Homes for Sale in 22727

• 

  

  

  /71

  $499,000

  $36K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,512 Sq Ft

  104 Half Penny Ln, Madison, VA 22727

  BRAND-NEW ROOF! Along with lots of other newer items including Well Pump, Gutters, Culligan Whole House Filter System and Paint. HVAC IS 2020. Discover the space, flexibility, and lifestyle offered by this beautifully maintained home on over 3 scenic acres in the desirable Malvern of Madison community.With more than 3,500 square feet of finished living space, 3 spacious bedrooms, and 3

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  104 Half Penny Ln, Madison, VA 22727
• 

  

  

  /22

  $285,000

  $14K PRICE DROP

  • Land
  • 10 Acres
  • $28,500 per Acre

  0 Goods Ln, Madison, VA 22727

  BEAUTIFUL 10-ACRE BUILDING LOT | MADISON COUNTY, VALocated in beautiful Madison County, this approximately 10-acre parcel offers an exceptional opportunity to build a custom home, create a small farmette, or secure a special piece of Virginia countryside.The property is currently a well-maintained hay field that has not been exposed to livestock or agricultural chemicals for at

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  0 Goods Ln, Madison, VA 22727
• 

  

  

  /37

  $415,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,744 Sq Ft

  319 N Main St, Madison, VA 22727

  Circa 1840 | A Timeless Madison Treasure Step back in time and own a remarkable piece of Madisons history. Constructed around 1840 by John Richard Gooding and proudly featured in The Historic Homes of Madison, this well-maintained Colonial residence pre-dates the Civil War and is rich with architectural character and enduring charm. From the moment you arrive, the classic columned front porch and

  Kelly Duckett-Corbin RE/MAX Gateway

  319 N Main St, Madison, VA 22727
• 

  

  

  /6

  $1,450,000

  • Land
  • 244 Acres
  • $5,943 per Acre

  0 Mount Zion Church Rd Unit 27296213, Madison, VA 22727

  244.34 acres located in Madison County, VA . Beautiful rolling farm land surronded by multiple streams with abudant wildlife. Mix of wooded (mature hardwoods and planted pines) and open pasture. Currently used for cattle. Great location for homesite, farm, or recreational land. - Fully fenced - 200 Amp electrical service on site- Multiple home sites with interior roadsystem in

  Peter Vick

  0 Mount Zion Church Rd Unit 27296213, Madison, VA 22727
• 

  

  /2

  $399,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  0 55b-1 Shelby Rd Unit VAMA2002922, Madison, VA 22727

  CONSTRUCTION STARTED!- MELBOURNE MODEL - LOT 55B-1 Located on 1.343 acres in beautiful Madison County. One level living with 3 bedrooms, 2 baths, and unfinished walk-out level basement with rough-in plumbing for future bath. The home includes granite countertops, stainless steel appliances, and LVP flooring throughout. Carpet in bedrooms. There is still time to make some selections! Call today

  Janet Holden CENTURY 21 New Millennium

  0 55b-1 Shelby Rd Unit VAMA2002922, Madison, VA 22727
• 

  

  /50

  $539,000

  Open Sun 1PM - 4PM

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

  60 Bee Gum Way, Madison, VA 22727

  Location Location! Private Subdivision on 3,03 acres on a corner lot beautifully lanscaped for privacy. Paved driveway leads you to Split level 3 Bedrooms 31/2 Bath Home with two Master Bedrooms. Fantastic Community amenities Club House, Pool, family visiting accomidations. As you enter Open to kitchen and dining off the right living room area. Opposite end you have 2 bedrooms and a office or

  Heather Parker Fairfax Realty 50/66 LLC

  60 Bee Gum Way, Madison, VA 22727
• 

  

  /28

  $299,900

  $30K PRICE DROP

  • Land
  • 10 Acres
  • $29,990 per Acre

  0 Elly Rd Unit 674426, Aroda, VA 22709

  Private 10-acre wooded parcel in the quiet Aroda area of Madison County. Gently rolling terrain with mature woods and a small stream through the lot. Survey completed with proposed septic drainfield location identified, and property corners and drainfield area are clearly marked. Access via a shared private driveway serving several nearby properties, with a power line along one side of the

  Tom Woolfolk KELLER WILLIAMS ALLIANCE - CHARLOTTESVILLE

  0 Elly Rd Unit 674426, Aroda, VA 22709
• 

  

  /8

  $89,900

  $5K PRICE DROP

  • Land
  • 1 Acre
  • $89,900 per Acre

  0 Main St, Madison, VA 22727

  In-town lot, Gravity flow septic system approved, wooded, shared driveway with 1 other lot.

