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Winchester, VA - homes for sale
118 of 118 results displayed
- New
$409,900Active3 beds 2 baths1,764 sq. ft.320 E Piccadilly St, WINCHESTER, VA 22601
MLS# VAWI2010018Listed by: COLONY REALTY - Coming SoonOpen Sat, 1 to 4pm
$310,000Coming Soon3 beds 1 baths423 Shenandoah Pl, WINCHESTER, VA 22601
MLS# VAWI2010016Listed by: KELLER WILLIAMS REALTY/LEE BEAVER & ASSOC. - New
$245,000Active2 beds 3 baths1,280 sq. ft.2967 Sorrell Ct, WINCHESTER, VA 22601
MLS# VAWI2010008Listed by: TRECK REALTY LLC - New
$489,900Active4 beds 3 baths2,100 sq. ft.620 Crystal Ct, WINCHESTER, VA 22601
MLS# VAWI2010000Listed by: REALTY FC - New
$279,000Active2 beds 1 baths759 sq. ft.424 Highland Ave, WINCHESTER, VA 22601
MLS# VAWI2010002Listed by: LONG & FOSTER REAL ESTATE, INC. - New
$279,000Active3 beds 2 baths1,144 sq. ft.106 W Southwerk St, WINCHESTER, VA 22601
MLS# VAWI2009996Listed by: ERA OAKCREST REALTY, INC. - Coming Soon
$339,900Coming Soon3 beds 2 baths2817 Papermill Rd, WINCHESTER, VA 22601
MLS# VAWI2009982Listed by: CENTURY 21 REDWOOD REALTY - New
$399,990Active3 beds 4 baths1,784 sq. ft.234 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009986Listed by: DRB GROUP REALTY, LLC - New
$1,100,000Active2.3 AcresPleasant Valley, WINCHESTER, VA 22601
MLS# VAFV2039602Listed by: COLDWELL BANKER PREMIER 
$224,900Pending3 beds 2 baths1,621 sq. ft.632 Watson Ave, WINCHESTER, VA 22601
MLS# VAWI2009994Listed by: PEARSON SMITH REALTY, LLC- New
$500,000Active4 beds 4 baths2,524 sq. ft.2643 Middle Rd, WINCHESTER, VA 22601
MLS# VAWI2009924Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - New
$549,900Active4 beds 3 baths2,234 sq. ft.1917 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009976Listed by: SAMSON PROPERTIES 
$419,900Pending3 beds 2 baths1,632 sq. ft.431 Jefferson St, WINCHESTER, VA 22601
MLS# VAWI2009944Listed by: COLONY REALTY- New
$389,990Active3 beds 4 baths1,784 sq. ft.218 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009978Listed by: DRB GROUP REALTY, LLC 
$337,000Active3 beds 2 baths1,280 sq. ft.19 W Germain St, WINCHESTER, VA 22601
MLS# VAWI2009802Listed by: COTTAGE STREET REALTY LLC
$389,900Pending4 beds 2 baths1,949 sq. ft.232 Myrtle Ave, WINCHESTER, VA 22601
MLS# VAWI2009914Listed by: LONG & FOSTER REAL ESTATE, INC.
$449,990Active4 beds 4 baths1,939 sq. ft.1809 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009962Listed by: D R HORTON REALTY OF VIRGINIA LLC
$449,990Active4 beds 4 baths1,920 sq. ft.1813 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009964Listed by: D R HORTON REALTY OF VIRGINIA LLC
$414,990Active4 beds 4 baths1,920 sq. ft.1821 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009960Listed by: D R HORTON REALTY OF VIRGINIA LLC
$599,000Pending3 beds 3 baths2,964 sq. ft.425 Briarmont Dr, WINCHESTER, VA 22601
MLS# VAWI2009926Listed by: KELLER WILLIAMS REALTY- Coming Soon
$735,000Coming Soon4 beds 3 baths1419 Ramseur Ln, WINCHESTER, VA 22601
MLS# VAWI2009932Listed by: RE/MAX ROOTS 
$739,900Pending4 beds 3 baths2,442 sq. ft.806 Mahone Dr, WINCHESTER, VA 22601
MLS# VAWI2009820Listed by: ERA OAKCREST REALTY, INC.
