Middletown, VA Homes

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  /54

  $2,999,900

  • 3 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  1115 Chapel Rd, Middletown, VA 22645

  Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern

  Lisa Blansett Mountains Edge Realty LLC

  1115 Chapel Rd, Middletown, VA 22645
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  /18

  $105,000 Sold Sep 19, 2025

  • Land
  • 6.26 Acres
  • $16,773 per Acre

  • 215 Days On Market

  Lot 36a Red Hawk Rd, Middletown, VA 22645

  Welcome to River Ridge Community. This 6+ acres wooded lot is prepped and ready for you to build your dream home. Whether you’re seeking a peaceful retreat, a weekend getaway, or a new permanent residence, this wooded property is your gateway to tranquility and natural beauty. The gravel driveway entrance and culvert have already been installed, the septic is approved for 3 bedroom septic

  Roger Tapscott Morris & Co. Realty, LLC

  Lot 36a Red Hawk Rd, Middletown, VA 22645
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  /43

  Est $837,292 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,604 Sq Ft

  322 Thomas Dr, Middletown, VA 22645

  322 Thomas Dr, Middletown, VA 22645
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  /55

  $459,000

  • 5 Beds
  • 2.5 Baths
  • 2,198 Sq Ft

  100 Coville St, Middletown, VA 22645

  Welcome home! Spacious craftsman style home in Villages at Middletown. The main level with large kitchen, dining and living room area is open and light-filled, making it perfect for entertaining. Walk out onto the back deck to enjoy the views with your morning coffee (or dine outside, there's plenty of room!)The upper level of this home boasts 5 bedrooms (or potentially use one as an office

  Amy Conover Samson Properties

  100 Coville St, Middletown, VA 22645
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  /12

  $549,999 Sold Sep 15, 2025

  • 1,610 Sq Ft
  • $342/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  107 Seventh St, Middletown, VA 22645

  Explore this beautiful Onyx model home! Just off the entry, you'll find two secondary bedrooms flanking a full bath. Toward the back of the home, there's a spacious open great room with an electric fireplace set in a tiled wall, a dining area with built-in cabinetry, a conveniet tech center and a covered patio. The kitchen offers a wide center island, a built-in pantry, luxury vinyl plank

  Richmond American Homes

  107 Seventh St, Middletown, VA 22645
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  /25

  Est $802,975 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,824 Sq Ft

  275 Thomas Dr, Middletown, VA 22645

  275 Thomas Dr, Middletown, VA 22645
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  /92

  $999,900

  • 5 Beds
  • 6 Baths
  • 5,335 Sq Ft

  190 Newell Dr, Middletown, VA 22645

  Experience peace and tranquility of life in one of Middletown's most desirable & beautifully maintained communities, "Sheridan Estates"—an intimate enclave of just 8 custom homes, offering an upscale yet welcoming atmosphere, perfect for those who value comfort, style, and serenity with NO HOA! A brief 5 miles to I-81 to Rt 66 makes it an easy commuting distance to downtown Washington DC. Only 1

  Michele Gibson Samson Properties

  190 Newell Dr, Middletown, VA 22645
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  /43

  $400,000 Sold Sep 12, 2025

  • 1,728 Sq Ft
  • $231/SF
  • 54 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1998

  152 Lusitano Ln, Middletown, VA 22645

  Follow Your Heart to the Castle at Hites Chapel. A Stunning 3 Story Contemporary Style Home sitting on 2.1 Acres among Massive Old Oaks and other Deciduous Tress and Flora. The 1700+ Sq. Ft. Home was Architect Designed for the Previous Owner with Dryvit exterior walls, Standing Seam metal roof and 2x6 sidewall construction for Energy Efficiency. The Home has Two Large Decks on the First and

  william sams Crossroads, Realtors

  152 Lusitano Ln, Middletown, VA 22645
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  /85

  Est $729,415 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 3,824 Sq Ft

  80 Little Sorrel Dr, Middletown, VA 22645

  80 Little Sorrel Dr, Middletown, VA 22645
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  /41

  $337,000

  • 3 Beds
  • 2.5 Baths
  • 1,307 Sq Ft

  119 Kensington Cir, Middletown, VA 22645

  Beautiful three-level townhome in the Enfield Knolls community of charming Middletown, VA. The open floor plan is filled with natural light and features a modern kitchen with stainless steel appliances and a moveable island that conveys. Enjoy durable luxury vinyl plank flooring, a composite deck for outdoor relaxation, and the convenience of bedroom-level laundry. With 3 bedrooms, 2.5 baths, and

  Natalie Langford ERA Oakcrest Realty, Inc.

