1,026

Middlesex, NY Homes

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  • 4755 S Hill Rd Unit 47, Middlesex, NY 14507
    4755 S Hill Rd Unit 47, Middlesex, NY 14507
    4755 S Hill Rd Unit 47, Middlesex, NY 14507
    /50

    $436,000

    $24K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    4755 S Hill Rd Unit 47, Middlesex, NY 14507

    Welcome to this exceptional second-owner custom chalet-style home, built in 1998 and nestled on 2.734 scenic acres in the desirable Naples Central School District. Surrounded by hundreds of acres of protected land, this private retreat offers breathtaking panoramic views of the Naples Valley, abundant wildlife, and the perfect balance of privacy, tranquility, and modern comfort. This beautifully

    Agent Photo

    Aimee Campbell

    Listing by Empire Realty Group

    4755 S Hill Rd Unit 47, Middlesex, NY 14507
  • 1519 S Lake Rd, Middlesex, NY 14507
    1519 S Lake Rd, Middlesex, NY 14507
    1519 S Lake Rd, Middlesex, NY 14507
    /50

    $4,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,090 Sq Ft
    • House for Rent

    1519 S Lake Rd, Middlesex, NY 14507

    FULLY FURNISHED SPECTACULAR WATERFRONT CANANDAIGUA LAKE DREAM LODGE. THIS AMAZING CANANDAIGUA LAKE HOME IS SITUATED ON 165FT OF WATERFRONT. YOU’LL BE AMAZED BY THE BEAUTY & TRANQUILITY OF THIS HOME. UPON ENTERING YOU’RE GREETED WITH A SPACIOUS FOYER. CATHEDRAL CEILING, WOOD BEAM FAMILY ROOM COMFORTABLY ACCOMMODATES ALL YOUR FAMILY & FRIENDS. ADDITIONAL SEATING IN THE SPERATE LIVING ROOM WITH AN

    Rich Testa Listing by Howard Hanna

    1519 S Lake Rd, Middlesex, NY 14507
  • 681 State Route 364, Middlesex, NY 14507
    681 State Route 364, Middlesex, NY 14507
    /2

    $565,000

    Sold Oct 24, 2025

    681 State Route 364, Middlesex, NY 14507

    • 3 Beds
    • 2.5 Baths
    • 1,559 Sq Ft
    • Built 2001

    Last Sold Summary

    • 16% Below List Price
    • $362/SF
    • 51 Days On Market

    Current Estimated Value $569,310

    Last Listing Agent Jon Bagley Listing by Griffith Realty Group

    681 State Route 364, Middlesex, NY 14507
  • 1592 Emerson Rd, Middlesex, NY 14507
    1592 Emerson Rd, Middlesex, NY 14507
    1592 Emerson Rd, Middlesex, NY 14507
    /25

    $219,900

    Pending
    • Land
    • 46.7 Acres
    • $4,709 per Acre

    1592 Emerson Rd, Middlesex, NY 14507

    Tucked away on a quiet dead-end stretch of Middlesex Road, this 46.7+/- acre wooded property offers the kind of privacy and natural character that land buyers search for in the Finger Lakes. As you step onto the property, the land immediately begins to rise from the road, gradually climbing toward the crest of a hill that hints at the views waiting above. Clear a small opening for a future cabin

    Agent Photo

    James Klossner

    Listing by Whitetail Properties Real Estate, LLC

    1592 Emerson Rd, Middlesex, NY 14507
  • 1890 Warren Rd, Middlesex, NY 14507
    1890 Warren Rd, Middlesex, NY 14507
    /2

    $397,500

    Sold Aug 03, 2026

    1890 Warren Rd, Middlesex, NY 14507

    • 3 Beds
    • 2.5 Baths
    • 2,322 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Above List Price
    • $171/SF
    • 10 Days On Market

    Current Estimated Value $347,350

    Last Listing Agent Danielle Clement Listing by Tru Agent Real Estate

    1890 Warren Rd, Middlesex, NY 14507
    • 883 State Route 245, Middlesex, NY 14507
      883 State Route 245, Middlesex, NY 14507
      /2

