Homes for Sale near Monroe County School District Virtual Instruction Program

• 

  

  

  /20

  $1,700,000

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft

  1224 2nd St, Key West, FL 33040

  Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of

  Jenna Stauffer Ocean Sotheby's International Realty

  1224 2nd St, Key West, FL 33040
• 

  

  

  /22

  $429,900

  $30K PRICE DROP

  • 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

  DANICA WATKINS Keller Williams Key West Compass Realty

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

  

  

  /44

  $999,995

  $49K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 838 Sq Ft

  3808 Duck Ave, Key West, FL 33040

  Wonderful Home with a Small Cottage, Salt Water Pool, and Off Street Parking, and 2 Brand New Roofs, on the Main House and the Guest Cottage!. Additionally- there is a New Insurance Mitigation report dated 8/28/2026! The Main Home has an open living room with cathedral ceilings, and a loft . The Kitchen has French Doors leading to a large deck, and a private back fenced yard. Chicago brick

  Elaine Coyle Keller Williams Key West Compass Realty

  3808 Duck Ave, Key West, FL 33040
• 

  

  

  /10

  $285,000

  5555 College Rd Unit 9, Key West, FL 33040

  OWNER FINANCING AVAILABLE!! Dock in a safe place for you vessel or liveaboard this boat slip with an overall length of 45' and width of 16' 1'. This floating concrete deep water boat slip has a 6' draft and is located in Sunset Marina in Key West, a locals favorite for 2 decades. Immediate access to gulf and easy access to Atlantic. Showers, laundry, dog walk, bike racks, convenience store, fuel

  Jim Spreitzer RE/MAX Keys Connection (KW)

  5555 College Rd Unit 9, Key West, FL 33040
• 

  

  

  /54

  $1,890,000

  • 2 Beds
  • 2 Baths
  • 1,495 Sq Ft

  516 Elizabeth St, Key West, FL 33040

  Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past.Listed on the National Register of Historic Places and awarded the Gold Star for Historic Preservations, 516

  Ellen Gvili Ocean Sotheby's International Realty

  516 Elizabeth St, Key West, FL 33040
• 

  

  /14

  $479,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  25D 10th Ave, Stock Island, FL 33040

  Corner lot with over 120 feet of street frontage in a part of Stock Island seeing continued investment and redevelopment. You own the land with NO HOA or lot rent, plus added privacy with no adjoining neighbors on two sides. A great opportunity for an owner or investor looking to get into an area with growing long-term potential.

  Zainya Zimmerer Berkshire Hathaway HomeServices Knight & Gardner Realty

  25D 10th Ave, Stock Island, FL 33040
• 

  

  /41

  $2,595,000

  $205K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,049 Sq Ft

  508 Grinnell St, Key West, FL 33040

  Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

  Marc Ulanowski Equestrian Sotheby's Internati

  508 Grinnell St, Key West, FL 33040
• 

  

  /80

  $2,400,000

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  2623 Gulfview Dr, Key West, FL 33040

  Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and

  Marlene Alvarez Keller Williams Key West Compass Realty

  2623 Gulfview Dr, Key West, FL 33040
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  /33

  $979,000

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  1500 5th St, Key West, FL 33040

  When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two

  Epperly - Celli Epperly - Celli Engel & Voelkers Key West

  1500 5th St, Key West, FL 33040
• 

  

  /28

  $799,000

  • 2 Beds
  • 2 Baths
  • 548 Sq Ft

  1422 Catherine St, Key West, FL 33040

  Welcome to 1422 Catherine Street in The Heart of Key West.Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom.The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new

  Bobby Coe RE/MAX Keys Connection (KW)

  1422 Catherine St, Key West, FL 33040
• 

  

  /4

  $949,000

  $146K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,520 Sq Ft

  818 Elizabeth St Unit Front, Key West, FL 33040

  Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 3038 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Please note that advanced notice is required to arrange showings.

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  818 Elizabeth St Unit Front, Key West, FL 33040
• 

  

  /72

  $3,398,000

  • 3 Beds
  • 4 Baths
  • 2,386 Sq Ft

  3034 Riviera Dr, Key West, FL 33040

  Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled canal frontage, complete with a new 24k lb boat lift and ~58' of new seawall, offering seamless ocean access. Step inside to experience the spacious living areas, illuminated by tons of natural light, with tile flooring throughout.

