Heritage Oaks Golf & Country Club Homes

• 

  

  

  /76

  $264,900

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft

  5320 Hyland Hills Ave Unit 2214, Sarasota, FL 34241

  Motivated Seller has authorized a major price improvement! Discover the charm of resort-style living in this beautiful Drummond model Veranda home. This fully furnished, maintenance-free unit boasts 2 bedrooms and 2 baths, featuring an open layout with two screened lanai spaces and a garage for your convenience. The cozy breakfast nook serves as an inviting eat-in area or can easily transform

  

  Suzy Kolaz

  KELLER WILLIAMS ON THE WATER S

  (941) 326-5915

  5320 Hyland Hills Ave Unit 2214, Sarasota, FL 34241
• 

  

  

  /32

  $4,750 per month

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • Condo for Rent

  5320 Hyland Hills Ave Unit 2225, Sarasota, FL 34241

  This Condo is FORE you!Monthly/Seasonal Availability & Pricing.Currently available:June - December 2025January - March 2026Our Heritage Oaks condo, located in the golf community of Heritage Oaks Golf & Country Club in Sarasota, FL is available for monthly/seasonal rental.Minimum 30-day stays, but seeking a 3-month minimum rental for the high season: Between

  5320 Hyland Hills Ave Unit 2225, Sarasota, FL 34241
• 

  

  /2

  $364,000 Sold Aug 20, 2025

  • 1,572 Sq Ft
  • $232/SF
  • 177 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  5150 Mahogany Run Ave, Sarasota, FL 34241

  Nestled in the pristine neighborhood of Heritage Oaks Golf & Country Club, this Buttonwood model Club Home offers an exceptional opportunity to experience Florida living at its finest and is being offered Turn-Key Furnished. This charming, well-maintained 2-bedroom, 2-bathroom, den/study, and 2-car garage home boasts a spacious open floor plan that's perfect for both entertaining and everyday

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5150 Mahogany Run Ave, Sarasota, FL 34241
• 

  

  

  /55

  Est $270,282 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft

  5310 Hyland Hills Ave Unit 2125, Sarasota, FL 34241

  5310 Hyland Hills Ave Unit 2125, Sarasota, FL 34241
• 

  

  

  /38

  $295,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft

  5240 Hyland Hills Ave Unit 1425, Sarasota, FL 34241

  Under contract-accepting backup offers. Exceptional Golf and Lake Views from This Renovated Heritage Oaks Condo!Enjoy one of the most picturesque views in Heritage Oaks—overlooking the signature 14th hole fairway and green with peaceful lake views—all from your custom-tiled, private second-story balcony. This updated 2-bedroom, 2-bath condo with a den/office combines comfort, style, and

  Mitch Helmuth HARRY ROBBINS ASSOC INC

  5240 Hyland Hills Ave Unit 1425, Sarasota, FL 34241
• 

  

  /26

  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Condo for Rent

  5241 Mahogany Run Ave Unit 425, Sarasota, FL 34241

  Looking for a Golf Community for your winter Getaway look know further, Heritage Oaks Golf and Country Club! Updated kitchen with stainless steel appliance package is perfect for the chef in the family, all the tools you need to make the perfect gourmet meal! Master bedroom offers a King size bed with an ensuite bathroom with dual sinks ample closet space and a walk in shower. Guest bathroom has

  Angela Bailey MONARCH PROPERTY GROUP LLC

  5241 Mahogany Run Ave Unit 425, Sarasota, FL 34241
• 

  /2

  $235,000 Sold Aug 08, 2025

  • 1,311 Sq Ft
  • $179/SF
  • 177 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241

  Nestled in the private community of Heritage Oaks Golf & Country Club, this Turn-Key Furnished "Carlton" model Veranda offers an unparalleled blend of luxury, convenience, and absolutely stunning views of water and the 12th and 13th holes of the golf course. This 2-bedroom, 2-bathroom second floor property provides an exceptional opportunity to enjoy resort-style, maintenance free living in one

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241
• 

  

  /58

  Est $338,512 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,684 Sq Ft

  5280 Hyland Hills Ave Unit 1824, Sarasota, FL 34241

  5280 Hyland Hills Ave Unit 1824, Sarasota, FL 34241
• 

  

