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1606 Flagler Ave, Key West
$905,000
2 Beds ⋅ 2 Baths ⋅ 615897 MLS
Renovated Midtown Key West Home | 2BR/2BA | 1,118 SF | Taken to Studs in 2021 | Off-Street Parking | Private Yard with Hot Tub. Just 5 Blocks to the Atlantic Ocean and beaches. Priced at $950,000, this single-level Midtown Key West home was taken to the studs and fully renovated in 2021, including new plumbing, new electric, roof, and impact windows and doors. 1,118 square feet of living space on a 3,608 SF lot, minutes from Smathers Beach, Higgs Beach, Ed Knight Pier, parks, restaurants, and island bike paths. The open-concept living and dining area connects to a modern kitchen with quartz countertops, stainless steel appliances including a smart refrigerator, a beverage bar, and a movable island. Consistent ceramic tile flooring runs throughout the home. The primary suite includes dual walk-in closets, an updated bathroom, and an in-suite washer and dryer. The large guest bedroom features a bay window with built-in seating and added storage in addition to a sizable closet. The charming guest bathroom has a jetted bathtub. Additional 2021 improvements include a French drain system, energy-efficient A/C, upgraded insulation, and moisture-resistant drywall--durable, low-maintenance features suited to island living. The fully fenced yardis a private outdoor retreat with a pergola-covered lanai, hot tub, garden beds, workshop, and extra storage. Rare off-street parking adds daily convenience in one of Key West's most desirable residential neighborhoods. Perfect primary Home, Secondary Home or Investment Property. Eligible for 30-day rentals. Move-in ready and easy to show.

1606 Flagler Ave, Key West

2417 Linda Ave, Key West
$902,000
3 Beds ⋅ 2 Baths ⋅ 619857 MLS
LOVELY 3 BEDROOM 2 BATH HOME WITH POOL AND PARKING!! Home has been owner occupied and well maintained. The property boasts a spacious lot that includes a pool, a deck area, a covered space for entertaining, tropical landscaping, and a fence for added privacy. Inside, the home features a thoughtful floor plan with a bright living room and an expansive family room, which has French doors leading outside. The kitchen is equipped with stainless steel appliances and offers ample cabinet space. There are three generously sized bedrooms, with the primary bedroom featuring a large walk-in closet. Home has two full baths. The home is equipped with central air conditioning and ductless AC cooling. Additionally, there is off-street parking, a laundry room, and a shed for extra storage. The location is conveniently close to shopping, schools, dining, and just a few blocks from the public boat ramp.

2417 Linda Ave, Key West

1417 8th St, Key West
$900,000
3 Beds ⋅ 3 Baths ⋅ 618188 MLS
Impeccably renovated Midtown retreat with guest cottage on a corner lot, framed by a classic white picket fence. This beautifully updated property offers a rare combination of charm, modern upgrades, and flexibility in one of Key West's most desirable residential neighborhoods. The 2-bedroom, 2-bath main house has been thoughtfully renovated throughout, featuring a brand-new kitchen, new metal roof (2022), new refrigerator, fully restored terrazzo floors, upgraded storage, and a fully renovated primary suite with ensuite bath and walk-in closet. Additional improvements include new central A/C ductwork, hurricane-rated sliding glass door, smart thermostat, retractable awning, new washer and dryer, and a new hot water heater. A generator with transfer switch adds peace of mind, while a newly built shed with hurricane tie-downs provides practical storage. The property is fully landscaped, including a native butterfly garden, creating a private tropical setting ideal for indoor-outdoor living. The separate 1-bedroom, 1-bath guest cottage offers excellent rental or guest accommodations with its own private entrance. The cottage features newly installed split A/C units, a renovated kitchen and bathroom with upgraded electrical and plumbing, hurricane-rated windows, and a new on-demand water heater. Cottage has option to come fully furnished. Set on a quiet corner lot, the fully enclosed fenced yard enhances privacy while offering both off-street and ample street parking—a true luxury in Key West. With a total of 3 bedrooms and 3 full baths, this property presents a compelling opportunity for full-time living, a second home, or a residence with strong rental income potential. Move-in ready, meticulously upgraded, and ideally located—this Midtown Key West home checks every box.

