Homes for Sale near May Sands Montessori School

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  /16

  $1,600,000

  • 8 Beds
  • 5 Baths
  • 1,830 Sq Ft

  928 Truman Ave Unit 101, Key West, FL 33040

  Old Town Multi-Use PropertyLocated on Truman Avenue, this distinctive property features five legal long-term rental apartments, making it ideal for steady income or employee housing.Unit 101, a CBS building, offers the potential for commercial conversion (buyer to verify), provided the residential units remain onsite, creating valuable flexibility.Highlights include:8 bedrooms and 5

  Allison Findlay Preferred Properties (KW)

  928 Truman Ave Unit 101, Key West, FL 33040
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  /60

  $2,095,000

  • 4 Beds
  • 3 Baths
  • 1,943 Sq Ft

  408 William St, Key West, FL 33040

  Freshly renovated throughout and nestled on one of Old Town's most coveted streets, you'll discover this captivating home steeped in rich history. The kitchen has new granite counters, new stainless-steel appliances & has been opened up to completely transform the space creating a modern feel and functional room. The Richard Roberts home, originally transported from Green Turtle Cay, Bahamas in

  Terri Spottswood Truman & Co. (KW)

  408 William St, Key West, FL 33040
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  /47

  $3,999,000

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

  919 Thomas St Unit 1A, Key West, FL 33040

  This property has a glamourous three bedroom, three and a half bath owners' unit with private pool and hot tub, plus three lucrative long-term rentals. It is the entire Lighthouse View Condominium Association, currently inactive. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence with its heated

  Mabry Binnicker Preferred Properties (KW)

  919 Thomas St Unit 1A, Key West, FL 33040
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  /39

  $2,250,000

  • 4 Beds
  • 3 Baths
  • 1,738 Sq Ft

  1015 Eaton St, Key West, FL 33040

  Situated in the coveted Historic Seaport neighborhood, 1015 Eaton Street offers charm and convenience, creating the ultimate Key West lifestyle. This meticulously reimagined Historic Eyebrow home offers 4 bedrooms and 3 bathrooms thoughtfully designed for quintessential island life. As you enter through the white picket fence, the home welcomes you with an inviting front porch, ideal for soaking

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1015 Eaton St, Key West, FL 33040
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  /37

  $1,650,000

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  613 Olivia St, Key West, FL 33040

  Welcome to 613 Olivia Street, a charming single-family home nestled in the heart of Old Town, Key West. Built in 1933, and located in the X Flood Zone, this historic residence offers 1,680 square feet of living space on two floors and on a 3,240 square foot lot. This property has been owner occupied for over 30 years. First time on the market in generations. Here is your chance to have that

  Bobby Coe RE/MAX Keys Connection (KW)

  613 Olivia St, Key West, FL 33040
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  /44

  $649,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 608, Key West, FL 33040

  Top floor sunset views! Discover this exceptional Oceanview 1-bedroom, 1-bathroom condo that perfectly blends comfort, style, and convenience. From the moment you step inside, you'll be greeted by a spacious living room designed for relaxation and year-round comfort, thanks to mini-split AC units and hurricane-grade soundproof windows and doors. Upgraded through the 2018 Airport Noise Improvement

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

  2601 S Roosevelt Blvd Unit 608, Key West, FL 33040
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  /42

  $623,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 319C, Key West, FL 33040

  A Key West Home with Style and EaseDiscover island living at its best; 2601 S. Roosevelt, #319-C is a beautifully, completely renovated condo located in the community of Key West by the Sea. This home blends modern touches with the relaxed feel of the tropics. Comfortable and spacious, this unit is conveniently located just a short walking distance to the white sandy Atlantic beaches, and a

  Wendy Moreira Keller Williams Key West Compass Realty

  2601 S Roosevelt Blvd Unit 319C, Key West, FL 33040
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  /9

  $1,701,000

  • 8 Beds
  • 4 Baths
  • 3,200 Sq Ft

  1621 Josephine St, Key West, FL 33040

  Prime 2 duplexes, each a 2/1 up & 2/1 down for a total of 8 bedrooms, 4 baths. Each unit has a generous covered porch extending the living area to the outdoors. Behind and between the 2 buildings is vacant land, room for a pool or outdoor storage, etc. Off-street parking for 4 cars. There's a lovely specimen Buttonwood tree at the entry to the property. A good investment for owner occupancy and