  /59

  $420,000

  • 2 Beds
  • 2 Baths
  • 1,585 Sq Ft

  5325 Chase Oaks Dr, Sarasota, FL 34241

  Embrace the ultimate Florida lifestyle at this furnished, beautiful end-unit Club Home in the renowned Heritage Oaks Golf & Country Club. This Arlington model is a perfect blend of comfort and recreation, offering two bedrooms, two baths, a flexible study/den, and 1,585 sq ft of meticulously maintained living space.The heart of the home is its open and airy layout, with a spacious kitchen

  Traci Bolen EXP REALTY LLC

  5325 Chase Oaks Dr, Sarasota, FL 34241
• 

  

  /46

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • Condo for Rent

  5280 Hyland Hills Ave Unit 1812, Sarasota, FL 34241

  Beautifully and Professionally remodeled 1st Floor 2 bedroom 2 bath condo with new furnishings. Comfort at its best! Tastefully remodeled and newly furnished with your complete satisfaction in mind. Join the Heritage Oaks Country Club for a nominal membership fee and golf until your heart's desire. Driving Range, tennis courts, gym with the latest equipment, social events of the country club

  Dino Theofilos FLORIDA CAPITAL REAL ESTATE

  5280 Hyland Hills Ave Unit 1812, Sarasota, FL 34241
• 

  /2

  $210,000 Sold Jul 31, 2025

  • 1,324 Sq Ft
  • $159/SF
  • 35 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  5330 Hyland Hills Ave Unit 2324, Sarasota, FL 34241

  Discover resort style living in Heritage Oaks at an exceptional price! Owners are motivated and want a new owner to enjoy this great condo that they have enjoyed. This condo is a must see along with the 14th hole view! One owner and well maintained are a few of the many benefits. Read on... Light and bright second floor unit with HIGH CEILINGS and open floor plan and one car garage. Enjoy

  Kathleen Goff KATHLEEN GOFF LICENSE R.E. BROKER

  5330 Hyland Hills Ave Unit 2324, Sarasota, FL 34241
• 

  /2

  Est $282,218 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,187 Sq Ft

  8817 Daybreak St, Sarasota, FL 34241

  8817 Daybreak St, Sarasota, FL 34241
• 

  

  /14

  $259,000

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  8540 Daybreak St, Sarasota, FL 34241

  NEW PRICE IMPROVMENT, PRICED BELOW MARKET VALUE FOR QUICK SALE AND THE HOA FEE is $140.00 less than the NEW ones the builder is offering, This is by far a better deal. Why wait on new construction when you can move right into this 2024 built, barely lived in 2 bedroom, 2.5 bath townhome in Skye Ranch. Looking for a bright, clean and fresh new start and pay less than the builder's current

  William Gonzalez W & CO REALTY

  8540 Daybreak St, Sarasota, FL 34241
• 

  

  /29

  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Condo for Rent

  5320 Hyland Hills Ave Unit 2222, Sarasota, FL 34241

  Welcome to the Lakeview 2 Bedroom 2 Bath Condo on Golf Course, a stunning property located in Heritage Oaks in the heart of Sarasota, FL. This condo offers two spacious bedrooms and two full bathrooms, and a den/study with a sofa sleeper, perfect for those who value comfort and convenience. The property is nestled within a golf community, providing residents with an opportunity to enjoy the sport

  Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

  5320 Hyland Hills Ave Unit 2222, Sarasota, FL 34241
• 

  /2

  $550,000 Sold Jul 02, 2025

  • 1,936 Sq Ft
  • $284/SF
  • 167 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  4451 Legacy Ct, Sarasota, FL 34241

  “PATIO HOME” with stunning golf course views and southern rear exposure in the MAINTENANCE FREE, SINGLE FAMILY HOME SECTION of Heritage Oaks Golf & Country Club. Boasting a NEW TILE ROOF IN 2021, IMPACT WINDOWS AND HURRICANE SHUTTERS ON BOTH THE COVERED FRONT ENTRY & REAR LANAI AND A NEW AIR CONDITIONING SYSTEM IN 2022, this tastefully appointed, 2 bedroom plus den, 2 bathroom Innisbrook floor

  Susan Mitchell MICHAEL SAUNDERS & COMPANY

  4451 Legacy Ct, Sarasota, FL 34241
• 

  /2

  Est $283,171 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  8544 Daybreak St, Sarasota, FL 34241

  8544 Daybreak St, Sarasota, FL 34241
• 

  