      Est $532,668

      Not Listed For Sale

      883 State Route 245, Middlesex, NY 14507

      • 4 Beds
      • 2 Baths
      • 1,752 Sq Ft
      • Built 1995
      883 State Route 245, Middlesex, NY 14507

  • 1316 Bay Dr, Middlesex, NY 14507
    1316 Bay Dr, Middlesex, NY 14507
    1316 Bay Dr, Middlesex, NY 14507
    /50

    $439,900

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,800 Sq Ft

    1316 Bay Dr, Middlesex, NY 14507

    Incredible Lakefront Family Home!! Tucked away in a serene park-like setting on 4 private acres, this exceptional four bedrm,2 1/2 bath home offers a rare opportunity to own one of only six homes on beautiful Emerson Lake. With over 380 ft of private lake frontage, you will enjoy unparalleled peace and tranquility on this non-motorized lake, where the sounds of nature replace the noise of boat

    Andrea Rohr Listing by Howard Hanna The Rohr Agency

    1316 Bay Dr, Middlesex, NY 14507
  • 1205 Upper Hill Rd, Middlesex, NY 14507
    1205 Upper Hill Rd, Middlesex, NY 14507
    /2

    $230,000

    Sold Sep 10, 2025

    1205 Upper Hill Rd, Middlesex, NY 14507

    • 2 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 2002

    Last Sold Summary

    • 15% Above List Price
    • $158/SF
    • 21 Days On Market

    Last Listing Agent Emily Martini Listing by Keller Williams Realty Gateway

    1205 Upper Hill Rd, Middlesex, NY 14507
    • 4342 Bootes Rd, Middlesex, NY 14507
      4342 Bootes Rd, Middlesex, NY 14507
      /2

      Est $397,044

      Not Listed For Sale

      4342 Bootes Rd, Middlesex, NY 14507

      • 3 Beds
      • 1 Bath
      • 1,188 Sq Ft
      • Built 1989
      4342 Bootes Rd, Middlesex, NY 14507

  • 6374 Glenn Ave, Middlesex, NY 14507
    6374 Glenn Ave, Middlesex, NY 14507
    6374 Glenn Ave, Middlesex, NY 14507
    /48

    $419,900

    Open Sun 12PM - 2PM
    • 2 Beds
    • 1 Bath
    • 902 Sq Ft

    6374 Glenn Ave, Middlesex, NY 14507

    SPECTACULAR CANANDAIGUA LAKE COTTAGE GETAWAY! This is what lake living is all about—a charming, character-filled cottage where you can spend your days on the water and your evenings relaxing with family and friends! Tucked away at the end of the street and just one house from Newago Cove, this special property offers an incredible opportunity to enjoy the Canandaigua Lake lifestyle!Enjoy

    Rich Testa Listing by Howard Hanna

    6374 Glenn Ave, Middlesex, NY 14507
  • 1369 Italy Valley Rd, Naples, NY 14512
    1369 Italy Valley Rd, Naples, NY 14512
    /2

    $349,900

    Sold Sep 25, 2025

    1369 Italy Valley Rd, Naples, NY 14512

    • 3 Beds
    • 1.5 Baths
    • 2,142 Sq Ft
    • Built 1900

    Last Sold Summary

    • $163/SF
    • 81 Days On Market

    Current Estimated Value $369,325

    Last Listing Agent Mary St George Listing by Real Broker NY, LLC

    1369 Italy Valley Rd, Naples, NY 14512
    • 5650 Widmer Rd, Middlesex, NY 14507
      5650 Widmer Rd, Middlesex, NY 14507
      /2

      Est $735,598

      Not Listed For Sale

      5650 Widmer Rd, Middlesex, NY 14507

      • 3 Beds
      • 1 Bath
      • 1,014 Sq Ft
      • Built 1976
      5650 Widmer Rd, Middlesex, NY 14507