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1621 Josephine St, Key West, FL 33040
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  /20

  $5,319,000

  • 24 Beds
  • 12 Baths
  • 9,000 Sq Ft

  1819 Atlantic Blvd, Key West, FL 33040

  PRIME OPPORTUNITY! 1819 Atlantic Blvd, 1719/21 Josephine St, 1723/25 Josephine St, 1821 Atlantic Blvd & 1823 Atlantic Blvd. EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 3 FOURPLEXES 12 units offering 9,000 sq ft of Floor Living Area, and 2 vacant lots for a total of 23,340 sq ft of land. All 12 units are each a 2/1, for a total of 24 bedrooms and 12 baths. Buyer to verify with the governing

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1819 Atlantic Blvd, Key West, FL 33040
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  /10

  $3,491,000

  • 16 Beds
  • 8 Baths
  • 6,000 Sq Ft

  1716 Bertha St, Key West, FL 33040

  EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 1714 Bertha St and 1716 Bertha St are two fourplexes with 16 bedrooms and 8 baths, 8 units of 2/1 each, comprising 6,000 sq ft of Floor Living Area on 8,755 sq ft of land, offered with the vacant lot adjacent to 1714 Bertha St, a bonus 5,765 sq ft lot comprising a total of 14,529 sq ft of land. Both buildings have new metal roofs as of 2024.

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1716 Bertha St, Key West, FL 33040
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  /15

  $5,197,000

  • 10 Beds
  • 9 Baths
  • 7,193 Sq Ft

  1005 Flagler Ave, Key West, FL 33040

  INVESTORS, DEVELOPERS, CONDO CONVERSION--1005 FLAGLER AVE AND 1009 FLAGLER AVE--Two fourplexes in the highly desirable Casa Marina neighborhood on 18,371 sq ft of land, with 7,193 sq ft of Floor Living Area, for a total of 10 bedrooms and 9 baths. 1005 Flagler is 4 units, 3 of which are 1/1, ground floor unit #1 is a 3/2 with a courtyard. There's an on site coin laundry, as well as a garage and

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1005 Flagler Ave, Key West, FL 33040
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  /47

  $3,999,000

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

  919 Thomas St Unit A,1-3, Key West, FL 33040

  This is the entire four-unit Lighthouse View Condominium Association. It is currently four lucrative long-term rentals. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence is secluded in the rear with its own private heated pool, hot tub and expansive garden with brick terrace. A free-standing two

  Mabry Binnicker Preferred Properties (KW)

  919 Thomas St Unit A,1-3, Key West, FL 33040
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  /32

  $1,680,000

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft

  1211 Catherine St, Key West, FL 33040

  This charming historic home is located just steps off vibrant White St and close to the beach, tennis courts, pickle ball and a short walk to famous Duval St. It's close to the action but in a tranquil area of the White St District.This property has many great features such as 10ft high ceilings through out the entire home, abundance of large windows, open floor plan with spacious living area,

  Haydee Stewart Bascom Grooms Real Estate (KW)

  1211 Catherine St, Key West, FL 33040
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  /35

  $580,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  3210 Eagle Ave, Key West, FL 33040

  NEW LISTING! Welcome to Key West Estates, a charming family community ideally situated just a short bike ride from the beautiful beaches, vibrant Duval Street, delightful restaurants, the theater, and shopping centers. This peaceful neighborhood features light one-way traffic and no HOA fees, making it a perfect place to call home.Step inside to discover an inviting open floor plan that

  Bobby Baker Brightwild Real Estate

  3210 Eagle Ave, Key West, FL 33040
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  /64

  $4,250,000

  • 5 Beds
  • 7 Baths
  • 2,681 Sq Ft

  1311 Grinnell St, Key West, FL 33040

  This stunning home in Casa Marina is a complete restoration of the original historic structure. Just 5 blocks from Higgs Beach and 6 blocks from Duval Street this property has a large master bedroom and two guest bedrooms on the main floor all with private baths and their own entrances opening to over 900 square feet of wraparound porches. The wide entrance hallway has an additional 1/2 bath and

  Jennifer Newman Truman & Co. (KW)