1417 8th St, Key West

1210 Virginia St, Key West
$900,000
3 Beds ⋅ 3 Baths ⋅ 616279 MLS
SOLD AS IS. This property has been a rental property for many years and needs repairs and renovations. The downstairs is vacant and easy to see. There are tenants upstairs, and we will not disturb them on initial showings. Currently this is a two-story legal duplex in the popular Bayview Park neighborhood in Old Town. It could be converted back to the original single-family home. There are a total of three bedrooms and 2.5 baths. As currently configured, the first floor has 2 bedrooms,1.5 baths and features 9.5-foot ceilings, doors with transom windows, and hardwood floors. French doors open to the rear yard and porch. The second-floor has 1 bedroom, 1 bath, hardwood floors and a large rear porch. The location of this current 2-unit property offers an investment potential or possible single family home conversion. Located just off White Street.

1210 Virginia St, Key West

1503-1509 Seminary St, Key West
$900,000
2 Beds ⋅ 1 Baths ⋅ 617066 MLS
Opportunity awaits in the heart of Midtown Key West! This rare double-lot offering includes two side-by-side parcels with endless potential for redevelopment or renovation. 1503 Seminary Street features a 2-bedroom, 1-bathroom single-family home built in 1943 with 1,160 sq. ft. of living area. The home offers a spacious layout ready for your personal touch — ideal for a full remodel or a complete redesign. 1509 Seminary Street currently includes a small structure in need of teardown, providing a clean slate for new construction, expansion of the adjacent home, or the creation of a private compound. Zoned residential and centrally located just minutes from beaches, shopping, dining, and Old Town, this is an exceptional investment for builders, developers, or anyone looking to create their own Key West .

1503-1509 Seminary St, Key West

3700 Northside Dr, Key West
$880,000
3 Beds ⋅ 2 Baths ⋅ 619269 MLS
This move-in ready property offers the perfect blend of comfort, functionality, and island charm. Thoughtfully updated, the home features durable vinyl flooring throughout and energy-efficient mini-split systems in every room, providing individualized climate control and lower utility costs. The spacious layout is ideal for both full-time living and investment potential. A private driveway offers convenient off-street parking, while the fully fenced backyard creates a private outdoor retreat--perfect for entertaining, relaxing, or accommodating pets. Additional highlights include in-unit laundry and a clean, modern interior that makes this home truly turnkey. Located in a desirable New Town neighborhood, you're just minutes from shopping, dining, schools, and all that Key West has to offer. Whether you're looking for a primary residence, second home, or investment opportunity, 3700 Northside Drive checks all the boxes.

3700 Northside Dr, Key West

2217 Harris Ave, Key West
$875,000
3 Beds ⋅ 3 Baths ⋅ 616050 MLS
Located in the heart of Key West and only 2 miles from Duval Street, this home is move in ready! The property was previously owner-occupied, meticulously maintained, and recently updated. The kitchen boasts stainless steel appliances, a granite island with a breakfast bar, a wine fridge, double oven, and ample cabinet and preparation space. The spacious living room features crown molding. The home offers luxury vinyl plank flooring, central air conditioning, laundry room, and over 1400 sq ft of living space. With 3 bedrooms and 3 bathrooms, including two en suite baths, the layout is ideal. The bonus room provides options for a home office space or guest room. The 5000 sq ft lot is enclosed by a 6ft privacy fence. There is room for a pool or enjoy as is with the covered deck area for entertaining allowing for additional outdoor dining/living space. Low maintenance tropical landscaping, this is the perfect island home, second home, or investment property for employee housing.

2217 Harris Ave, Key West

2007 Flagler Ave, Key West
$875,000
6 Beds ⋅ 5 Baths ⋅ 616010 MLS
Discover a smart investment opportunity and a relaxed lifestyle right in Key West's Midtown. This actively leased duplex is ideally located, just steps from Key West High School and close to beaches, restaurants and postcard-worthy sunsets. With two spacious units, the property generates a robust monthly income of $9000, totaling approximately $108,000 annually. Whether you're an investor looking for strong returns or a buyer dreaming of island living with built-in income, this property delivers exceptional flexibility. Live in one unit and lease the other, or rent out both for maximum cash flow. The interiors are updated, offering generous bedrooms and a flexible layout. Zoned for multi-family use and located on a 5000 sq ft lot, this 2-story duplex is an excellent opportunity for savvy buyers looking for both ROI and tropical tranquility in paradise.

