231

Winter Haven, FL Homes for Sale under $100,000

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  • /48

    $53,000

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft

    188 Edelweiss Dr, Winter Haven, FL 33881

    Swiss Village / Lot #188 / 2 Bedroom/2 Bath / 1,290 Sq. Ft. / $53,000.00 This immaculate, corner lot home, has so much to offer a buyer at a price that you can afford! The pictures do not do it justice, but just a few of the upgraded features are: A/C & Roof that are just 2 years old Double Carport (only 1 year old) with tie downs New Bathroom Vanities in both bathrooms Handicap Commodes Huge

    Jennifer Torres CRF Communities

    188 Edelweiss Dr, Winter Haven, FL 33881
  • /31

    $65,000

    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    77 Bern Dr, Winter Haven, FL 33881

    Swiss Village / Lot #77/ 2 Bed/ 2 Bath / 1,584 Sq. Ft./ REDUCED TO $65,000.00 !! Reasonable offers will be considered by the Seller. This gorgeous home has been updated with: Sprinkler System Leaf Filter on Gutters Painted inside and out Laundry in the shed with sink Luxury Vinyl Plank Flooring Roof And so much more! It offers a formal dining room, new appliances, and large bedrooms! It has a

    Jennifer Torres CRF Communities

    77 Bern Dr, Winter Haven, FL 33881
  • /22

    $24,900

    • 1 Bed
    • 1 Bath
    • 618 Sq Ft

    5601 Cypress Gardens Rd Unit M14B, Winter Haven, FL 33884

    Cozy Retreat for Seniors - Move-In Ready & Fully Furnished! Located in Hammondell, a pet friendly, 55+ community situated in Winter Haven, Florida. Homes in this community are on lot leased land. Owning the home, but not the land, you pay a monthly lot rent of $640.00 whichgives you and your guest access to the amenities of the community, Lawn Mowing & Basic Cable TV are also included in the lot

    Bette Johnson Renee's Resales

    5601 Cypress Gardens Rd Unit M14B, Winter Haven, FL 33884
  • /23

    $75,000

    • Land
    • 0.23 Acre
    • $326,087 per Acre

    312 Ulrich Ave, Winter Haven, FL 33881

    Build your dream home or next investment property on this vacant residential lot located at 312 Ulrich Avenue in Winter Haven, Florida. The property is under 0.25 acres and is ready to build, making it an excellent opportunity for homeowners, builders, or investors.Situated in an established neighborhood with convenient access to schools, shopping, dining, and major roadways, this lot offers

    Angel Ayala KELLER WILLIAMS ADVANTAGE III

    312 Ulrich Ave, Winter Haven, FL 33881
  • /60

    $60,000

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    229 Fairway Cir, Winter Haven, FL 33881

    Don't miss this immaculate 2BR/2BA, 1248 sq. ft. home in the highly sought-after 55+ gated community, Swiss Golf & Tennis, in sunny Central Florida. Whether you're looking for a permanent home or a seasonal getaway, this home is for you. Swiss Golf is one of the few lot lease parks with reasonable monthly lot rent. Buyers are able to inherit the seller's current lot rent of $487 for the remainder

    Cynthia Cole Sunset Home Sales

    229 Fairway Cir, Winter Haven, FL 33881
  • /50

    $44,900

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    842 9 Iron Ct, Winter Haven, FL 33881

    Discover Lifestyle and Leisure in Central Florida! Welcome home to this 2BR/2BA sanctuary with tons of space inside & out! This home is conveniently located on a large corner lot in the heart of the 55+ Hidden Golf community. Immaculate, well-maintained, and FULLY FURNISHED, making this residence a true TURNKEY opportunity. With an open concept, the home resonates space and comfort. The popular

