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

$4,495,000

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 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
1311 Truman Avenue
$2,279,000.

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

Florida Keys real estate

1720 South Street
$1,525,000

This fabulous 4BR/3.5BA home was built with wonderful finishes in 2005 by one of KW's top contractors. There's a beautiful open kitchen/living/dining room that opens out to a heated pool and patio with ipe decking and a retractable 27' awning. The kitchen has all Miele appliances, granite counter tops and cherry cabinetry, a wet bar with ice maker and wine cooler, a large walk in pantry and laundry area, 2 zone AC / heat and a central vacuum system. There is an office on the ground floor with pocket doors for privacy. All windows are double glazed for sound and insulation and there are metal roll down shutters for all the openings. Built above the flood plain, this is a comfortable home that includes a 2 car carport and loads of storage. 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

1515-1523 Florida Street & 1400 Johnson Street
$1,385,000

Wonderful home and income in beautiful area that runs entire block from Johnson St to Laird St encompassing 2 corners. Huge triplex property sits on 11,263sf of land, features a large 3 bedroom, 2.5 bath owners unit with a heated pool and spa and massive yard along with a 3 bedroom, 2 bath unit and a 2 bedroom, 2 bath unit. Each unit has their own private yard, washer & dryer, impact rated windows, tile and wood floors. 1515, 1519, 1523 Florida Street and 1400 Johnson Street are all included in the sale. More information on this property

Key West Real Estate

610-616 Petronia Street
$1,299,900

Wonderful compound in the heart of Old Town just a block & half off Duval Street. Configured as four separate buildings & licensed as 3 residential units. Two charming 1BR/1BA cottages & 2 additional cottages that can be combined as a 2BR/2BA or a 1BR/1BA cottage + a studio cottage. Enjoy a tropical pool, vaulted ceilings, private back porches & washer/dryer for each unit. Perfect for extended family & friends or a home with income! 2 off-street parking, X zone. Next door, 608 Petronia is on the market also. Tenants in place, needs 24hr notice to show. Can easily be converted to 3 condominiums. 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

1022 Fleming Street
$1,225,000

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

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
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
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

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

807 Catherine Street
$629,900

This ideal centrally located Conch style home has been recently updated including a beautiful new bath and kitchen that includes stainless steel appliances, quartz countertops and glass back splash. The charming home has very tall ceilings, Dade County Pine Walls, wood floors and a very nice floor plan. The living/dining area and kitchen are located at the rear of the home adjacent to a covered porch overlooking the private nicely landscaped rear yard with outdoor half bath and koi pond. Additionally there is a sleeping loft or storage area and lots of exterior storage. 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

608 Petronia Street
$599,900

Great hidden gem in Old Town just 2 blocks from Duval & tucked away on a private lane off Petronia Street. With 2 bedrooms and 2 baths this home has been renovated with Brazilian hardwood floors, a gas stove and an outdoor deck & jacuzzi. There is off street parking & room for a small pool. Walk to everything!! More information on this property

Key West Real Estate
526 William Street, #4
$499,000

Beautifully restored one bedroom condo in the Heart of Old Historic Key West. Delancey Hall was built in late 1800's and converted into 5 luxury condo's in 2001. This particular condo is located on second floor to the front of the building overlooking William St. Spacious outdoor balcony to enjoy outdoor dining or lounging. Granite kitchen with double counter tops overlooking living area. Excellent lighting throughout, Dade county Pine walls and beautiful hard wood floors. Shared pool with brick patio and grilling area. Call listing agent for appointment today. 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 for sale
616 White Street

$479,000

Along a row of historic shotgun cottages on White Street, is this 2BR/1BA cottage that is in good condition. Currently rented on a long term basis, the house is ready for upgrades and there is room for a pool. There's a nice deck at the rear and a lovely garden beyond that. Within easy biking and walking distance to everything Key West has to offer. More information on this property
Key West real estate for sale
717 Fort Street

$399,800

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
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

Cozy Cottage Old Town Key West Real Estate
100 Geraldine Street
$235,000

Cozy cottage located nearby Fort Zachary Taylor and within a short walk to local shops and restaurants. 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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