2007 Flagler Ave, Key West

1800 Atlantic Blvd Unit 408A, Key West
$875,000
2 Beds ⋅ 2 Baths ⋅ 616590 MLS
Welcome to the view you've been looking for! This 2 bedroom, 2 bath top floor condo has a balcony that spans the length of the unit and has glass sliding doors from each room for natural light and views of the open ocean, ready to make it your own. The condo boasts a partially vaulted wood ceiling for added style. This place is the island dream with a beautiful pool, hot tub and even private beach access just steps from the building. The complex also has a fitness center and tennis courts for the active islander. Gated garage parking, and secured building access for safety and privacy of the residents and guests. This location, this floor, this view - is priced to sell, and pictures do not do the view justice. Go see! *Sold as is, no warranties, no Warranty deed. *Offers shall include a fully signed conflict of interest statement.

1800 Atlantic Blvd Unit 408A, Key West

1613 Josephine St, Key West
$871,000
2 Beds ⋅ 3 Baths ⋅ 620175 MLS
**Low Insurances totaling $4300/year** Furnished and move in ready, this beautifully appointed Midtown Key West half townhouse offers the perfect blend of comfort and island living. The open floor plan features high ceilings, abundant natural light, and a spacious living, dining, and kitchen area, along with a convenient half bath on the main level. Upstairs the private bedroom suites provide comfortable accommodations and separation from the living space. Enjoy plenty of room for outdoor entertaining, relaxing, and dining al fresco, along with ample off street parking ...a rare Key West convenience. Centrally located near beaches, restaurants, shopping and all that Key West has to offer this property is ideal as a primary residence, vacation home or investment opportunity.

1613 Josephine St, Key West

732 Olivia St, Key West
$865,000
1 Beds ⋅ 1 Baths ⋅ 617321 MLS
Unlock the charm and potential of Old Town Key West living! Tucked away in the heart of Old Town, just a few blocks from world-famous Duval Street, 732 Olivia Street offers a rare opportunity to own a charming piece of Key West history. This one-bedroom, one-bath cottage with a versatile loft has been lovingly held by the same owner for over 45 years. Situated on a generous sized lot, the property invites you to bring your vision and create your own island retreat. Whether you're dreaming of a cozy getaway or a full renovation, the potential here is undeniable. Adding to the appeal, the home includes a 1/10 ownership in a shared 10-space parking area, conveniently accessible through the rear gate. Located in the desirable X flood zone, this home combines historic charm, prime location, and unique perks, making it an exceptional find in the heart of Key West. Don't miss out, schedule your private showing today and start your next chapter in Key West!

732 Olivia St, Key West

729 Windsor Ln, Key West
$865,000
2 Beds ⋅ 1 Baths ⋅ 615169 MLS
Charming Historic Gem in the Heart of Old Town Key West! Welcome to 729 Windsor Lane—a rare opportunity to own a piece of Key West history nestled in one of the island's most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint that's almost unheard of in Old Town, along with the luxury of coveted off-street parking. Step inside to discover a thoughtfully updated interior that blends historic charm with modern comfort. The remodeled bathroom features stylish tilework, updated fixtures, and a spa-like feel, while the upgraded kitchen boasts contemporary cabinetry, sleek countertops, and stainless steel appliances—perfect for preparing everything from a quiet Key West breakfast to tropical cocktails on the patio. Surrounded by lush native foliage, the property offers a serene, private setting just steps from Duval Street, world-class dining, art galleries, entertainment, and more—while maintaining the tranquility of a quiet residential neighborhood. For investors, the unbeatable location just a short stroll from Duval Street, renowned restaurants, nightlife, galleries, and cultural attractions makes this property ideal for monthly vacation rentals or long-term leasing to locals. For second-home buyers, it offers an effortless blend of privacy and proximity to the action, in a quiet residential neighborhood. Truly your home away from home. And for the historic home lover, this residence offers a chance to preserve and personalize a piece of Key West's architectural heritage with room to enhance over time and make it your own. With its historic architecture, upgraded amenities, and rare lot size, this home offers endless potential to create your tropical dream oasis. Whether you're looking for a charming island retreat, a vacation rental, or a full-time residence, 729 Windsor Lane delivers the perfect blend of location, lifestyle, and opportunity.