  • 2190 Warren Rd, Middlesex, NY 14507
    2190 Warren Rd, Middlesex, NY 14507
    2190 Warren Rd, Middlesex, NY 14507
    /6

    $180,000

    • Land
    • 45 Acres
    • $4,000 per Acre

    2190 Warren Rd, Middlesex, NY 14507

    Beautiful land located in Italy, NY. Approximate address is 2190 Warren Road, Italy, NY. Tons of potential. Buildable parcel with a pond and natural springs, lots of hardwood (red and white oak; walnut; maple), selectively harvested in 2010 (never before). Last surveyed in 2024 at 44.47 acres (Lot 1 in the map). Wooded neighboring lots on all sides. Abundant wildlife (deer, turkey, bear) and lots

    Derek Eisenberg Listing by Continental Real Estate Group

    2190 Warren Rd, Middlesex, NY 14507
  • 6351 N Vine Valley Rd, Middlesex, NY 14507
    6351 N Vine Valley Rd, Middlesex, NY 14507
    /2

    $38,000

    Sold Nov 28, 2025

    6351 N Vine Valley Rd, Middlesex, NY 14507

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft
    • Built 2002

    Last Sold Summary

    • 15% Below List Price
    • $95/SF
    • 98 Days On Market

    Last Listing Agent Rich Testa Listing by Howard Hanna

    6351 N Vine Valley Rd, Middlesex, NY 14507
    • 232 Bagley Rd, Rushville, NY 14544
      232 Bagley Rd, Rushville, NY 14544
      /2

      Est $206,826

      Not Listed For Sale

      232 Bagley Rd, Rushville, NY 14544

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1990
      232 Bagley Rd, Rushville, NY 14544

  • 34 Vine Valley Park, Middlesex, NY 14507
    34 Vine Valley Park, Middlesex, NY 14507
    34 Vine Valley Park, Middlesex, NY 14507
    /46

    $39,000

    • Land
    • 0 Sq Ft

    34 Vine Valley Park, Middlesex, NY 14507

    There is still time to enjoy the season at Vine Valley Park! This tastefully decorated 2-bedroom, 1 bath cottage is ready for you to relax and enjoy all that Canandaigua Lake has to offer. Enjoy private lake access, boat launch, community center, and general store. Seasonal living approximately April 15th-October 15th. Annual fee is $10,500 plus $2500 for dock space. Home only, land not included.

    Kurt Ledgerwood Listing by Griffith Realty Group

    34 Vine Valley Park, Middlesex, NY 14507
  • 1060 State Route 364, Middlesex, NY 14507
    1060 State Route 364, Middlesex, NY 14507
    /2

    $295,000

    Sold Feb 13, 2026

    1060 State Route 364, Middlesex, NY 14507

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft
    • Built 1897

    Last Sold Summary

    • 2% Below List Price
    • $154/SF
    • 40 Days On Market

    Current Estimated Value $307,299

    Last Listing Agent Susan Glenz Listing by Keller Williams Realty Gateway

    1060 State Route 364, Middlesex, NY 14507
    • 5621 Water St, Middlesex, NY 14507
      5621 Water St, Middlesex, NY 14507
      /2

      Est $208,623

      Not Listed For Sale

      5621 Water St, Middlesex, NY 14507

      • 3 Beds
      • 1 Bath
      • 1,552 Sq Ft
      • Built 1885
      5621 Water St, Middlesex, NY 14507

  • 198 E Lake Rd, Rushville, NY 14544
    198 E Lake Rd, Rushville, NY 14544
    198 E Lake Rd, Rushville, NY 14544
    /50

    $599,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    198 E Lake Rd, Rushville, NY 14544

    An Exceptionally Rare & Updated CANANDAIGUA LAKE WATERFRONT RETREAT Offering Privacy, Adventure & Spectacular Views Perched above the sparkling waters of Canandaigua Lake, this extraordinary private retreat captures breathtaking, MILLION-DOLLAR PANORAMIC VIEWS and offers unparalleled opportunity to own one of the region's most secluded waterfront sanctuaries. Nestled on 2.6 SCENIC ACRES