    Cynthia Cole Sunset Home Sales

    842 9 Iron Ct, Winter Haven, FL 33881
  • /33

    $39,900

    • 1 Bed
    • 1 Bath
    • 616 Sq Ft

    836 Sandtrap Cir, Winter Haven, FL 33881

    Hidden Golf Club 55+ Community- Mostly furnished home with many recent updates featuring 1 bedroom, 1 bath, plus a BONUS ROOM with its own entrance-perfect for guests, office, or hobby space. Open kitchen flows into living area. Spacious 11x17 screened room that adds extra living space and a shed that includes laundry. Located on a large, beautifully landscaped lot with no rear neighbors and a

    Brandi Sappington CRF Communities

    836 Sandtrap Cir, Winter Haven, FL 33881
  • /38

    $24,500

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    709 Century Ln, Winter Haven, FL 33881

    Cozy furnished home with no rear neighbors, ready for you to move right in! Nestled in an active and friendly 55+ community close to the pool and clubhouse. Highlights of Home- Newer AC (2023) - Split plan layout - Private lot with no rear neighbors! Enjoy the comfort of indoor laundry, 2 spacious screened rooms- one on each side of the house, and outdoor patio space perfect for relaxing. Home

    Brandi Sappington CRF Communities

    709 Century Ln, Winter Haven, FL 33881
  • /18

    $16,900

    • 2 Beds
    • 1 Bath
    • 616 Sq Ft

    868 Sandtrap Cir, Winter Haven, FL 33881

    Charming fixer-upper in a friendly 55+ community, offering a wonderful opportunity for the right buyer to bring out its full potential. This 2-bedroom, 1-bath home features a bright, open layout with plenty of natural light. Spacious Florida room. The home does need some updating and is priced with that in mind. Roof and AC need attention, will need refrigerator and some sections of flooring

    Brandi Sappington CRF Communities

    868 Sandtrap Cir, Winter Haven, FL 33881
  • /61

    $44,900

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    95 Greenview Dr, Winter Haven, FL 33881

    Motivated seller! Looking for the perfect getaway in sunny Florida? Look no further! This charming 2-bedroom, 2-bathroom home is nestled in the highly sought-after, gated community of Swiss Golf & Tennis. Lot lease is currently $683 a month. Wake up to stunning golf course views from your very own Florida room, or immerse yourself in nature while relaxing in the screened-in room, the perfect spot

    Patti Alvin Sunset Home Sales

    95 Greenview Dr, Winter Haven, FL 33881
  • /66

    $74,500

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    1082 Eagle Dr, Winter Haven, FL 33881

    Price Reduced 5K! Move-in ready and fully furnished, this well-maintained 2-bedroom, 2 bath home on a corner lot offers a spacious layout with large bedrooms and an open kitchen. Newer Roof and AC both new in 2024 for peace of mind. Guest bed and bath offer sliding door for privacy. Bonus room for office space or craft room. The bright Florida room adds extra living space and is perfect for

    Brandi Sappington CRF Communities

    1082 Eagle Dr, Winter Haven, FL 33881
  • /33

    $29,500

    • 1 Bed
    • 1 Bath
    • 520 Sq Ft

    439 Dolphin Dr, Winter Haven, FL 33881

    Hidden Cove West / Lot #439 / 1 Bedroom/1 Bath / 520 Sq. Ft. / $29,500.00 This cozy home is nestled in a beautiful cul-de-sac and is on a large lot. It has been updated, boasting: New Hot Water Heater New Luxury Vinyl Plank Flooring New A/C with Heat Pump, New Windows, Generator Hooked Directly int the Home Roof (only 2 years old) Freshly Painted Two Sheds Wood Kitchen Cabinets Florida Room (that

    Jennifer Torres CRF Communities

    439 Dolphin Dr, Winter Haven, FL 33881
  • /21

    $29,900

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    116 Hideaway Ln Unit 116, Winter Haven, FL 33881

    2 Bedroom | 1 Bath | 728 sq ft | $29,900 EXCITING OFFER: Enjoy 0 Lot Rent until January 1, 2026! Hidden Cove Lot 116 is your affordable opportunity to own a home in a gated, 55+ Central Florida community! This 2 bedroom home is walking distance to the lakefront clubhouse and amenities! This home boasts: - All new siding - New metal roof - New carport - Newly rescreened screen room - BRAND NEW A/C