  Bonnie Coffey Samson Properties

  0 Main St, Madison, VA 22727
• 

  

  /51

  $519,000

  New Construction

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

  240 Windmill Ln, Madison, VA 22727

  Welcome home to this beautifully crafted new construction offering 3 bedrooms, 2 full baths, and a full unfinished walkout basement with rough-in plumbing, providing endless potential for future living space, recreation room, &/or additional bedrooms (4 bedroom septic). Designed with both style and functionality in mind, this home features a desirable split-bedroom floor plan, luxury vinyl plank

  Carl Broyles Montague, Miller & Company

  240 Windmill Ln, Madison, VA 22727
• 

  

  /18

  $299,000

  • Land
  • 10 Acres
  • $29,900 per Acre

  LOT 2 S F T Valley Rd, Madison, VA 22727

  Amazing Opportunity to own 10 acres on Scenic Byway 231!! Perc approved for a 4 bedroom conventional septic. Level building spot about half way up the mountain. Beautiful views from this parcel. Seasonal creek. Lots of wildlife.

  Dana Williams EXP Realty, LLC

  LOT 2 S F T Valley Rd, Madison, VA 22727
• 

  

  /58

  $377,700

  • 4 Beds
  • 2 Baths
  • 2,028 Sq Ft

  247 Little Church Ln, Madison, VA 22727

  Renovated One-Level Home on 2.17 Acres! This move-in-ready home has been thoughtfully renovated with modern comfort and style in mind. Features include a new kitchen, new HVAC system, new flooring, new windows, and beautifully updated bathrooms. The elegant primary bedroom provides a comfortable and inviting retreat. Enjoy the convenience of one-level living while having approximately 2.17 acres

  Jaime Pinto Funkhouser Real Estate Group

  247 Little Church Ln, Madison, VA 22727
• 

  

  /46

  $674,900

  • 4 Beds
  • 4 Baths
  • 2,991 Sq Ft

  1515 Desert Rd, Madison, VA 22727

  Whole House Generator!Welcome home to your own private retreat in the heart of Reva. Set on 3 peaceful acres surrounded by mature trees and picturesque countryside, this property offers the perfect balance of privacy, comfort, and outdoor living.From the moment you arrive, you'll appreciate the inviting covered front porch that wraps around to an expansive covered deck, creating

  Kerry Shannon Pearson Smith Realty, LLC

  1515 Desert Rd, Madison, VA 22727
• 

  

  /71

  $200,000

  • 4 Beds
  • 2.5 Baths
  • 2,932 Sq Ft

  150 N Main St, Madison, VA 22727

  List price is starting bid only. Home will be sold at auction 9/14/2026 @12pm. Contact us or your favorite real estate professional to view this home! Buying at auction is easy and transparent you can get financing!! Historic 4 BR/2.5 BA multi-tenant home on 1.619 +/- acres (circa 1820) -- Detached 30'x36' shop/garage/storage building -- Currently used as a duplex, but easily converted to a

  John Nicholls Nicholls Auction Marketing Group

  150 N Main St, Madison, VA 22727
• 

  

  /69

  $475,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  2303 W Hoover Rd, Haywood, VA 22722

  Recently renovated with the intention of being a forever home, this charming 1940s farmhouse was lovingly transformed while preserving the character, warmth, and timeless appeal that make it so special. Each project was completed with quality, durability, and longevity in mind.With 1,144 square feet, the home offers just enough space to get away to the extraordinarily scenic countryside

  Robin Garbe Century 21 Redwood Realty

  2303 W Hoover Rd, Haywood, VA 22722
• 

  

  /18

  $309,000

  • Land
  • 10.34 Acres
  • $29,884 per Acre

  LOT 1 S F T Valley Rd, Madison, VA 22727

  Absolutely breathtaking lot on Scenic Highway 231!!!!!! Entrance is in place and approved by VDOT. 4 bedroom perc site approximately half way up the mountain on a lovely flat knoll. Almost 180 degrees of Mountain Views from the building spot. Wildlife trails everywhere! This is a rare opportunity!!!

