Key West, FL Homes for Sale under $100,000

/66
$26,000

$5K PRICE DROP
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040

Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
Explore Key West
/70
$49,900
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040

Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lock door unit - where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café--everything you need for a

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040
/58
$32,500
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040

Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard

Stephanie Herrmann

Truman & Co. Real Estate

617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040
/68
$59,900

$9K PRICE DROP
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040

Experience elevated waterfront ownership with this deeded timeshare in the highly desirable Building C at the Galleon Resort. This penthouse end-corner unit boasts one of the most sought-after spots in the resort, showcasing unobstructed, head-on views of the Gulf of Mexico.The residence features vaulted ceilings, extra windows for enhanced natural light, and multiple balconies designed to

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040
/58
$49,900
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040

Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove

Stephanie Herrmann

Truman & Co. Real Estate

617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040
/66
$32,500
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit B-51 Penthouse Week, Key West, FL 33040

Top floor unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit B-51 Penthouse Week, Key West, FL 33040
/68
$37,500
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit B-24 Week 45, Key West, FL 33040

Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of the most spectacular sunsets in all of Key West.Filled with natural light, the residence also features a private balcony perfectly positioned to capture the stunning waterfront scenery above the

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit B-24 Week 45, Key West, FL 33040
/44
$59,900

$9K PRICE DROP
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040

Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. 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

Stephanie Herrmann

Truman & Co. Real Estate

617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040
/11
$3,350
- 2 Beds
- 1 Bath
1614 Dennis St Unit B, Key West, FL 33040

Newtown annual rental is now available to RENT! 2 bed 1 bath large deck! Convenient location near Key West Highs and just a short ride to down town. Can be rented ASAP, comes with washer and dryer fro your unit! First Month and security deposit to get started. Tenant pays utilities.

Matthew Sheehan

Ocean Sotheby's International Realty

1614 Dennis St Unit B, Key West, FL 33040
/57
$59,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit A52 wk32, Key West, FL 33040

PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy this deeded week 32 and celebrate Lobster Week and the Rum Festival yearly with the rest of Key West. The Penthouse boasts expansive, straight-on views of the Gulf of Mexico, Pool and hot tub, the private beach, and the Tiki Bar, where a local guitarist performs nearly every day or night. There

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit A52 wk32, Key West, FL 33040
/32
$5,500
- 3 Beds
- 3 Baths
- 1,380 Sq Ft
59 Palm Dr, Key West, FL 33040

Enjoy the Keys lifestyle in this stunning canal-front 3-bedroom, 3-bathroom elevated modular home, located in the desirable Bay Point neighborhood, just behind Baby's Coffee. Available for $5,500 per month, this 2015-built home offers modern amenities and a spacious layout perfect for comfortable living. The lower level features a bedroom with a full bath, 9-foot ceilings, and access to a covered

Dan Serban

Key West Luxury Real Estate Inc (KW)

59 Palm Dr, Key West, FL 33040
/41
$42,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit B41 Week 1, Key West, FL 33040

Views of the famous Key West Sunset, Gulf of Mexico and pool await you when you arrive at this 4th-floor end- deeded timeshare unit. The live music from the Tiki bar saunters up to the balconies. This highly desirable winter week is magical enjoy the warm weather and Christmas boat parades while Key West is all dressed up for the holidays. Enjoy the private beach, pool, hot tub, sauna, outdoor

Stephanie Herrmann

Truman & Co. Real Estate

617 Front St Unit B41 Week 1, Key West, FL 33040
/34
$5,500
- 3 Beds
- 3 Baths
- 1,380 Sq Ft
37 Palm Dr, Key West, FL 33040

Turnkey Waterfront Living in Saddlebunch Key - $5,500/month This fully furnished 3 bed, 3 bath canal-front home offers the ultimate Keys lifestyle just behind Baby's Coffee. Enjoy quick access to open water with your own boat lift, perfect for fishing or sunset cruising. Spacious open-concept living, updated kitchen, and outdoor entertaining areas make this a perfect getaway or full-time

Dan Serban

Key West Luxury Real Estate Inc (KW)

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

PENTHOUSE! Beautiful straight-on views of the Gulf, 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. Stay or rent it

Stephanie Herrmann

Truman & Co. Real Estate

617 Front St Unit A52 Penthaus Week 32, Key West, FL 33040
/41
$62,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit A-52 Penthaus Week 5, 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

617 Front St Unit A-52 Penthaus Week 5, Key West, FL 33040
/53
$62,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit A52 Penthouse WK 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 Eve celebrations, including live music, fireworks, and iconic Duval Street

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit A52 Penthouse WK 52, Key West, FL 33040
/63
$43,000
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit C-21 Week 22, Key West, FL 33040

Experience deeded ownership of the same week each year (Week 22) at the highly desirable Galleon Resort. This timeshare offers a fantastic location and some of the most spectacular sunsets in Key West.Filled with light, the unit features a private balcony overlooking the Gulf and Marina. Enjoy views of passing sails and evening cruises, along with warm Gulf breezes and live acoustic music

Stephanie Herrmann Truman & Co. Real Estate

617 Front St Unit C-21 Week 22, Key West, FL 33040
/27
$26,900

$3K PRICE DROP
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit D42/42 Swing Float, Key West, FL 33040