    Rich Testa Listing by Howard Hanna

    198 E Lake Rd, Rushville, NY 14544
  • 0 Warren Rd Unit R1656614, Middlesex, NY 14507
    0 Warren Rd Unit R1656614, Middlesex, NY 14507
    /2

    $15,000

    Sold Jun 10, 2026

    0 Warren Rd Unit R1656614, Middlesex, NY 14507

    • Land
    • 2.28 Acres
    • $6,579 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 119 Days On Market

    Last Listing Agent Nathan Fox Listing by Berkshire Hathaway HS Zambito

    0 Warren Rd Unit R1656614, Middlesex, NY 14507
    • 1115 Mertz Rd, Middlesex, NY 14507
      1115 Mertz Rd, Middlesex, NY 14507
      /2

      Est $282,516

      Not Listed For Sale

      1115 Mertz Rd, Middlesex, NY 14507

      • 3 Beds
      • 2 Baths
      • 1,170 Sq Ft
      • Built 2002
      1115 Mertz Rd, Middlesex, NY 14507

  • 4522 State Route 364, Penn Yan, NY 14527
    4522 State Route 364, Penn Yan, NY 14527
    4522 State Route 364, Penn Yan, NY 14527
    /5

    $55,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,867 Sq Ft

    4522 State Route 364, Penn Yan, NY 14527

    2 story 3-bedroom 1 bath home sitting on.32 acres of land. Property line on driveway side goes through a shared barn. House is being sold in AS IS condition. No showings after 5pm as there is no electricity in the home

    Dale Lane Listing by Keuka Lake & Land Realty

    4522 State Route 364, Penn Yan, NY 14527
  • 1119 S Lake Rd, Middlesex, NY 14507
    1119 S Lake Rd, Middlesex, NY 14507
    /2

    $750,000

    Sold Feb 27, 2026

    1119 S Lake Rd, Middlesex, NY 14507

    • 3 Beds
    • 1 Bath
    • 750 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $1,000/SF
    • 88 Days On Market

    Current Estimated Value $789,073

    Last Listing Agent Holly Creek Listing by Howard Hanna

    1119 S Lake Rd, Middlesex, NY 14507
    • 840 Timberlane Rd, Middlesex, NY 14507
      840 Timberlane Rd, Middlesex, NY 14507
      /2

      Est $437,130

      Not Listed For Sale

      840 Timberlane Rd, Middlesex, NY 14507

      • 1 Bed
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1999
      840 Timberlane Rd, Middlesex, NY 14507

  • 5087 Hagerty Rd, Middlesex, NY 14507
    5087 Hagerty Rd, Middlesex, NY 14507
    5087 Hagerty Rd, Middlesex, NY 14507
    /37

    $490,000

    Pending
    • Land
    • 64.11 Acres
    • $7,643 per Acre

    5087 Hagerty Rd, Middlesex, NY 14507

    Idyllic 64 ACRES with large POND in the Heart of the Finger Lakes Region, conveniently located between Canandaigua Lake and Keuka Lake! This picturesque parcel has great potential for recreational use, farming, building your dream home or get-a-way, or further potential development! This serene setting offers a fine blend of woodlands, clearings & farm fields. Approx 40’ x 50’ POLE BARN built in

    Marty Mendola Listing by Edelweiss Properties Realtors, LLC

    5087 Hagerty Rd, Middlesex, NY 14507
  • 1140 State Route 364, Middlesex, NY 14507
    1140 State Route 364, Middlesex, NY 14507
    1140 State Route 364, Middlesex, NY 14507
    /23

    $151,500

    Sold Mar 26, 2026

    1140 State Route 364, Middlesex, NY 14507

    • 3 Beds
    • 1.5 Baths
    • 1,119 Sq Ft
    • Built 1870

    Last Sold Summary

    • 5% Below List Price
    • $135/SF
    • 81 Days On Market

    Current Estimated Value $163,066

    Last Listing Agent Deyanira Voll Listing by Keller Williams Realty Gateway

    1140 State Route 364, Middlesex, NY 14507
    • 6301 S Vine Valley Rd, Middlesex, NY 14507
      6301 S Vine Valley Rd, Middlesex, NY 14507
      /2

