St Unit S-LL-1A,1B,1C,1D, Stock Island, FL 33040
• 

  

  /17

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  3001 Riviera Dr, Key West, FL 33040

  Charming 3 bedroom/2 bath single-family home ideally located just a half block from the Riviera Canal boat ramp, offering convenient boating access and a desirable Key West location. This well-maintained property features custom cabinetry and built-ins throughout, central air conditioning, and an en-suite primary bedroom. The kitchen showcases custom finishes, a stylish backsplash, and a

  The Spottswood Team Truman & Co. (KW)

  3001 Riviera Dr, Key West, FL 33040
• 

  

  /54

  $2,999,500

  • 2 Beds
  • 2 Baths
  • 1,770 Sq Ft

  401 Emma St Unit H, Key West, FL 33040

  Beautifully updated and styled with plush new interior designed furnishings, 401 Emma Street Unit H is a vacation rental townhome that has BOTH Ocean and Harbor views in the heart of Truman Annex. Enjoy gorgeous sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered

  Ralph Sanchez Century 21 All Keys Inc (KW)

  401 Emma St Unit H, Key West, FL 33040
• 

  

  /56

  $2,549,000

  • 3 Beds
  • 4 Baths
  • 2,469 Sq Ft

  2924 Riviera Dr, Key West, FL 33040

  Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room and kitchen give you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was stripped to the concrete block walls and rebuilt (with

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  2924 Riviera Dr, Key West, FL 33040
• 

  

  /43

  $1,999,999

  • 4 Beds
  • 3 Baths
  • 1,632 Sq Ft

  1708 Laird St, Key West, FL 33040

  Tucked into the heart of Midtown Key West, this striking 4 bedroom, 3 bathroom concrete home is where modern design meets island rhythm.Behind a private electric gate, you'll discover a home that feels like a quiet retreat lush landscaping, full irrigation, off street parking, and a sense of privacy that's rare and refreshing.Step inside and the tone changes... in the best way.Large windows and

  Jenny Perry Preferred Properties (KW)

  1708 Laird St, Key West, FL 33040
• 

  

  /73

  $1,410,000

  • 3 Beds
  • 3 Baths
  • 1,610 Sq Ft

  1507 19th St, Key West, FL 33040

  Beautifully maintained 3-bedroom, 2.5 bath pool home located in the highly desirable Newtown neighborhood of Key West. This property offers the perfect balance of indoor comfort and outdoor island living.A flagstone pathway leads to your private, quaint, floating dock on Sunrise Canal, providing convenient access to launch kayaks, paddleboards, and personal watercraft. From here, you can explore

  Marlene Alvarez Keller Williams Key West Compass Realty

  1507 19th St, Key West, FL 33040
• 

  

  /75

  $4,200,000

  • 4 Beds
  • 4 Baths
  • 2,458 Sq Ft

  3 Evergreen Ave, Key West, FL 33040

  New 2025 waterfront construction on the final canal in Key Haven--an architectural entertainer designed for seamless indoor-outdoor living just 5 minutes from Key West. Unlike typical Keys homes, this residence was designed around outdoor living, offering over 2,400 Sq.Ft. of covered entertaining space seamlessly connected to the interior. Completed in 2025, this striking modern waterfront

  Lisa Swanson Coldwell Banker Schmitt Real Estate Co.

  3 Evergreen Ave, Key West, FL 33040
• 

  

  /53

  $1,994,999

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft

  1607 Sunshine Dr, Key West, FL 33040

  Welcome to your ideal island escape at 1607 Sunshine Drive in vibrant Key West, FL! This newer-construction 2014 single-family home offers the modern coastal lifestyle you want - built to the latest building codes for improved insurance options- featuring impact glass windows and doors, metal roof, concrete siding, and an elevated structure above base flood for added peace of mind.Step inside to

  Jimmy Lane Island Life Realty Experts

  1607 Sunshine Dr, Key West, FL 33040
• 

  

  /59

  $4,495,000

  • 4 Beds
  • 5 Baths
  • 2,806 Sq Ft

  1614 Washington St, Key West, FL 33040

  Architect-designed and purpose-built for modern island living, 1614 Washington Street delivers a rare combination of durability, intelligence, and refined restraint. This is a luxury home defined not by excess, but by performance, longevity, and thoughtful design. Constructed with solid masonry, impact-rated windows and doors, and positioned above flood elevation, the home offers a level of

