Homes for Sale near May Sands Montessori School

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  /48

  $3,675,000

  • 3 Beds
  • 4 Baths
  • 2,438 Sq Ft

  1020 Southard St, Key West, FL 33040

  This stunning Gingerbread-style home seamlessly blends historic charm with modern luxury right in the heart of Old Town . A covered wraparound porch welcomes you into a bright, window-lined foyer, leading to an elegant living and dining area. Throughout, gorgeous pine floors and walls highlight the home's timeless character.The open gourmet kitchen, featuring high-end appliances, flows into the

  Terri Spottswood Truman & Co. (KW)

  1020 Southard St, Key West, FL 33040
• 

  

  

  /35

  $2,350,000

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  1116 Elgin Ln, Key West, FL 33040

  Nestled in the heart of Key West's Historic Seaport District, this outstanding two-story residence is a true architectural gem. Tucked away on a tranquil lane with coveted off-street parking, the home's origins date back to the 1850s, showcasing timeless craftsmanship with stunning historic details, including rich Dade County Pine walls and flooring. Designed with both elegance and functionality

  Team Kaufelt Truman & Co. (KW)

  1116 Elgin Ln, Key West, FL 33040
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  /88

  $7,495,000

  • 5 Beds
  • 7 Baths
  • 4,000 Sq Ft

  616 Eaton St, Key West, FL 33040

  Nestled in the heart of Key West's historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern

  Terri Spottswood Truman & Co. (KW)

  616 Eaton St, Key West, FL 33040
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  /72

  $2,250,000

  • 3 Beds
  • 4 Baths
  • 2,110 Sq Ft

  1104 South St, Key West, FL 33040

  ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina district with unique design 1104 South St will appeal to those who demand the best in quality design, finishes, and lifestyle. The indoor-outdoor spaces are seamlessly connected by stack-away sliding-glass doors, promoting a flawless integration of outdoor/indoor living with architectural detailing that adds a

  Tommy Mack Coastal Collection Real Estate Inc.

  1104 South St, Key West, FL 33040
• 

  

  

  /43

  $2,950,000

  • 3 Beds
  • 3 Baths
  • 1,519 Sq Ft

  610 Griffin Ln, Key West, FL 33040

  Tucked away on a quiet lane in the heart of Old Town Key West, this one-of-a-kind compound blends island charm and character. Offering three distinct dwellings wrapped around a serene brick courtyard and heated cocktail pool, this property is a rare gem providing ultimate privacy while just steps from world-class dining, shopping, and entertainment.The main house is a light-filled updated

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  610 Griffin Ln, Key West, FL 33040
• 

  

  /43

  $2,800,000

  • 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 International Realty

  508 Grinnell St, Key West, FL 33040
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  /54

  $1,069,000

  • 4 Beds
  • 2 Baths
  • 1,785 Sq Ft

  2418 Patterson Ave, Key West, FL 33040

  Investment opportunity! This Duplex features a 3 bedroom and 1 bath main home with carport, separate addresses (Front & Rear) & utilities. The 1 bed/1 bath concrete block structure is 553 square feet, built in 1958 with its own driveway and side yard. There is a small shed for extra storage. The combined (under market) rentals are just over $4,500/month with leases in effect through June 2026 for

  Andrea Weitz Island Life Realty Experts

  2418 Patterson Ave, Key West, FL 33040
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  /12

  $580,000

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3930 S Roosevelt Blvd Unit 104E, Key West, FL 33040

  This beautifully updated 3-bedroom, 2-bathroom condo captures the relaxed charm of Key West living. Located on the first floor of the East wing, this bright and spacious unit features an open layout with abundant natural light. The kitchen is equipped with stainless steel GE appliances along with a GE Profile - washer/dryer combo. Sliding glass doors lead to a private balcony, perfect for

  Key West Luxury Finders Preferred Properties (KW)

  3930 S Roosevelt Blvd Unit 104E, Key West, FL 33040
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  /26

  $1,449,000

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft

  627 Whitehead St, Key West, FL 33040

  Prime Old Town Mixed-Use Property - Live, Work, or Invest! Ideally situated in Old Town Key West, this Historic Residential Office (HRO) zoned property offers a rare opportunity for both residential and commercial use. Previously, home to a successful spa, it's perfectly suited for continuing as a business or transforming into a private residence. Filled with character, the space features