  Dana Williams EXP Realty, LLC

  LOT 1 S F T Valley Rd, Madison, VA 22727
• 

  

  /136

  $5,850,000

  • 3 Beds
  • 2 Baths
  • 3,023 Sq Ft

  1830 Thrift Rd, Madison, VA 22727

  Woodbourne Estate, circa 1810, is a National and Virginia registered historic landmark set on 53 acres in Madison County, less than 90 miles from Washington, D.C. Nestled in the foothills of the Blue Ridge Mountains, the property combines two extraordinary elements: the award-winning Bald Top Brewing Company and the beautifully restored Woodbourne Manor. Together they create a rare chance to

  Daniel Langberg Virginia Estates, Inc.

  1830 Thrift Rd, Madison, VA 22727
• 

  

  /31

  $249,900

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  258 Laurel Dr, Madison, VA 22727

  Escape to your own slice of nature in this cozy 1-bedroom, 1-bath cottage tucked away on 4.1 wooded acres, with Garth Run access on the back of the property. Inside, the home offers warm, natural charm with wood cabinetry and butcher block countertops in the kitchen, complemented by newer stainless steel appliances that bring a modern touch to the classic cottage feel. Recent updates include a

  Carrie Brown Montague, Miller & Company

  258 Laurel Dr, Madison, VA 22727
• 

  

  /45

  $3,400,000

  • 5 Beds
  • 3 Baths
  • 2,760 Sq Ft

  3111 S Seminole Trail, Madison, VA 22727

  Beautiful 115± acre countryside property in Madison County offering open fields, established fencing and a peaceful rural setting ideal for horses, farming or a private country estate. The land features multiple paddocks, run-in sheds, and a charming brick manager’s residence, providing immediate usability while allowing flexibility for future improvements. The gently rolling acreage offers

  Sharon Merrick HOWARD HANNA ROY WHEELER REALTY CO.- CHARLOTTESVILLE

  3111 S Seminole Trail, Madison, VA 22727
• 

  

  /18

  $345,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  399 Shelby Rd, Madison, VA 22727

  This newly renovated 3-bed, 2-bath home in Madison County makes it easy to picture your life here, waking up to panoramic mountain views, sipping coffee on your deck, and coming back to a space that feels warm and effortless. Inside, the granite countertops and luxury vinyl plank flooring throughout add a clean, modern feel that’s both beautiful and practical for everyday living. The open layout

  Ryan Dickerson Samson Properties

  399 Shelby Rd, Madison, VA 22727
• 

  

  /4

  $99,900

  • Land
  • 3.07 Acres
  • $32,541 per Acre

  0 Malvern Dr Unit VAMA2002938, Madison, VA 22727

  Gorgeous 3+ Acre Building Lot in Sought After Malvern. Lot offers a ton of wide open space to build your forever home! Parcel can also be purchased with neighboring property - 359 Malvern Drive.

  Philip Thornton Long & Foster Real Estate, Inc.

