Windermere, FL Homes

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  /23

  Est $562,262 Not Listed For Sale

  11486 Misty Oak Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Built 2016

  11486 Misty Oak Aly, Windermere, FL 34786

  Last Sold Summary

  • 2% Above List Price
  • $282/SF
  • 9 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Bertrand Bouchenot PINELOCH INVESTMENTS, INC
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  /66

  $3,699,000

  • 3 Beds
  • 5 Baths
  • 4,262 Sq Ft

  4812 Alexandra Garden Ct, Windermere, FL 34786

  Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a

  Rob Rahter STOCKWORTH REALTY GROUP

  4812 Alexandra Garden Ct, Windermere, FL 34786
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  /2

  $1,500,000 Sold Apr 25, 2025

  3606 Lake Buynak Rd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,083 Sq Ft
  • Built 1989

  Last Sold Summary

  • 25% Below List Price
  • $487/SF
  • 195 Days On Market

  Current Estimated Value $1,450,821

  Last Listing Agent Narda Miranda EXP REALTY LLC

  3606 Lake Buynak Rd, Windermere, FL 34786
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  /28

  Est $412,588 Not Listed For Sale

  13303 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,441 Sq Ft
  • Built 2020

  13303 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $306/SF
  • 24 Days On Market

  Last Sold Price $441,500

  Last Listing Agent Charles Kohlinger BHHS FLORIDA REALTY
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  /64

  $725,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,129 Sq Ft

  13649 Zori Ln, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to this beautifully maintained four-bedroom, four-bath home in the desirable Providence Community, in the top-rated Windermere school district. Bright, open living spaces feature 10-foot ceilings, elegant architectural details, and a thoughtful split multigenerational floor plan for everyday living and entertaining. The spacious owner’s suite offers

  Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  13649 Zori Ln, Windermere, FL 34786
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  /2

  $285,000 Sold Sep 19, 2025

  8277 Maritime Flag St Unit 205, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $196/SF
  • 39 Days On Market

  Current Estimated Value $291,896

  Last Listing Agent Raymond Glenn LAKESIDE REALTY WINDERMERE INC

  8277 Maritime Flag St Unit 205, Windermere, FL 34786
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  /2

  Est $428,944 Not Listed For Sale

  11405 Brownstone St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Built 2015

  11405 Brownstone St, Windermere, FL 34786

  Last Sold Summary

  • 6% Below List Price
  • $243/SF
  • 76 Days On Market

  Last Sold Price $457,500

  Last Listing Agent Philip Foo FUTURE HOME REALTY INC
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  /9

  $5,995,000 New Construction

  • 5 Beds
  • 6 Baths
  • 6,000 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  /2

  $700,000 Sold Apr 17, 2025

  9058 Reflection Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,651 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $192/SF
  • 280 Days On Market

  Current Estimated Value $722,925

  Last Listing Agent Marcos Del Nero LA ROSA REALTY KISSIMMEE

  9058 Reflection Pointe Dr, Windermere, FL 34786
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  /2

  Est $467,917 Not Listed For Sale

  7653 Ripplepointe Way, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,212 Sq Ft
  • Built 2015

  7653 Ripplepointe Way, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $223/SF
  • 86 Days On Market

  Last Sold Price $492,500

  Last Listing Agent Nina Oh JUPITER PROPERTIES, INC
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  /40

  $516,000

  • 3 Beds
  • 2.5 Baths
  • 1,876 Sq Ft

  8648 Powder Ridge Trail, Windermere, FL 34786

  LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door.Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a

  Renan Serretiello NOVA REAL ESTATE SERVICES INC

  8648 Powder Ridge Trail, Windermere, FL 34786
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  /2

  $530,000 Sold Aug 15, 2025

  12868 Holdenbury Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $215/SF
  • 39 Days On Market

  Current Estimated Value $536,063

  Last Listing Agent Victor Nawrocki VISION HOME REAL ESTATE, LLC

  12868 Holdenbury Ln, Windermere, FL 34786
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  /61

  Est $1,104,953 Not Listed For Sale

  8361 Torcello Isle Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 4,176 Sq Ft
  • Built 2018

  8361 Torcello Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 4% Below List Price
  • $275/SF
  • 22 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Sherri Palmer EXP REALTY LLC
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  /46

  $785,000

  • 3 Beds
  • 2.5 Baths
  • 2,379 Sq Ft

  5018 River Gem Ave, Windermere, FL 34786

  Welcome to 5018 River Gem Avenue, an exceptional one-story pool estate with serene pond views in the prestigious Summerport community of Windermere, perfectly positioned for luxury living, convenience, and resort-style enjoyment — only 20 minutes from the Disney Theme Parks, Disney Springs, premier shopping, dining, and major roadways. This 3-bedroom, 2.5-bath, 2,379 sq ft showpiece features a