  Richard Haskins Buy The Keys

  3034 Riviera Dr, Key West, FL 33040
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  /25

  $343,500

  $40K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  3312 Northside Dr Unit 405, Key West, FL 33040

  IMPORTANT UPDATE TO NOTE: SELLER WILL PROVIDE A $5,000 CREDIT THAT CAN BE USED FOR CLOSING COSTS OR CONDO FEES!!Excellent as an investment, primary residence, second home, or rental property. This condo is conveniently located in a shopping area with easy access to Duval and US 1. It is one of the few gated communities in Key West with secure entry. You have ample parking, storage, pool,

  Karen Angle Coldwell Banker Schmitt Real Estate Co.

  3312 Northside Dr Unit 405, Key West, FL 33040
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  /48

  $1,249,000

  $30K PRICE DROP

  • 2 Beds
  • 3.5 Baths
  • 1,824 Sq Ft

  25 Seaside South Ct, Key West, FL 33040

  Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels.You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  25 Seaside South Ct, Key West, FL 33040
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  /33

  $779,000

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 648 Sq Ft

  906 Truman Ave Unit 2, Key West, FL 33040

  Turnkey Old Town Key West condo! 2 Bedrooms/2 Full Baths/ Fully Furnished/Pool-side/Rentals through March 2027!Welcome to your turnkey piece of Old Town Key West. This first-floor, poolside 2 Bedroom.2 Bath condo is fully furnished, ready to enjoy now, and comes with future rentals already booked through March 2027. Whether you're looking for a Key West getaway or an established vacation

  Elaine Coyle Keller Williams Key West Compass Realty

  906 Truman Ave Unit 2, Key West, FL 33040
• 

  

  /53

  $2,250,000

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

  912 Pohalski St, Key West, FL 33040

  Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available.There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy

  Bobby Coe RE/MAX Keys Connection (KW)

  912 Pohalski St, Key West, FL 33040
• 

  

  /31

  $1,100,000

  $199K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  414 Virginia St, Key West, FL 33040

  Price Reduced!!! Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price. Please ask Listing Agent about historical significance of this property.

  414 Virginia St, Key West, FL 33040
• 

  

  /61

  $999,000

  New Construction $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  49G Miriam St, Stock Island, FL 33040

  This newly built 2026 home on Stock Island delivers what buyers rarely find in the Florida Keys: true new construction, built to current code, with a fully legal guest suite and insurance costs designed to be as manageable as possible -- all priced under $1.1M.The main residence offers 3 bedrooms, 2 bathrooms, and over 1,500 square feet of thoughtfully designed living space elevated 18 feet

  Jimmy Lane Island Life Realty Experts

  49G Miriam St, Stock Island, FL 33040
• 

  

  /17

  $175,000

  $60K PRICE DROP

  5555 College Rd Unit 5, Key West, FL 33040

  Well-positioned 30' wet slip located at Sunset Marina on the gated side of the property. This floating concrete dock can accommodate a vessel up to 35' in length and offers deep water access with a 6' control depth -- perfect for easy navigation to both the Gulf and Atlantic waters.Sunset Marina is a full-service marina with on-site fuel, bait, and marina store. Owners of slips on the

  Jimmy Lane Island Life Realty Experts

  5555 College Rd Unit 5, Key West, FL 33040
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  /58

  $1,350,000

  $1M PRICE INCREASE

  • 1,760 Sq Ft

  1300 Ashby St, Key West, FL 33040

  Your place in Key West awaits. Located in Midtown, just minutes from the energy of Duval Street, this updated two-unit property offers the flexibility to live here, escape here, or explore its income potential. Whether you're looking for a full-time residence, a tropical getaway, or a property that can help offset the cost of ownership, this is an opportunity to experience Key West on your own

  Samira Garcia Luxe Properties

  1300 Ashby St, Key West, FL 33040
• 

  

  /20

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft

  2116 Fogarty Ave, Key West, FL 33040

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light.The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white

  Jenna Blackwell Berkshire Hathaway HomeServices Knight & Gardner Realty

  2116 Fogarty Ave, Key West, FL 33040
• 

  