  1311 Grinnell St, Key West, FL 33040
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  /39

  $1,600,000

  • 3 Beds
  • 3 Baths
  • 1,897 Sq Ft

  1033 Catherine St, Key West, FL 33040

  RECENTLY REDUCED - PRICED TO SELL!!! Step into Key West history with a modern twist at the Kali Zoi House, a well-maintained gem nestled in lush tropical surroundings in Old Town. Originally built in the early 1900s & updated in 1988, this fully furnished home offers nearly 1,900sqft of spacious living. Located near everything- Duval Street, beaches, shopping, & entertainment, this home combines

  Madeleine Lowe Expert Realty LLC (HQ)

  1033 Catherine St, Key West, FL 33040
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  /33

  $1,649,500

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

  28 Seaside Ct S, Key West, FL 33040

  Discover the ultimate coastal retreat in this exquisite ocean view townhome, where luxury meets convenience in a serene gated environment. This three-level masterpiece exemplifies modern coastal living, with resilient construction designed to endure nature's elements while captivating the eye.Enjoy effortless movement throughout the home with a private elevator leading you to spacious living

  Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  28 Seaside Ct S, Key West, FL 33040
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  /22

  $2,895,000

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  1100 South St, Key West, FL 33040

  Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, 'A FAREWELL TO ARMS.'' This sprawling single story property spans an impressive 8100 square feet, occupying a

  Key West Luxury Finders Preferred Properties (KW)

  1100 South St, Key West, FL 33040
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  /11

  $449,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  25D 10th Ave, Stock Island, FL 33040

  Come share in the ''Key West'' address on ''up & coming'' Stock Island. Excellent opportunuty for a CASH BUYER! Just minutes from Key West proper, yet nestled in a tranquil area, with world-class dining, entertainment & beaches close at hand. Attractive price point in this charming mobile home on a generously sized corner lot with soft St. Augustine grass beneath your feet,. Plenty of room to

  Robin Mitchell Keller Williams Key West Compass Realty

  25D 10th Ave, Stock Island, FL 33040
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  /30

  $2,290,000

  • 4 Beds
  • 5 Baths
  • 2,376 Sq Ft

  1730 United St, Key West, FL 33040

  Exceptional newly built (2023) 4-bedroom, 4 1/2-bath home situated on a corner lot in Key West, featuring a large saltwater, heated pool and hot tub. This home offers a blend of luxury and practicality with highlights including: a corner lot location, soaring ceilings on both levels, crown molding, and a full ensuite bath in every bedroom. The open-concept first floor is perfect for entertaining,

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1730 United St, Key West, FL 33040
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  /26

  $980,000

  • 2 Beds
  • 2 Baths
  • 1,095 Sq Ft

  1312 Catherine St, Key West, FL 33040

  This charming duplex has much to offer. A great location, two very nice one bedroom, one bath units, each with their own entry and outdoor space and it's in move in condition. The first floor features a primary bedroom with Dade Pine walls and a large closet. The kitchen/living/dining area opens to the private exterior deck. Upstairs the 1/1 has high ceilings and natural light. It has a porch in

  Laura McChesney Preferred Properties (KW)

  1312 Catherine St, Key West, FL 33040
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  /19

  $729,000

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  617 Fleming St Unit 6, Key West, FL 33040

  You can't beat this location, it's superb! This delightful 1/1 condo in the coveted Campbell Courtyard has a well-documented rental history as a monthly vacation rental. Secure and private, the Campbell Courtyard is a long-established small association of only 9 units. The front porch looks out to the pool. Offered fully furnished, this is a must see!

  Tyler Caudell Key West Realty, LLC (KW)

  617 Fleming St Unit 6, Key West, FL 33040
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  /47

  $2,195,000

  • 3 Beds
  • 4 Baths
  • 1,522 Sq Ft

  816 Ashe St, Key West, FL 33040

  This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance

  Bascom Grooms Bascom Grooms Real Estate (KW)

  816 Ashe St, Key West, FL 33040
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  /30

  $998,000

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft

  608 Roberts Ln, Key West, FL 33040

  OLD TOWN CONCH HOUSE on a lovely Lane tucked away but close to all of your favorite shops, cafes and Key West attractions! First time on the market in over 45 years! This historic home built by the Roberts Family is located on a quiet cul-de-sac lane in Old Town Key West. Tucked away and just off Frances St, 608 Roberts Lane (formerly known as Cates Lane as well as Darwin Court dates back to the

  Bascom Grooms Bascom Grooms Real Estate (KW)

  608 Roberts Ln, Key West, FL 33040
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  /18

  $689,000

  • Land

  5950 Peninsular Ave Unit 674, Key West, FL 33040

  Florida Keys living beckons at this oceanfront marina community. Aptly named Oceanside Marina. Includes parking, dock-box, electric/water hookup as well as laundry/bath facilities. Docks received complete refurbishment in 2017. Adjacent hotel built in 2017 offers 6 pools, restaurant, dog park, hourly shuttles downtown, fuel dock, kayak tours, charter fishing. Live aboard your vessel or rent out

  Zachary Bentley Coastal Collection Real Estate Inc.

