Old Town Homes

/41
$69,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit C54 Week 36, Key West, FL 33040

Experience premium waterfront ownership with this deeded timeshare in the highly coveted Building C at the Galleon Resort1 This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple balconies that

Stephanie Herrmann

Truman & Co. Real Estate

(786) 751-6835

617 Front St Unit C54 Week 36, Key West, FL 33040
Explore Old Town
/13
$3,500 per month
- 1 Bed
- 1 Bath
- 300 Sq Ft
- Property for Rent
828 Fleming St, Key West, FL 33040

Available now, this brand-new Old Town studio offers a rare blend of style, comfort, and location on one of the Historic District's most desirable blocks. Thoughtfully redesigned with beautiful white oak hardwood floors, and a bright, refined interior, the home brings a fresh, elevated feel to classic Key West living. An assigned garden nook extends the living space outdoors, while a full-size

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(786) 982-0974

828 Fleming St, Key West, FL 33040
/45
$2,900,000 Sold Jan 09, 2026

1224 Florida St, Key West, FL 33040
- 5 Beds
- 6 Baths
- 2,760 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $1,051/SF
- 56 Days On Market
Current Estimated Value $2,875,337

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

1224 Florida St, Key West, FL 33040

/47
Est $3,308,296 Not Listed For Sale

621 Eaton St, Key West, FL 33040
- 5 Beds
- 6 Baths
- 2,448 Sq Ft
- Built 1933
621 Eaton St, Key West, FL 33040

Last Sold Summary
- 2% Above List Price
- $1,328/SF
- 18 Days On Market
Last Sold Price $3,250,000

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

/29
$775,000 Pending
- 3 Beds
- 2 Baths
- 1,292 Sq Ft
1115 Varela St, Key West, FL 33040

Nestled on a charming street in the heart of Old Town Key West, 1115 Varela Street is the renovation project that you have been waiting for. This historic treasure would be a perfect project for an investor, developer or anyone looking to restore a historic Key West gem. Currently configured as a 3BD/2BA with a large outside deck and an ideal positioned detached unfinished utility shed. The lot

Terry Garcia

Keller Williams Key West Compass Realty

(786) 244-8439

1115 Varela St, Key West, FL 33040
/20

$2,854 - $3,961 per month

Lofts at Bahama Village

1 - 3 Beds

750 Fort St, Key West, FL 33040

Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a

750 Fort St, Key West, FL 33040
/4
$1,200,000 Sold Nov 20, 2025

1108 Whitehead St, Key West, FL 33040
- Land
Last Sold Summary
- 0 Days On Market
Last Listing Agent Terri Spottswood Truman & Co. (KW)

1108 Whitehead St, Key West, FL 33040

/37
Est $2,149,865 Not Listed For Sale

711 Ashe St, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,058 Sq Ft
- Built 1993
711 Ashe St, Key West, FL 33040

Last Sold Summary
- 1% Below List Price
- $2,056/SF
- 10 Days On Market
Last Sold Price $2,175,000

Last Listing Agent Team Kaufelt Truman & Co. (KW)

/22
$774,000
- 2 Beds
- 1 Bath
- 1,057 Sq Ft
1102 Whitehead St, Key West, FL 33040

Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden

Margarita Villoch

Island Group Realty (KW)

(645) 205-0763

1102 Whitehead St, Key West, FL 33040
/28
$5,500 per month
- 2 Beds
- 2.5 Baths
- 1,288 Sq Ft
- House for Rent
1124 Eaton St, Key West, FL 33040

Welcome to your Key West paradise at 1124 Eaton Street! Located in the heart of Old Town, this charming 2-bedroom, 2.5-bath home offers the perfect launchpad for your Key West adventure. Enjoy the luxury of a private off-street patio ideal for entertaining or a quiet retreat. Forget the hassle of parking with your own private parking space. Just a short walk to the Seaport, you'll have easy