    Jennifer Torres CRF Communities

    116 Hideaway Ln Unit 116, Winter Haven, FL 33881
  • /30

    $64,900

    • 1,344 Sq Ft

    152 Sago Palm Way Unit 362, Winter Haven, FL 33880

    This 2006 Double-wide is located in a gated active 55 plus community. 2018 Shingled roof, A/C installed in 2022, and a new 2025 hot water heater. Partially furnished. Kitchen has a lot of counter space and cabinets with additional counter- top and extra storage space underneath. Washer and dryer located off kitchen. Breakfast eating area and formal dining room. Master bath has both walk-in shower

    Russ Lattin CRF Communities

    152 Sago Palm Way Unit 362, Winter Haven, FL 33880
  • /35

    $59,900

    • 1 Bed
    • 1 Bath

    4320 Dundee Rd Unit 36, Winter Haven, FL 33884

    This IMMACULATE Beach Bungalow is the Perfect Dream Home come true! Located in the Pristine ALL-AGE community of Southern Duck RV Resort in central Florida! With Exquisite curb appeal, first notice the pristine landscaping, clean-coated driveway under carport, and outdoor back patio with raised pavers for an evening under the warm Florida stars! This adorable cottage offers every modern

    Linda Wilson Sunset Home Sales

    4320 Dundee Rd Unit 36, Winter Haven, FL 33884
  • /11

    $49,500

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    47 Azalea Dr Unit AZ-47, Winter Haven, FL 33881

    This Beautiful new home features 768 sq. ft. of well-designed living space, 2 bedrooms, and 1 bathroom. Open Floor plan, entertain while cooking. Floors are grey vinyl planked with light tones throughout the home. All new appliances and double stainless-steel sinks. Nice size lot with concrete sidewalk and driveway, off street parking. With restaurants, and shopping all nearby, this community

    Sherri Streight Four Star Homes, Inc.

    47 Azalea Dr Unit AZ-47, Winter Haven, FL 33881
  • /2

    $69,900

    • 2 Beds
    • 2 Baths

    66 Stebbins Dr Unit 66, Winter Haven, FL 33884

    Tori Coil Grove Shores

    66 Stebbins Dr Unit 66, Winter Haven, FL 33884
  • /32

    $74,900

    • 2 Beds
    • 2 Baths
    • 1,701 Sq Ft

    60 Bern Dr Unit 60, Winter Haven, FL 33881

    Swiss Village / Lot #60 / 2 Bedroom/ 2 Bath/ 1,701 Sq. Ft. / $74,900.00 This gorgeous home has been meticulously taken care of and updated with: New Flooring A/C Roof 13x9 Florida Room Bathrooms Fully furnished, this spacious home allows you plenty of room for storage and moving about (not that you will want to stay home with all of the amenities & activities available). You will love being a

    Jennifer Torres CRF Communities

    60 Bern Dr Unit 60, Winter Haven, FL 33881
  • /22

    $84,900

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft

    1420 Wild Dunes Ct Unit 58, Winter Haven, FL 33881

    2 Bedroom | 2 Bath | 1,148 sq ft | $84,900 Immaculate home in a premier 55+ Community! Four Lakes Golf Club lot 58 is a meticulously maintained home, nestled in a sunny Central Florida. Situated on a desirable perimeter lot adjacent to a serene Florida preserve, this home offers the perfect blend of privacy and tranquility. Priced well at just $84,900- ideal for seasonal escapes or year-round