      Est $296,100

      Not Listed For Sale

      6301 S Vine Valley Rd, Middlesex, NY 14507

      • 1 Bed
      • 1 Bath
      • 651 Sq Ft
      • Built 1980
      6301 S Vine Valley Rd, Middlesex, NY 14507

  • 6380 Vine Valley Rd, Middlesex, NY 14507
    6380 Vine Valley Rd, Middlesex, NY 14507
    6380 Vine Valley Rd, Middlesex, NY 14507
    /46

    $99,900

    Open Sun 12PM - 2PM
    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    6380 Vine Valley Rd, Middlesex, NY 14507

    SPECTACULAR CANANDAIGUA LAKE AT VINE VALLEY PARK! RARE AND BEST LOCATION WITH IMMEDIATE MILLION DOLLAR LAKE VIEW! THIS IS THE MOST AFFORDABLE WAY TO BE ON CANANDAIGUA LAKE. OVER 500'+ OF SAND AND SHALE BEACH AREA! GREAT SPOT TO DOCK YOUR BOAT TOO! TURNKEY READY TO MOVE IN AND ENJOY! BEAUTIFUL AND IMMCACULATE...... WELCOMING YOU AND YOUR GUEST IS AN ENTERTAINMENT SIZED COVERED PORCH WITH LAKE

    Rich Testa Listing by Howard Hanna

    6380 Vine Valley Rd, Middlesex, NY 14507
  • 1571 Emerson Rd, Middlesex, NY 14507
    1571 Emerson Rd, Middlesex, NY 14507
    /2

    $195,000

    Sold Dec 12, 2025

    1571 Emerson Rd, Middlesex, NY 14507

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $305/SF
    • 121 Days On Market

    Current Estimated Value $206,021

    Last Listing Agent Tammy Hullings Listing by Amanda Grover Real Estate, LLC

    1571 Emerson Rd, Middlesex, NY 14507
    • 763 Newago Ave, Middlesex, NY 14507
      763 Newago Ave, Middlesex, NY 14507
      /2

      Not Listed For Sale

      763 Newago Ave, Middlesex, NY 14507

      • 3 Beds
      • 2 Baths
      • 1,614 Sq Ft
      • Built 1967
      763 Newago Ave, Middlesex, NY 14507

  • 28 Vine Valley Park, Middlesex, NY 14424
    28 Vine Valley Park, Middlesex, NY 14424
    28 Vine Valley Park, Middlesex, NY 14424
    /37

    $15,000

    $21K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 450 Sq Ft

    28 Vine Valley Park, Middlesex, NY 14424

    Welcome to Vine Valley Park and the perfect Finger Lakes retreat! This beautiful 1-bedroom, 1-bath mobile home offers a wonderful opportunity to enjoy summers on Canandaigua Lake. Enjoy the lake view from the deck, offering the perfect spot to relax and take in the beautiful surroundings. Enjoy all that Vine Valley Park has to offer, including a community center, general store, public boat launch

    Kurt Ledgerwood Listing by Griffith Realty Group

    28 Vine Valley Park, Middlesex, NY 14424
  • 5170 Sunnyside Rd, Middlesex, NY 14507
    5170 Sunnyside Rd, Middlesex, NY 14507
    /2

    $575,000

    Sold Oct 03, 2025

    5170 Sunnyside Rd, Middlesex, NY 14507

    • 2 Beds
    • 1.5 Baths
    • 1,206 Sq Ft
    • Built 2021

    Last Sold Summary

    • 15% Below List Price
    • $477/SF
    • 130 Days On Market

    Current Estimated Value $653,639

    Last Listing Agent Brian Schmitt Listing by Finger Lakes Premier Prop.

