Key West real estate and luxury estates for sale from Truman & Co. Real estate in the keys of florida is a great investment for a vacation home or residential purchase. Truman & Company hosts some of the finest Key West estates, waterfront condos, residential and commercial Key West real estate for sale. Stop in and see us or call our Florida Keys real estate number at 305-292-2244
Key West real estate offered by Truman & Co.
Key West real estate in Old Town Old Town Key West FL homes
Key West condos - oceanfront living, water view
Residential real estate in florida keys
Multi-unit Key West real estate
Key West oceanfront real estate
Key West vacant land and lots real estate
Key West FL commercial real estate


Key West Old Town Real Estate

Key West real estate listing photo
744 Windsor Lane

$4,245,000

Incomparable recently renovated home on an estate sized lot in the heart of the historic district. The secluded home is sleek and modern with a large open floor plan including a showplace kitchen, a lavish master suite, three guest bedrooms with gorgeous ensuite bathrooms, large artist studio, multiple covered porches and spectacular outdoor living area with built-in kitchen. The expansive gardens are beautifully landscaped with meandering paths and one of the largest residential pools in Key West. This well designed private Old Town oasis embraces the indoor/outdoor Key West lifestyle with walls of sliding glass doors and lots of windows. More information on this property
Key West Waterfront Real Estate
906 Johnson Street
$3,795,000

Luxury meets location on the coveted & peaceful Johnson Street of the Casa Marina District. A rare opportunity awaits to enjoy 3820 sqft in a sprawling parklike setting. You will marvel at the large open spaces that grace this home both inside & out. Beautifully appointed 5bd/6ba + studio. Two 1bd guest suites enjoy exterior entrances, mini kitchens, full bath & living areas. Walled for privacy & beautifully landscaped with large pool complimented by outdoor kitchen for the ultimate in entertaining. 3 blocks from the beach, tennis courts & dining. This unsurpassed combination is not to be missed. More information on this property

Key West Waterfront Real Estate
45 Sunset Key Drive
$2,595,000

Fulfill your fantasy of living on a small tropical island. Only a 5 minute ferry ride from Key West, Sunset Key is a luxury retreat with resort like amenities including two tennis courts, beautiful homeowner’s beach and access to spa, gym, restaurant and concierge services. This beautiful three bedroom, three bath home has an open floor plan with sunny rooms, high ceilings, crown molding, tile and wood floors, designer details throughout and is in perfect condition. The home is sited on a private lot with a wrap-a-round porch, private master suite deck, beautifully landscaped yards and heated pool. A third floor porch provides great views of the island and water beyond. There is 24 hour Ferry service from the Westin Resort to Sunset Key. More information on this property

Key West Real Estate
623 William Street
$2,150,000

Impressive renovation of a fantastic Victorian home on a beautiful street in Old Town. Historic Preservation Award winning, this 3BR/3.5BA has a huge updated kitchen with granite counters, Wolf & Sub Zero appliances & centrally located. Enjoy a large master bedroom with vaulted ceilings overlooking the pool and pool cottage. Detail and charm permeate the home with Dade county pine floors & walls, home office, formal living and dining areas along with a light filled family room with accordion style wall that opens to the heated pool & deck. Outdoor shower & off street parking off Carsten Ln. More information on this property

Key West Waterfront Real Estate
1311 Truman Avenue
$1,995,000

Now priced over $300,000 below recent appraisal! Gracious Victorian home c.1905 sits on a huge lot (14,000SF) in the Historic District. Beautiful Dade County pine floors, moldings and trim including the original staircase and high ceilings on two floors. Original windows and double story wrap around porches. Completely renovated in 1999, this home features a main house (2940 SF) with 4BR/4.5 BA and a 3BR/3BA guest house. A large covered dining porch, beautiful swimming pool with mature gardens, off street parking and loads of privacy. More information on this property