  Kate Green Old Town Realty

  627 Whitehead St, Key West, FL 33040
• 

  

  /28

  $1,295,000

  • 2 Beds
  • 2 Baths
  • 805 Sq Ft

  612 Mickens Ln, Key West, FL 33040

  Come check out the Magic on Mickens Lane!Nestled in the heart of Old Town Key West, 612 Mickens Lane offers a unique blend of historic charm and modern potential. This single-family home, built in 1901, encompasses 805 square feet of living space, featuring 2 bedrooms and 1.5 bathrooms, with a great outdoor entertaining area. The property is situated in the X-Flood Zone on a 2,250 square foot

  Bobby Coe RE/MAX Keys Connection (KW)

  612 Mickens Ln, Key West, FL 33040
• 

  

  /65

  $5,750,000

  • 6 Beds
  • 6 Baths
  • 3,751 Sq Ft

  906 Johnson St, Key West, FL 33040

  Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths

  Regan Butler Truman & Co. (KW)

  906 Johnson St, Key West, FL 33040
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  /28

  $795,000

  • 3 Beds
  • 3 Baths
  • 1,136 Sq Ft

  E33 12th Ave, Stock Island, FL 33040

  Discover this beautifully updated 3-bedroom, 3-bathroom home in the up-and-coming Stock Island, where new development is transforming the area into a vibrant island hotspot! This hidden gem features wood-look tile flooring throughout, an open-concept kitchen and living space, impact windows and doors, and recessed lighting for a bright, modern feel. A privacy brick wall surrounds the property,

  Samantha Barrabeitg Expert Realty LLC (HQ)

  E33 12th Ave, Stock Island, FL 33040
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  /25

  $824,000

  • 1 Bed
  • 2 Baths
  • 814 Sq Ft

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

  Experience the epitome of beachfront living at the Key West Beachside Resort and Residences! This stunning corner suite invites you to live like you're on vacation every day. Inside, designer-grade finishes and furnishings create an atmosphere of refined elegance. Travertine flooring flows throughout the spacious living areas, complemented by an open gourmet kitchen featuring granite countertops,

  Karen Verri Ocean Sotheby's International Realty

  3841 N Roosevelt Blvd Unit 121, Key West, FL 33040
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  /4

  $3,250,000

  • 5 Beds
  • 6 Baths
  • 2,500 Sq Ft

  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 new construction of this single-family home. Planned for a 5 bed, 5 1/2 bath, pool home. Buyer still has time to choose design materials and possible floor plan changes . Soaring ceilings on both levels, crown molding, and a full ensuite bath in every bedroom. The open-concept first

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1513 Seminary St, Key West, FL 33040
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  /24

  $1,375,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  20 Aster Terrace, Key West, FL 33040

  This fully upgraded 2 bedroom 1 bathroom canal front home offers open water views and deep water access. Completely renovated, plumbing, electrical, impact doors and windows, custom cabinetry in kitchen and bath, porcelain countertops and backsplash, built in closets and electric water heater. A brand-new 60' x 8' concrete seawall adds durability and value. Enjoy coastal living and island life

  Jenny Perry Preferred Properties (KW)

  20 Aster Terrace, Key West, FL 33040
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  /25

  $1,149,000

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

  1210 Virginia St, Key West, FL 33040

  Currently this is a two-story duplex in the popular Bayview Park neighborhood in Old Town. It could be converted back to the original single-family home. There are a total of three bedrooms and 2.5 baths. As currently configured, the first floor has 2 bedrooms,1.5 baths and features 9.5-foot ceilings, doors with transom windows, and hardwood floors. French doors open to the rear yard and porch.

  The Behmke Group Keller Williams Key West Compass Realty

  1210 Virginia St, Key West, FL 33040
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  /34

  $1,599,000

  • 3 Beds
  • 3 Baths
  • 1,764 Sq Ft

  1730 Flagler Ave, Key West, FL 33040

  Welcome to this charming 3-bedroom, 3-bath home in the heart of Key West, offering a perfect blend of comfort and potential. Located in the sought-after Midtown neighborhood, this home is just a short distance from the beautiful Higgs Beach and vibrant shopping areas, making it an ideal spot for both relaxation and convenience.Outside, discover your own private oasis with a stunning pool and hot

  Marc Spivey Keller Williams Key West Compass Realty

  1730 Flagler Ave, Key West, FL 33040
• 

  