  0 Malvern Dr Unit VAMA2002938, Madison, VA 22727
• 

  

  /18

  $2,472,000

  • Land
  • 23.09 Acres
  • $107,059 per Acre

  0 Main St N Unit VAMA2002616, Madison, VA 22719

  Discover an exceptional opportunity to acquire three contiguous land parcels totaling 23.103 acres in a highly desirable location between N. Main Street and Business Route 29 in Madison VA. Offering a rare combination of Business (B1) and Residential (R1) zoning, this property provides outstanding flexibility for commercial development, residential housing, or a mixed‐use project.Parcel 1 –

  Kim Gallihugh CENTURY 21 New Millennium

  0 Main St N Unit VAMA2002616, Madison, VA 22719
• 

  

  /3

  $312,000

  $40K PRICE INCREASE

  • Land
  • 2.83 Acres
  • $110,247 per Acre

  0 Seminole Trail Unit VAMA108074, Madison, VA 22727

  Commercial Opportunity adjoining Madison Plaza Food Lion Center. Exceptionally well located land parcels with public utilities available. Development plan has all the approvals for a business park with future uses including restaurants, office, retail and service businesses. The property is located at a traffic light across US 29 from the Madison County High School and the southern crossover.

  Bill Gentry Jefferson Land & Realty, Inc.

  0 Seminole Trail Unit VAMA108074, Madison, VA 22727
• 

  

  /57

  $600,000

  • 3 Beds
  • 3 Baths
  • 2,621 Sq Ft

  398 Ruth Hollow Fire Trail, Madison, VA 22727

  Set on 10.88 wooded acres just 7 miles from the Town of Madison, this move-in-ready 3BD/3BA home sits on an elevated, private lot and has been fully renovated. The main level offers approx. 1,700 finished sq ft, a 1,100+ sq ft finished walkout basement and a covered porch with wooded views. The ideal blend of privacy and convenience. Inside, the open layout includes a fully updated kitchen, new

  JENNIFER KIRBY MONTAGUE, MILLER & CO. - WESTFIELD

  398 Ruth Hollow Fire Trail, Madison, VA 22727
• 

  

  /65

  $1,625,000

  Coming Soon

  • 3 Beds
  • 3 Baths
  • 3,802 Sq Ft

  3638 Oak Park Rd, Madison, VA 22727

  Enjoy your morning coffee from the expansive deck while watching your horses or livestock graze in the beautifully maintained pastures secured by three-board fencing, with the tops of the Blue Ridge Mountains in the distance. Set on 44± acres & bordered on 3 sides by meandering streams, the property offers exceptional privacy & is a nature lover's sanctuary, where you can watch the purple martins

  Gayle Harvey GAYLE HARVEY REAL ESTATE, INC

  3638 Oak Park Rd, Madison, VA 22727
• 

  

  /12

  $715,000

  • Land
  • 42 Acres
  • $17,024 per Acre

  TM 39-31&33b Thrift Rd, Madison, VA 22727

  "White Oak Run" - this is one of the most stunning land parcels in Central Virginia. Long State road frontage, with elevated building site, looking at the Blue Ridge and Old Rag Mountain. 42+ Acres that are in land use taxation. Soil evaluation for a four bedroom septic. Land is in predominantly mature hardwoods, and approximately eleven acres open. Several springs feed White Oak Run. New access

  Bill Gentry JEFFERSON LAND & REALTY

  TM 39-31&33b Thrift Rd, Madison, VA 22727
• 

  

  /57

  $424,900

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  359 Malvern Dr, Madison, VA 22727

  Quintessential Malvern! Do not miss this gorgeous light-filled gem in sought after Malvern. Situated on almost 4 acres, this architecturally interesting home is truly one of a kind! Nestled amongst the mature trees and landscaping, the property offers abundant privacy, yet this community is conveniently located a short distance from major commuter routes. Offering a traditional, though

  Philip Thornton Long & Foster Real Estate, Inc.

  359 Malvern Dr, Madison, VA 22727
• 

  

  /6

  $1,450,000

  $400K PRICE DROP

  • Land
  • 244.34 Acres
  • $5,934 per Acre

  0 Mount Zion Church Rd Unit 2604632, Madison, VA 22727

  244.34 acres located in Madison County, VA• 200 Amp electrical service on site• Multiple home sites• Interior road system in place• Property subject to nutrient credit and streamrestoration easements• 91.4 acres in the nutrient credit easement- plantedin loblolly pines in 2023• Great recreation land with abundant wildlife Includes 4 tax

  Peter Vick Commonwealth Residential Rlty

  0 Mount Zion Church Rd Unit 2604632, Madison, VA 22727
• 

  

  /36

  $699,000

  • Land
  • 29.52 Acres
  • $23,679 per Acre

  0 Hurt Hollow Rd, Banco, VA 22711

  Amazing opportunity to own 29.5 Acres in Madison County near the Shenandoah National Park! This property offers multiple elevated building sites with potential views of Double Top Mountain! There is a creek meandering along the bottom of the property. Trails are already in place to take a walk and enjoy everything nature has to offer! Plenty of wildlife!