Key West Real Estate
1416 White Street
$1,895,000

Refined taste & elegant styling are everywhere you look in this Casa Marina neighborhood stunner. Nearly 3,000 sf of living space featuring Brazilian cherry floors, high trey ceilings, 4BR/3.2BA + den, whole home generator, custom cabinetry, granite counters impact glass & more. In-ground heated pool & spa with waterfall are the stars of the lushly landscaped back yard with off-street parking tucked between the cultivated forestry of the front yard. Truly a home that has to be experienced to be appreciated. More information on this property

Key West Real Estate
1017 Margaret Street
$1,895,000

This beautiful Old Town property includes a 2 story home with classic Conch architecture, a large guest cottage, pool and covered parking on a 7100+ SF lot. The home has an open floor plan with a large living /dining area opening to the pool through French doors, top of the line kitchen, pantry and powder room. Upstairs are 2 master suites with vaulted ceilings, walk-in closets, private porches and spacious baths. The charming guest cottage has 2 bedrooms, large bath, vaulted ceiling and Dade County pine walls. Spectacular outdoor space with gardens, pool and spa, covered parking and large storage closet. Additionally there is surround sound, central vac, and smart home capability. A must see and cannot be appreciated with a drive-by. More information on this property

Key West real estate
1226 Von Phister Street

$1,725,000.

This striking home is on a beautiful block of Von Phister - completely renovated and expanded in 2007 with great attention to detail for easy island living. Over 2400 sf of living space with 4 bedrooms, 4 baths, plus a separate poolside cottage with a half bath. The spacious kitchen/dining/living area has two sets of glass doors that open out onto a travertine porch overlooking the pool and patio. All of the windows and doors are impact glass. The house was built with high ceilings and large rooms, loads of closets, each fitted out for optimum organization, 2 zone air conditioning, and a laundry room. The gardens are mature and lush - and there is also a relaxing covered outdoor dining pavilion. More information on this property
Key West real estate
1625 Johnson Street

$1,695,000.

Elegant Simplicity - A total renovation of this handsome house originally built in 1958, within 4 bedrooms and 4 baths, all new impact windows and doors, a sparkling new 34' pool, all situated on a double lot. Great floor plan includes a large living area with high ceilings, open kitchen/dining area that overlooks the pool and gardens. Loads of light and air throughout. Completely walled for privacy with off street parking for two cars. More information on this property
Key West real estate
608 Angela Street

$1,625,000

Stunning Old Town home saturated in history. A classic beauty built in 1890, lovingly restored & renovated, formerly the home of Phillip Burton. 3BR/2BA, new pine floors, Dade County Pine walls, 12-ft ceilings, granite countertops with stainless steel Viking appliances, new tile floors in baths, lovely spacious porch, master suite with French doors opening to heated tile pool with new equipment & coping. Great new outdoor bar & gates. Generator, off-street parking and 2002 Sea Ray 280 Sundancer for the full Key West lifestyle. More information on this property
Key West Real Estate
1311 Villa Mill Alley

$1,450,000

Resting near the end of one of the most sought after Alley's in Key West, this spacious yet cozy home is lushly landscaped and perfect for entertaining. With 4BR/3BA you have your choice of upstairs or downstairs master bedroom, huge covered porch upstairs and covered patio downstairs. Enjoy meandering grounds and large lagoon pool that make this home a tropical treat. 3 off st. parking spots. This is a potential short sale transaction subject to lender approval. More information on this property
Key West Real Estate
530 William Street

$1,450,000

Elegant Historic Home located in the most desirable area of Old Town. Large spacious rooms in main house. Downstairs has Formal living dining, eat-in kitchen, 2 bedrooms 1 bath. Upstairs also full kitchen 2 bedrooms and 1 bath. Two meters with separate heating and cooling units. Easily converted back to a grand single family home. Also, included 725 and 727 Southard Street cottage. Each is Living room, 1 bedroom 1 bath and kitchen. total of 4 units. Grand home in great condition. Well maintained. Must see to appreciate. More information on this property