$185,000Pending3 beds 1 baths1,232 sq. ft.376 Charles St, WINCHESTER, VA 22601
MLS# VAWI2009942Listed by: REAL BROKER, LLC- Coming Soon
$449,000Coming Soon3 beds 3 baths25 W Southwerk St, WINCHESTER, VA 22601
MLS# VAWI2009902Listed by: COLONY REALTY 
$279,999Pending2 beds 2 baths954 sq. ft.407 Van Fossen St, WINCHESTER, VA 22601
MLS# VAWI2009922Listed by: SAMSON PROPERTIES
$889,000Active5 beds 5 baths4,957 sq. ft.1540 Meadow Branch Ave, WINCHESTER, VA 22601
MLS# VAWI2009860Listed by: COLONY REALTY
$389,900Active2 beds 2 baths1,550 sq. ft.1885 Rosser Ln, WINCHESTER, VA 22601
MLS# VAWI2009918Listed by: OLIVETREE PROPERTY GROUP
$290,000Active2 beds 1 baths817 sq. ft.580 York Ave, WINCHESTER, VA 22601
MLS# VAWI2009852Listed by: THE VASQUEZ GROUP LLC
$349,900Pending3 beds 1 baths1,196 sq. ft.249 West Street St, WINCHESTER, VA 22601
MLS# VAWI2009908Listed by: LONG & FOSTER REAL ESTATE, INC.
$285,000Active2 beds 2 baths780 sq. ft.2519 Hockman Ave, WINCHESTER, VA 22601
MLS# VAWI2009854Listed by: HOFFMAN REALTY
$650,000Active4 beds 4 baths3,474 sq. ft.132 Amherst St, WINCHESTER, VA 22601
MLS# VAWI2009872Listed by: COLONY REALTY
$80,000Active0.13 Acres520 Highland Ave, WINCHESTER, VA 22601
MLS# VAWI2009882Listed by: SAMSON PROPERTIES
$80,000Active0.08 Acres24 N Pleasant Valley Rd, WINCHESTER, VA 22601
MLS# VAWI2009884Listed by: SAMSON PROPERTIES
$409,990Pending4 beds 4 baths1,889 sq. ft.1806 Blythe Way, WINCHESTER, VA 22601
MLS# VAWI2009856Listed by: D R HORTON REALTY OF VIRGINIA LLC- Open Sat, 12 to 2pm
$469,900Active3 beds 3 baths2,100 sq. ft.1025 S Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009836Listed by: SAMSON PROPERTIES 
$310,000Pending3 beds 2 baths1,530 sq. ft.712 Frederick Ave, WINCHESTER, VA 22601
MLS# VAWI2009832Listed by: CRUM REALTY, INC.
$499,000Active3 beds 3 baths2,293 sq. ft.3137 Eton Pl, WINCHESTER, VA 22601
MLS# VAWI2009840Listed by: ERA OAKCREST REALTY, INC.
$484,900Active3 beds 3 baths1,992 sq. ft.703 S Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009838Listed by: SAMSON PROPERTIES- Open Sat, 1 to 3pm
$300,000Active3 beds 1 baths1,789 sq. ft.501 Battle Ave, WINCHESTER, VA 22601
MLS# VAWI2009808Listed by: PEARSON SMITH REALTY, LLC 
$175,000Active0.37 Acres719 Kennedy Dr, WINCHESTER, VA 22601
MLS# VAWI2009810Listed by: COLONY REALTY
$549,900Pending3 beds 2 baths1,800 sq. ft.435 Mikey Ct, WINCHESTER, VA 22601
MLS# VAFV2038896Listed by: ERA OAKCREST REALTY, INC.
