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
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Multi-unit Key West real estate
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Key West Old Town Real Estate

Key West real estate listing photo
1006-1008 Fleming Street

$2,975,000

Exquisitely restored & renovated, this captivating Old Town home on a rare large lot is truly perfect & in mint condition. Enjoy a fabulous great room w/soaring ceilings & a new Heart of Pine wall that completely opens up to pool & lush private gardens. Totaling 4 bdrms/4.5 baths including 2 guest houses. Since these owners purchased this compound they have done nothing but refine every detail of this fabulous property. Upgrades include a generator, privacy wall & gate, sprinkler system, pool retiled & refinished, day kitchen in pool house, & off st pkg for 2, hurricane shutters, security, sound & camera system throughout, new doors, landscaping, window treatments & much more! More information on this property
Key West Waterfront Real Estate
626 William Street
$2,950,000

A Historic Masterpiece. Come revel in this homage to the art filled mansions of long ago. Sitting in the heart of Old Town with 5BR/4.5BA, including a 1BR/1BA guest cottage, you can relax by one of the largest pools in Key West or indulge in your artistic endeavors in the detached studio/office. A massive great room & flowing design elements incorporated by previous owner Jerry Herman make entertaining a delight. The master bedroom has soaring ceilings & a pair of his & her closets bigger than most Manhattan apartments! Balconies, access to Baker's Ln via an electronically locked gate, Dynasty & SubZero appliances, storage for over 3000 bottles of wine, 25KW whole home generator, video security system, intercom system, off street parking for 8 SMART cars, 18 feet above sea level, even a well to water the extensive grounds! This is one of the rare properties that can truly say it has it all! More information on this property

Key West Waterfront Real Estate
717 White Street
$2,600,000

Subtropical Modernist Architecture. Preconstruction offering for an upscale home to be built at the corner of White and Newton Streets. This thoughtfully designed home has high end finishes throughout with a spacious open living area and 3 bedrooms, 3.5 baths. The home has two light filled structures separated by a courtyard with pool, covered dining, outdoor kitchen, fireplace and projection cinema. The main living area and master suite are on one side while the 2 guest rooms are in the other. Storage has been carefully designed to maximize space and create a place for everything. There are outdoor spaces, off-street parking for 2 cars, native landscaping and evening lighting. Minimalist modern style with careful attention to every detail. More information on this property

Florida Keys real estate

727 Love Lane
$1,500,000

Desirable Love Lane: Complete renovation just completed from New piers to new roof. Home taken down to the studs and rebuilt! Vaulted ceiling in Living room, private office. Beautiful Kitchen dining area. Large covered patio off Kitchen. Laundry room and storage room off patio. Landscaped and ready to move in immediately. Most desired location in Old Town, walk to Restaurants, Seaport, Theatre and Duval St or enjoy quiet private setting at the end of Love Lane. 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

1024 Southard Street
$1,295,000

Wonderful Old Town home on a beautiful block with a huge light filled great room that you will never want to leave! Eight French doors lead out to a heated salt generated pool with waterfall feature as well as a separate back yard garden & lounging area with a jacuzzi/spa. This artfully renovated home has 2BR/2BA + an office, stylish Ip decking, outdoor shower, even gated & bricked off street parking! More information on this property

Key West Real Estate

717 Southard Street
$1,289,000

Elegance and Luxury is what you will experience as you enter the foyer of this magnificent Old Town Beauty. Built in 1866 and located atop of Solares Hill, this home underwent a complete renovation, introducing all the modern amenities while maintaining the historic integrity of the property. 3 bedrooms all ensuite, including a spacious master suite with third floor library and separate office. Gourmet kitchen overlooking the open floor plan of dining and living room. Luscious tropical landscaping, cozy patio and cocktail pool offer ideal outdoor space, while one off street parking spot will accommodate your vehicle. Make an appointment to see this showcase today! More information on this property