  Dana Williams EXP Realty, LLC

  0 Hurt Hollow Rd, Banco, VA 22711
• 

  

  /3

  $411,500

  • Land
  • 3.74 Acres
  • $110,027 per Acre

  0 Seminole Trail Unit VAMA108070, Madison, VA 22727

  Commercial Opportunity adjoining Madison Plaza Food Lion Center. Exceptionally well located land parcels with public utilities available. Development plan has all the approvals for a business park with future uses including restaurants, office, retail and service businesses. The property is located at a traffic light across US 29 from the Madison County High School and the southern crossover.

  Bill Gentry Jefferson Land & Realty, Inc.

  0 Seminole Trail Unit VAMA108070, Madison, VA 22727
• 

  

  /70

  $524,900

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  359 Malvern Dr, Madison, VA 22727

  Quintessential Malvern! Do not miss this gorgeous light-filled gem in sought after Malvern. Situated on over 7 acres, this architecturally interesting home is truly one of a kind! Nestled amongst the mature trees and landscaping, the property offers abundant privacy, yet this community is conveniently located a short distance from major commuter routes. Offering a traditional, though functional,

  Philip Thornton Long & Foster Real Estate, Inc.

  359 Malvern Dr, Madison, VA 22727
• 

  

  /50

  $4,450,000

  • 5 Beds
  • 6 Baths
  • 5,153 Sq Ft

  4578 Ruth Rd, Madison, VA 22727

  Set amidst 17 beautifully landscaped acres, Monte Ventoso is an extraordinary Italian-inspired villa offering the ambiance of a private Mediterranean retreat in the foothills of the Blue Ridge Mountains. Ideally positioned between Washington, D.C. and Charlottesville, VA, the estate combines exceptional privacy with convenient accessibility. A handcrafted fountain imported from Italy creates a

  COURT NEXSEN MCLEAN FAULCONER INC., REALTOR

  4578 Ruth Rd, Madison, VA 22727
• 

  

  /69

  $675,000

  $15K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 4,544 Sq Ft

  66 Wrights Ln, Madison, VA 22727

  Escape to the peaceful beauty of Madison County with this beautifully maintained 3 bedroom, 3.5 bathroom ranch home nestled on nearly 5 private acres. Offering the convenience of one-level living plus a fully finished basement, this spacious home provides plenty of room for everyday living, entertaining, and relaxing. The thoughtfully designed floor plan features a welcoming living area with a

  Cindy Reed EXP Realty, LLC

  66 Wrights Ln, Madison, VA 22727
• 

  

  /67

  $450,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  803 Weaver Hollow Rd, Banco, VA 22711

  Charming Country Retreat on Nearly 8 Acres — Peaceful Setting with Endless Potential! Nestled in the heart of the countryside yet conveniently located just a short drive to Madison, Culpeper, Graves Mountain Lodge, White Oak Canyon, Shenandoah National Park, the Rapidan River, and countless outdoor adventures, this solidly built one-level home offers the perfect blend of privacy, comfort, and

  Kelly Duckett-Corbin RE/MAX Gateway

  803 Weaver Hollow Rd, Banco, VA 22711
• 

  

  /132

  $875,000

  • 4 Beds
  • 3.5 Baths
  • 4,497 Sq Ft

  202 Innovation Ln, Madison, VA 22727

  Welcome home to this stunning brick, stone, and vinyl sided Colonial nestled on 3.86 picturesque acres in the heart of Madison County. Offering over-sized living spaces, timeless curb appeal, and endless possibilities, this exceptional property is the perfect blend of elegance, comfort, and country living.Inside, you'll find four spacious bedrooms and three full baths, with generous room

  Brenda Payne Long & Foster Real Estate, Inc.