  /62

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,585 Sq Ft

  5217 Chase Oaks Dr, Sarasota, FL 34241

  Welcome to Heritage Oaks Golf and Country Club, one of Sarasota’s premier luxury golf course communities. Nestled within lush, meticulously landscaped grounds, Heritage Oaks offers an exceptional country club lifestyle with resort-style amenities designed for comfort, recreation, and elegance. Residents enjoy access to an 18-hole championship golf course, a professional-grade Pro Shop, a putting

  Marina Solo KW SUNCOAST

  5217 Chase Oaks Dr, Sarasota, FL 34241
• 

  

  /15

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • House for Rent

  4420 Chase Oaks Dr, Sarasota, FL 34241

  Seasonal rate has been reduced to $5200.00! Available for March and April 2025 due to tenant cancellation! Enjoy this 2 bedroom 2/bath Villa with sweeping views of the Golf Course from the screened rear patio. Formal Dining room for your evening dinners. Updated kitchen with all the tools one needs to make a 3 course meal for friends and family. A bonus den off the kitchen for your business needs

  Angela Bailey MONARCH PROPERTY GROUP LLC

  4420 Chase Oaks Dr, Sarasota, FL 34241
• 

  /2

  $367,675 Sold Jun 30, 2025

  • 1,572 Sq Ft
  • $234/SF
  • 77 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  5283 Chase Oaks Dr, Sarasota, FL 34241

  Welcome to Heritage Oaks Golf & Country Club, Sarasota's private, gated, golfing neighborhood. This wonderful "Buttonwood" club home features 2 bedrooms, 2 bathrooms, a den/study with french doors allowing it to be used as a third bedroom, and a sizable 2 car garage. Ideal for full time owners or seasonal residents, this lovely property has more than enough space for owners and their guests and

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5283 Chase Oaks Dr, Sarasota, FL 34241
• 

  /2

  Est $289,385 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  8548 Daybreak St, Sarasota, FL 34241

  8548 Daybreak St, Sarasota, FL 34241
• 

  

  /45

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,684 Sq Ft

  5251 Mahogany Run Ave Unit 521, Sarasota, FL 34241

  Welcome to your dream home, a beautifully updated, fully furnished, 2nd-story condo offering a harmonious blend of luxury, comfort, and resort-style living in one of Sarasota’s most sought-after communities. Ideally positioned, this home features breathtaking panoramic views of the 13th Fairway and a tranquil pond, offering a peaceful setting to enjoy your morning coffee or evening glass of wine

  Joey Lamielle RE/MAX ALLIANCE GROUP

  5251 Mahogany Run Ave Unit 521, Sarasota, FL 34241
• 

  

  /41

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Condo for Rent

  5330 Hyland Hills Ave Unit 2312, Sarasota, FL 34241

  Turn-key. Also available SHORT-TERM. Welcome to this cozy 2 bedrooms, 2 baths with a Den first floor unit with amazing pond and golf course views. Located in the luxury resort style gated community of Heritage Oaks Golf and Country Club which offers 24/7 guard service, clubhouse, restaurant, bar and grill lounge, 5 swimming pools, tennis courts, fitness center, a calendar of events, and a golf

  Veronica Alves WILLIAM RAVEIS REAL ESTATE

  5330 Hyland Hills Ave Unit 2312, Sarasota, FL 34241
• 

  /2

  $245,000 Sold Jun 27, 2025

  • 1,324 Sq Ft
  • $185/SF
  • 98 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  5250 Hyland Hills Ave Unit 1514, Sarasota, FL 34241

  Take a look at this first floor "Drummond" model veranda home that is a unique opportunity to live and play in one of the best kept secrets in Sarasota - Heritage Oaks Golf & Country Club! With expansive views of water and the signature 14th hole of the golf course, this is the property you have been waiting for and is being sold Turn-Key Furnished. The maintenance free property is conveniently

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5250 Hyland Hills Ave Unit 1514, Sarasota, FL 34241
• 

  

  /35

  Est $304,122 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft

  5310 Hyland Hills Ave Unit 2117, Sarasota, FL 34241

  5310 Hyland Hills Ave Unit 2117, Sarasota, FL 34241
• 

  

  /53

  $319,900

  • 2 Beds
  • 2 Baths
  • 1,684 Sq Ft

  5240 Hyland Hills Ave Unit 1426, Sarasota, FL 34241

  Welcome to the largest Veranda model in Heritage Oaks Golf & Country Club—a rare second floor, end-unit offering exceptional space, natural light, and turnkey furnishings for a seamless move-in experience. Step inside to discover new luxury vinyl flooring throughout the living areas, bedrooms, and den—offering both style and durability. The bright, open-concept design seamlessly connects the