    Cheryl Dobbs CRF Communities

    1420 Wild Dunes Ct Unit 58, Winter Haven, FL 33881
  • /22

    $27,000

    • 2 Beds
    • 1.5 Baths

    433 Flamingo Way, Winter Haven, FL 33881

    Charming 2 Bedroom, 1.5 Bath Doublewide Home located in a peaceful 55+ community on a quiet dead-end street. Features Include: -Spacious screened porch - perfect for relaxing -Beautiful bay window that brings in natural light -Ceiling fans for added comfort -Kitchen equipped with refrigerator, stove, dishwasher, and microwave -Freshly updated with new flooring and paint throughout

    Yvonne Straub Lake Deer Mobile Hamlet

    433 Flamingo Way, Winter Haven, FL 33881
  • /38

    $65,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    757 Century Ln, Winter Haven, FL 33881

    Fully furnished, move-in-ready home in a great location in highly sought after 55+ community. This cozy home is close to clubhouse, lake and restaurant! Highlights include -Newer AC -No rear neighbors -Spacious open layout with dedicated dining space -Walk in closets in bedrooms -Large storage shed. This home gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained

    Brandi Sappington CRF Communities

    757 Century Ln, Winter Haven, FL 33881
  • /31

    $32,000

    • 3 Beds
    • 3 Baths
    • 1,772 Sq Ft

    93 Misty Meadow Rd, Winter Haven, FL 33881

    ** Exclusive Listing! Age 55+ Land Lease Community. Contact listing agent below for ALL showings and offers.** As soon as you set your eyes on this truly unique and super spacious double wide and single wide combination, you'll know it's the one you've been looking for! Priced right at $32,000, the 1974 double wide measures 23x52, the 1976 single wide addition measures 12x48, for an

    Shawna Kemp Mobile Home Spot Inc.

    93 Misty Meadow Rd, Winter Haven, FL 33881
  • /32

    $72,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    8 Captain Kidd Ln SW, Winter Haven, FL 33880

    Charming Home with 2-Bedroom, 2-Bath and Lake Shipp Views in Shipp Reck Harbor Homes in Shipp Reck Harbor community are on lot leased land Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $474 which gives you and your guest access to the amenities of the community, basic cable & trash pick-up. Looking for your perfect Florida retreat or forever home? This

    Bette Johnson Renee's Resales

    8 Captain Kidd Ln SW, Winter Haven, FL 33880
  • /58

    $99,000

    • 2 Beds
    • 2 Baths
    • 1,568 Sq Ft

    148 Greenview Dr, Winter Haven, FL 33881

    Enjoy resort-style living in this completely remodeled home with large bedrooms and walk in closets. Located in highly sought after 55+ Community! This home is like brand new- a must see! Dedicated dining space and breakfast nook. Home Features -New roof and A/C - only 2 years old -Modern kitchen with new cabinets, granite countertops, and new stainless-steel appliances -All new windows -new

    Brandi Sappington CRF Communities

    148 Greenview Dr, Winter Haven, FL 33881
  • /3

    $73,500

    • Land
    • 2.54 Acres
    • $28,937 per Acre

    26-28-22-000000-0340 Lake Buckeye Rd, Winter Haven, FL 33881

    A VACANT LOT IN WINTER HAVEN IN POLK COUNTY!!!

    Sean Seward Keller Williams Island Life RE

    26-28-22-000000-0340 Lake Buckeye Rd, Winter Haven, FL 33881
  • /65

    $53,990

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    40 Lake Charlotte Dr E, Winter Haven, FL 33880

    Welcome to 40 Lake Charlotte Dr. E, a Meticulously Renovated 2-bedroom, 2-bathroom home in Winter Haven's premier community. This exceptional property offers extensive interior remodeling that transforms everyday living into an extraordinary experience. This home features upgraded windows in both the dining and living areas, allowing the spaces to flood with natural light. A spacious 12x36

    Chrissy Walter Sunset Home Sales

    40 Lake Charlotte Dr E, Winter Haven, FL 33880
  • /36

    $49,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    474 Lake Henry Cir, Winter Haven, FL 33881