  /29

  $819,000

  • 1 Bed
  • 1 Bath
  • 622 Sq Ft

  1105 Olivia St, Key West, FL 33040

  This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Completely turnkey and perfectly suited as a winter home or seasonal Key West escape, it offers the opportunity to simply arrive, settle in, and enjoy island life from day one.Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers

  Epperly - Celli Epperly - Celli Engel & Voelkers Key West

  1105 Olivia St, Key West, FL 33040
• 

  

  /70

  $2,595,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,931 Sq Ft

  1501 Florida St, Key West, FL 33040

  Price Reduction. Excellent opportunity to purchase a luxurious, modern, and refined single-family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living spaceand situated on a 5,896 S. F. corner lot. This CBS home has

  Jason Barroso Century 21 All Keys Inc (KW)

  1501 Florida St, Key West, FL 33040
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  /36

  $950,000

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1800 Atlantic Blvd Unit 218B, Key West, FL 33040

  Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along

  Donna Pezzi Keller Williams Key West Compass Realty

  1800 Atlantic Blvd Unit 218B, Key West, FL 33040
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  /63

  $1,375,000

  $175K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,387 Sq Ft

  9 Mccoy Cir Unit 9, Key West, FL 33040

  Experience quintessential island living in this stunning waterfront townhome at Flagler's Landing, where sweeping Gulf views meet a central Key West location with private boat dockage. This elevated residence offers ~1,387 sq ft of living space with open water views from the main living areas, private balcony, and both upstairs bedrooms. Designed for effortless entertaining, the main level

  Karen Verri Ocean Sotheby's International Realty

  9 Mccoy Cir Unit 9, Key West, FL 33040
• 

  

  /12

  $299,000

  • Land
  • 2,178 Sq Ft
  • $5,980,000 per Acre

  2001 Flagler Ave, Key West, FL 33040

  2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

  Everett Watkins Keller Williams Key West Compass Realty

  2001 Flagler Ave, Key West, FL 33040
• 

  

  /28

  $1,995,000

  $395K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft

  1620 Jamaica Dr, Key West, FL 33040

  NEW PRICE!! Key West WATERFRONT Home with a POOL! This expansive two-story residence has everything you need, featuring a first-floor primary suite, ample off-street parking, and a canal for boating enthusiasts, along with a fantastic pool area complete with a tiki hut for shaded relaxation. With 4 bedrooms and 3 bathrooms, this home spans 2,080 sq. ft. and is just minutes away from Old Town Key

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1620 Jamaica Dr, Key West, FL 33040
• 

  

  /36

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft

  103 Key Haven Rd, Key West, FL 33040

  Welcome to 103 Key Haven Road! This home is on an over-sized lot, which overlooks a small bay, and has mangrove and sunset views. The expansive back yard feels very private and has a large patio area. There is plenty of room for your boat along the seawall, and it is the perfect spot to watch sunset. The 3 bedroom home is livable as it is, or you can add your own current updates.

  Elaine Coyle Keller Williams Key West Compass Realty

  103 Key Haven Rd, Key West, FL 33040
• 

  

  /30

  $1,299,999

  $179K PRICE DROP

  • 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

  Joyce Craul Expert Realty LLC (HQ)

  1306 Virginia St, Key West, FL 33040
• 

  

  /78

  $2,100,000

  $295K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,820 Sq Ft

  13A 12th Ave, Key West, FL 33040

  80 Feet on One Of The Deepest Canals in the 33040 Zip Code. A13 and A14 12th Avenue sit side by side on Stock Island's waterfront, combining for 80 feet of canal frontage across two 4,800-square-foot parcels. A13 is an 1,820-square-foot CBS home that features four-bedrooms, three bathrooms home with a private dock on one of the deepest canals in the 33040 zip code. The layout offers flexibility

  Krystal Thomas eXp Realty LLC Southernmost Branch

  13A 12th Ave, Key West, FL 33040
• 

  

  /8

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  C1 9th Ave, Stock Island, FL 33040

  This 4 Bedroom 2-bathroom doublewide sits on a corner fenced lot with ample parking. This home has a roof that is only a few years old as well as newer central A/C. Currently it is being used as a rental with good monthly income. And you own the land

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  C1 9th Ave, Stock Island, FL 33040
• 

  

  /7

  $399,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  32C 10th Ave, Key West, FL 33040