  Lindsay Nock MICHAEL SAUNDERS & COMPANY

  5240 Hyland Hills Ave Unit 1426, Sarasota, FL 34241
• 

  

  /33

  $6,500 per month

  • 4 Beds
  • 2 Baths
  • 2,187 Sq Ft
  • House for Rent

  4630 Chase Oaks Dr, Sarasota, FL 34241

  Booked through April 2025. - Escape to a world of refined luxury at this exclusive retreat within the prestigious Heritage Oaks Golf & Country Club. Enveloped by 24/7 guard service, this remarkable rental home in Sarasota, nestled on Florida's captivating Gulf Coast, presents an unrivaled opportunity for an unforgettable getaway. Emanating opulence, Heritage Oaks Golf and Country Club boasts an

  Michael Sorensen STRINGER MANAGEMENT INC

  4630 Chase Oaks Dr, Sarasota, FL 34241
• 

  /2

  $305,000 Sold Jun 26, 2025

  • 1,684 Sq Ft
  • $181/SF
  • 128 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  5330 Hyland Hills Ave Unit 2311, Sarasota, FL 34241

  Come take a look at this gorgeous 1st floor Abbey model Veranda in Heritage Oaks Golf & Country Club being sold Turn-Key Furnished. This wonderful property features 2 bedrooms, 2 full bathrooms, a den/study that can double as a third bedroom, and a 1 car detached garage. With almost 1,700 square feet of interior living space, there is more than enough room for full time owners or seasonal

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5330 Hyland Hills Ave Unit 2311, Sarasota, FL 34241
• 

  

  /80

  Est $399,150 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,572 Sq Ft

  5141 Peppermill Ct Unit 14, Sarasota, FL 34241

  5141 Peppermill Ct Unit 14, Sarasota, FL 34241
• 

  

  /67

  $405,000

  • 2 Beds
  • 2 Baths
  • 1,585 Sq Ft

  5092 Mahogany Run Ave, Sarasota, FL 34241

  Heritage Oaks Golf & Country Club! ** Step into an Arlington model end-unit Club Home, nestled gracefully on the 11th fairway. This is a turn-key furnished home that offers indoor and outdoor living, enhanced by crown molding that adds an extra layer of elegance. Step into the kitchen that offers ample cabinets and a cozy breakfast nook. The open floor plan allows for plenty of engagement while

  Rick Trapp EXP REALTY LLC

  5092 Mahogany Run Ave, Sarasota, FL 34241
• 

  

  /19

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • Condo for Rent

  5320 Hyland Hills Ave Unit 2225, Sarasota, FL 34241

  2BR/2BA Condo, Seasonal Rental - Heritage Oaks Golf & Country Club, OFF SEASON AVAILABILITY ONLYThis Condo is FORE you!Our Heritage Oaks condo, located in the golf community of Heritage Oaks Golf & Country Club in Sarasota, FL is available for monthly/seasonal rental.Minimum 30-day stays, but seeking a 3-month minimum rental for the season:In season pricing: January-

  Dave Holt PMI SARASOTA

  5320 Hyland Hills Ave Unit 2225, Sarasota, FL 34241
• 

  /2

  $435,000 Sold Jun 18, 2025

  • 1,585 Sq Ft
  • $274/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  5223 Chase Oaks Dr, Sarasota, FL 34241

  You will not want to miss the opportunity to take a look at this outstanding, updated "Arlington" Club Home in Heritage Oaks Golf & Country Club that is being sold Fully Furnished. This wonderful end unit features 2 bedrooms, 2 bathrooms, a den/study with closet that can be used as a third bedroom, and an attached 2-car garage. The owners have spared no expense with the gorgeous updates that have

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5223 Chase Oaks Dr, Sarasota, FL 34241
• 

  

  /6

  Est $319,052 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,191 Sq Ft

  8785 Daybreak St, Sarasota, FL 34241

  8785 Daybreak St, Sarasota, FL 34241
• 

  

  /62

  $329,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,684 Sq Ft

  5211 Mahogany Run Ave Unit 126, Sarasota, FL 34241

  Under contract-accepting backup offers. Updated & Partially Furnished Condo in Heritage Oaks Golf & Country ClubWelcome to 5211 Mahogany Run Ave #126, a beautifully updated second-floor END UNIT condo in the sought-after Heritage Oaks Golf & Country Club! This move-in-ready residence offers stunning golf course views and an array of recent upgrades, including fresh paint, new LVP

