Summerland Key, FL Homes for Sale

/24
$1,595,000
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
182 Venetian Way, Summerland Key, FL 33042

Experience classic Florida Keys waterfront living in this spacious canal-front retreat on Sugarloaf Key, offering boating access, expansive indoor-outdoor living, and just a short drive to Key West. 3,000 square feet of finished living space including 4 bedrooms and 3 baths. Situated on a wide canal with ample room for a future dock, offering the opportunity to create your own boating paradise.

James Olive LoKation Real Estate

182 Venetian Way, Summerland Key, FL 33042
/40
$689,000
- 1 Bed
- 1 Bath
- 820 Sq Ft
2231 Middle Torch Rd, Summerland Key, FL 33042

Imagine having the freedom to create your own secluded retreat in the heart of the Lower Florida Keys. This remarkable offering includes two adjacent 2.5-acre parcels, combining for approximately 5 acres--an exceptionally rare amount of land in the Florida Keys. Existing improvements include two separate residences, each offering one bedroom and one bathroom. One parcel is improved with a

Justyn Ewald Expert Realty LLC

2231 Middle Torch Rd, Summerland Key, FL 33042
/30
$180,000
- Land
- 6,098 Sq Ft
- $1,285,714 per Acre
27347 Martinique Ln, Ramrod Key, FL 33042

Rare Opportunity in the Desirable Lower Florida Keys! This property offers the chance to secure a piece of paradise and create your own future plans.This property provides great boating access to the Atlantic along with the Gulf. Enjoy the relaxed island lifestyle of the Keys boating, fishing, snorkeling at the reef, watersports, beaches, and the all natural beauty of the Keys. Also Just

Heather Mason Coastal Collection Real Estate Inc.

27347 Martinique Ln, Ramrod Key, FL 33042
/38
$674,999
- 2 Beds
- 2 Baths
- 770 Sq Ft
701 Spanish Main Dr Unit 123, Cudjoe Key, FL 33042

YOUR FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully furnished 2-bedroom, 2-bath home combines water views, exceptional boating access, comfortable island living, and resort-style amenities just seconds from open water.Situated on a wide 60' canal, boaters will love the 35' concrete

Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

701 Spanish Main Dr Unit 123, Cudjoe Key, FL 33042
/41
$949,000
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
342 Spanish Main Dr, Summerland Key, FL 33042

Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

Monika Rydzak eXp Realty LLC KW Branch

342 Spanish Main Dr, Summerland Key, FL 33042
/31
$982,600
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access.

Jonathan Minerick Homecoin.com

701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
/45
$1,269,000
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
116 Spanish Main Dr, Summerland Key, FL 33042

Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

Margaret Crowley Florida Keys Realty Group

116 Spanish Main Dr, Summerland Key, FL 33042
/4
$189,000
- Land
- 0 Sq Ft
29859 Overseas Hwy #20, Big Pine, FL 33043

Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across

Liza Dieppa Coldwell Banker Realty

29859 Overseas Hwy #20, Big Pine, FL 33043
/43
$735,000

$45K PRICE DROP
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
27024 Shannahan Rd, Summerland Key, FL 33042

Well-maintained elevated home offering the perfect combination of comfort, functionality, and peace of mind. Built above flood elevation, this move-in-ready property features an open-concept floor plan with spacious living and dining areas, durable flooring throughout, and a bright kitchen with abundant cabinetry, stainless steel appliances, and generous counter space.The covered and

Jenna Stauffer Ocean Sotheby's International Realty

27024 Shannahan Rd, Summerland Key, FL 33042
/34
$899,000
- 1 Bed
- 1 Bath
- 552 Sq Ft
31342 Avenue I, Big Pine Key, FL 33043

This recently built canal front home is situated in a highly desirable area of Big Pine just minutes to the open water. The home has a bright open kitchen with plenty of cabinets, stainless appliances, attractive tile backsplash and built in table with seating overlooking the living area.......From the bedroom with adjoined bathroom there are partial ocean views. There is also a utility room with