  5950 Peninsular Ave Unit 674, Key West, FL 33040
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  /59

  $4,300,000

  • 4 Beds
  • 5 Baths
  • 3,204 Sq Ft

  22 Floral Ave, Key West, FL 33040

  This 4b/4.5ba luxurious home boasts Gulf of Mexico & deep canal waterfront living in Key West. It includes hurricane shutters, impact windows, metal roof with solar panels, and automated blinds. Ample parking with 2 large garages & driveway for 3 cars. 1st floor has a Chef's kitchen, a dining room perfect for hosting parties, a luxurious master suite with walk-in custom closets and the en-suite

  22 Floral Ave, Key West, FL 33040
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  /3

  $1,299,000

  • Land

  1513 Seminary St, Key West, FL 33040

  Discover an incredible opportunity in the heart of Key West! This 7,500 sq. ft. lot is cleared, ready for the construction of your dream single-family home. With a transferable building permit in hand, the possibilities are endless. Enjoy the perfect blend of privacy and convenience, just moments from everything Key West has to offer. Don't miss out on this rare chance to create your ideal

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1513 Seminary St, Key West, FL 33040
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  /20

  $3,295,000

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  728 Love Ln, Key West, FL 33040

  Located in Old Town Key West, and on one of the most sought after tranquil lanes, sits this perfectly updated home in the X zone. Upon entering, the foyer seamlessly flows into an open-concept living room and kitchen. You're welcomed by a breathtaking cathedral ceiling that enhances the sense of space, while large pocket doors draw your gaze to the outdoors. An expansive lanai extends the living

  Key West Luxury Finders Preferred Properties (KW)

  728 Love Ln, Key West, FL 33040
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  /41

  $1,249,000

  • 4 Beds
  • 3 Baths
  • 1,740 Sq Ft

  1215 Bay St, Key West, FL 33040

  This charming four-bedroom, three-bathroom duplex is a rare find, nestled on a generous 7,500 sq. ft. lot that provides plenty of room for relaxation, gardening, or entertaining. Surrounded by lush foliage, the property offers a serene sense of privacy and seclusion, making it a perfect retreat. Centrally located, you'll enjoy easy access to shopping, dining, and the beach, with Old Town Key West

  Justyn Ewald Expert Realty LLC (HQ)

  1215 Bay St, Key West, FL 33040
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  /17

  $2,175,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1115 Fleming St, Key West, FL 33040

  This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone else's overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890

  Derek Epperly Keys Atlantic Realty

  1115 Fleming St, Key West, FL 33040
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  /21

  $1,450,000

  • 6 Beds
  • 3 Baths
  • 2,434 Sq Ft

  1401 5th St, Key West, FL 33040

  Rare Opportunity: Three Charming Homes on Adjacent Lots - Unlimited Potential!Discover the perfect investment opportunity with these three vintage 2-bedroom, 1-bathroom homes, nestled on separate adjoining lots and being sold together as a single package. Situated in a desirable location, this unique offering provides incredible flexibility for visionary buyers.Each home offers cozy layouts that

  Stacy Stahl Realty ONE Group Destination

  1401 5th St, Key West, FL 33040
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  /23

  $990,000

  • 3 Beds
  • 3 Baths
  • 1,296 Sq Ft

  308 Peacon Ln, Key West, FL 33040

  Yes - not too good to be true or a misprint! Priced to sell for just $990,000 with this $400,000 price reduction. Rare 2 unit property in Old Town! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  308 Peacon Ln, Key West, FL 33040
• 

  

  /23

  $735,000

  • 2 Beds
  • 1 Bath
  • 643 Sq Ft

  409 Margaret St Unit 202 / B, Key West, FL 33040

  Close to the Historic Seaport, restaurants, art galleries, and more!. Recently renovated, this 2 bedroom, 1 bath condo has high impact windows and door, washer/ dryer, tankless hot water heater, new flooring, kitchen, mini splits, appliances, and is being sold furnished! Prime Old Town location, walk or bike to everything! This is easy island living- close to everything, and no need for a car.

