Oakland, FL Homes

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  $535,000 Sold Feb 24, 2026

  9029 Sonoma Coast Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • Built 2021

  Last Sold Summary

  • $266/SF
  • 64 Days On Market

  Current Estimated Value $531,658

  Last Listing Agent Abraham Mendez NONA LEGACY POWERED BY LA ROSA

  9029 Sonoma Coast Dr, Oakland, FL 34787
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  Est $1,486,838 Not Listed For Sale

  10081 Atwater Bay Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,920 Sq Ft
  • Built 2024

  10081 Atwater Bay Dr, Oakland, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $408/SF
  • 5 Days On Market

  • Last Sold Price $1,600,000
  • Feb 21, 2025

  Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC
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  $597,990 Pending

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  3112 Namaste Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. This lovely Riviera Next Gen® single-story home features an attached private suite with its own living room, kitchenette, bedroom and bathroom. In the main home is an open space layout in the kitchen, nook and family room, which extends to the covered patio through sliding glass doors for outdoor living. There is a flex space to accommodate

  Ben Goldstein LENNAR REALTY

  3112 Namaste Dr, Oakland, FL 34787
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  $387,900 Sold Jul 17, 2025

  1509 Sweet Apple St, Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $214/SF
  • 144 Days On Market

  Current Estimated Value $393,408

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  1509 Sweet Apple St, Oakland, FL 34787
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  Est $475,727 Not Listed For Sale

  14047 Lochend Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 1,996 Sq Ft
  • Built 2024

  14047 Lochend Way, Oakland, FL 34787

  Last Sold Summary

  • 7% Above List Price
  • $223/SF

  • Last Sold Price $445,000
  • Sep 03, 2024

  Last Listing Agent Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY
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  $637,325 Pending

  • 4 Beds
  • 3 Baths
  • 2,102 Sq Ft

  17138 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley floorplan by Dream Finders Homes features 2,102 square feet of well-designed living space across two stories. This home includes 4 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17138 Ingram Hills Aly, Oakland, FL 34787
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  $585,000 Sold Aug 20, 2025

  15114 Field Daisy Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 2025

  Last Sold Summary

  • $273/SF

  Current Estimated Value $579,626

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  15114 Field Daisy Dr, Oakland, FL 34787
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  Est $465,683 Not Listed For Sale

  9267 Gran Teatro Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft
  • Built 2024

  9267 Gran Teatro Dr, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $264/SF
  • 82 Days On Market

  • Last Sold Price $484,990
  • Feb 28, 2025

  Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY
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  $519,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft

  2618 Bobcat Chase Blvd, Oakland, FL 34787

  Welcome to this beautiful 3 bedroom, 2 bath home featuring 1,565 square feet of inviting living space in Longleaf at Oakland. From the moment you step inside, you’ll feel the warmth and charm throughout, with a bright, open floor plan designed for both comfortable everyday living and easy entertaining.The spacious living and custom dining area flow seamlessly, creating a welcoming atmosphere

  Elena Santiago THE REAL ESTATE COLLECTION LLC

  2618 Bobcat Chase Blvd, Oakland, FL 34787
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  $455,000 Sold Jun 11, 2025

  13418 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $288/SF
  • 185 Days On Market

  Current Estimated Value $459,542

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  13418 Princess St, Oakland, FL 34787
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  Est $1,255,453 Not Listed For Sale

  1080 Canyon Creek Trail, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,852 Sq Ft
  • Built 2024

  1080 Canyon Creek Trail, Oakland, FL 34787

  Last Sold Summary

  • $327/SF
  • 15 Days On Market

  • Last Sold Price $1,259,910
  • Mar 20, 2025

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY
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  $2,750,000

  • 5 Beds
  • 6 Baths
  • 4,373 Sq Ft

  812 Johns Point Dr, Oakland, FL 34787

  Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout.Designed for effortless entertaining, the open-concept layout

  Any Alves WRA BUSINESS & REAL ESTATE

  812 Johns Point Dr, Oakland, FL 34787
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  $954,900 Sold Oct 09, 2025

  4637 Golden Birch Ave, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,272 Sq Ft
  • Built 2025

  Last Sold Summary

  • $224/SF
  • 0 Days On Market

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  4637 Golden Birch Ave, Oakland, FL 34787
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  Est $1,043,164 Not Listed For Sale

  1056 Sadler Oaks Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,711 Sq Ft
  • Built 2024

  1056 Sadler Oaks Way, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $387/SF
  • 129 Days On Market

  • Last Sold Price $1,050,000
  • Feb 14, 2025

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY
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  $665,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  2986 Good Vibes Way, Oakland, FL 34787