Rob Severin Rob Severin Real Estate Co

31342 Avenue I, Big Pine Key, FL 33043
/42
$799,000

$50K PRICE DROP
- 3 Beds
- 2 Baths
- 984 Sq Ft
937 Loggerhead Ln, Summerland Key, FL 33042

Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf Key area, offering space, privacy, and modern upgrades throughout. Designed for easy coastal living, the home features durable Hardie board siding, a long-lasting metal roof, tile flooring throughout, and an energy-efficient

Richard Haskins Buy The Keys

937 Loggerhead Ln, Summerland Key, FL 33042
/49
$779,000

$41K PRICE DROP
- 2 Beds
- 2 Baths
- 1,076 Sq Ft
1817 Watson Blvd, Big Pine Key, FL 33043

Nestled in the heart of Big Pine Key, this 2-bedroom, 2-bath canal-front ranch style home offers a rare opportunity to enjoy the Florida Keys lifestyle while investing for exceptional future potential. Situated on an oversized 1 1/2 lot with direct boating access out to open water in 3 mins, this property is a true waterfront gem. The existing home provides comfortable island living with abundant

Paul Rogers Coldwell Banker Schmitt RE Co.

1817 Watson Blvd, Big Pine Key, FL 33043
/9
$800,000
- Land
- 7,840 Sq Ft
- $4,444,444 per Acre
28525 Jolly Roger Dr, Little Torch Key, FL 33042

Rare actively permitted waterfront homesite with existing concrete seawall/dock on Little Torch Key with exceptional boating access, approved engineered house plans, and protected salt-pond and nature-preserve views across the street. The property is offered with an active Monroe County building permit and approved plans for an elevated concrete 3-bedroom, 2-bath residence with approximately

Nate Meyer Meyer and Boumerhi Realty LLC

28525 Jolly Roger Dr, Little Torch Key, FL 33042
/4
$189,000
- Land
- 0 Sq Ft
29859 Overseas Hwy, Big Pine Key, FL 33043

Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across the

Liza Dieppa Coldwell Banker Realty

29859 Overseas Hwy, Big Pine Key, FL 33043
/7
$170,000
- Land
- 5,662 Sq Ft
- $1,307,692 per Acre
Lot 27 Dorn Rd, Torch Key, FL 33042

If you love fishing, love the water, and hate the big crowds, this is the place for you! Upon arrival, the first thing you will notice is the peace and quiet. Easy access to the Gulf of America and Atlantic Ocean. This property is adjacent to my other listing which is owned by the same person. This would be an excellent opportunity to own a double lot on Big Torch Key! Adjacent property (blue

Dylan Calhoun Luxe Properties

Lot 27 Dorn Rd, Torch Key, FL 33042
/26
$745,000
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
28441 Meyer Rd, Summerland Key, FL 33042

This canal-front home offers the perfect blend of comfort, convenience, and the laid-back Florida Keys lifestyle. Located on a corner lot and built with durable CBS construction. This home features a spacious open floor plan, exceptional outdoor living, and direct boating access to Pine Channel. The outdoor amenities are truly a boater's dream. A brand-new 60-foot dock with boat slip, 17,000-lb.

Deni Heintzelman KeyIsle Realty

28441 Meyer Rd, Summerland Key, FL 33042
/42
$699,000

$86K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,224 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. Or you may just want to demo the house and build your Keys Dream Home on two

Karen Haack Coldwell Banker Schmitt RE Co.

