Waterfront Homes for Sale in Summerland Key, FL

/13
$1,350,000
- 3 Beds
- 2 Baths
- 1,488 Sq Ft
22777 Jolly Roger Dr, Summerland Key, FL 33042

Stop dreaming and start packing. This rare canal-front gem features a 2.75 assumable mortgage for qualified buyers—a game-changer in today’s market! Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even

Olivia Poto GARRISON REALTY GROUP LLC

22777 Jolly Roger Dr, Summerland Key, FL 33042
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/52
$3,899,000
- 6 Beds
- 6 Baths
- 3,029 Sq Ft
1557 Long Beach Dr, Big Pine Key, FL 33043

Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meets income opportunity. This beautifully updated waterfront property allows you to live the Florida Keys lifestyle while hosting it or operate a turnkey hospitality investment in one of the most sought-after settings in the Lower Keys. The property has undergone an extensive renovation over

Surelis Yanes Miami Portfolio Collection

1557 Long Beach Dr, Big Pine Key, FL 33043
/52
$1,449,000
- 3 Beds
- 3 Baths
- 1,820 Sq Ft
845 Pirates Rd, Summerland Key, FL 33042

Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to open water, making it ideal for fishing and island adventures.Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas overlooking the canal. Boaters will

Sandra Dolowy KeyIsle Realty

845 Pirates Rd, Summerland Key, FL 33042
/49
$950,000 Open Fri 10AM - 12PM
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
29175 Aster Ln, Big Pine Key, FL 33043

Discover exceptional Florida Keys living in this impeccably kept 3-bedroom, 2-bath waterfront residence on Big Pine Key featuring direct, bridge-free access to Pine Channel--an authentic boater's paradise. Built for performance, longevity, and security, this property includes a metal roof, impact-resistant windows and doors, Hardie Board siding plus solar panels delivering reduced energy costs,

Scott Brisson KeyIsle Realty

29175 Aster Ln, Big Pine Key, FL 33043
/72
$595,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
/8
$1,450,000
- Land
- 0.14 Acre
- $10,357,143 per Acre
00000 Lagoon Dr, Summerland Key, FL 33042

Excellent opportunity to build your dream in paradise. This 6,140 sq foot lot with 70.65 ft. of water frontage has a beautiful open water and ocean view. This is the last lot available in this established subdivision Summerland Cove. Easy access to both the Atlantic Ocean and the Gulf of Mexico.

Marc Ulanowski Equestrian Sotheby's International Realty Inc.

00000 Lagoon Dr, Summerland Key, FL 33042
/50
$1,595,000
- 3 Beds
- 2 Baths
- 1,995 Sq Ft
643 Indies Rd, Summerland Key, FL 33042

Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

Greg MacLaren Internet Realty of the Florida Keys

643 Indies Rd, Summerland Key, FL 33042
/12
$495,000
- Land
701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

Anay Ramos Miami New Realty

701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
/7
$500,000
- Land
53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

Build your dream home in prestigious Sugarloaf Shores, an upscale coastal waterfront community just 20 minutes from the magic of Key West. This oversized 16,361 SqFt canal-front lot offers approximately 80 feet of waterfront frontage with excellent boating access to both the Atlantic Ocean and Florida Bay.The property includes permits for dock installation, clearing, and grading, with ROGO

Anay Ramos Miami New Realty

53 Sugarloaf Dr, Sugarloaf Shores, FL 33042
/45
$519,000
- 2 Beds
- 2 Baths
- 758 Sq Ft
701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

Amanda Taylor Bluescape Real Estate

701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
/34
$469,000
- 1 Bed
- 1.5 Baths
- 735 Sq Ft
701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home offers

Bea Evelyn Citron Compass Florida, LLC

701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
/49
$1,499,000
- 4 Beds
- 3 Baths
- 1,800 Sq Ft
27372 W Indies Dr, Summerland Key, FL 33042

Offered for the first time, this custom-built 4 bedroom, 3 bathroom waterfront residence on Ramrod Key showcases refined coastal design, exceptional craftsmanship, and magnificent ocean views. Completed in 2020, the two-story stilted home was thoughtfully designed to maximize light, views, and seamless indoor-outdoor living, with one master bedroom ensuite on each level for comfort and

Sandra Dolowy KeyIsle Realty

27372 W Indies Dr, Summerland Key, FL 33042
/49
$2,100,000
- 4 Beds
- 3 Baths
- 2,440 Sq Ft
22542 Jolly Roger Dr, Summerland Key, FL 33042

This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay—creating a rare and commanding presence along the shoreline.Broad covered

Lauren Dunn Coldwell Banker Schmitt R.E.