  Under Construction. Welcome to the Steely, an innovative two-story Next Gen® home. This home features a private suite with a separate entrance, living area, kitchenette, bedroom, bathroom and laundry, ideal for multigenerational households. The main home is host to an inviting open-concept layout that blends the kitchen, living and dining areas, while a luxe owner’s suite at the back of the home

  Ben Goldstein LENNAR REALTY

  2986 Good Vibes Way, Oakland, FL 34787
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  $694,490 Sold Mar 16, 2026

  3064 Namaste Dr, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,385 Sq Ft
  • Built 2026

  Last Sold Summary

  • $205/SF

  Current Estimated Value $477,667

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  3064 Namaste Dr, Oakland, FL 34787
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  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 5 Baths
  • 3,794 Sq Ft
  • Built 2025

  Unlisted Address

  Last Sold Summary

  • $470/SF

  • Last Sold Price $1,783,268
  • Jul 30, 2024

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $606,440 Pending

  • 4 Beds
  • 3 Baths
  • 2,102 Sq Ft

  17156 Ingram Hills Aly, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES !!!! The Berkley at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Berkley model. This impressive 2,102 sq. ft. residence features 4 bedrooms, 3 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  17156 Ingram Hills Aly, Oakland, FL 34787
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  $3,894,945 Sold Mar 13, 2026

  517 N Pollard St, Winter Garden, FL 34787

  • 6 Beds
  • 7 Baths
  • 4,636 Sq Ft
  • Built 2026

  Last Sold Summary

  • 26% Above List Price
  • $840/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  517 N Pollard St, Winter Garden, FL 34787
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  Not Listed For Sale

  13007 Tollcross Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft
  • Built 2024

  13007 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • $290/SF

  • Last Sold Price $626,549
  • Aug 15, 2024

  Last Listing Agent Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY
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  $525,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  2259 White Feather Loop, Oakland, FL 34787

  Under contract-accepting backup offers. INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling

  Chuck Burt YOUNG REAL ESTATE

  2259 White Feather Loop, Oakland, FL 34787
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  $430,000 Sold Jul 16, 2025

  1113 Prado Ln, Oakland, FL 34787

  • Land
  • 16,117 Sq Ft
  • $1,162,162 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  1113 Prado Ln, Oakland, FL 34787
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  Est $805,223 Not Listed For Sale

  9462 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft
  • Built 2024

  9462 Emerald Berry Dr, Oakland, FL 34787

  Last Sold Summary

  • $251/SF
  • 62 Days On Market

  • Last Sold Price $804,990
  • Jan 05, 2025

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
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  $674,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  12919 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026Bungalow featuring a private in-law suite above a detached 2-car garage. A charming covered entry welcomes you into an open and expansive floor plan with seamless flow between the great room, kitchen, and dining area — ideal for both everyday living and entertaining.Enjoy

  Dayene Grubert ORLANDO TBI REALTY LLC

  12919 Westhaven Oak Dr, Oakland, FL 34787
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  $600,000 Sold Apr 28, 2026

  2606 Bobcat Chase Blvd, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,473 Sq Ft
  • Built 2019

  Last Sold Summary

  • 10% Below List Price
  • $243/SF
  • 168 Days On Market

  Current Estimated Value $706,476

  Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
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  Est $838,000 Not Listed For Sale

  5590 Orange Orchard Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,853 Sq Ft
  • Built 2021

  5590 Orange Orchard Dr, Oakland, FL 34787

  Last Sold Summary

  • 10% Below List Price
  • $328/SF
  • 3 Days On Market

  • Last Sold Price $935,000
  • Sep 26, 2024

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS
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  $688,240 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,147 Sq Ft

  3120 Namaste Dr, Oakland, FL 34787

  Under Construction. The Summerlin checks all your boxes! This breath taking two-story home features an expansive design with a convenient three-car garage. The first floor features an open-concept family room that complements a chef-ready kitchen and a cozy dining room, plus a private office and a spacious lanai. On the same level is the tranquil owner’s suite with an attached bathroom. Found

  Ben Goldstein LENNAR REALTY

  3120 Namaste Dr, Oakland, FL 34787
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  $449,490 Sold Jul 22, 2025

  2915 Transformation Way, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft
  • Built 2025

  Last Sold Summary

  • $250/SF
  • 4 Days On Market

  Last Listing Agent Ben Goldstein LENNAR REALTY

  2915 Transformation Way, Oakland, FL 34787
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  Est $784,886 Not Listed For Sale