$589,000Active3 beds 2 baths1,974 sq. ft.832 Winder Ct, WINCHESTER, VA 22601
MLS# VAWI2009800Listed by: REALTY ONE GROUP OLD TOWNE
$320,000Pending4 beds 2 baths1,344 sq. ft.1610 S. Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009664Listed by: SAMSON PROPERTIES
$360,000Pending3 beds 4 baths1,784 sq. ft.226 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009794Listed by: DRB GROUP REALTY, LLC
$365,000Pending3 beds 4 baths1,784 sq. ft.217 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009792Listed by: DRB GROUP REALTY, LLC
$199,900Active0.16 Acres1415 Ramseur Ln, WINCHESTER, VA 22601
MLS# VAWI2009784Listed by: COLDWELL BANKER PREMIER- Open Sat, 12 to 2pm
$419,900Active3 beds 2 baths2,219 sq. ft.945 Allen Dr, WINCHESTER, VA 22601
MLS# VAWI2009776Listed by: REALTY ONE GROUP OLD TOWNE 
$389,990Pending3 beds 4 baths1,784 sq. ft.214 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009620Listed by: DRB GROUP REALTY, LLC
$347,500Active3 beds 1 baths907 sq. ft.217 Myrtle Ave, WINCHESTER, VA 22601
MLS# VAWI2009772Listed by: REALTY ONE GROUP OLD TOWNE- Open Sat, 1 to 3pm
$339,900Active3 beds 1 baths960 sq. ft.2952 Grace St, WINCHESTER, VA 22601
MLS# VAWI2009724Listed by: WEICHERT, REALTORS 
$569,900Pending3 beds 2 baths2,154 sq. ft.1412 Magruder Court, WINCHESTER, VA 22601
MLS# VAWI2009712Listed by: COLONY REALTY
$339,000Active2 beds 1 baths1,249 sq. ft.45 And 45 1/2 Race St, WINCHESTER, VA 22601
MLS# VAWI2009722Listed by: CORCORAN MCENEARNEY
$280,000Pending3 beds 2 baths1,120 sq. ft.13 E Hart St, WINCHESTER, VA 22601
MLS# VAWI2009706Listed by: MARKETPLACE REALTY
$649,000Pending5 beds 3 baths3,420 sq. ft.501 Jefferson St, WINCHESTER, VA 22601
MLS# VAWI2009708Listed by: COLONY REALTY
$450,000Active4 beds 3 baths1,634 sq. ft.21 W Pall Mall St, WINCHESTER, VA 22601
MLS# VAWI2009682Listed by: KELLER WILLIAMS REALTY
$464,900Active4 beds 3 baths1,960 sq. ft.418 Circle Dr, WINCHESTER, VA 22601
MLS# VAWI2009680Listed by: SAMSON PROPERTIES
$415,000Pending3 beds 2 baths1,716 sq. ft.307 Fox Dr, WINCHESTER, VA 22601
MLS# VAWI2009686Listed by: COLONY REALTY
$339,000Active4 beds -- baths1,249 sq. ft.45 And 45 1/2 Race St, WINCHESTER, VA 22601
MLS# VAWI2009612Listed by: CORCORAN MCENEARNEY- Open Sun, 3 to 5pm
$435,000Active4 beds 2 baths2,408 sq. ft.519 Whitacre St, WINCHESTER, VA 22601
MLS# VAWI2009672Listed by: SAMSON PROPERTIES 
$310,000Active3 beds 1 baths1,134 sq. ft.27 Jackson Ave, WINCHESTER, VA 22601
MLS# VAWI2009632Listed by: ERA OAKCREST REALTY, INC.
$384,900Active2 beds 2 baths1,186 sq. ft.711 E Cork St, WINCHESTER, VA 22601
MLS# VAWI2009596Listed by: SPRING HILL REAL ESTATE, LLC.