  202 Innovation Ln, Madison, VA 22727
• 

  

  /70

  $649,900

  • 4 Beds
  • 4.5 Baths
  • 3,120 Sq Ft

  1245 Parish Rd, Reva, VA 22735

  Nestled on 9.1 private acres in beautiful Madison County, this spacious 4-bedroom, 4.5-bath home offers the perfect combination of comfortable living, peaceful surroundings, and room to spread out.The inviting family room features a wood stove, creating a warm and welcoming gathering space, while the adjoining dining room offers French doors leading to a large rear deck overlooking the

  Kim Gallihugh CENTURY 21 New Millennium

  1245 Parish Rd, Reva, VA 22735
• 

  

  /9

  $379,500

  $79K PRICE DROP

  • Land
  • 10.56 Acres
  • $35,938 per Acre

  48-13o,13v&13u Courthouse Mountain Rd, Madison, VA 22727

  Three exceptionally well located land parcels along Courthouse Mountain Road; adjacent to the Town of Madison. The wooded parcels have soil evaluations for (3) bedroom septic systems. REC electric service available. All parcels are in hardwood timber and accessible from a private road (Toscana Lane). It is uncommon to have parcels with the feeling of privacy and yet within a two minute drive to

  Bill Gentry JEFFERSON LAND & REALTY

  48-13o,13v&13u Courthouse Mountain Rd, Madison, VA 22727
• 

  

  /44

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  2242 Shelby Rd, Madison, VA 22727

  Lovely Rancher with full finished basement. Nice size kitchen, Fireplace in the living room, Separate Dining rm, 2 bedrooms on the main level, 1 bedroom in the basement, 2 full baths, freshly painted upstairs interior. Roof replaced 4 years ago, Washer and Dryer fairly new conveys, HVAC replaced in 2025, Dbl Pane Tilt Windows, 3 Acres fully fenced with extensive landscaping. Walk-in gun safe in

  Bonnie Coffey Samson Properties

  2242 Shelby Rd, Madison, VA 22727
• 

  

  /10

  $50,000

  • Land
  • 1.07 Acres
  • $46,729 per Acre

  0 Washington St, Madison, VA 22727

  List price is starting bid only. Land will be sold 9/14/2026 @12pm. Contact us or your favorite real estate professional to view this home! Buying at auction is easy and transparent you can get financing!! 1.073 +/- acre multi-use vacant land parcel -- The parcel fronts Washington St. and has 140' +/- of road frontage -- Excellent opportunity for potential residential, commercial or investment

  John Nicholls Nicholls Auction Marketing Group

  0 Washington St, Madison, VA 22727
• 

  

  /17

  $430,000

  • Land
  • 39.18 Acres
  • $10,975 per Acre

  TM 24-1 Mitchell Mountain Rd, Haywood, VA 22722

  This is a newly surveyed 39+ acre parcel, located within a short drive to the Towns of Madison and Culpeper; but still in a area surrounded by other large farms and land tracts. The subject property has long State road frontage, and is in Forestal Land Use Taxation. The land is wholly wooded, in a balanced mix of assorted hardwood timber and mountain laurel. There are two spring fed creeks

  Bill Gentry JEFFERSON LAND & REALTY

  TM 24-1 Mitchell Mountain Rd, Haywood, VA 22722
• 

  

  /93

  $749,900

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  1765 Oneals Rd, Madison, VA 22727

  Amazing Views-Amazing Home! Thoughtfully crafted, meticulously renovated and expanded in 2025/26, this amazing 3-bedroom, 2-bath ranch-style home blends modern luxury with timeless country charm across 1,872 square feet of custom-designed main floor living space, offering a harmonious blend of luxury and comfort in a serene rural setting. The front concrete walkway and curved steps welcome you to

  Mr. Mike Butters EXP Realty, LLC

  1765 Oneals Rd, Madison, VA 22727

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