31033 Hibiscus Dr, Big Pine Key, FL 33043
/40
$4,400,000

New Construction $75K PRICE INCREASE
- 5 Beds
- 5.5 Baths
- 3,119 Sq Ft
231 E Shore Dr Unit 6, Summerland Key, FL 33042

Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

231 E Shore Dr Unit 6, Summerland Key, FL 33042
/7
$1,600,000
- Land
- 1.01 Acres
- $1,584,158 per Acre
0 Racoon Run, Big Pine Key, FL 33043

Rare opportunity to own 1 acre in beautiful Big Pine Key, Florida! Build your dream island retreat in one of the most desirable areas of the Lower Keys. Enjoy the natural beauty, tropical surroundings, boating, fishing, snorkeling, and the laid-back Florida Keys lifestyle. Big Pine Key is known for its peaceful atmosphere, abundant wildlife, and proximity to the National Key Deer Refuge.

Sara Baldomero Ribot HOME PRIME REALTY LLC

0 Racoon Run, 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
/70
$1,435,000

$50K PRICE DROP
- 4 Beds
- 2 Baths
- 2,310 Sq Ft
29562 Saratoga Ave, Big Pine Key, FL 33043

Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and

Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

29562 Saratoga Ave, Big Pine Key, FL 33043
/51
$749,900
- 3 Beds
- 2 Baths
- 1,116 Sq Ft
1821 Bittersweet Ave, Big Pine Key, FL 33043

A Boating/Fishing Dream Home....This Canal Front Stilt home sits on an oversized corner lot, in ''Key Deer Refuge'', beautiful wild-life and Key Deer abound, 2/bedroom, 2/bath, a 3rd bonus room, you may use as a bedroom or office, a spacious Living/Dining/Kitchen with lots of light, stainless appliances, impact windows, Bamboo/tile floors. Enjoy the Florida Keys Lifestyle on your Boat docked

Brenda Alexander Lokation Real Estate

1821 Bittersweet Ave, Big Pine Key, FL 33043
/3
$64,750
- Land
0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

ROGO Lot. Letter on hand from Monroe County granting 2 points

Jenna Stauffer Ocean Sotheby's International Realty

0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
/38
$1,185,000
- 3 Beds
- 2 Baths
- 1,188 Sq Ft
706 Caribbean Dr E, Summerland Key, FL 33042

OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop,

Donna Pezzi Keller Williams Key West Compass Realty

706 Caribbean Dr E, Summerland Key, FL 33042
/45
$493,000

$36K PRICE DROP
- 2 Beds
- 2 Baths
- 758 Sq Ft
701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

PRICE DROPPED AGAIN below 500k! MOTIVATED SELLER!This is THE lowest 2BR/BA priced home in Venture Out on Cudjoe Key!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 &

Amanda Taylor Bluescape Real Estate

701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
/49
$749,900

$25K PRICE DROP
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
19543 Navajo St, Cudjoe Key, FL 33042

3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

Pamela Stangler Expert Realty LLC

19543 Navajo St, Cudjoe Key, FL 33042
/6
$1,775,000
- 4 Beds
- 4 Baths
- 1,671 Sq Ft
193 Galleon Ln, Cudjoe Key, FL 33042

Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

Joaquin Merlo-Garzon CRANELUXE

193 Galleon Ln, Cudjoe Key, FL 33042
/4
$595,000

$80K PRICE DROP
- Land
- 13,503 Sq Ft
- $1,919,355 per Acre
2080 Coral Way, Big Pine Key, FL 33043

Rare opportunity to own a stunning ocean view double lot with 107 feet of canal frontage in sought-after Big Pine Key! Currently #5 in ROGO, this prime property comes with approved building plans—available upon request. The spacious lot offers ample room for your dream home with direct canal access and breathtaking open-water views. Buyers may have the ability to modify the existing plans—please

Kelly Acosta ARGO GROUP PROPERTIES LLC

2080 Coral Way, Big Pine Key, FL 33043
/33
$239,000

$10K PRICE DROP
- 1 Bed
- 1 Bath
- 368 Sq Ft
701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room.The property is currently occupied by a long-term

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 533, Cudjoe 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
/9
$514,900
- Land
- 2,613 Sq Ft
- $8,581,667 per Acre
701 Spanish Main Dr Unit LOT 266, Cudjoe Key, FL 33042

Premier Waterfront RV Lot in Venture Out | 35' Seawall, Ocean Views & Proven Rental Income!Whether you are looking for your own personal Florida Keys getaway or a high-performing investment property, this lot offers the perfect blend of luxury, location, and lucrative returns. Boasting a consistent rental history, this turn-key property is a proven income producer with established guest

Carmen Brake Waterfront Keys Realty Inc.