  Elaine Coyle Keller Williams Key West Compass Realty

  409 Margaret St Unit 202 / B, Key West, FL 33040
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  /35

  $1,399,000

  • 2 Beds
  • 3 Baths
  • 960 Sq Ft

  231 Southard St, Key West, FL 33040

  For the first time, the Key West home of famed landscape architect and Martha Stewart co-star Fernando Wong is available. Welcome to your dream townhouse nestled in the heart of the exclusive Truman Annex, just steps away from the restaurants, shops and bars on Duval Street. This professionally decorated 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern comfort and island

  Carrie Howe Keller Williams Key West Compass Realty

  231 Southard St, Key West, FL 33040
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  /42

  $749,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 632, Key West, FL 33040

  Experience Ultimate Elegance at Key West's Marriott Beachside Resort. This offering includes two luxurious, fully furnished units--a Signature King Room and a Resort View Suite--each designed to deliver an exceptional blend of comfort and sophistication. Together, they provide flexibility as a full-time residence, vacation retreat, or income-producing rental property with two coveted TRANSIENT

  Tommy Mack Coastal Collection Real Estate Inc.

  3841 N Roosevelt Blvd Unit 632, Key West, FL 33040
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  /35

  $4,400,000

  • 3 Beds
  • 4 Baths
  • 2,744 Sq Ft

  3741 Eagle Ave, Key West, FL 33040

  3741 Eagle Avenue - A Masterpiece of Coastal Luxury This stunning 3 bedroom, 3.5 bath fully furnished residence on a generous 10,800 SF lot offers unparalleled coastal elegance at an impressive elevation of 10.5ft. The new concrete construction features an open concept with cathedral ceilings and large impact sliding doors throughout. Premium materials, high-end appliances, and thoughtful layout

  Jenny Perry Preferred Properties (KW)

  3741 Eagle Ave, Key West, FL 33040
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  /29

  $1,295,000

  • 2 Beds
  • 3 Baths
  • 960 Sq Ft

  208 Fleming St, Key West, FL 33040

  Owner is a licensed real estate agent and listing agent.Charming End Unit Townhome in the Heart of Truman Annex, Key WestNestled in the highly sought-after Truman Annex, this exceptional end unit townhome offers the perfect blend of privacy, luxury, and tropical living. Boasting an unbeatable location just steps from the vibrant attractions of Old Town Key West and the serene beauty of Fort

  Tracy Dubensky Real Estate Management of Key West, LLC

  208 Fleming St, Key West, FL 33040
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  /26

  $1,599,900

  • 5 Beds
  • 3 Baths
  • 2,007 Sq Ft

  1415 United St, Key West, FL 33040

  INVESTOR ALERT! Great opportunity to own a 3 unit building centrally located in Key West with off Street parking and plenty of room for a pool. The downstairs front unit is a 2BD/1BA, has an open floor plan with lots of windows allowing for plenty of natural light and a cute front porch. The upstairs unit is a 1BD/1BA and the rear third unit is another 2BD/1BA. The multi unit building sits on a

  Team Spottswood/Vazquez Truman & Co. (KW)

  1415 United St, Key West, FL 33040
• 

  

  /28

  $645,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 107 B, Key West, FL 33040

  Island living starts here -- ground-level, steps from thee pool, and just across from Smathers Beach. This handicap-accessible 1BD/1BA condo in Key West by the Sea offers no-stairs entry, a private patio, and rare garden space -- ideal for full-time living, a tropical getaway, or a smart investment.The interior features an open, light-filled layout with impact windows and an updated kitchen

  Kathryn Baldwin Berkshire Hathaway HomeServices Knight & Gardner Realty

  2601 S Roosevelt Blvd Unit 107 B, Key West, FL 33040
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  /28

  $875,000

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  817 Eaton St Unit 1, Key West, FL 33040

  MOTIVATED SELLERS' A must see this desirable beautiful bright condo located in the heart of historic Old Town area. This charming 1 bedroom 1 bath home offers high ceilings, with open spacious floor plan. The perfect spot within walking distance of great restaurants and a few blocks to the Historic Seaport and the famous Duval Street. OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

  Letisia Powell Robert Slack LLC

  817 Eaton St Unit 1, Key West, FL 33040

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