  Nicole Betz KW COASTAL LIVING III

  5211 Mahogany Run Ave Unit 126, Sarasota, FL 34241
• 

  

  /14

  $2,800 per month

  • 2 Beds
  • 2 Baths
  • 1,585 Sq Ft
  • Apartment for Rent

  5064 Mahogany Run Ave, Sarasota, FL 34241

  AVAILABLE FOR THE OFF SEASON MONTHS FOR 2025. GATED! Heritage Oaks Golf and Country Club! Come in and be impressed with this gorgeous Arlington 2 bed/2 bath model plus den villa in one of Sarasota's most sought after communities. This lanai overlooks the 11th green. No carpet! Quartz countertops, SS appliances in the kitchen. 3 New 55" TVs. Heritage Oaks is a gated and "bundled" community that

  Robin De Busk STRINGER MANAGEMENT INC

  5064 Mahogany Run Ave, Sarasota, FL 34241
• 

  /2

  $324,000 Sold Jun 10, 2025

  • 1,684 Sq Ft
  • $192/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  5220 Hyland Hills Ave Unit 1211, Sarasota, FL 34241

  This is the one! Take a look at this completely updated "Abbey" floor plan veranda in Heritage Oaks Golf & Country Club that is being sold FullyFurnished. Featuring 2 bedrooms, 2 bathrooms, a den/study, and a 1 car garage, this property is perfect for a seasonal resident or full time owner. As soon as you step through the front door, you're greeted with a ton of natural light and the abundance of

  Doug Figgins ROSEBAY INTERNATIONAL REALTY, INC

  5220 Hyland Hills Ave Unit 1211, Sarasota, FL 34241
• 

  

  /44

  Est $269,732 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft

  5280 Hyland Hills Ave Unit 1812, Sarasota, FL 34241

  5280 Hyland Hills Ave Unit 1812, Sarasota, FL 34241
• 

  

  /50

  $859,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,624 Sq Ft

  4532 Chase Oaks Dr, Sarasota, FL 34241

  With views of the Golf Course and Water, this Single Family "POOL" Home is BETTER than New..."MOVE-IN READY" and located in the Desirable community of "HERITAGE OAKS GOLF & COUNTRY CLUB" in Sarasota, FL Beautifully Updated...2,624sq ft of "SPACIOUS" and "OPEN" living space, 3-bedroom 2.5-bath with a den, and 2-car garage. A true cook's kitchen with granite countertops, stainless steel

  Kristy Heitl EXIT KING REALTY

  4532 Chase Oaks Dr, Sarasota, FL 34241
• 

  

  /56

  $2,871 per month

  • 2 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • Condo for Rent

  5301 Mahogany Run Ave Unit 1023, Sarasota, FL 34241

  Welcome to Tranquil Waters! This breathtaking second-floor 2-bedroom, 2-bathroom lakefront condo is located in the highly established Heritage Oaks Golf and Country Club. Nuzzled in nature, this tropical lakefront condo is the perfect location for you and your family to make memories that will last a lifetime! Heritage Oaks Golf and Country Club have resort-style amenities galore! The

  Andy Moore GULF COAST REALTY & MANAGEMENT

  5301 Mahogany Run Ave Unit 1023, Sarasota, FL 34241
• 

  /2

  $315,500 Sold May 14, 2025

  • 1,373 Sq Ft
  • $230/SF
  • 203 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  8787 Winter Breeze Way, Sarasota, FL 34241

  Pre-Construction. To be built. MLS#A4599917 REPRESENTATIVE PHOTOS ADDED. December 2024. The Jasmine townhome offers 1,337 sq. ft. of living space, 3 bedrooms, 2.5 baths, a 1-car garage, and more. Enter the home from the front porch and directly into the heart of the gathering room and the open-concept kitchen that is equipped with an expansive island. Sharing the first-floor space is a half bath,

  Michelle Campbell TAYLOR MORRISON RLTY OF FLA

  8787 Winter Breeze Way, Sarasota, FL 34241
• 

  

  /7

  Est $308,473 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,202 Sq Ft

  8865 Daybreak St, Sarasota, FL 34241

  8865 Daybreak St, Sarasota, FL 34241

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