22542 Jolly Roger Dr, Summerland Key, FL 33042
/41
$849,000
- 2 Beds
- 2 Baths
- 960 Sq Ft
154 Cutthroat Dr, Summerland Key, FL 33042

Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New fence with double gates and an entrance gate, gutters, landscaping, tile flooring, freshly painted

Pamela Stangler Expert Realty LLC

154 Cutthroat Dr, Summerland Key, FL 33042
/64
$669,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

OCEANFRONT TRANSIENT RENTAL IN VENTURE OUT - CUDJOE KEYAmazing open water views of the sparkling Atlantic set the tone the moment you arrive. From this premier waterfront location, you'll enjoy sweeping vistas of the marina, lagoon, Tiki hut, and the iconic Bird Point sanctuary. Sunrise glows over endless blue water, creating a peaceful and ever-changing coastal backdrop.Positioned on a 35-foot

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
/77
$440,000
- Land
701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and walkway,

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
/35
$1,250,000
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
29662 Independence Ave, Big Pine Key, FL 33043

Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

Halley Haack Coldwell Banker Schmitt RE Co.

29662 Independence Ave, Big Pine Key, FL 33043
/31
$809,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
31226 Hollerich Dr, Big Pine Key, FL 33043

Buy a slice of the Florida Keys with this sturdy CBS 2-2 located in one of the most convenient locations available! Boating is a short ride to Bogie channel which offers easy access to both the Gulf of Mexico and the Atlantic! World-class fishing at your fingertips! Also nearby is Big Pine Park, and many amenities like the Winn-Dixie shopping center. More about the house; the first floor

Wyatt Tucker Action Keys Realty of the Lower FL Keys LLC

31226 Hollerich Dr, Big Pine Key, FL 33043
/39
$799,000
- 2 Beds
- 2 Baths
- 984 Sq Ft
744 Blackbeard Rd, Summerland Key, FL 33042

Welcome to your piece of Keys living in this charming 2 bedroom, 2 bathroom home in Little Torch Key on the ocean side. Enjoy a lovely west-facing screen porch overlooking the canal for a quiet morning coffee or to view the colors of the evening sunset. This fully fenced stilted modular home offers direct boating access to Pine Channel and Newfound Harbour for some of the best boating in the

Debra Farrell Island Welcome Real Estate

744 Blackbeard Rd, Summerland Key, FL 33042
/82
$3,699,000
- 4 Beds
- 3.5 Baths
- 1,744 Sq Ft
17183 Coral Dr, Summerland Key, FL 33042

Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

Jan Fritz Coldwell Banker Schmitt RE Co.

17183 Coral Dr, Summerland Key, FL 33042
/47
$445,000
- Land
701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
/7
$799,990
- Land
- 0.18 Acre
- $4,444,389 per Acre
28525 Jolly Roger Dr, Little Torch Key, FL 33042

RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

Fazana Haniff FHG Realty, LLC.

28525 Jolly Roger Dr, Little Torch Key, FL 33042
/73
$1,099,000
- 5 Beds
- 2 Baths
- 1,888 Sq Ft
3836 No Name Rd, Big Pine Key, FL 33043

Introducing No Name Retreat - Rare waterfront opportunity with exceptional development potential featuring 140 feet of direct water frontage and expansive 14,420 sq ft lot. The property currently includes a full duplex plus an additional buildable vacant lot, offering endless possibilities for investors, builders, or someone looking for extra room next door. Live on the water while generating

Saara Staten Engel & Volkers Marathon

3836 No Name Rd, Big Pine Key, FL 33043
/10
$350,000
- Land
30324 Frigate Ln, Big Pine Key, FL 33043

CLEARED WATERFRONT CORNER LOT IN TROPICAL BAY with active building permit! Build your dream CBS home in a wonderful subdivision. Building permit is good till 2028! Large dock already in place. 20' on short side and 55 feet on the long side. Seller financing possible.

Derrick Johnson Coco Plum Real Estate

30324 Frigate Ln, Big Pine Key, FL 33043
/30
$989,000
- 3 Beds
- 3 Baths
- 1,314 Sq Ft
3633 Blue Lagoon St, Big Pine Key, FL 33043

This meticulously maintained 3-bedroom, 3-bath home in Big Pine Key offers exceptional privacy with state owned non-buildable land on both sides of this tranquil property. With 1,314 square feet of living space, it features an open floor plan, strand woven bamboo floors, two en-suite bedrooms and a nice sized third bedroom.The kitchen includes custom granite countertops, soft close cabinets,

David Kaufmann Century 21 Circle

3633 Blue Lagoon St, Big Pine Key, FL 33043
/62
$1,149,000
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
417 Pirates Rd, Summerland Key, FL 33042

Welcome to this beautifully updated canal-front home in the highly desirable Jolly Roger Estates on Little Torch Key! Offering 3 bedrooms, 2 baths, 1,170 sq ft of living space plus a 110 sq ft flex/office area, this meticulously maintained waterfront home features a desirable split floor plan with an open layout, remodeled kitchen with quartz countertops and LG ThinQ smart refrigerator and range,