  /23

  $1,299,999

  • 3 Beds
  • 2 Baths
  • 1,109 Sq Ft

  709 Chapman Ln, Key West, FL 33040

  Located in the heart of historic Key West in the X Flood Zone (no flood insurance required), this beautifully renovated conch cottage offers a perfect blend of classic charm and modern comfort. Just three blocks from Duval Street and half a block from the Truman Annex, it sits in a quiet yet walkable neighborhood close to top attractions. This flexible two- or three-bedroom home features tall

  Terri Spottswood Truman & Co. (KW)

  709 Chapman Ln, Key West, FL 33040
• 

  

  /45

  $2,495,000

  • 4 Beds
  • 8 Baths
  • 4,013 Sq Ft

  1028 Truman Ave, Key West, FL 33040

  Prime Mixed-Use Investment Opportunity in Key West!Built in 2021 to current building codes, this exceptional four-unit commercial and residential compound is a rare find in the heart of Key West. A perfect 1031 Exchange candidate, this versatile property includes two licensed townhouse residences and two licensed commercial units, offering excellent income potential and flexibility.The commercial

  Team Spottswood/Vazquez Truman & Co. (KW)

  1028 Truman Ave, Key West, FL 33040
• 

  

  /21

  $1,200,000

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  817 Terry Ln, Key West, FL 33040

  This idyllic Old Town Key West home offers an extraordinary location and super-coveted parking. Light, Bright and in move-in condition, this furnished, turn-key oasis works well as an exceptional rental property and/or second home. Your own Key West pied a terre. Outstanding features include vaulted wood ceilings, loft, wood floors, oak cabinets, and a private deck perfect for al fresco dining

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  817 Terry Ln, Key West, FL 33040
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  /29

  $330,000

  • 1 Bath
  • 408 Sq Ft

  3312 Northside Dr Unit 401, Key West, FL 33040

  Exclusive opportunity for investors! This property is attractively priced for a quick sale. Competitive rates for Key West Neighborhood. Enjoy Key West in this efficiency minutes from the Gulf waters. Catch a glimpse from your private yet very spacious balcony with partial waterviews. The recently renovated kitchenette has all stainless steel appliances across from the quartz breakfast countertop

  Baris Leyla Coastal Collection Real Estate Inc.

  3312 Northside Dr Unit 401, Key West, FL 33040
• 

  

  /23

  $2,250,000

  • 3 Beds
  • 3 Baths
  • 2,715 Sq Ft

  30 Key Haven Rd, Key West, FL 33040

  June 11- Flooring complete, Cabinets in, walls painted, waiting for countertops, stucco, landscape. UPDATED PHOTOS. Check back often! Luxury Waterfront Living in a Highly Desirable Boating Community.Live in elegance in this fully renovated 3-bedroom, 3-bathroom en-suites concrete home, designed for modern coastal living. Every detail of this residence has been meticulously updated, including ALL

  Natallie Liz Expert Realty LLC (HQ)

  30 Key Haven Rd, Key West, FL 33040
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  /44

  $4,850,000

  • 4 Beds
  • 3 Baths
  • 3,154 Sq Ft

  1523 Patricia St, Key West, FL 33040

  Discover the epitome of island elegance with this stunning Spanish Mediterranean-style home situated on an expansive 10,000+ sq. ft. corner lot in the heart of Key West. This exceptional property offers over 3,100 sq. ft. of living space, featuring 4 spacious bedrooms and 3 full bathrooms. Step inside to find a light-filled living and dining area that seamlessly opens to a lush tropical oasis,

  Team Spottswood/Vazquez Truman & Co. (KW)

  1523 Patricia St, Key West, FL 33040
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  /44

  $1,695,000

  • 3 Beds
  • 3 Baths
  • 1,284 Sq Ft

  1211 Knowles Ln, Key West, FL 33040

  Discover the timeless charm of this beautifully remodeled historic home located in Old Town, Key West. This fully furnished 3 bedroom, 2.5 bath property boasts lovingly restored Dade County Pine, and combines classic craftsmanship with modern comforts. 1211 Knowles Ln features a 300 sq.ft. loft currently used as a 3rd bedroom, office and storage ! Both front and side porches invite you to relax

  Emily Lombard Ocean Sotheby's International Realty

  1211 Knowles Ln, Key West, FL 33040
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  /32

  $3,795,000

  • 4 Beds
  • 5 Baths
  • 2,628 Sq Ft

  1610 South St, Key West, FL 33040

  This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builder's constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between