Lisa Karp LoKation Real Estate - Pompano Beach

1124 Eaton St, Key West, FL 33040
/34
$1,550,000 Sold Jun 02, 2025

1400 Virginia St, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
- Built 1923
Last Sold Summary
- 3% Below List Price
- $1,160/SF
- 124 Days On Market
Current Estimated Value $1,646,926

Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

1400 Virginia St, Key West, FL 33040

/7
Est $1,630,107 Not Listed For Sale

324 Truman Ave, Key West, FL 33040
- 4 Beds
- 5 Baths
- 2,020 Sq Ft
- Built 1944
324 Truman Ave, Key West, FL 33040

Last Sold Summary
- 9% Above List Price
- $743/SF
- 262 Days On Market
Last Sold Price $1,500,000

Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

/41
$59,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit A52 Week 32, Key West, FL 33040

PENTHOUSE! Beautiful straight on views of the Gulf of Mexico, Pool, Beach, Sunsets, and Tiki Bar. Enjoy week 32 in this Timeless Timeshare and celebrate Lobster Week and the Rum Festival. The Galleon resort has Elevators, a rooftop deck, a gated parking garage, a sauna, an exercise room, and the Pirates Cove Cafe and Outdoor gas grills, which are located on the Marina side of the Galleon. In

Stephanie Herrmann

Truman & Co. Real Estate

(645) 225-2567

617 Front St Unit A52 Week 32, Key West, FL 33040
/20
$18,964 per month
- 2 Beds
- 2 Baths
- 2,023 Sq Ft
- Condo for Rent
536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040

The advertised rate of $18,964/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040
/12
$1,050,000 Sold Mar 03, 2026

619 Front St Unit 21, Key West, FL 33040
- Land
Last Sold Summary
- 5% Below List Price
- 86 Days On Market
Last Listing Agent Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

619 Front St Unit 21, Key West, FL 33040

/26
Est $560,060 Not Listed For Sale

1209 William St Unit 7, Key West, FL 33040
- 1 Bed
- 1 Bath
- 486 Sq Ft
- Built 1928
1209 William St Unit 7, Key West, FL 33040

Last Sold Summary
- 10% Below List Price
- $1,276/SF
- 9 Days On Market
Last Sold Price $620,000

Last Listing Agent Gwendolyn Esbensen Berkshire Hathaway HomeServices Knight & Gardner Realty

/42
$69,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit C41 Week 50, Key West, FL 33040

On the Gulf of Mexico this 4th floor end unit Timeshare is on the water and overlooks the Key West Marina. 2 bed 2bath with sofa couch sleeps 6. Week 50 is a very sought after week which offers ideal winter weather, a relaxed island atmosphere and peak rental demand. Enjoy the decorative Christmas boat parades from your own personal view balconies and experience Key West all dressed up for the

Stephanie Herrmann

Truman & Co. Real Estate

(645) 300-5987

617 Front St Unit C41 Week 50, Key West, FL 33040
/7
$3,800 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Property for Rent
311 Amelia St Unit 1, Key West, FL 33040

Fully furnished 1 bedroom, 1 bathroom townhome in Bahama Village. Close to beaches and park. Walking distance to Duval Street. Fully fenced and private entrance. Monthly rent includes utilities. One small pet allowed.

Joyce Craul Expert Realty LLC (HQ)

311 Amelia St Unit 1, Key West, FL 33040
/32
$835,000 Sold Apr 13, 2026

1401 Simonton St Unit 20, Key West, FL 33040
- 2 Beds
- 3 Baths
- 907 Sq Ft
- Built 2006
Last Sold Summary
- 5% Below List Price
- $921/SF
- 160 Days On Market
Current Estimated Value $848,925

Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

1401 Simonton St Unit 20, Key West, FL 33040

/29
Est $1,447,590 Not Listed For Sale

1219 Grinnell St Unit B, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,360 Sq Ft
- Built 1990
1219 Grinnell St Unit B, Key West, FL 33040

Last Sold Summary
- $1,066/SF
- 55 Days On Market
Last Sold Price $1,450,000

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

/16
$9,888,000
- 3 Beds
- 2 Baths
- 2,071 Sq Ft
1430 Vernon Ave Unit 1-2, Key West, FL 33040

Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West.As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing

Irina Pytlik

Keys Top Realty LLC

(786) 981-9652

1430 Vernon Ave Unit 1-2, Key West, FL 33040
/20
$7,920 per month
- 2 Beds
- 3 Baths
- 1,345 Sq Ft
- Condo for Rent
629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040

The advertised rate of $7,920/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040
/30
$930,000 Sold Aug 01, 2025

608 Roberts Ln, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1933
Last Sold Summary
- 41% Below List Price
- $547/SF
- 189 Days On Market
Current Estimated Value $1,053,191

Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

608 Roberts Ln, Key West, FL 33040

/39
Est $2,267,119 Not Listed For Sale

623 Simonton St Unit 9, Key West, FL 33040
- 3 Beds
- 4 Baths
- 2,160 Sq Ft
- Built 1997
623 Simonton St Unit 9, Key West, FL 33040

Last Sold Summary
- 26% Above List Price
- $833/SF
- 48 Days On Market
Last Sold Price $1,800,000

Last Listing Agent Terri Spottswood Truman & Co. (KW)

/69
$3,168,000
- 3 Beds
- 3 Baths
- 2,262 Sq Ft
524 Southard St, Key West, FL 33040

Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character. Inside, soaring 14'

Tommy Mack

Coastal Collection Real Estate Inc.

(786) 396-7585

524 Southard St, Key West, FL 33040
/5
$3,600 per month
- 2 Beds
- 1 Bath
- Property for Rent
1110 White St Unit 2, Key West, FL 33040

2-bedroom,1-bath apartment in prime Key West location .Walking distance to Sandy's cafe ,Fausto's Food Palace ,and local shops ,and just minutes from the beach .Conveniently located near restaurants ,grocery stores ,and laundry facilities.Enjoy the convenience of having everything you need just steps away in one of Key West's most desirable areas

Ernie Cruz Berkshire Hathaway HomeServices Knight & Gardner Realty

1110 White St Unit 2, Key West, FL 33040
/53
$3,500,000 Sold Aug 08, 2025

407-415 Olivia St, Key West, FL 33040
- 6 Beds
- 5 Baths
- 3,171 Sq Ft
- Built 1964
Last Sold Summary
- 18% Below List Price
- $1,104/SF
- 134 Days On Market
Current Estimated Value $3,594,728

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

407-415 Olivia St, Key West, FL 33040

/31
Est $1,897,879 Not Listed For Sale

603 Angela St Unit 2, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,440 Sq Ft
- Built 1997
603 Angela St Unit 2, Key West, FL 33040

Last Sold Summary
- 13% Above List Price
- $1,163/SF
- 70 Days On Market
Last Sold Price $1,675,000

Last Listing Agent Team Kaufelt Truman & Co. (KW)

/37
$1,375,000
- 3 Beds
- 2 Baths
- 1,690 Sq Ft
524 White St, Key West, FL 33040

Welcome to ParotHdHideaway!Located in the heart of the Historic District, just steps to world famous Duval Street, 5 minutes to Higgs Beach, and Garrison Bight Marina being literally around the corner, this location is UNBEATABLE.Featuring almost 1700 Square Feet of indoor living space, this Gem mixes Old Town Conch Charm with contemporary living and comfortably sleeps 6 adults.On the first floor

Mike Kane

Internet Realty of the Florida Keys

(305) 853-8613

524 White St, Key West, FL 33040
/18
$5,429 per month
- 2 Beds
- 2 Baths
- 893 Sq Ft
- Condo for Rent
120 Angela St Unit SI ID1384034P, Key West, FL 33040

The advertised rate of $5,429/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

120 Angela St Unit SI ID1384034P, Key West, FL 33040
/31
$750,000 Sold Oct 03, 2025

1428 Virginia St, Key West, FL 33040
- 4 Beds
- 2 Baths
- 2,236 Sq Ft
- Built 1933
Last Sold Summary
- 16% Below List Price
- $335/SF
- 111 Days On Market
Current Estimated Value $841,319

Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

1428 Virginia St, Key West, FL 33040

/22
Est $1,320,587 Not Listed For Sale

800 Fleming St Unit C1, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,550 Sq Ft
- Built 1910
800 Fleming St Unit C1, Key West, FL 33040

Last Sold Summary
- 1% Above List Price
- $845/SF
- 53 Days On Market
Last Sold Price $1,310,000

Last Listing Agent Heather Carruthers Berkshire Hathaway HomeServices Knight & Gardner Realty

/40
$62,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit A-52 Week 52, Key West, FL 33040

Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events.