  Endless Potential on Stock Island! Fantastic opportunity to own a 3,570 sq. ft. lot featuring an existing 1980 2-bed, 2-bath mobile home. Ideal for handymen, investors, or builders seeking a prime Keys project. Keep and renovate the current home for affordable living/rental income, or capitalize on the lot to explore building new. No HOA fees and located just minutes from Key West's premier

  Letisia Powell Robert Slack LLC

  32C 10th Ave, Key West, FL 33040
• 

  

  /28

  $679,500

  $18K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  3029 N Roosevelt Blvd Unit 11, Key West, FL 33040

  Welcome to your slice of paradise in the highly sought-after Key Cove community in Key West, FL, where island living meets enjoyable comfort. This beautifully designed townhome offers the perfect blend of coastal charm and modern convenience. Featuring a bright, open-concept layout, the living and dining spaces flow seamlessly with the well appointed kitchen. Ideal for entertaining or unwinding

  Christopher Orth Berkshire Hathaway HomeServices Knight & Gardner Realty

  3029 N Roosevelt Blvd Unit 11, Key West, FL 33040
• 

  

  /17

  $499,000

  $35K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,222 Sq Ft

  6800 Maloney Ave Unit 13, Stock Island, FL 33040

  PRICE DROP: $35K reduction!This Harbor Shores home on Stock Island packs 1,222 square feet with vaulted ceilings, granite counters, central AC, and 3BR with 3 full baths. Large closets in every room.HOA is $230/month and covers cable, common area maintenance and sewer. Strong option for long-term rental or employee housing.Harbor Shores is a waterfront community with a private boat

  Forrest Shearin Berkshire Hathaway HomeServices Knight & Gardner Realty

  6800 Maloney Ave Unit 13, Stock Island, FL 33040
• 

  

  /91

  $3,750,000

  $245K PRICE DROP

  • 7 Beds
  • 7.5 Baths
  • 3,015 Sq Ft

  919 Thomas St, Key West, FL 33040

  Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character

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

  919 Thomas St, Key West, FL 33040
• 

  

  /5

  $2,800

  • 2 Beds
  • 1 Bath

  6630 Maloney Ave Unit 7D, Key West, FL 33040

  Ernie Cruz Berkshire Hathaway HomeServices Knight & Gardner Realty

  6630 Maloney Ave Unit 7D, Key West, FL 33040
• 

  

  /44

  $1,100,000

  $300K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,156 Sq Ft

  2914 Fogarty Ave, Key West, FL 33040

  Nestled within lush tropical landscaping, this unique Key West home offers serene privacy and island charm just minutes from everything. A winding brick pathway leads you through mature palms and gardens to an inviting covered entryway. Inside, the home features spacious open living areas with exposed beam ceilings, a functional kitchen, and two classic tiled bathrooms, including a glass-block

  Janice Perez Keller Williams Key West Compass Realty

  2914 Fogarty Ave, Key West, FL 33040
• 

  

  /24

  $1,350,000

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft

  564 Porter Ln, Key West, FL 33040

  President's Walk townhome in the Truman Annex. This is a two-bedroom, 2.5-bathroom unit that also includes a deeded carport. It is a great location close to the community pool and all the downtown attractions that Key West has to offer. It features an open floor plan with kitchen, half bath, dining and living areas that open to the rear and side yard! Upstairs are two-bedroom ensuites with

  Behmke The Compass Realty (KW)

  564 Porter Ln, Key West, FL 33040
• 

  

  /40

  $1,074,000

  $24K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft

  1445 S Roosevelt Blvd Unit 412, Key West, FL 33040

  Fully furnished TRANSIENT LICENSED condos in Coconut Mallory Marina & Resort — listed separately but offered together as a rare investment package. Known as The Poolside Cottages (Units #412 & #411), these charming 1BR/1BA cottages sit steps from the pool with private patios, vaulted ceilings, updated interiors, and sleeping space for up to six guests per unit. Each comes turnkey and ready for

  Jonathan Minerick Homecoin.com

  1445 S Roosevelt Blvd Unit 412, Key West, FL 33040
• 

  

  /34

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 885 Sq Ft

  1025 Elgin Ln, Key West, FL 33040

  Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay

  Jimmy Lane Island Life Realty Experts

  1025 Elgin Ln, Key West, FL 33040

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