729 Windsor Ln, Key West

44 Spoonbill Way Unit # 1, Key West
$860,000
3 Beds ⋅ 3 Baths ⋅ 619360 MLS
Priced to SELL. Seller is relocating. The views take center stage. Some homes feel like an escape. This one feels like eternal vacation, a place where luxury unfolds softly, until you're fully wrapped in its calm. At 44#1 Spoonbill, the arrival is its own quiet ceremony. Fresh brick pavers form a polished pathway through tropical greens, guiding you toward a home that seems to glow from w/in. The light a little warmer, as if the entire space has been curated for serenity. Inside, refinement meets dreamscape. Travertine floors stretch across the main level like cool, polished stone, while bamboo rises up the stairs, traversing across the second floor, a warm, golden luxury that whispers of handcrafted detail. Every window carries elevated elegance: multi-level Ocean View window treatments that shift the sunlight from sheer radiance to velvety calm, filtering the day in layers of soft, coastal luxury. Through upgraded impact slider on lower level, the world opens into a living masterpiece. #15 tee box/fairway stretching into perfect green geometry, the #17 fairway bending toward breathtaking SUNSET LAKE. The water itself glowing w/sky reflections, ducks wander, egrets glide, the pond sparkles. Pure tranquility w/a touch of wild grace. The kitchen carries its own polished upgrades, anchored by granite countertops, brand-new stainless range, gleaming modern sophistication, new stainless microwave, new Bosch dishwasher; stainless French door refrig./freezer. On the main level, the reimagined guest bath delivers boutique-hotel refinement--a new walk-in shower, glass doors, w/upgraded finishes. The 3rd bdrm. (downstairs) is a bonus, perhaps office/study area. Upstairs, primary suite feels like a private retreat. Expansive slider opens to an oasis via a screened veranda w/breathtaking vista! Generous-sized en-suite guest bdrm. has a cozy veranda overlooking the quiet cul-de-sac. The best of Rees-Jones designed Golf Course living! 24-hr. Res. Services! Come live the dream!

44 Spoonbill Way Unit # 1, Key West

1222 Florida St, Key West
$855,000
3 Beds ⋅ 1 Baths ⋅ 620399 MLS
Discover the timeless charm of Key West living at 1222 Florida Street, ideally positioned in the highly sought-after White Street Gallery District. Just a short stroll from Higgs Beach, the White Street Pier, neighborhood parks, tennis and pickleball courts, and less than a mile from the restaurants, boutiques, galleries, and nightlife of iconic Duval Street, this location offers the perfect balance of tranquility and convenience. Offering approximately 1,580 square feet of living space, the residence features an inviting floor plan filled with natural light and comfortable gathering spaces designed for everyday living and effortless entertaining. Spacious bedrooms and flexible living areas provide versatility for a primary residence, seasonal escape, or investment property. With 2 bedrooms and 1 bathroom on the first floor and a huge loft room upstairs. Outdoor living is an essential part of the island lifestyle, and this property offers the opportunity to create your own private tropical oasis with room to add a pool or simply bring your furniture and enjoy the privacy with a fully fenced yard and off street parking. The surrounding neighborhood is celebrated for its tree-lined streets, historic charm, vibrant arts community, and exceptional walkability. Spend your mornings biking to the beach, afternoons exploring local galleries and evenings enjoying world-class dining! Located in a 28-day rental zoning.

1222 Florida St, Key West

53 Spoonbill Way, Key West
$855,000
4 Beds ⋅ 3 Baths ⋅ 617596 MLS
BIG PRICE REDUCTION!!!!! MUST SEE! Meticulously Maintained Tropical Escape. This townhome is located within the gates of the prestigious Key West Golf Course community. The home has a large floor plan which features tropical architecture with a cottage feel. Resort style amenities include 24 hour security, 2 community pools, a clubhouse with a fitness center and a 18 hole golf course. This lovely townhome is located on the desired Spoonbill Way cul-de-sac that provides lots of privacy. As you enter through the beautiful white picket fence, you will notice the professional tropical landscaping which includes a sprinkler system. An inviting front porch awaits you arrival. In the home, you will immediately notice a fully renovated kitchen with solid countertops and stainless appliances. The beautiful new floors throughout will draw your attention. The home has a bedroom and full bath on main level. Upstairs are 3 additional bedrooms with vaulted ceilings and a full hall bathroom. Included in the upstairs bedrooms is a spacious master suite. The master has a renovated en-suite bathroom along with a large linen closet. The custom-built walk in master closet exceeds expectations for anyone with a large wardrobe. With a large floor plan, private street, tropical landscaping, upgrades, custom pantry and custom master closet this home is truly ''One Of A Kind'' A special find in Key West!