  Richard Patten Your Keys Real Estate, LLC

  1614 Washington St, Key West, FL 33040
• 

  

  /9

  $675,000

  • 3 Beds
  • 3 Baths
  • 1,358 Sq Ft

  3314 Northside Dr Unit 13 & 13A, Key West, FL 33040

  Two well kept condo units at Solana Village in Key West's New Town neighborhood represents a solid investment opportunity. Conveniently situated near local schools, government offices, retail centers, a movie theater, and marinas, the property offers both lifestyle and income potential.The second-floor unit (13) is a 2-bedroom, 2-bathroom with all-tile flooring and a private balcony, while the

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  3314 Northside Dr Unit 13 & 13A, Key West, FL 33040
• 

  

  /41

  $587,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 108, Key West, FL 33040

  Welcome to island living at its finest in this beautifully maintained 1-bedroom, 1-bathroom ground-floor unit at the highly desirable Key West by the Sea.This light-filled residence offers a comfortable open layout with tile flooring throughout, a spacious living area, and a seamless flow to your private deck, where you can enjoy tropical breezes and garden views just steps from the pool.

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  2601 S Roosevelt Blvd Unit 108, Key West, FL 33040
• 

  

  /35

  $695,000

  • 2 Beds
  • 3 Baths
  • 900 Sq Ft

  18 Golf Club Dr, Key West, FL 33040

  Introducing this stunning new listing with the best lake view on the golf course, this meticulously maintained and updated 2-bedroom, 2 1/2-bathroom, 900 sqft townhome in Key West Golf Course community offers serene vistas of the 6th hole. Ideally positioned near the community entrance for easy access, this home features a host of impressive updates including a custom kitchen renovation, wood

  Solaris Gregory Expert Realty LLC (HQ)

  18 Golf Club Dr, Key West, FL 33040
• 

  

  /23

  $899,995

  • 2 Beds
  • 2 Baths
  • 798 Sq Ft

  3625 Seaside Dr Unit 25304, Key West, FL 33040

  Enjoy the view of the Salt Ponds & catch sunset from the balcony of this 2 bedroom / 2 bath Transient Licensed condo. Good investment opportunity to have your own place in Key West and generate rental income when you are not here to offset carrying costs. The condo comes fully furnished (turnkey) and has been updated with LVP flooring throughout, renovated baths with tiled, glass enclosed walk-in

  Shad Knapp Beach Club Brokers (KW)

  3625 Seaside Dr Unit 25304, Key West, FL 33040
• 

  

  /30

  $1,395,000

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  1306 Virginia St, Key West, FL 33040

  LEGAL DUPLEX with INVESTMENT OPPORTUNITY.Located in the Old Town Key West neighborhood in the X Flood zone, this historic property presents many opportunities. Increase the square footage and/or covert to a single family home. Bring your creativity to this historic charmer.Currently set up as a Legal Duplex with 2 bedrooms/1 bath downstairs, and 1 bedroom/ 1 bath upstairs with separate electric

  Joyce Craul Expert Realty LLC (HQ)

  1306 Virginia St, Key West, FL 33040
• 

  

  /21

  $250,000

  • Land

  5555 College Rd Unit 8, Key West, FL 33040

  Lowes cost liveaboard slip for 45' x 15' boat in Key West. Live in Paradise for only $250,000 and circa $592/month (HOA fee/property taxes) + utilities.Well-protected 120 slip marina on leeward side of the island, with state of the art Bellingham floating concrete docks. Deeded dockominium (you own bay bottom rights). Easy access to Gulf of Mexico, Atlantic Ocean and The Caribbean.Has mailboxes

  Jerry Hughes Old Town Realty

  5555 College Rd Unit 8, Key West, FL 33040
• 

  

  /12

  $215,000

  5555 College Rd Unit 6 (starfish), Key West, FL 33040

  Sunset Marina offers a range of amenities and attractions that make it a desirable destination for live aboard boaters and visitors alike. Starfish # 6 is a 30 ft boat slip that accommodates a max of 35 ft overall boat length. The marina features a variety of boat slips that can accommodate different sizes of vessels, providing easy access to the water. A convenient fuel dock is available for

  Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  5555 College Rd Unit 6 (starfish), Key West, FL 33040
• 

  

  /58

  $1,250,000

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

  1409 4th St, Key West, FL 33040

  Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of living space. The open-concept layout features a large living room, a well-appointed kitchen with an adjoining dining area, and plenty of natural light. There's also a garage, laundry room, and

  Keys Team Bryant and Kat Expert Realty LLC (HQ)

  1409 4th St, Key West, FL 33040
• 

  

  /15

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 895 Sq Ft

  1311 Newton St, Key West, FL 33040

  This charming conch retreat property has been completely renovated and refurbished to contemporary standards and expectations: two bedrooms, two baths, an impressive great room, tranquil pool area, and one of the best geographic locations on the island. This lodging is named the Conch Republic Retreat in reference to Key West's laid-back attitude and, more specifically, to its Meadows

  Louis Condos Home Edge Inc. (KW)

  1311 Newton St, Key West, FL 33040
• 

  

  /47

  $1,399,000

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  617 Fleming St Unit 4, Key West, FL 33040

  Looking for a gorgeous, lock and go, 2-bedroom condo in a perfect downtown Key West location? Just 1 1/2 blocks from Duval, on iconic Fleming Street, sits your dream Key West escape in the historic Campbell Building. This condo is gorgeous and its location can't be beat! A stone's throw from the action and the historic Seaport District, unit 4 is fully remodeled and looks directly down onto

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  617 Fleming St Unit 4, Key West, FL 33040
• 

  

  /53

  $1,885,000

  • 4 Beds
  • 2 Baths
  • 2,242 Sq Ft

  1416 Catherine St, Key West, FL 33040

  Priced to Sell - Exceptional Value in Old Town Key West! Opportunity meets island charm in this recently updated 4-bedroom, 2-bath home located in Old Town -- just a short walk or bike ride to everything Key West has to offer. Listed below market value for a swift sale, this is your chance to own a true tropical retreat at an incredible price. A classic white picket fence welcomes you in, leading

  Jody Clark Key West Luxury Real Estate Inc (KW)

  1416 Catherine St, Key West, FL 33040
• 

  

  /25

  $799,000

  • 1 Bed
  • 2 Baths
  • 814 Sq Ft

  3841 N Roosevelt Blvd Unit 121, Key West, FL 33040

  Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of beachfront living at the Key West Beachside Resort and Residences. This stunning waterfront corner suite invites you to live like you are on vacation every day. This is a rare to come on the market opportunity, as there are only three one-bedroom units on the entire property, and this beachfront location remains the most desired.

  Karen Verri Ocean Sotheby's International Realty

  3841 N Roosevelt Blvd Unit 121, Key West, FL 33040
• 

  

  /68

  $1,950,000

  • 5 Beds
  • 3 Baths
  • 2,146 Sq Ft

  530 White St, Key West, FL 33040

  Wonderful large home with a 7400 square foot yard!. Currently configured as 3 units, this property can be lived in as is or renovated for maximum potential. Located on the corner of White street and Stump lane, this property has beautiful grounds, room for a large pool, a workshop, decking, and off street parking. The First level features 2 units, each one has 2 bedrooms and 1 bath. Each unit is

  Elaine Coyle Tropical Properties Real Estat (KW)

  530 White St, Key West, FL 33040
• 

  

  /34

  $635,000

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3675 Seaside Dr Unit 342, Key West, FL 33040

  Welcome to your private slice of paradise at 3675 Seaside Dr Unit 342 -- a desirable end unit offering added privacy, extra natural light, and a peaceful coastal setting. Thoughtfully designed, this bright and airy residence features open living spaces perfect for both everyday comfort and effortless entertaining.The well-appointed kitchen flows seamlessly into the dining and living areas,

  Joanne Allen Berkshire Hathaway HomeServices Knight & Gardner Realty

  3675 Seaside Dr Unit 342, Key West, FL 33040
• 

  

  /50

  $3,699,000

  • 4 Beds
  • 5 Baths
  • 2,810 Sq Ft

  1501 Georgia St, Key West, FL 33040

  1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and

  The Spottswood Team Truman & Co. (KW)

  1501 Georgia St, Key West, FL 33040
• 

  

  /24

  $844,000

  • 3 Beds
  • 1 Bath
  • 1,342 Sq Ft

  1425 Eliza St, Key West, FL 33040

  3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own.

  Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  1425 Eliza St, Key West, FL 33040
• 

  

  /45

  $1,193,000

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft

  1713 Rose St, Key West, FL 33040

  Welcome to 1713 Rose Street! This is your chance to purchase a well-maintained 3/2 pool home in Mid Town West! As its namesake suggests, Rose is one of the sweetest streets in midtown. Two blocks from the beaches, it is nestled away with its three sister streets, in a quiet, serene neighborhood full of wonderful residents. A 5 minute walk to White Street Pier, Higgs Beach, Salute Restaurant,

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  1713 Rose St, Key West, FL 33040
• 

  

  /22

  $619,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  804 South St Unit 3, Key West, FL 33040

  This is a must see unique and airy tropical second story condo in the Southpark Condominium Association. Lush vegetation surrounds the property and the private pool area located in the beautiful Casa Marina neighborhood. This upstairs 1 Bedroom/1 Bathroom offers relaxation on either the front covered porch or the rear private deck with a motorized awning for your comfort and convenience. Inside

  Mike Caron Keller Williams Key West Compass Realty

  804 South St Unit 3, Key West, FL 33040
• 

  

  /4

  $649,500

  • Land
  • 0.11 Acre
  • $6,117,237 per Acre

  1610-1612 Dennis St, Key West, FL 33040

  SELLER FINANCING AVAILABLE! Seller willing to negotiate terms for owner financing while you develop this parcel. Options are open as Seller wants to move this property.Development opportunity now even more affordable! This property includes the rights to build duplex or attached townhomes in prime midtown location. Live in one unit and collect rental income from the other. Great proximity to

  Mark MacLaughlin R.W.A. Realty Inc

  1610-1612 Dennis St, Key West, FL 33040
• 

  

  /62

  $1,575,000

  • 4 Beds
  • 3 Baths
  • 2,050 Sq Ft

  3405 16th Terrace, Key West, FL 33040

  Spacious, Turn-key Retreat on one of New Town's Largest Lots: Welcome to a rare opportunity in New Town - set on an oversized 14,000+ sq.ft. lot, one of the largest in the neighborhood. This 4- bedroom, 2.5 bath home offers the space, flexibility and outdoor living today's buyers are searching for, all in a move-in ready package. The backyard is the true showstopper. A 14 x 28 ft. swimming pool

  Suzanne Moore Truman & Co. (KW)

  3405 16th Terrace, Key West, FL 33040
• 

  

  /35

  $999,999

  • 3 Beds
  • 3 Baths
  • 1,452 Sq Ft

  1018 Georgia St, Key West, FL 33040

  Income producing Duplex in Old Town Key West! Fully renovated offering strong income potential and turnkey condition. Recent upgrades include a new roof, siding, impact windows, updated kitchens and baths, and new flooring in the rear unit.The downstairs features two lockout units--rear unit projected at $2,800/month with large private backyard, and front unit at $2,300/month. Upstairs treetop

  Diana Fiddes Coldwell Banker Schmitt Key Largo

  1018 Georgia St, Key West, FL 33040
• 

  

  /37

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,211 Sq Ft

  1440 17th St, Key West, FL 33040

  DUPLEX! Discover the perfect blend of flexibility, privacy, and income potential in this beautifully updated Key West duplex--ideal for families, extended living, or savvy investors. The main residence is a spacious 2-bedroom, 1-bath home thoughtfully updated in 2026 with a brand-new kitchen featuring modern cabinetry, sleek quartz countertops, a tile backsplash, and new stainless appliances.

  Dawn McComish Lokation Real Estate

  1440 17th St, Key West, FL 33040
• 

  

  /46

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,559 Sq Ft

  1720 Patricia St, Key West, FL 33040

  Perfect Home in the Heart of Key West - Renovated with Pool Near BeachIdeally located in the heart of Key West, this recently renovated three-bedroom, two-bath home is just a short stroll to Higgs Beach, White Street Pier, nearby parks, and popular tennis and bocce courts. It's a fantastic opportunity to own a move-in ready home in one of Key West's most desirable neighborhoods.Inside, the

  Richard Haskins Buy The Keys

  1720 Patricia St, Key West, FL 33040

Showing Results 121 - 160, Page 4 of 10