  119 Kensington Cir, Middletown, VA 22645
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  /26

  $449,000 Sold Sep 08, 2025

  • 1,900 Sq Ft
  • $236/SF
  • 59 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2023

  131 Birmingham Dr, Middletown, VA 22645

  It's Time to Rediscover the Shenandoah Valley again, here between the Blue Ridge Mountains & the Foothills to the Allegheny Mountains is a small town feel with short access to many state parks lies this Spacious Home with Room to Grow! Come Check out this 4-bedroom 2.5 bath on 3 levels. Main level has a Family room that is Open to the Kitchen That's Nice & Bright with an Island & Stainless-Steel

  Richard Kozlowski Long & Foster Real Estate, Inc.

  131 Birmingham Dr, Middletown, VA 22645
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  /25

  Est $199,934 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 910 Sq Ft

  23 Guard Rd, Middletown, VA 22645

  23 Guard Rd, Middletown, VA 22645
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  /75

  $365,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,484 Sq Ft

  2425 Third St, Middletown, VA 22645

  Welcome home to Third St!!! The sellers are motivated and the home is simply waiting for you!!! This lovely and well maintained split foyer is on one acre of unrestricted property and also boasts quite a number of upgrades! There is lots of space for entertaining, particularly outside with a fairly level landscape, and in the home there are ample rooms to work with. This home has lots of

  Nicole Lewis Coldwell Banker Premier

  2425 Third St, Middletown, VA 22645
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  /60

  $645,000 Sold Aug 29, 2025

  • 2,401 Sq Ft
  • $269/SF
  • 34 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  111 Jackson Place, Middletown, VA 22645

  All brick home that backs to the 4th & 5th green of Sly Fox Golf Course on 1 acre! No HOA. Comcast internet. Public water & sewer. This home has been updated with new roof (2024), new windows on front and side of home, custom shutters and plantation blinds throughout. HVAC 2016, Water Heater 2025. Amazing patio and hardscape out back that overlooks the golf course! Upgraded kitchen w/all

  Traci Shoberg RE/MAX Roots

  111 Jackson Place, Middletown, VA 22645
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  /17

  Est $551,701 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  3586 Reliance Rd, Middletown, VA 22645

  3586 Reliance Rd, Middletown, VA 22645
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  /30

  $180,000

  • 1 Bed
  • 1 Bath
  • 1,905 Sq Ft

  7189 Middle Rd, Middletown, VA 22645

  ARE YOU LOOKING FOR A FLIP, RENTAL OR AIRBNB? HERE IS YOUR PLACE! 2 DWELLINGS AND GARAGE ON 1.41 ACRES. FORMERLY HAWKINS GROCERY BUILT IN 1946. FUEL TANKS HAVE BEEN REMOVED AND SELLERS HAVE SOIL REPORTS AND THEY ARE CLEAN. NO WELL ON PROPERTY. THERE ARE 3 CISTERNS. HOUSES SHARE CONVENTIONAL SEPTIC.

  Jacquelyn Rizzari MarketPlace REALTY

  7189 Middle Rd, Middletown, VA 22645
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  /44

  $539,900 Sold Aug 27, 2025

  • 2,308 Sq Ft
  • $234/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  200 High St, Middletown, VA 22645

  Fantastic Opportunity – One-Owner Country Charmer! Don’t miss this great opportunity to own a beautifully two-story home on a landscaped 1.26-acre lot, conveniently located near shopping and I-81. This spacious home offers 4 bedrooms and 2.5 bathrooms. The sunny kitchen features an island bar, solid surface countertops, and double ovens—perfect for cooking and gathering. It opens to a large

  Brett Sowder RE/MAX Roots

  200 High St, Middletown, VA 22645
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  /88

  Est $623,282 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  2857 Reliance Rd, Middletown, VA 22645

  2857 Reliance Rd, Middletown, VA 22645
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  /19

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  2432 Laurel Ln, Middletown, VA 22645

  This recently updated three-bedroom, two-bath home is available in the charming town of Middletown, VA. Conveniently located near Main Street, you will quickly appreciate the vibrant community, which features locally owned restaurants, shops, and various community events. The home boasts modern finishes and is filled with an abundance of natural light. The semi-open concept kitchen and living

  Jen Moore ERA Oakcrest Realty, Inc.

