Search for Old Town South Homes

Old Town South

Proximity & Location = A Great Neighborhood!

Old Town South is the area between Casa Marina and Truman Avenue. Old Town South runs from the southernmost end of Truman Avenue north to White Street then east to United Street and jogging the waterfront beginning at Simonton Street.

Just like Old Town North, the homes are rich in history and the architecture is the quintessential Conch Home style with a sprinkle of modern architecture adjacent to the Casa Marina neighborhood. Proximity and location make this section of Key West an ideal area to live. Everything that Old Town North has to offer is only a short bike ride away, as well as the many recreation opportunities available in the Casa Marina area. The always bustling El Siboney Cuban restaurant is located within this district on Catherine and Margaret Streets. For more restaurants and art galleries, saunter down to the quieter side of Duval Street south of Truman. You can sip wine and people watch at Grand Vin, savor the best homemade ice cream at Flamingo Crossing or have breakfast, lunch or dinner at Banana Cafe. For a variety of shops and restaurants, Duval Square between Simonton, Virgina & Duval Streets is a short drive or bike ride away. Be sure to visit The Key West Butterfly Conservatory for a tranquil respite or if you need to entertain your children or grandchildren!

New Listings in Old Town South

1318 Duncan St Unit APT 3, Key West
$544,900
1 Beds ⋅ 1 Baths ⋅ 621579 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit APT 3, Key West
1011 Whitehead St, Key West
$3,795,000
3 Beds ⋅ 5 Baths ⋅ 621561 MLS
Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

1011 Whitehead St, Key West
615 Amelia St, Key West
$1,699,000
2 Beds ⋅ 3 Baths ⋅ 621509 MLS
Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-bedroom, two-and-a-half-bath single family home offers inviting indoor and outdoor spaces centered around a tropical pool courtyard. The open living and dining area features wide sliding glass doors leading to a covered deck, creating an easy flow for relaxing or entertaining. Beyond the deck, lush landscaping surrounds the pool and patio, with space for outdoor dining and lounging. The kitchen offers white cabinetry, ample storage, and a windowed breakfast nook, while a vaulted ceiling gives one of the bedrooms an airy feel. The roof and windows were upgraded in 2024. Located in Flood Zone X, annual insurance costs are approximately $6,407. From morning coffee on the deck to afternoons beside the pool, this home brings together comfortable living and a convenient Old Town location.

615 Amelia St, Key West
220 Angela St A & B, Unit A&B, Key West
$1,999,999
4 Beds ⋅ 4 Baths ⋅ 621502 MLS
KEY WEST LIFESTYLE !!!!!! Prime Old Town Duplex Just Two Blocks Off Duval. (each unit also available for sale ) Exceptional investment and island living opportunity in the heart of Old Town Key West. 220 Angela Street offers a classic two-story Conch duplex featuring two private residences (Units A & B), each designed for effortless indoor-outdoor living. Both units boast functional multi-level layouts, central A/C, dedicated interior laundry, and expansive upstairs and downstairs wrap-around porches overlooking lush tropical surroundings. The fully fenced grounds provide a private, shaded yard and the ultimate Old Town luxury: rare off-street parking. Live in one unit while generating passive income from the other, or hold as an income-producing multi-family portfolio piece in one of the nation's strongest rental markets. Situated on a quiet residential stretch just steps from Duval Street, Bahama Village dining, Fort Zachary Taylor State Park & Beach, and the Truman Waterfront. KEYWEST EVENTS : https://www.keywestchamber.org/visit.html

220 Angela St A & B, Unit A&B, Key West
418 Amelia St, Key West
$989,000
2 Beds ⋅ 2 Baths ⋅ 621361 MLS
Built in 1899, 418 Amelia Street is where Key West history, privacy, and the perfect location converge. Behind classic wood siding and Bahama shutters, this two-bedroom, two-bath residence with a bonus loft/finished attic makes thoughtful and intentional use of its 861 interior square feet, featuring an updated kitchen and an easy flow that extends naturally outdoors to the large covered deck and garden. A private, palm-shaded plunge pool anchors the garden, the privacy fence creating your own secluded retreat in the heart of the island. Traditional Conch architecture, mature tropical landscaping and intimate outdoor living endow the property with a sense of place that gives authentic Key West. Less than a block from Upper Duval, the home sits within easy reach of the Hemingway Home, Southernmost Point, art galleries, fine dining restaurants and the quieter residential streets of Old Town. This hidden gem offers the rare ability to step directly into the energy of Key West and return home to a private oasis steps away from it all. For the buyer seeking a 2-bedroom Old Town home with a private pool, tropical garden, and an exceptional walkable location, 418 Amelia Street is the one you've been waiting for.