Key West Real Estate

403 Emma Street #A
$1,255,000

Sit back and relax next to your own private salt pool at this one of kind home in Mill's Place. Located in the prestigious Truman Annex this 2BR/2.5BA is a rare find with its own salt pool & patio area. It has an open floor plan, trey ceiling, custom built in's, plantation shutters, full dining room, eat-in kitchen, stainless steel appliances, crown molding, overlooking the unique pool setting, off street parking & more. Only a quick jaunt to Duval St. & all downtown Key West has to offer! The unit will convey with the special Truman Annex transient rental license. Seller has not rented property. (Buyer to verify rental restrictions). Buyer to pay one time Capital Contribution of $1,500 at closing. More information on this property

Key West Real Estate

306 Peacon Lane
$1,229,000

Delightful home that has been superbly renovated in the heart of the Historic Seaport District. Mere foot steps to the hotspots of Caroline St while simultaneously being tucked away on a very low traffic and quiet lane, this home takes location to the max! All the historical charm of a home built in the mid 1800's combined with thoughtful updates like an open concept kitchen, pool with water feature, tons of closet space and even an outdoor shower! High ceiling and Dade county pine artfully blended with newer Ipe floors in the addition, Jenn-Air & Bosch appliances outfit the kitchen, off street parking and so much more that has to been seen to be appreciated. This home was also featured on HGTV's Island Life series. More information on this property

Key West Real Estate

109 Front Street #314
$1,195,000

Penthouse unit in the waterfront Harbor Place condominium in exclusive Truman Annex. This 2BR/2.5BA unit has stunning sunset views, impact glass windows and doors, two balconies, transient license & two deeded & covered parking spots. Harbor Place sits on the beautiful Truman Waterfront with fantastic views, waterfront pool & proximity to all the hotspots of Old Town Key West. More information on this property

Key West Real Estate

1022 Fleming Street
$1,095,000

Beautifully located in Prime Old Town Historic District, this handsome two story house was built around the turn of the century. Lovingly cared for and well maintained, it is currently used as a single family house, but is legal a duplex with a living/dining/kitchen area on each floor. There are double story wrap around porches with lovely views of the neighborhood and lot's of original Dade county pine on the walls and newer oak floors on both floors. Loads of light everywhere, there are 2 bedrooms and a bath on each floor. The pool is solar heated and surrounded by a lovely deck and gardens. More information on this property

Key West Real Estate

814 Ashe Street
$999,000

Spacious and beautifully constructed home, located in the heart of Old Town. No expense spared in this GE Smart Home. Impact windows and doors throughout, large granite and stainless steel kitchen overlooking expansive and bright living area. All bedrooms are spacious with ensuite luxury bathrooms and lots of closet space and stunning hard wood floors. Inground private heated pool and patio for dining and lounging. X-5oo flood zone just a few blocks from all Key West best attractions. Call listing agent for private viewing today. More information on this property

Key West Real Estate

1100 Williams Lane
$999,000

Tucked back on a quiet lane off a quiet street, this home is just waiting for YOU to discover it! Constructed in 2008, it is spacious with a modern great room. Features include large closets, three floors, impact glass throughout, heated pool, composite decking, stainless steel appliances, hard wood floors upstairs with tile floors downstairs, private bathrooms for all the bedrooms and so much more! Off street parking in an area where that is worth more than gold! Home is in the X-500 zone for flood insurance. More information on this property

818 Carsten Lane, Key West
818 Carsten Lane
$949,000

Delightful cottage on coveted Old Town Key West Lane. Behind the white picket fence a beautiful front porch welcomes you to to this perfectly appointed home. Dade County Pine floors, walls and ceilings throughout the original home that opens up to a fabulous addition with vaulted ceilings. A wall of glass doors fold open to enjoy a covered patio overlooking tropical gardens and views of the heated pool. The kitchen boasts custom cabinetry that has been built around Haitian Art, granite counters and high end appliances. Offered furnished so you could start enjoying this home immediately. It truly doesn't get more charming than this! More information on this property

Southernmost Cabana Resort
1019 Simonton Street #103
$934,600

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1019 Simonton St #103 is a two story, 3BR/3BA end unit with fornt and rear porches. More information on this property

1514 Von Phister
$900,000

Privacy Abounds: 3BR/2.5BA family home with tile flooring, lots of custom built-ins, a large kitchen with a pass through to the outdoor wetbar and fridge poolside. Overlooking the pool is the 1BR/1BA guest house with living room, bedroom, bath and loft - ideal for Mother In Law or office. Heated pool and spa, lush private gardens with off street parking and a koi pond. More information on this property