  Anastasia Fischer KELLER WILLIAMS SOUTH TAMPA

  5018 River Gem Ave, Windermere, FL 34786
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  /2

  $580,000 Sold Sep 22, 2025

  12867 Penshurst Ln, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 3 Days On Market

  Current Estimated Value $576,673

  Last Listing Agent Stefany Marcelino RE/MAX INNOVATION

  12867 Penshurst Ln, Windermere, FL 34786
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  /40

  Est $493,771 Not Listed For Sale

  13856 Summerport Trail Loop, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • Built 2016

  13856 Summerport Trail Loop, Windermere, FL 34786

  Last Sold Summary

  • $235/SF
  • 3 Days On Market

  Last Sold Price $495,000

  Last Listing Agent Skyler Warden COLDWELL BANKER REALTY
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  /30

  $450,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  13752 Bressler Aly, Windermere, FL 34786

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ask about a lender provided RATE BUY-DOWN CREDIT on this home ~ Seller may consider buyer concessions if made in an offer ~ Welcome to effortless living in the heart of Windermere! This fantastic 3-bedroom, 2.5-bath townhome in the highly desirable Vineyards/Horizon West community offers modern upgrades, a

  Jennifer Wemert WEMERT GROUP REALTY LLC

  13752 Bressler Aly, Windermere, FL 34786
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  /2

  $695,000 Sold Jun 13, 2025

  116 Main St, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • Built 1958

  Last Sold Summary

  • $548/SF
  • 91 Days On Market

  Current Estimated Value $712,046

  Last Listing Agent Adam Judd METROPOLIS R.E. SOLUTIONS, LLC

  116 Main St, Windermere, FL 34786
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  /43

  Est $750,663 Not Listed For Sale

  8711 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,419 Sq Ft
  • Built 2015

  8711 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • $219/SF
  • 10 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC
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  /45

  $2,315,000

  • 5 Beds
  • 4 Baths
  • 3,461 Sq Ft

  5067 Sawyer Cove Way, Windermere, FL 34786

  STUNNING CUSTOM ESTATE in the EXCLUSIVE GATED community of Sawyer Sound - a private enclave of 20 luxury homes, ideally located across the street from Windermere Prep, and close to excellent dining and premiere entertainment. Built under the meticulous supervision of its owners, one of whom is an accomplished interior designer, this home showcases curated exceptional quality finishes and

  Denise Crabbe REVEL REALTY LLC

  5067 Sawyer Cove Way, Windermere, FL 34786
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  /2

  $305,000 Sold Jun 06, 2025

  8276 Maritime Flag St Unit 110, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $212/SF
  • 62 Days On Market

  Current Estimated Value $305,660

  Last Listing Agent Evan Caulfield STOCKWORTH REALTY GROUP

  8276 Maritime Flag St Unit 110, Windermere, FL 34786
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  /37

  Est $442,099 Not Listed For Sale

  13477 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,756 Sq Ft
  • Built 2020

  13477 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $271/SF
  • 54 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Jen Dantas THE FLORIDA LOUNGE REALTY LLC
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  /31

  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,124 Sq Ft

  5413 Walsh Pond Ct, Windermere, FL 34786

  Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in

  Brenda Jebailey HAVEN PROPERTY GROUP LLC

  5413 Walsh Pond Ct, Windermere, FL 34786
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  /2

  $653,250 Sold Mar 28, 2025

  12761 Westside Village Loop, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $265/SF
  • 9 Days On Market

  Current Estimated Value $645,268

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  12761 Westside Village Loop, Windermere, FL 34786
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  /95

  Est $871,912 Not Listed For Sale

  11947 Otterbrooke Trail, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,407 Sq Ft
  • Built 2013

  11947 Otterbrooke Trail, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $264/SF
  • 58 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Caroline De Castro Marcellini COMPASS FLORIDA, LLC
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  /22

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  11434 Jasper Kay Terrace Unit 1120, Windermere, FL 34786

  Beautifully maintained condo located in the highly desirable Lakeside Lakes of Windermere community. Situatedon the third floor with elevator access, this residence features a spacious split floor plan offering both privacy and functionality. The open concept living and dining area flows seamlessly to a private balcony perfect for enjoying your morning coffee or relaxing evenings.The

  alonso delgado REALTY ONE GROUP MVP

  11434 Jasper Kay Terrace Unit 1120, Windermere, FL 34786
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  /46

  $825,000 Sold May 15, 2025

  8738 Iron Mountain Trail, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,127 Sq Ft
  • Built 2013

  Last Sold Summary

  • 13% Below List Price
  • $264/SF
  • 313 Days On Market

  Current Estimated Value $823,767

  Last Listing Agent Crystal Washington Booth CENTURY 21 BE3

  8738 Iron Mountain Trail, Windermere, FL 34786
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  /42

  Est $698,418 Not Listed For Sale

  11813 Cave Run Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,935 Sq Ft
  • Built 2014

  11813 Cave Run Ave, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $245/SF
  • 16 Days On Market

  Last Sold Price $719,000

  Last Listing Agent Jaime Leizan EXP REALTY LLC
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  /2