Own one week in Key West Every Year! DEEDED ANNUAL TIMESHARE! Similar to fractional ownership, here is your chance to own ONE WEEK PER YEAR in Key West for life! Enjoy 7 nights PER YEAR in a large 2bd, 2ba condo at the Galleon Resort in Key West! Sleeps up to 6 adults. This SWING FLOAT week is deeded as D42/42 but it excludes Fantasy Fest or Boat race weeks. This unit typically Floats to the 2nd

Mary Bradford LIST FOR LESS, LLC

617 Front St Unit D42/42 Swing Float, Key West, FL 33040
/2
$15,000
- 1 Bed
- 1 Bath
- 500 Sq Ft
323 Whitehead St Unit 702 wks 12, Key West, FL 33040

Own Week 12 at The Banyan Resort and enjoy one of the most sought-after times of year in Key West. Nestled in the heart of Old Town, this charming one-bedroom loft suite offers the perfect island getaway just steps from the energy of Duval Street. Unit 702 comfortably accommodates up to four guests and features a unique loft-style design with a spiral staircase leading to a semi-private bedroom

Monika Rydzak eXp Realty LLC KW Branch

323 Whitehead St Unit 702 wks 12, Key West, FL 33040
/5
$2,800
- 2 Beds
- 1 Bath
6630 Maloney Ave Unit 7D, Key West, FL 33040

Ernie Cruz Berkshire Hathaway HomeServices Knight & Gardner Realty

6630 Maloney Ave Unit 7D, Key West, FL 33040
/9
$20,000

$5K PRICE INCREASE
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040

Selling weeks 42 and 43. High Tourist season. Fantasy Fest and Halloween. 2 Bedroom Villa, Ocean view sunrise view, Princess balcony

Jenny Murphy Keller Williams Key West Compass Realty

3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040
/2
$2,500
5950 Peninsular Ave Unit 640, Key West, FL 33040

Prestigious boat slip for rent at Ocean's Edge Marina, suitable for boats up to 50FT located on the North pier with ample water access boasting a 6ft control depth. Features include a nearby fuel station and access to the hotel pool for tenants. Ideal for water enthusiasts seeking a premium marina experience. Daily, monthly or long term rentals available. Air bnb's or houseboats are not allowed.

Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

5950 Peninsular Ave Unit 640, Key West, FL 33040
/18
$3,450
- 2 Beds
- 2 Baths
- 1,175 Sq Ft
Unlisted Address

Fully furnished La Brisa condo available through September 30, 2026. Electric, water and wi-fi included up to $200 per month. Washer and dryer in the unit. Covered carport, storage unit, central a/c, salt ponds view. Secured entry and building. La Brisa has an EV charging station, car wash area, tennis/pickleball court, barbecues, heated pool and hot tub and saunas No smoking, no pets, background

Suzanne Washburn Coldwell Banker Schmitt Real Estate Co. (KW)

Unlisted Address
/9
$20,000
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
3675 S Roosevelt Blvd Unit week 43, Key West, FL 33040

Selling week 42 and 43. High Tourist season. Fantasy Fest and Halloween. These weeks can be sold as deeded weeks or as points to add to an existing portfolio. Across from Smathers beach. There is an ocean view and amazing Sunrise views. Princess Balcony. 2 Bedroom Villa.

Jenny Murphy Keller Williams Key West Compass Realty

3675 S Roosevelt Blvd Unit week 43, Key West, FL 33040
/13
$2,000
- 1 Bed
- 1 Bath
- 396 Sq Ft
55 Boca Chica Rd Unit 451, Key West, FL 33040

Just 10 miles from downtown Key West! This Seaside resort mobile home has a covered deck that maximizes indoor-outdoor living with a relaxed space to take in the views. Added storage space can be found in the shed off the deck. Not only is it close to Key West, the 1 bedroom, 1 bath unit has a fantastic location inside the community, situated on Fantasy Island, just a short walk from the Seaside

Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

55 Boca Chica Rd Unit 451, Key West, FL 33040
/5
$3,500
- 2 Beds
- 1 Bath
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
/17
$3,995
- 2 Beds
- 1.5 Baths
- 780 Sq Ft
81 Golf Club Dr, Key West, FL 33040

For Rent - Key West Golf Club Community Beautifully updated 2 bedroom, 1.5 bath townhome located in the highly desirable gated Key West Golf Club community on Stock Island. This 780 sq ft home offers a perfect blend of comfort, style and island living. This home features beautifully renovated kitchen and bathrooms, along with an open and inviting living space. Step outside to a spacious, private

Nicole Gruenauer Key West Luxury Real Estate Inc (KW)

81 Golf Club Dr, Key West, FL 33040

Florida Monroe County

Home Prices in Key West, FL

The median home sale price in Key West, FL is $1,100,000, consistent with the median home sale price year-over-year. Homes in Key West sell in 107 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $1,100,000	Median Single Family Sale Price $1,300,000
Median Townhouse Sale Price $682,500	Median 2 Bedroom Sale Price $894,500
Median 1 Bedroom Sale Price $615,000	Average Price Per Sq Ft $992
Number of Homes for Sale 227	Last 12 months Home Sales 408
Months of Supply 6.70	Median List Price $1,300,000
Median Change From 1st List Price 8%	Median Home Sale Price YoY Change 0%

How to Buy a Home How to Finance a Home How to Sell a Home

In Key West, there are currently 27 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Key West, FL. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

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