Southernmost Cabana Resort
609 Virginia Street
$883,000

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 609 Virginia St is a two story, 2BR/3BA end unit with front and rear porches as well as a rear balcony. More information on this property

Southernmost Cabana Resort
611 Virginia Street
$873,000

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 611 Virginia St is a two story, 3BR/3BA end unit with downstairs front and rear porches as well as a rear balcony. More information on this property

Southernmost Cabana Resort
617 Virginia Street
$873,000

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and ameneties of Duval St. Get one before they are gone! 617 Virginia St is a two story, 3BR/3BA end unit with front and back porches as well as a rear balcony. More information on this property

Southernmost Cabana Resort
1025 Simonton Street
$871,700

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1025 Simonton St is a two story, 3BR/3BA end unit with front and rear porches as well as a rear balcony. More information on this property

Southernmost Cabana Resort
1029 Simonton Street
$871,700

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1029 Simonton St is a two story, 3BR/3BA end unit with front and rear porches as well as a rear balcony. More information on this property

Southernmost Cabana Resort
1019 Simonton Street #102
$868,000

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1019 Simonton St #102 is a two story, 2BR/3BA with downstairs front and rear porches as well as a front balcony overlooking the pool area. More information on this property

Southernmost Cabana Resort
1027 Simonton Street
$836,625

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1027 Simonton St is a two story, 2BR/3BA end unit with front and rear porches as well as a rear balcony. More information on this property

Southernmost Cabana Resort
1023 Simonton Street
$831,625

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1023 Simonton St is a two story, 2BR/3BA townhome with front and rear porches as well as a front balcony. More information on this property

Key West Real Estate
218 Olivia Street
$825,000

Amazing 3 story Old Town hidden retreat. This home features beautiful Mexican tiles and wood floors, high ceilings, European style open kitchen with stainless steel appliances, 3 bedroom ensuite baths. A wonderful loft master bedroom with views into the treetops. There is also a big porch perfect for entertaining, family dinners and just relaxing. An outdoor shower and a bathtub are an extra bonus. This home is located a few blocks off busy Duval St. and a short walk away from the Truman waterfront and Fort Zachary Taylor park and beach. Here you don't need more than a bike to get around. More information on this property

Key West Real Estate
324 Julia Street
$799,000

Here's a wonderful property in the historic district that offers flexible living. This is a unique 5 bedroom property with income potential and an easy lifestyle. The house is charming with 1 BR/1Bath with pool, patio and outdoor shower at the rear with 4 bedrooms and a bath at the front. Off street parking for at least one car and lush landscaping all around. Well located within easy walking distance to all that Old Town has to offer. More information on this property

Key West Real Estate
1211 Packer Street
$769,000

Built by a contractor for himself, this home is a wonderful surprise that completely opens up to a free form edged pool, IPE decking and great back yard. Enjoy 3 BD/2BA's + an office inside the main house & a separate licensed 1/1 mother-in law cottage with sky lights, new roof & wood floors. Dade County pine is used throughout with impact window & sliders, Brazilian cherry floors, natural stone tiles and hardy board concrete siding. This renovated & very private home is completely fenced with 6ft side fences and a 12ft CBS back wall with mature landscaping & gardens. There is an onsite well for watering. Three off street parking spots. More information on this property

Southernmost Cabana Resort
1017 Simonton Street #101
$764,375

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1017 Simonton St #101 is a one level end unit with 2BR/2BA, front porch & attic with pull down stairs. More information on this property

Southernmost Cabana Resort
1017 Simonton Street #102
$759,375

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1017 Simonton St #102 is a one level unit with 2BR/2BA, front porch & attic with pull down stairs. More information on this property