Maggie Beall Lokation Real Estate

417 Pirates Rd, Summerland Key, FL 33042
/22
$1,150,000 Open Sat 11AM - 2PM
- 2 Beds
- 2 Baths
- 1,060 Sq Ft
1331 Hudgins Dr, Summerland Key, FL 33042

Construction Location & Orientation A Beautifully Appointed Canal Front Fortress All Concrete: Floors Walls Stairs Walk-Around Ramp Driveway Deck & Seawall. All Solar Glazed and Insulated Impact windows Enter the Unique Palm Tree Stained-glass Impact door to 24-inch Travertine floors and Nine-foot ceilings throughout. The Master Bedroom has French doors with a Tropical Stained-Glass Floral

Camilo Perez Home Sold Realty, LLC

1331 Hudgins Dr, Summerland Key, FL 33042
/27
$350,000
- 2 Beds
- 1 Bath
- 672 Sq Ft
701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

Bea Evelyn Citron Compass Florida, LLC

701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
/42
$750,000
- 3 Beds
- 1.5 Baths
- 1,008 Sq Ft
31033 Hibiscus Dr, Big Pine Key, FL 33043

Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Additional highlights include an on-demand hot water heater, a seawall, and

Karen Haack Coldwell Banker Schmitt RE Co.

31033 Hibiscus Dr, Big Pine Key, FL 33043
/4
$400,000
- Land
- 1,400 Acres
- $286 per Acre
27378 Jamaica Ln, Summerland Key, FL 33042

ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

Patricia Borges Borges Realty Group LLC

27378 Jamaica Ln, Summerland Key, FL 33042
/75
$915,000 Open Fri 10:30AM - 1:30PM
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

This is the house for your boat!ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront residence. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water & an unmatched

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
/21
$459,000
- 1 Bed
- 1 Bath
- 668 Sq Ft
701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
/61
$1,675,000
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
1163 de Lussan Ln, Summerland Key, FL 33042

Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift

Jan Fritz Coldwell Banker Schmitt RE Co.

1163 de Lussan Ln, Summerland Key, FL 33042
/53
$2,375,000
- 5 Beds
- 4 Baths
- 2,772 Sq Ft
205 S Point Dr, Summerland Key, FL 33042

Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views.The primary suite is a private

Dawn McComish Lokation Real Estate

205 S Point Dr, Summerland Key, FL 33042
/41
$799,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
1634 Lantana Ln, Big Pine Key, FL 33043

Custom-built 2-bedroom, 2-bathroom home (1987) situated on a boating canal in the sought-after Eden Pines neighborhood of Big Pine Key where the Key Deer roam. Short stilted home located on a 6,000 sq. ft. lot the property offers 60 feet of concrete seawall ideal for your boat of choice, with excellent boating access via Pine Channel. Boaters should note two bridges en route with approximate

Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

1634 Lantana Ln, Big Pine Key, FL 33043
/28
$758,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
3856 Donna Rd, Big Pine Key, FL 33043

30k Price Improvement, Priced to SELL, Motivated Seller, Bring all Offers. Sportsman Paradise. 2 Bedroom House with Permitted Concrete BOAT RAMP, concrete sea wall, concrete fish cleaning table with Permitted downstairs bathroom. Real short idle to open water. Back country fishing, lobster diving/snorkel and stone crabs right in your back yard. Easy access to to Atlantic & Looe Key. Lots of

Alan Ballas Alan Ballas Realty

3856 Donna Rd, Big Pine Key, FL 33043
/4
$275,000
- Land
27426 Martinique Ln, Summerland Key, FL 33042

Vacant 6,000 SF lot in desirable Ramrod Key, ideally positioned near the world-class Looe Key Reef and just a five-minute boat ride to Picnic Island. This property offers an exceptional opportunity to build in one of the Lower Keys' most sought-after lifestyle locations. Walking distance to local favorites including The Tiki Bar and Boondocks Grille & Draft House. Buyer to obtain building permit

Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

27426 Martinique Ln, Summerland Key, FL 33042
/44
$1,149,000
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
27426 Martinique Ln, Summerland Key, FL 33042

Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

27426 Martinique Ln, Summerland Key, FL 33042
/21
$575,000
- 2 Beds
- 2 Baths
- 861 Sq Ft
701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and

Mary Conklin Action Keys Realty of the Lower FL Keys LLC

701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
/7
$190,000
- Land
- 6,000 Acres
- $32 per Acre
1145 Hakluyt Ln, Cudjoe Key, FL 33042

Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

Daniel Pacheco United Realty Group Inc

1145 Hakluyt Ln, Cudjoe Key, FL 33042

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