701 Spanish Main Dr Unit LOT 266, Cudjoe Key, FL 33042
/41
$799,000

$170K PRICE DROP
- 2 Beds
- 2 Baths
- 1,277 Sq Ft
29544 Independence Ave, Big Pine Key, FL 33043

LOCATION and PRICE is the KEY to this charming, one level coastal retreat. 75' canal-frontage, 2 bedrooms, 2 full baths plus a bonus all-season sunroom. Property is furnished with many upgrades. Generous and impressive living space is perfect for entertaining and family gatherings. Grab a siesta or your favorite beverage while overlooking the canal from the sunroom or on the covered patio. Pine

Jennifer Sylvia Keller Williams Key West Compass Realty

29544 Independence Ave, Big Pine Key, FL 33043
/71
$2,069,000
- 3 Beds
- 2 Baths
- 1,849 Sq Ft
1733 Sunrise Dr, Big Pine Key, FL 33043

Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

Norman De la Cruz Florida Realty of Miami Corp

1733 Sunrise Dr, Big Pine Key, FL 33043
/47
$1,200,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
637 Caribbean Dr E, Summerland Key, FL 33042

Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromatic palette, the interiors feel fresh, cohesive, and effortlessly sophisticated--ready for you to start living the Keys lifestyle. Step outside to a relaxing porch overlooking a 60' wide, crystal-clear flow-through canal--perfect

Donna Pezzi Keller Williams Key West Compass Realty

637 Caribbean Dr E, Summerland Key, FL 33042
/15
$895,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
135 Tortuga Ln, Summerland Key, FL 33042

If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and

Kathleen Reed Bruno Realty Group, Inc

135 Tortuga Ln, Summerland Key, FL 33042
/64
$1,800,000

$190K PRICE DROP
- 3 Beds
- 2 Baths
- 1,841 Sq Ft
3127 Stewart Rd, Summerland Key, FL 33042

Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

Pamela Stangler Expert Realty LLC

3127 Stewart Rd, Summerland Key, FL 33042
/34
$1,469,000

New Construction $80K PRICE DROP
- 3 Beds
- 3 Baths
- 1,500 Sq Ft
27374 Guadaloupe Ln, Summerland Key, FL 33042

*Construction process underway. Expected completion November/December 2026Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your

Nick Boumerhi Meyer and Boumerhi Realty LLC

27374 Guadaloupe Ln, Summerland Key, FL 33042
/4
$1,999,000

$751K PRICE DROP
- 3 Beds
- 1 Bath
- 1,020 Sq Ft
32029 Marginella Dr, Big Pine Key, FL 33043

Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stone's throw away from Big Pine Key, this nearly 2-acre property presents

Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

32029 Marginella Dr, Big Pine Key, FL 33043
/31
$998,000

Open Sat 1PM - 3PM $57K PRICE DROP
- 3 Beds
- 2 Baths
- 1,225 Sq Ft
83 Sugarloaf Dr, Summerland Key, FL 33042

Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

83 Sugarloaf Dr, Summerland Key, FL 33042
/38
$1,270,000

$120K PRICE DROP
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
174 Tortuga Ln, Cudjoe Key, FL 33042

Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Built in 2020 for peace of mind and

Sarah Bixby eXp Realty LLC

174 Tortuga Ln, Cudjoe Key, FL 33042

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