  2432 Laurel Ln, Middletown, VA 22645
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  /34

  $391,550 Sold Aug 19, 2025

  • 1,352 Sq Ft
  • $290/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  310 Coville St, Middletown, VA 22645

  COMING SOON - June 26th, like new construciton in amazing location with easy access to I-81 Open house expectd on June 29th. Main level living in this 2020-built Ryan Homes community, Villages at Middletown. Three bed, two full bath on 1352 square foot main level with split bedroom layout and open kitchen/living space. Upgraded cabinetry in the kitchen and baths, premium grade vinyl floor(perfect

  Doug Rapport Berkshire Hathaway HomeServices PenFed Realty

  310 Coville St, Middletown, VA 22645
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  /35

  Est $596,400 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  2768 Reliance Rd, Middletown, VA 22645

  2768 Reliance Rd, Middletown, VA 22645
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  /12

  $799,000

  • Land
  • 3.84 Acres
  • $208,073 per Acre

  0 Reliance Rd Unit VAFV2024656, Middletown, VA 22645

  Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond

  Jim Guisewhite Commercial Specialists

  0 Reliance Rd Unit VAFV2024656, Middletown, VA 22645
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  /58

  $660,000 Sold Aug 14, 2025

  • 2,671 Sq Ft
  • $247/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2022

  7040 Valley Pike, Middletown, VA 22645

  Tucked away on 2 peaceful acres surrounded by mature trees, this stunning 4 bedroom, 2.5 bath home offers both privacy and luxury. One bedroom is perfect for a home office or flex space. The expansive gourmet kitchen features granite countertops, under-cabinet lighting, and ample cabinet space—perfect for the home chef. Enjoy durable LVP flooring throughout and beautifully tiled bathrooms,

  Daryl Stout RE/MAX Real Estate Connections

  7040 Valley Pike, Middletown, VA 22645
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  /37

  Est $508,350 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  2722 Reliance Rd, Middletown, VA 22645

  2722 Reliance Rd, Middletown, VA 22645
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  /2

  $5,750,000

  • Land
  • 41.57 Acres
  • $138,321 per Acre

  226 Reliance Rd, Middletown, VA 22645

  41.5 acres of prime interstate land perfect for a commercial or industrial development. Zoned acres B2 and remaining RA.

  Jason Aikens RE/MAX Roots

  226 Reliance Rd, Middletown, VA 22645
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  /52

  $870,500 Sold Jul 31, 2025

  • 3,010 Sq Ft
  • $289/SF
  • 75 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2023

  810 Huttle Rd, Middletown, VA 22645

  UNIQUE TO THIS HOME, MAIN LEVEL PRIMARY, WITH SECONDARY FAMILY ROOM ON THE UPPER LEVEL. THIS IS A MUST SEE...Brand new home crafted by a premier custom builder, showcasing exceptional quality, modern design, and thoughtful details throughout.Step inside to be greeted by an array of custom features and high-end finishes designed to elevate your living experience. The elegant

  Kathy Colville Century 21 Redwood Realty

  810 Huttle Rd, Middletown, VA 22645
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  /84

  Est $766,584 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,432 Sq Ft

  902 Forest Grove Rd, Middletown, VA 22645

  902 Forest Grove Rd, Middletown, VA 22645
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  /14

  $595,000

  • Land
  • 1.38 Acres
  • $431,159 per Acre

  0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645

  Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high

  Kevin Smith Sager Real Estate

  0 Reliance Rd Unit VAFV2013246, Middletown, VA 22645
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  /57

  $494,000 Sold Jul 31, 2025

  • 2,180 Sq Ft
  • $227/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  131 Seventh St, Middletown, VA 22645

  Modern comfort meets small-town charm in this nearly new home! Built just one year ago, this well-maintained property features 3 official bedrooms plus a non-conforming 4th bedroom—perfect for guests, a home office, or extra living space. Enjoy an open-concept layout, a bright loft area, and a spacious walkout basement with tons of potential. The fully fenced backyard is ideal for pets, play, or

  Grace Eberly Realty ONE Group Old Towne

  131 Seventh St, Middletown, VA 22645
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  /50

  Est $2,095,342 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  171 Crest River Dr, Middletown, VA 22645

  171 Crest River Dr, Middletown, VA 22645
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  /56

  $410,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,776 Sq Ft

  2137 Reliance Rd, Middletown, VA 22645

  Welcome to this beautifully updated ranch-style home nestled in the Shenandoah Valley — offering a blend of comfort, charm, and breathtaking views on 2.34 private acres. This cozy 3-bedroom, 1.5-bath home features a dining room, a spacious living room with a gas fireplace, hardwood floors, and stunning mountain views to take in right from your window. Start your mornings with a cup of coffee on