    5170 Sunnyside Rd, Middlesex, NY 14507
    • 5400 Sunnyside Rd, Middlesex, NY 14507
      5400 Sunnyside Rd, Middlesex, NY 14507
      /2

      Est $575,606

      Not Listed For Sale

      5400 Sunnyside Rd, Middlesex, NY 14507

      • 3 Beds
      • 1 Bath
      • 1,320 Sq Ft
      • Built 1953
      5400 Sunnyside Rd, Middlesex, NY 14507

  • 52 Vine Valley Park, Middlesex, NY 14507
    52 Vine Valley Park, Middlesex, NY 14507
    52 Vine Valley Park, Middlesex, NY 14507
    /48

    $64,900

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 720 Sq Ft

    52 Vine Valley Park, Middlesex, NY 14507

    Vine Valley Park 3 bedroom one bathroom home on Lot 52. YOU ARE BUYING HOME ONLY, NOT LAND. Seasonal use property FULLY FURNISHED. 700' of lake frontage with new T-dock for hoists. Seller has owned home for 30 plus yrs. Great place to make lifetime family memories and new friends. Close knit Community. General store with some prepared foods, Community Center, boat launch and public beaches at end

    Tammy Hullings Listing by Amanda Grover Real Estate, LLC

    52 Vine Valley Park, Middlesex, NY 14507
  • 1234 Phelps Rd, Middlesex, NY 14507
    1234 Phelps Rd, Middlesex, NY 14507
    /2

    $199,000

    Sold Jan 02, 2026

    1234 Phelps Rd, Middlesex, NY 14507

    • 4 Beds
    • 2.5 Baths
    • 2,467 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Above List Price
    • $81/SF
    • 66 Days On Market

    Current Estimated Value $212,609

    Last Listing Agent Chad Loblaw Listing by Brix & Maven Realty Group LLC

    1234 Phelps Rd, Middlesex, NY 14507
    • 1561 S Lake Rd, Middlesex, NY 14507
      1561 S Lake Rd, Middlesex, NY 14507
      /2

      Not Listed For Sale

      1561 S Lake Rd, Middlesex, NY 14507

      • 10 Beds
      • 2 Baths
      • 3,000 Sq Ft
      • Built 1898
      1561 S Lake Rd, Middlesex, NY 14507

  • 105 Indian Vilage Park, Middlesex, NY 14507
    105 Indian Vilage Park, Middlesex, NY 14507
    105 Indian Vilage Park, Middlesex, NY 14507
    /22

    $35,000

    • 1 Bed
    • 1 Bath
    • 264 Sq Ft

    105 Indian Vilage Park, Middlesex, NY 14507

    THIS IS A GREAT LOW MAINTENANCE WAY TO SPEND TIME ON CANANDIAGUA LAKE AND GET YOUR FEET WET ! Canandaigua Lake access from Indian Village Park lot 105. This sale includes a park model tiny home on lot #105 and the storage shed. This is a 1994 Casa Villa model "1379 Villa Royal" 1 bedroom , 1 full bath unit. Enjoy the shade and outdoor dining if it rains under the attached covered deck. This is a

    Jim Moon Listing by Howard Hanna Lake Group

    105 Indian Vilage Park, Middlesex, NY 14507
  • 1795 Upper Hill Rd, Middlesex, NY 14507
    1795 Upper Hill Rd, Middlesex, NY 14507
    /2

    $240,000

    Sold Jun 15, 2026

    1795 Upper Hill Rd, Middlesex, NY 14507

    • 2 Beds
    • 1 Bath
    • 1,440 Sq Ft
    • Built 1998

    Last Sold Summary

    • $167/SF
    • 0 Days On Market

    Current Estimated Value $246,281

    Last Listing Agent Kurt Ledgerwood Listing by Griffith Realty Group

    1795 Upper Hill Rd, Middlesex, NY 14507
    • 5960 N Vine Valley Rd, Rushville, NY 14544
      5960 N Vine Valley Rd, Rushville, NY 14544
      /2

      Est $413,244

      Not Listed For Sale

      5960 N Vine Valley Rd, Rushville, NY 14544

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 2009
      5960 N Vine Valley Rd, Rushville, NY 14544

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