    Hidden Cove West / Lot #474 / 2 Bed/2 Bath / 924 Sq. Ft. / $49,900.00 GORGEOUS HOME REDUCED 7K!! This popular floor plan offers plenty of room and storage! It is furnished and boasts: New wiring, LVP Flooring, New windows, New Underpinning, Outside Paint, and Hurricane Shutters!! This is truly a TURN-KEY HOME where all it takes is for you to show up with your clothes to be moved in! Located in a

    Jennifer Torres CRF Communities

    474 Lake Henry Cir, Winter Haven, FL 33881
  • /20

    $52,900

    • 2 Beds
    • 2 Baths

    42 Berna Cir, Winter Haven, FL 33884

    PRICE REDUCTION. A beautifully upgraded property in a vibrant community, where relaxation meets recreation! This unique home offers a blend of comfort, style, and convenience, making it an ideal choice for anyone seeking a serene lifestyle. Step inside to discover the elegance of Pergo floors complemented by stylish high baseboard molding, creating a warm and inviting atmosphere. The entire

    Emily Muscarella

    42 Berna Cir, Winter Haven, FL 33884
  • /22

    $59,990

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    5406 Laurel Oak Dr, Winter Haven, FL 33880

    OPEN TO OFFERS!!! Discover your perfect 55+ retreat in this 2-bedroom, 2-bathroom home nestled within Winter Haven's premier 55+ active adult community. This handyman special presents an excellent opportunity for those who appreciate potential over perfection. The seller sweetens the deal with a generous up to $15,000 flooring allowance and a contractor ready to install your preferred flooring

    Chrissy Walter Sunset Home Sales

    5406 Laurel Oak Dr, Winter Haven, FL 33880
  • /55

    $49,999

    225 Alpine Dr, Winter Haven, FL 33881

    NEW SUNROOM (THE FRAME AND ROOF) Welcome to 225 Alpine Dr in Swiss Village, a cozy 2-bed, 2-bath home nestled in a gated 55+ community. This charming property offers a peaceful lifestyle with stunning views of Lake Henry from its north-facing sunroom. Step inside to find a well-maintained interior featuring a spacious kitchen with all appliances included. Recent updates make this home move-in

    Chrissy Walter Sunset Home Sales

    225 Alpine Dr, Winter Haven, FL 33881
  • /36

    $69,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    268 Hummingbird Ln, Winter Haven, FL 33884

    NEW LOWER PRICE! 2-Bedroom 2-Bath home has new luxury vinyl plank and ceramic tile flooring, Updated kitchen boasts island with seating, stainless steel appliances, and white cabinets. Bonus room off kitchen is currently being used as a dining room. Both bathrooms have been updated. Large main bedroom has walk-in shower and dual sinks. Enclosed Florida room with ceramic tile flooring adds to the

    Leslie Yokshas Flamingo Mobile Home Sales

    268 Hummingbird Ln, Winter Haven, FL 33884
  • /45

    $55,900

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    602 Century Dr, Winter Haven, FL 33881

    Welcome to this beautifully maintained, fully furnished turnkey home in active 55+ community! Enjoy an adorable, fenced courtyard perfect for relaxing and enhancing curb appeal. Inside, you'll find unique Spanish tile and charming accents throughout, complemented by beautiful newer flooring. The spacious bedrooms offer generous closet space, while the large climate-controlled lanai provides a

    Brandi Sappington CRF Communities

    602 Century Dr, Winter Haven, FL 33881
  • /29

    $99,000

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    1717 Woodmount Ln Unit 530, Winter Haven, FL 33881

    1717 Woodmount Lane - Lot 530 3 Bedrooms | 2 Bathrooms | 1,736 Sq Ft Discover a home where the kitchen truly steals the show! This beautifully designed 3-bedroom, 2-bath home in Four Lakes Golf Club is perfect for anyone who loves to cook, entertain and gather with friends and family. The standout feature of this home is the expansive, entertainer's kitchen offering counter space galore and