  Kimberlee Wergland Realty ONE Group Old Towne

  2137 Reliance Rd, Middletown, VA 22645
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  /66

  $620,000 Sold Jul 21, 2025

  • 2,416 Sq Ft
  • $257/SF
  • 33 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  168 Thomas Dr, Middletown, VA 22645

  Well-maintained 4BR/2.5BA custom-built home nestled on a 2.54 acre lot in the sought-after Stonewall Estates neighborhood, bordering Sly Fox Golf Course.Features include a large main-level master suite with vaulted ceiling and French doors that access the large Trex deck. Master bath includes jetted corner tub with his/her separate vanities and ceramic tile floors. Open floor plan

  Ken Evans RE/MAX Real Estate Connections

  168 Thomas Dr, Middletown, VA 22645
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  /60

  Est $545,086 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,272 Sq Ft

  253 Lakeland Cir, Middletown, VA 22645

  253 Lakeland Cir, Middletown, VA 22645
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  /6

  $199,900 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,053 Sq Ft

  2085 Chapel Rd, Middletown, VA 22645

  Welcome home to this charming 2-bedroom, 1-bath Cape Cod just outside the town limits of Middletown, VA! Offering comfort and convenience in a peaceful setting, this home is full of character and potential. Don’t miss the opportunity to make it yours—more photos coming soon!

  Abby Walters Preslee Real Estate

  2085 Chapel Rd, Middletown, VA 22645
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  /27

  $318,000 Sold Jul 19, 2025

  • 1,494 Sq Ft
  • $213/SF
  • 43 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1909

  7979 Main St, Middletown, VA 22645

  Welcome home to 7979 Main St in the quaint little town of Middletown! This 3 Bedroom, 1.5 bath early 1900s colonial is just beaming with charm! With its location right on Main St, enjoy walking to the local shops or just sit outside on your lovely front porch and relax and have a front row seat to all of Middletown’s local festivities! It actually has a wonderful, serene backyard space with a

  Becky Wallace Pearson Smith Realty, LLC

  7979 Main St, Middletown, VA 22645
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  /37

  Est $347,126 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  330 Catletts Ford Rd, Middletown, VA 22645

  330 Catletts Ford Rd, Middletown, VA 22645
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  /55

  $1,250,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,696 Sq Ft

  112 Woods Way, Middletown, VA 22645

  Privacy and Relaxation! Sited well off the road at the high point of a secluded 35 acre site with 400 feet of Shenandoah River frontage this home features expansive windows; solid log construction; a stunning, centrally located, wood-burning fireplace and chimney; gourmet kitchen with stainless steel appliances; and a wrap-around deck above the undisturbed woodlands and North Fork of the

  Bradley Boland Keller Williams Realty Dulles

  112 Woods Way, Middletown, VA 22645
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  /7

  $251,000 Sold Jul 18, 2025

  • Land
  • 0.54 Acre
  • $464,815 per Acre

  • 144 Days On Market

  7881 Main St, Middletown, VA 22645

  Prime Commercial & Residential Opportunity in Historic Middletown!Located in the heart of Middletown’s Historic District, 7881 Main St offers a unique opportunity for commercial and residential development. Zoned B-1 in Frederick County, this 0.54-acre lot allows for a variety of uses, including retail, office, restaurant, personal services, and residential. The property can be subdivided

  Johnny Mendez William G. Buck & Assoc., Inc.

  7881 Main St, Middletown, VA 22645
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  /101

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  3850 Long Meadow Rd, Middletown, VA 22645

  3850 Long Meadow Rd, Middletown, VA 22645
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  /19

  $2,300,000 Under Contract

  • Land
  • 183.19 Acres
  • $12,555 per Acre

  0 Reliance Rd Unit VAWR139520, Middletown, VA 22645

  Large tract of land bordering the Sly Fox Golf Club. 183 wooded acres suitable for subdivision. The seller has created a sketch showing 36 lots for this subdivision that is BY RIGHT SO it cannot be denied! there are 24 1-acre lots; 9 ten-acre lots; 2 - 22 acre lots; and 1 - 20 acre lot & innternal streets that would stem from Reliance Rd. Tax Map #11 13 (55.2704 ac), TM#11 12 (103.00 ac), TM# 11

  Tana Hoffman Sager Real Estate

  0 Reliance Rd Unit VAWR139520, Middletown, VA 22645

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