Stephanie Herrmann

Truman & Co. Real Estate

(844) 967-2396

617 Front St Unit A-52 Week 52, Key West, FL 33040
/20
$8,796 per month
- 4 Beds
- 3.5 Baths
- 1,797 Sq Ft
- Condo for Rent
1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040

The advertised rate of $8,797/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 29, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040
/35
$1,675,000 Sold Jun 02, 2025

1075 Duval St Unit 1, Key West, FL 33040
- 2 Beds
- 2.5 Baths
- 1,225 Sq Ft
- Built 1987
Last Sold Summary
- $1,367/SF
- 4 Days On Market
Current Estimated Value $1,566,173

Last Listing Agent Richard Haskins Buy The Keys

1075 Duval St Unit 1, Key West, FL 33040

/2
Est $793,643 Not Listed For Sale

951 Caroline St Unit 5, Key West, FL 33040
- 1 Bed
- Built 2003
951 Caroline St Unit 5, Key West, FL 33040

Last Sold Summary
- 1% Below List Price
Last Sold Price $785,000

Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

/12
$735,000
- 2 Beds
- 1 Bath
- 745 Sq Ft
906 Truman Ave Unit 1, Key West, FL 33040

This performing vacation rental sold as shown is a beautiful property which exudes a sense of warmth and character from the moment you set eyes on it. As you approach the home, you are greeted by a picturesque facade that captures the essence of Key West architecture. The vibrant colors and tropical landscaping create a welcoming atmosphere that invites you to step inside and explore further.

Darrin Smith

Key West Luxury Real Estate Inc (KW)

(645) 238-6011

906 Truman Ave Unit 1, Key West, FL 33040
/18
$5,900 total monthly price
- 2 Beds
- 1.5 Baths
- 850 Sq Ft
- Townhouse for Rent
634 Louisa St, Key West, FL 33040

Newly Renovated, furnished Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a

634 Louisa St, Key West, FL 33040
/23
$600,000 Sold Jul 15, 2025

651 William St Unit 1, Key West, FL 33040
- 1 Bed
- 1 Bath
- 599 Sq Ft
- Built 1933
Last Sold Summary
- 28% Below List Price
- $1,002/SF
- 191 Days On Market
Current Estimated Value $657,683

Last Listing Agent Barbara Bowers Preferred Properties (KW)

651 William St Unit 1, Key West, FL 33040

/8
Est $776,565 Not Listed For Sale

951 Caroline St Unit 1, Key West, FL 33040
- 1 Bed
- Built 2003
951 Caroline St Unit 1, Key West, FL 33040

Last Sold Summary
- 1% Below List Price
- 58 Days On Market
Last Sold Price $785,000

Last Listing Agent Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

Showing Results 1 - 40, Page 1 of 18

Florida Monroe County Key West Old Town

Learn more about living in Old Town

Home Trends in Old Town, FL

On average, homes in Old Town, Key West sell after 109 days on the market compared to the national average of 56 days. The median sale price for homes in Old Town, Key West over the last 12 months is $1,450,000, up 14% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,450,000

Median Single Family Sale Price

$1,595,000

Median Townhouse Sale Price

$1,450,000

Median 2 Bedroom Sale Price

$879,000

Median 1 Bedroom Sale Price

$692,000

Average Price Per Sq Ft

$1,260

Number of Homes for Sale

Last 12 months Home Sales

121

Months of Supply

9.80

Median List Price

$1,650,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

14%

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Old Town Homes

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Home Trends in Old Town, FL

Housing Trends