  Randal Longo Keys Realty Redefined LLC

  1610 South St, Key West, FL 33040
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  /52

  $2,495,000

  • 3 Beds
  • 3 Baths
  • 1,325 Sq Ft

  115 Front St Unit 101, Key West, FL 33040

  Step into a piece of history, reimagined for modern luxury. This stunning 3-bedroom, 3-bath condominium is located in the historic Naval Administration Building within the prestigious, award-winning Truman Annex. Completely renovated to the highest contemporary standards, this one-of-a-kind residence boasts soaring exposed beam ceilings, ultra-thick concrete walls and ceilings for unparalleled

  Jimmy Lane Island Life Realty Experts

  115 Front St Unit 101, Key West, FL 33040
• 

  

  /20

  $599,000

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft

  119 Golf Club Dr, Key West, FL 33040

  Charming Key West Retreat in the Exclusive Key West Golf Club Community. This particular unit has been recently painted inside and outside.Welcome to 119 Golf Club Drive, a beautifully updated townhome offering the perfect blend of comfort, style, and resort-style living. As you step inside, you'll be greeted by an inviting open floor plan bathed in natural light. The main level features a modern

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

  119 Golf Club Dr, Key West, FL 33040
• 

  

  /27

  $799,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  900 Thomas St, Key West, FL 33040

  Nestled in the ''X'' flood zone of Old Town Key West, this charming one level, two bedroom and one bathroom home offers the perfect blend of historic character and modern convenience. Featuring classic island architecture, the property boasts a spacious open floor plan, high ceilings, and beautiful hardwood floors throughout. Located mere steps from Key West's vibrant downtown, renowned

  Jimmy Lane Island Life Realty Experts

  900 Thomas St, Key West, FL 33040
• 

  

  /22

  $689,000

  • 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 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 the condo

  Mike Caron Keller Williams Key West Compass Realty

  804 South St Unit 3, Key West, FL 33040
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  /26

  $508,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  5031 5th Ave Unit 57, Key West, FL 33040

  Beautiful Home with Sunset Views Located in a gated community with resort-quality amenities, this 2-bedroom, 2-bathroom home is a boater's dream, just minutes from both the Atlantic and the Gulf by boat. Situated on a canal with breathtaking, unobstructed sunset views, this property is in the beautiful community of Sunset Harbor at Cow Key Marina. No HOA Fees or Property Taxes. Dock your boat

  Sean Crosier Homepie, Inc

  5031 5th Ave Unit 57, Key West, FL 33040
• 

  

  /35

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  1617 Jamaica Dr, Key West, FL 33040

  NEW PRICE!! CANAL HOME IN KEY WEST!! Fabulous Canal Home in Key West. Spacious CBS three bedroom, two bath home in Riviera Shores. Perfect island home is private and offers plenty of indoor and outdoor living areas including bricked courtyards, verandas, and deck spaces. This home has beautiful grounds and tropical landscape for relaxing in your hammock or enjoying the canal. The primary

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1617 Jamaica Dr, Key West, FL 33040
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  /44

  $2,095,000

  • 2 Beds
  • 3 Baths
  • 1,312 Sq Ft

  216 Fleming St, Key West, FL 33040

  Located in the prestigious gated Truman Annex, this beautifully appointed 2-bedroom, 2.5-bath home offers refined coastal living just steps from Duval Street and Truman Waterfront. Thoughtfully designed with elegant finishes and an open, airy layout, this residence is perfect for those seeking a private sanctuary in Old Town.A private entrance welcomes you into a turn-key interior, where Serena &

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  216 Fleming St, Key West, FL 33040
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  /42

  $474,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  5031 5th Ave Unit 61, Key West, FL 33040

  >>>>> Agents: Buyer agent friendly - see listing agent regarding Comp. The Virtual Tour: It's a must see! >>>>>> A BOATER'S DREAM! Cash buyers preferred. Million Dollar views for half the price in a gated community with resort quality amenities! Purchase home for $474,900 and lease the land for just $1,442 per month. NO HOA FEES OR PROPERTY TAXES! Located in the beautiful Sunset Harbor Waterfront

  Sean Crosier Homepie, Inc

  5031 5th Ave Unit 61, Key West, FL 33040
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  /76