Key West Real Estate

201 Virginia Street
$925,000

Island Gem with 3 bedroom, 3 baths, Pool and Off street parking. Excellent finishes are used throughout including stone and wood floors, granite countertops in the kitchen and baths and wind impact windows and doors. The home has an up to date floorplan with an open living/dining and kitchen opening to a covered porch and stunning pool with water feature. Also on the main level is a guest bedroom and bath. Upstairs are two oversized master suites both with walk-in closet, and bath with separate tub and shower. One of the master suites includes a large loft area with stairs to a rooftop widows walk with spectacular panoramic views of Key West and the waterfront. More information on this property

Southernmost Cabana Resort
1019 Simonton Street #103
$924,000

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 #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

Key West Real Estate

2 Fletchers Lane
$899,000

Wonderful, turn-key, 2 story Old Town home with beautiful Brazilian cherry floors, custom kitchen cabinets & Dade County pine walls. Obviously built by a ship builder, you can feel the custom woodwork quality throughout. Each bedroom enjoys lots of privacy with a split floor plan plus a guest cottage. Totaling 3 bedrooms & 3.5 baths with a great room that opens completely to the outdoors. Tropical landscaping and new Trex decking surround the heated pool & spa. The third bedroom cottage can double as guest quarters or a bar entertaining area with according style windows that open it up completely. Fully fenced for privacy & located between Grinnell & Margaret Streets, you can walk to everything from this unique property 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
421 Catherine Street
$799,000

Charming and meticulously renovated 2 bedroom 2.5 bath home in Old town Key West. The home has a breezy front porch for relaxing and watching the interesting neighborhood stroll past. The interior is impeccable with Brazilian Cherry Floors, and vaulted ceilings. There is a bedroom and bath on the first floor, a top of the line kitchen, half bath, surround sound system, wet bar with wine cooler, and living room which opens through French doors to the private back yard. There is a master bedroom and bath with walk-in closet and a balcony on the second floor. New roof and hurricane shutters. More information on this property

Key West Real Estate
1403 Olivia Street
$765,000

This is a charming traditional Conch house and is located in the popular Meadows neighborhood. The comfortable home has been well maintained and has much Dade Co. pine, original stair case, and wood floors. The home is set back from the street with and inviting front porch that overlooks a colorful garden. The rear yard is fenced, has a garden shed and decking. 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

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

612 Mickens
$600,000

2010 Certificate of Excellence Star: Award winning preservation home. Quiet street in Old Town with dedicated walking lane to Whitehead St. All new interior. 2 bedroom , 1 and 1/2 bath and a study. Covered porches, front and back. Seperate laundry shed. No detail overlooked! More information on this property

1004 Watson Street
$599,000

Old Town Duplex: Renovated and move in condition. Left side is 2 bedroom, 2 baths. Right side 3 bedrooms 1 bath with extra loft. Wonderful Old Town location in X500 Zone. New roof being installed. New windows and A/C. More information on this property

615 Mickens Lane
$575,000

Private Home tucked away on quiet lane. 1/2 Block to Whitehead St. Recently renovated Kitchen and Baths. New deck installed. Vaulted ceilings. French doors opening to private deck area. Walking distance to shops, restaurants, Fort Zachary Taylor. Great Location! 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
307 Amelia Street
$399,000

The perfect Island Getaway and beautifully restored from Foundation to Roof. Just a short stroll to Duval on Quiet One way Street. 2 Bedrooms and 1 bath, with Pine floors and Dade County Pine walls throughout. New windows & New Metal roof, this Cottage has been completely restored and is in excellent condition. Kitchen overlooks living rooms and pocket doors on bedrooms can open entire cottage. Call Listing agent for appointment today. More information on this property

Key West Real Estate
1110 Olivia Street
$399,000

Short Sale: Adorable cottage in Old town. Walking distance to Duval St. Desirable X Zone. Potential short sale transaction subject to lender approval which may require a commission adjustment between the listing agent and selling agent regardless of the MLS offer of compensation. More information on this property

Key West Real Estate
812 Fleming Street, #7
$349,000

Check out the only unit available in the wonderful Seafoam Building. This charming & private Old Town condo has tons of character with 9ft tall ceilings, Dade County pine everywhere and a great balcony overlooking the pool & lush landscaping. Third floor, 1BR/1BA unit with 518 sq ft of living space sitting in the back of the building where it is very quiet. Seafoam Condominiums consists of eight condominiums & two commercial units. 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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