    Cheryl Dobbs CRF Communities

    1717 Woodmount Ln Unit 530, Winter Haven, FL 33881
  • /29

    $89,900

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    148 Sweet Cir, Winter Haven, FL 33884

    NEW ROOF OCTOBER 2025!!! NEW HVAC 2025!!! Won't find these newbies on very many homes. Fully furnished 2 bedroom/2 bath home in Orange Manor West. Enjoy your mornings/evenings on your spacious, enclosed lanai. Located in Southeast Winter Haven this park offers easy access to a variety of local restaurants, grocery stores and attractions. This fully furnished home comes with one share of Orange

    Darlene Bice BHHS FLORIDA PROPERTIES GROUP

    148 Sweet Cir, Winter Haven, FL 33884
  • /18

    $42,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    132 Mandarin Dr SE, Winter Haven, FL 33884

    Stress-Free Retirement Awaits in this Immaculate and Turnkey Home! Homes in Orange Manor East, a pet friendly, 55+ community are on lot leased land in Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $536 which gives you and your guest access to the amenities of the community. Trash also included in the lot fee. Discover the perfect blend of comfort

    Bette Johnson Renee's Resales

    132 Mandarin Dr SE, Winter Haven, FL 33884
  • /23

    $54,500

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    21 Kinsmen Dr, Winter Haven, FL 33884

    MORE PHOTOS COMING SOON. Must see this lovely 2 bedroom, 2 bath double wide mobile home in sought after Orange Manor West community. Owners have left some furnishings, leaving space for you to purchase and furnish you new home just the way you like it. Perfect home for those cold winters up north or make it your year round residence. This home is on leased land with a monthly fee of $513, which

    Emily Muscarella

    21 Kinsmen Dr, Winter Haven, FL 33884
  • /78

    $45,000

    • 2 Beds
    • 2 Baths
    • 1,177 Sq Ft

    41 Morningside Rd, Winter Haven, FL 33881

    ** Exclusive Listing! Age 55+ Land Lease Community. Contact listing agent below for ALL showings and offers.** You'll know you're looking at your new home as soon as you step inside this comfortably spacious and uniquely appointed 1980 Fuqua Prestige. Priced right at $45,000, and measuring 23x44, plus the 11x15 Florida room, the home will provide an approximate total of 1170 square feet of

    Shawna Kemp Mobile Home Spot Inc.

    41 Morningside Rd, Winter Haven, FL 33881
  • /2

    $40,000

    • Land
    • 0.1 Acre
    • $400,000 per Acre

    0 26th St NW, Winter Haven, FL 33881

    Great opportunity to buy land in the fastest growing city in Florida. Primo location.

    Angela Chapman CAPITAL REALTY GROUP FLORIDA

    0 26th St NW, Winter Haven, FL 33881
  • /51

    $75,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    707 Red Cypress Ln, Winter Haven, FL 33881

    2006 home in Cypress Creek Village, a premier 55+ community, will allow 40+! Super cute home with split bedroom plan with 2 large bedrooms, 2 baths, and a den! Spacious and open floor plan with an open-concept living area. Fully furnished with laminate flooring in the main areas, all window treatments remain. LIVING ROOM 17' 6 X 15' 9 Welcome to your new home! Spacious, Bright, and Open to the

    Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

    707 Red Cypress Ln, Winter Haven, FL 33881
  • /55

    $67,500

    • 2 Beds
    • 2 Baths
    • 1,188 Sq Ft

    63 Greenview Dr, Winter Haven, FL 33881

    Price Reduced! Charming Updated and modern, furnished home with privacy and stunning water views! Located in an active 55+ Community. 2 spacious bedrooms with large walk-in closets and indoor laundry room. Large, screened room with gorgeous pond view and double carport. Many updates including -Newer Roof (2023) -Newer dishwasher -New garbage disposal. This vibrant 55+ gated golf community offers

    Brandi Sappington CRF Communities

    63 Greenview Dr, Winter Haven, FL 33881

Showing Results 121 - 160, Page 4 of 6

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