  $555,000

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  61 Golf Club Dr Unit 255, Key West, FL 33040

  FINAL Price Improvement! Ideal INVESTOR OPPORTUNITY! Seller just accepted a SOLID 18-mos. rental. Ideal tenants, professionals, new to KW. Superb location/pristine/exceptionally large extended rear yard. Tranquility awaits @ gated Key West Golf Club. Savor the first AM beverage on beautiful, screened veranda. Absorb majestic sunrise colors. Eastern tropical breezes flow. Serene vista overlooks

  Robin Mitchell Keller Williams Key West Compass Realty

  61 Golf Club Dr Unit 255, Key West, FL 33040
• 

  

  /21

  $1,500,000

  • 4 Beds
  • 2 Baths
  • 2,019 Sq Ft

  1327 Duncan St, Key West, FL 33040

  Are you ready to build??? after talking with City Planning the new owner will be able to possibly renovate the main house and build a second new house or build two new houses after your plans have gone through permitting process or possibly renovate the main house and build a second new house Buyer to verify...Make your offer today.Welcome to 1327 Duncan Street, this property offers a 3

  Barbara Crespo Keller Williams Key West Compass Realty

  1327 Duncan St, Key West, FL 33040
• 

  

  /22

  $2,200,000

  • 3 Beds
  • 4 Baths
  • 1,445 Sq Ft

  719 Bakers Ln, Key West, FL 33040

  A Rare Opportunity in Key West's Historic Heart - 719 Bakers LaneNestled in the tranquil charm of Old Town Key West, 719 Bakers Lane offers an exceptional chance to craft your dream home in the island's most coveted location. This nearly finished 3-bedroom, 3.5-bath residence presents the rare opportunity to pick your own finishes, fixtures, appliances and landscaping and skip the endless

  Scott Forman Royal Palms Realty (KW)

  719 Bakers Ln, Key West, FL 33040
• 

  

  /39

  $849,000

  • 4 Beds
  • 3 Baths
  • 1,320 Sq Ft

  11 Kestral Way, Key West, FL 33040

  This updated 4-bedroom, 3-bathroom townhome in the gated Key West Golf Club community is a prime investment opportunity and active vacation rental. Offering privacy, comfort, and resort-style living, it's just minutes from downtown Key West, beaches, and world-class dining.Inside, an open, light-filled floor plan features crown molding, neutral tile flooring, and refined finishes. The

  Austin Kimbler Expert Realty LLC (HQ)

  11 Kestral Way, Key West, FL 33040
• 

  

  /33

  $1,799,900

  • 3 Beds
  • 4 Baths
  • 1,572 Sq Ft

  908 Catherine St, Key West, FL 33040

  Essentially a Brand-New Home at an Unbeatable Price Per Square Foot!Nestled in the coveted X flood zone, this historic Key West gem has been completely reimagined from the inside out. With all-new plumbing, electrical, roof, and impact-resistant windows, this property offers the charm of the past with the peace of mind of modern construction.Step beyond the charming Caribbean gate and into a

  Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

  908 Catherine St, Key West, FL 33040
• 

  

  /57

  $2,600,000

  • 5 Beds
  • 3 Baths
  • 2,303 Sq Ft

  710 Ashe St Unit Front and Back, Key West, FL 33040

  Welcome to 710 Ashe Street, a masterfully restored 1889 Eyebrow home, where historic charm and contemporary comfort converge in one of Key West's most sought-after locations. This exceptional property, complete with a detached guest house, offers a versatile and elegant living experience--perfect for families, in-laws, or lucrative rental opportunities (rental figures available upon request). The

  Team Kaufelt Truman & Co. (KW)

  710 Ashe St Unit Front and Back, Key West, FL 33040
• 

  

  /26

  $999,000

  • 2 Beds
  • 1 Bath
  • 1,021 Sq Ft

  710 Ashe St Unit Rear, Key West, FL 33040

  Tucked away on one of the best streets in Old Town Key West, 710 Ashe Street Rear is a beautifully remodeled 2 bedroom, 1 bath residence offering the perfect balance of family living and an optional vacation rental opportunity. Upon entering, an expansive open floor plan invites you in, with the living, dining, and kitchen areas flow effortlessly into one another. Framed by four sets of French

  Team Kaufelt Truman & Co. (KW)

  710 Ashe St Unit Rear, Key West, FL 33040

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