  14205 Lanyard Way, Oakland, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,076 Sq Ft
  • Built 2024

  14205 Lanyard Way, Oakland, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $254/SF
  • 0 Days On Market

  • Last Sold Price $779,990
  • Mar 31, 2025

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $519,000

  • 4 Beds
  • 2 Baths
  • 2,046 Sq Ft

  1270 Stationside Dr, Oakland, FL 34787

  Nested right along the scenic West Orange Trail, this spacious 4 bedroom, 2 bath home offers the perfect balance of recreation and relaxation. The open interior flows seamlessly to private pool, creating an ideal oasis for Florida living. Located for ultimate convenience, just 15 mins from Downtown Winter Garden with The Turnpike nearby for an easy commute. Enjoy being 30 mins of Orlando's world

  Ky Lam HOME INVEST REALTY INC

  1270 Stationside Dr, Oakland, FL 34787
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  $380,000 Sold Jul 25, 2025

  2203 Gopher Tortoise Terrace, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $235/SF
  • 57 Days On Market

  Current Estimated Value $375,590

  Last Listing Agent Dawn Thomas KELLER WILLIAMS REALTY AT THE LAKES

  2203 Gopher Tortoise Terrace, Oakland, FL 34787
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  Est $779,657 Not Listed For Sale

  1404 High Springs Ln, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,059 Sq Ft
  • Built 2020

  1404 High Springs Ln, Winter Garden, FL 34787

  Last Sold Summary

  • 7% Above List Price
  • $239/SF
  • 92 Days On Market

  • Last Sold Price $730,000
  • Feb 26, 2025

  Last Listing Agent Kaitlin LaMacchia DENIZ REALTY PARTNERS LLC
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  $600,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft

  1119 Bobcat Chase Blvd, Oakland, FL 34760

  Prepare to be captivated by this enchanting 4-bedroom, 2.5-bath pool home, nestled amidst mature oaks that lend an air of timeless charm. Located in the idyllic community of Long Leaf, this home boasts the best lot in the neighborhood—complete with a cozy fire pit that begs for evening gatherings under the stars.Step inside to discover a kitchen adorned with tasteful taupe cabinetry,

  Erica Diaz HOMEVEST REALTY

  1119 Bobcat Chase Blvd, Oakland, FL 34760
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  $525,000 Sold Oct 22, 2025

  233 Largovista Dr, Oakland, FL 34787

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 93 Days On Market

  Current Estimated Value $513,283

  Last Listing Agent Rachael Segarra EXP REALTY LLC

  233 Largovista Dr, Oakland, FL 34787
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  Est $812,255 Not Listed For Sale

  9516 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft
  • Built 2024

  9516 Emerald Berry Dr, Oakland, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $261/SF
  • 13 Days On Market

  • Last Sold Price $837,210
  • Nov 30, 2024

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
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  $574,990 New Construction

  • 4 Beds
  • 2 Baths
  • 2,532 Sq Ft

  3108 Namaste Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Under Construction. It’s what you have been waiting for, the Estero. This exquisite home emphasizes elegance and ease of living. Heading down the foyer there is a formal dining room that compliments a chef-ready kitchen, casual breakfast nook and spacious family room, plus an beautiful lanai. Framing the sides of the home are three secondary

  Ben Goldstein LENNAR REALTY

  3108 Namaste Dr, Oakland, FL 34787
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  $719,000 Sold Jun 05, 2025

  17858 Adrift Rd, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,113 Sq Ft
  • Built 2022

  Last Sold Summary

  • 10% Below List Price
  • $340/SF
  • 97 Days On Market

  Current Estimated Value $703,433

  Last Listing Agent John R. Gordon EXP REALTY LLC

  17858 Adrift Rd, Oakland, FL 34787
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  Est $602,542 Not Listed For Sale

  12891 Westhaven Oak Dr, Oakland, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 1,908 Sq Ft
  • Built 2024

  12891 Westhaven Oak Dr, Oakland, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $340/SF

  • Last Sold Price $649,233
  • Aug 02, 2024

  Last Listing Agent Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY
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  $949,990 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,227 Sq Ft

  8911 Sonoma Coast Dr, Oakland, FL 34787

  Under contract-accepting backup offers. This 5-bedroom, 4 full bath + powder bath Torrey model sits on a premium pond-view lot and is loaded with upgrades throughout. The home is in impeccable condition and truly move-in ready.The home is FULLY AUTOMATED: control lights, exhaust fans, and the pool from your phone. Plus, PAID-OFF solar panels keep electric bills very low.Enjoy an open

  John Silva JOHN SILVA REALTY & ASSOCIATES

  8911 Sonoma Coast Dr, Oakland, FL 34787
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  $852,105 Sold Jul 02, 2025

  5307 Citrus Leaf Blvd, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $258/SF
  • 33 Days On Market

  Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

  5307 Citrus Leaf Blvd, Oakland, FL 34787

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