  $3,000,000 New Construction

  • 5 Beds
  • 5 Baths
  • 2,565 Sq Ft

  19 Main St, Windermere, FL 34786

  Under Construction. New Construction in Downtown Windermere Waterfront on the Butler Chain of Lakes!Experience modern lakefront living in the heart of the golf cart–friendly Town of Windermere. This brand-new construction home is currently under construction with an anticipated completion date of late Summer 2026. The residence will offer approximately 2,500 square feet of living space and

  Milena Fernandes GOLDEN GROUP REALTY LLC

  19 Main St, Windermere, FL 34786
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  /2

  $1,240,000 Sold May 02, 2025

  7587 Lake Albert Dr, Windermere, FL 34786

  • 6 Beds
  • 6.5 Baths
  • 5,149 Sq Ft
  • Built 2014

  Last Sold Summary

  • 5% Below List Price
  • $241/SF
  • 40 Days On Market

  Current Estimated Value $1,255,435

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  7587 Lake Albert Dr, Windermere, FL 34786
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  /92

  Est $2,193,388 Not Listed For Sale

  11817 Vinci Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 5,023 Sq Ft
  • Built 2012

  11817 Vinci Dr, Windermere, FL 34786

  Last Sold Summary

  • $438/SF
  • 36 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Hojin Chang RE/MAX
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  /38

  $870,000

  • 5 Beds
  • 3.5 Baths
  • 3,724 Sq Ft

  8767 Iron Mountain Trail, Windermere, FL 34786

  The Melville floor plan features a functional and well-designed layout with formal living and dining areas, a spacious primary suite, an open-concept family room and a versatile flex space that can be used as a game room or adapted to suit a variety of lifestyle needs. Located in the desirable Windermere Trails community, the property offers convenient access to area lakes, daily essentials,

  Gilson Rodrigues KARDOSH REALTY

  8767 Iron Mountain Trail, Windermere, FL 34786
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  /2

  $600,000 Sold Jul 09, 2025

  5063 Carillon Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 2004

  Last Sold Summary

  • $249/SF
  • 7 Days On Market

  Current Estimated Value $586,606

  Last Listing Agent Jared Dunn LIVE MVRK LLC

  5063 Carillon Ln, Windermere, FL 34786
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  /29

  Not Listed For Sale

  14264 Desert Haven St Unit GE, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2012

  14264 Desert Haven St Unit GE, Windermere, FL 34786

  Last Sold Summary

  • $215/SF
  • 106 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Jennifer McCarty ORCHARD BROKERAGE, LLC
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  /56

  $789,000

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  13609 Ancilla Blvd, Windermere, FL 34786

  Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony,

  Fernanda Soares Santos de Oliveira WRA BUSINESS & REAL ESTATE

  13609 Ancilla Blvd, Windermere, FL 34786
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  /2

  $820,000 Sold Mar 06, 2026

  416 Magnolia St, Windermere, FL 34786

  • 2 Beds
  • 1.5 Baths
  • 2,115 Sq Ft
  • Built 1915

  Last Sold Summary

  • 7% Below List Price
  • $388/SF
  • 74 Days On Market

  Current Estimated Value $861,964

  Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

  416 Magnolia St, Windermere, FL 34786
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  /30

  Est $507,762 Not Listed For Sale

  13347 Overstreet Rd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 2013

  13347 Overstreet Rd, Windermere, FL 34786

  Last Sold Summary

  • 2% Above List Price
  • $243/SF
  • 46 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Eve Metlis WATSON REALTY CORP
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  /16

  $950,000

  • 4 Beds
  • 3 Baths
  • 2,224 Sq Ft

  13542 Gorgona Isle Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  13542 Gorgona Isle Dr, Windermere, FL 34786
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  /2

  $1,650,000 Sold Sep 29, 2025

  4108 Downeast Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,150 Sq Ft
  • Built 1979

  Last Sold Summary

  • 50% Below List Price
  • $524/SF
  • 208 Days On Market

  Current Estimated Value $1,635,755

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  4108 Downeast Ln, Windermere, FL 34786
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  /10

  Not Listed For Sale

  Lot 2 Down Park Ln, Windermere, FL 34786

  Lot 2 Down Park Ln, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market

  Last Sold Price $1,795,000

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

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