53 Spoonbill Way, Key West

1014 17th Ter, Key West
$850,000
3 Beds ⋅ 2 Baths ⋅ 617017 MLS
Welcome to 1014 17th Terrace in the highly desired neighborhood of Perlman Heights in Key West. This charming home offers a warm and welcoming atmosphere in one of the most sought-after areas of new town. Owned by only one owner, this property is waiting for you to make it your own. Located just two blocks from the Gulf and conveniently close to all local shopping centers, this home provides exceptional access to everyday amenities and services. Whether you need groceries, dining options, or retail stores, everything is within easy reach, making everyday living effortless. Situated near some of the best schools in the area, this three-bedroom, two-bathroom home is also perfect for families. A sparkling pool with fencing provides privacy, security and tropical charm. The spacious driveway provides parking for a car or coveted boat trailer storage! There is plenty of additional off-street parking as well. With its excellent location near top-rated schools and convenient access to shops and beaches, this property offers the perfect balance of comfort, convenience, and community. Don't miss this fantastic opportunity to own a beautiful home in new town!

1014 17th Ter, Key West

3608 Northside Dr, Key West
$850,000
5 Beds ⋅ 3 Baths ⋅ 615928 MLS
This beautifully maintained home is perfectly situated in a desirable family-oriented neighborhood, just steps from Cozumel Park. Designed to accommodate families or multi-generational living, the property features a versatile layout: a 3-bedroom, 2-bathroom main house and a separate 2-bedroom, 1-bathroom mother-in-law suite with its own private entrance. Upgrades Include: new hurricane-impact doors and windows, a 4-year-old AC system, a metal roof with recently upgraded special screws for enhanced longevity. The spacious corner lot provides ample parking, including a convenient carport, while the fenced side yard offers a private oasis, perfect for entertaining or relaxing. With its thoughtful design and prime location, this home seamlessly blends functionality, comfort, and convenience. Don't miss this exceptional opportunity!

3608 Northside Dr, Key West

308 Peacon Ln, Key West
$850,000
3 Beds ⋅ 3 Baths ⋅ 612553 MLS
Yes - not too good to be true or a misprint! Priced to sell for just $990,000 with this $400,000 price reduction. Rare 2 unit property in Old Town! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was converted into a legal 2-unit property with separate water & electric accounts. The configuration is upstairs (large 1 BR & 1 BA with a sleeping loft) and downstairs (2 BR & 1.5 BA) units, with an exterior staircase. Both units have a front & rear porch, balcony, or deck. For your parking convenience, an off-street spot is in front of the property. Prime location, opportunity & value!

308 Peacon Ln, Key West

2601 S Roosevelt Blvd Unit 305A, Key West
$840,000
2 Beds ⋅ 1 Baths ⋅ 617052 MLS
Experience breathtaking oceanfront living from every room in this bright, third-floor corner residence at Key West By The Sea. With extra windows along the side, natural light fills the space, highlighting views of the Atlantic and creating a serene ambiance throughout. The open-concept living and dining area flows onto a private balcony, the perfect spot to enjoy morning coffee or evening breezes while overlooking Smather's Beach. Both bedrooms offer beautiful water views. The primary with direct ocean vistas and the guest room overlooking both the pool and the sea are filled with light. Thoughtful upgrades include impact-rated doors and windows, a nearly new central A/C system, freshly painted interiors, and the convenience of an in-unit washer and dryer, a rare feature in this community. Even more exceptional is the private storage locker located directly across the hall, a valuable and seldom-available addition. Key West By The Sea is a gated, oceanfront community with resort-style amenities, including two large pools (one heated), tennis courts, a clubhouse, on-site parking, a pet walking trail, and bike racks. Residents enjoy easy access to Smather''s Beach and the wide oceanfront promenade for walking, jogging, or biking into Old Town to enjoy Key West's world-class dining and entertainment. Call today to see this direct ocean view gem! Owner is a licensed Florida Realtor.

2601 S Roosevelt Blvd Unit 305A, Key West

3625 Seaside Dr Unit 25312, Key West
$835,000
2 Beds ⋅ 2 Baths ⋅ 614351 MLS
Here is a rare opportunity to own a nightly vacation rental condo in Key West with a transient license, allowing for highly profitable short-term rentals. Rental history is available in the documents tab. Located in the sought-after Sunrise Suites Resort, this property offers a long history of consistent rental income. Investors can take over future bookings, ensuring a seamless transition and steady revenue stream. Situated on the third floor, this 2-bedroom, 2-bathroom unit overlooks the tennis courts, providing scenic views and a relaxed atmosphere. Sunrise Suites offers an array of resort-style amenities, including a lagoon-style pool surrounded by lush tropical landscaping, a community BBQ area perfect for grilling your fresh catch, tennis courts for an evening match, and an on-site gym for staying active. The unit itself has been updated with new flooring, a/c, washer/dryer hookup and a fresh coat of paint.

3625 Seaside Dr Unit 25312, Key West