418 Amelia St, Key West
1216 Packer St, Key West
$1,299,000
2 Beds ⋅ 2 Baths ⋅ 621345 MLS
Experience the charm and ideal location that make Old Town Key West so special. Located in the desirable X Flood Zone, this two-bedroom, two-bath home offers an inviting layout filled with classic island character. A wine refrigerator provides a convenient touch for entertaining or enjoying a chilled bottle at the end of the day. The outdoor space is a true highlight, featuring a spacious 31-by-11-foot saltwater pool equipped with both a heater and chiller for year-round enjoyment. Ideally situated just minutes from Duval Street, restaurants, galleries, and shops, this home provides easy access to everything that makes Key West such a unique place to live and enjoy.

1216 Packer St, Key West
1075 Duval St Unit C1 & C2, Key West
$1,349,000
2 Baths ⋅ 621255 MLS
Situated in Duval Square along Key West's Duval Street, this approximately 1,592 SqFt commercial property consists of two combined condominium units currently configured as a restaurant. Step inside to a spacious dining area, a commercial kitchen, and an inviting layout designed to accommodate both locals and all of the visitors drawn to Key West each year. Outdoor seating adds to the island atmosphere and gives guests the opportunity to enjoy the tropical surroundings that define the Key West dining experience. For an owner-operator, this is an opportunity to put a new concept into an established restaurant space. For an investor, it offers ownership of commercial real estate in one of the island's most sought-after corridors. Bring your concept, your vision, and your appetite for opportunity to life!

1075 Duval St Unit C1 & C2, Key West
411 Louisa St, Key West
$6,750,000
5 Beds ⋅ 5 Baths ⋅ 621141 MLS
Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment. This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable neighborhoods. Enter through the white picket fence and tropical courtyard to your grand Key West estate, where every detail has been thoughtfully designed. The first floor is set for entertaining, featuring a spacious living area and a chef's kitchen with stone countertops, an oversized island, custom cabinetry, and premium Sub-Zero, Viking, and Wolf appliances. A generous walk-in pantry adds extra storage convenience. The primary suite, also on the ground level, overlooks the pool and boasts a spa-inspired bath with dual showers, a freestanding soaking tub (with air bubble massage) and a large walk-in closet with one of two laundry areas. Outdoors, enjoy your private resort-style backyard with an oversized pool, covered lounge, and outdoor kitchen complete with gas grill, ice maker, and mini-fridge, perfect to grill up those fresh catches or hotdogs for the kids. Sonos speakers throughout set the tone to enjoy a relaxed Key West lifestyle. A floating living room staircase leads to two inviting guest rooms and a full bath. Two additional bedrooms currently serve as offices, each with en suite baths and private entrances, ideal for guest suites, studios, or remote workspaces (one includes a kitchenette). A climate-controlled standalone workshop offers a perfect space for projects, hobbies, or extra storage. Designed for both resilience and comfort, the home includes impact-rated doors and windows, a 30 KW Cummins diesel generator with 500-gallon fuel tank, smart home automation for lighting and shades, and off-street parking for two vehicles.

411 Louisa St, Key West
1004 Watson St Unit 2, Key West
$750,000
2 Beds ⋅ 2 Baths ⋅ 621130 MLS
Positioned in the coveted X flood zone, this 2-bedroom, 2-bathroom townhome perfectly blends Old Town charm with modern convenience. As one of only two units in an exclusive boutique setting, it provides exceptional privacy just steps from local wellness hubs, neighborhood cafes, and historic sites. The efficient galley kitchen is outfitted with granite countertops and stainless-steel appliances, while the primary suite serves as a tribute to island heritage with historic Dade County Pine. Outdoor living is seamlessly integrated with a classic front porch for morning coffee and a fully fenced rear deck designed for private, starlit dinners. Complete with a transferable A/C warranty, and the flexibility of a primary home or monthly rental, this residence offers an effortless Key West lifestyle.

1004 Watson St Unit 2, Key West
1422 Catherine St, Key West
$789,000
2 Beds ⋅ 2 Baths ⋅ 621112 MLS
Welcome to 1422 Catherine Street in The Heart of Key West. Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom. The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new floors and totally updated. Outdoors is a perfect courtyard for dining under the stars or just hanging out and solving all the world's problems. There are also washer and dryer hook ups and an outdoor shower. This home is perfect for full time residents, second home or a great rental property. Call today for your private showing!

1422 Catherine St, Key West
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