Southernmost Cabana Resort
1017 Simonton Street #103
$759,375

Treat yourself to something special... a brand new home in Old Town Key West! This intimate 21 home enclave in the heart of the island is an opportunity not to be missed. Homes will range from 2 to 3 bedrooms, 1200 to 1500 square feet, all will feature high end finishing, impact glass & low maintenance fees. The homes will exceed building code requirements so owners can enjoy lower then average insurance and utility costs. The grounds include a community pool and each unit has parking. Only steps to the sights and amenities of Duval St. Get one before they are gone! 1017 Simonton St #103 is a one level unit with 2BR/2BA, front porch & attic with pull down stairs. More information on this property

803 Catherine Street
$679,000

Classic Shotgun Style Cottage just 3 blocks from Duval in center of Old Town. With 2BD and 1BA, this updated cottage has bedrooms off the hallway and then opens to a spacious updated kitchen & living area. Silestone countertops with breakfast bar, stainless steel appliances and custom cabinetry for the gourmet chef. Three double French doors with impact glass lead out to wonderful patio with lots of space for outdoor dining, sitting area and plenty of room for a pool or tropical garden. X-500 Flood Zone so no flood insurance is required. Perfect Old Town cottage! More information on this property

4 Aronovitz Ln
$659,000

Awesome Old Town location tucked away between Duval St and Whitehead St on quiet Aronovitz Lane. Recently renovated baths. Deck and walkway replaced 2013. Loft bedroom and full bath not included in Sq Ft. Very spacious home. Must see to appreciate. More information on this property

Key West Real Estate
1009 Simonton Street, #3
$499,000

This beautiful office condominium is located near the intersection of Truman Avenue and Simonton Street. This commercial space comprises the second and third floors of the free standing building and consists of a reception area, two large offices, storage and bath on main level with the upper level being an open floor plan with full bath. Also included are two reserved parking spaces. More information on this property

Key West Real Estate
904 Terry Lane, #1
$399,000

Hidden gem in the heart of Bahama Village. This 4 unit condo enclave is tucked down a quiet lane just steps from all the downtown hotspots Key West has to offer. All 4 homes are 1BR/1BA, renovated in 2006 & full of charm. Enjoy granite counters, walk in closets, central AC, & even laundry hookups. This unit has tile flooring and is on the ground floor at the front of the building. Interior photos are of Unit 4. Off-Street Parking. More information on this property

Key West Real Estate
904 Terry Lane, #2
$399,000

Hidden gem in the heart of Bahama Village. This 4 unit condo enclave is tucked down a quiet lane just steps from all the downtown hotspots Key West has to offer. All 4 homes are 1BR/1BA, renovated in 2006 & full of charm. Enjoy granite counters, walk in closets, central AC, & even laundry hookups. This unit has tile flooring and is on the ground floor at the front of the building. Interior photos are of Unit 4. Off-Street Parking. More information on this property

Key West Real Estate
904 Terry Lane, #3
$399,000

Hidden gem in the heart of Bahama Village. This 4 unit condo enclave is tucked down a quiet lane just steps from all the downtown hotspots Key West has to offer. All 4 homes are 1BR/1BA, renovated in 2006 & full of charm. Enjoy granite counters, walk in closets, central AC, & even laundry hookups. This unit has tile flooring and is on the ground floor at the front of the building. Interior photos are of Unit 4. Off-Street Parking. More information on this property

Key West Real Estate
904 Terry Lane, #4
$399,000

Hidden gem in the heart of Bahama Village. This 4 unit condo enclave is tucked down a quiet lane just steps from all the downtown hotspots Key West has to offer. All 4 homes are 1BR/1BA, renovated in 2006 & full of charm. Enjoy granite counters, walk in closets, central AC, & even laundry hookups. This unit has tile flooring and is on the ground floor at the front of the building. Interior photos are of Unit 4. Off-Street Parking. More information on this property

Key West real estate for sale
717 Fort Street

$349,000

Cozy duplex located nearby Fort Zachary Taylor and within a short walk to local shops and restaurants. Each unit is a 1 Bedroom / 1 Bath and has the potential for great income! More information on this property
   
   

Truman & Co. Real Estate Services - Key West, FL
1205 Truman Avenue . Key West . Florida . 33040
Telephone: 305.292.2244 :: Fax: 305.292.2202 :: Email: inquiry@trumanandcompany.com

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