$370,000Pending4 beds 3 baths1,868 sq. ft.126 N Euclid Ave, WINCHESTER, VA 22601
MLS# VAWI2009594Listed by: REAL BROKER, LLC
$250,000Pending3 beds 2 baths1,682 sq. ft.21 E Germain St, WINCHESTER, VA 22601
MLS# VAWI2009356Listed by: CENTURY 21 ENVISION
$559,900Pending4 beds 3 baths2,644 sq. ft.436 Westside Station Dr, WINCHESTER, VA 22601
MLS# VAFV2038424Listed by: SAMSON PROPERTIES- Open Sun, 1 to 3pm
$464,000Active3 beds 3 baths2,805 sq. ft.407 Jefferson St, WINCHESTER, VA 22601
MLS# VAWI2009590Listed by: COLDWELL BANKER PREMIER 
$439,990Active4 beds 4 baths1,920 sq. ft.1805 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009538Listed by: D R HORTON REALTY OF VIRGINIA LLC
$449,990Active4 beds 4 baths1,939 sq. ft.1817 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009540Listed by: D R HORTON REALTY OF VIRGINIA LLC
$369,990Pending3 beds 4 baths1,784 sq. ft.222 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009526Listed by: DRB GROUP REALTY, LLC
$359,990Pending3 beds 4 baths1,784 sq. ft.230 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009528Listed by: DRB GROUP REALTY, LLC
$379,990Pending3 beds 4 baths1,784 sq. ft.209 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009524Listed by: DRB GROUP REALTY, LLC
$455,000Active6 beds 3 baths1,552 sq. ft.2250 Roosevelt Blvd, WINCHESTER, VA 22601
MLS# VAWI2009326Listed by: SPRING HILL REAL ESTATE, LLC.
$265,000Pending2 beds 1 baths882 sq. ft.204 Shenandoah Ave, WINCHESTER, VA 22601
MLS# VAWI2009534Listed by: KELLER WILLIAMS REALTY
$405,000Pending3 beds 2 baths1,802 sq. ft.414 S Cameron St, WINCHESTER, VA 22601
MLS# VAWI2009506Listed by: REALTY ONE GROUP OLD TOWNE
$345,000Pending3 beds 2 baths1,066 sq. ft.105 W Oates Ave, WINCHESTER, VA 22601
MLS# VAWI2009494Listed by: CENTURY 21 NEW MILLENNIUM
$279,900Pending3 beds 2 baths1,332 sq. ft.2901 Sorrell Ct, WINCHESTER, VA 22601
MLS# VAWI2009322Listed by: CENTURY 21 REDWOOD REALTY
$279,000Active3 beds 1 baths907 sq. ft.208 Shenandoah Ave, WINCHESTER, VA 22601
MLS# VAWI2009462Listed by: COLONY REALTY
$330,000Pending3 beds 1 baths1,237 sq. ft.117 W Oates Ave, WINCHESTER, VA 22601
MLS# VAWI2009446Listed by: REALTY ONE GROUP OLD TOWNE
$294,990Pending3 beds 1 baths1,205 sq. ft.627 Watson Ave, WINCHESTER, VA 22601
MLS# VAWI2009434Listed by: SAMSON PROPERTIES
$519,900Pending3 beds 2 baths2,177 sq. ft.216 Fairmont Ave, WINCHESTER, VA 22601
MLS# VAWI2009418Listed by: RE/MAX ROOTS
$700,000Pending4 beds 4 baths4,417 sq. ft.1006 Armistead St, WINCHESTER, VA 22601
MLS# VAWI2009256Listed by: EXP REALTY, LLC
$305,000Pending3 beds 2 baths1,214 sq. ft.204 Barrington Ln, WINCHESTER, VA 22601
MLS# VAFV2038616Listed by: CENTURY 21 REDWOOD REALTY
$365,000Pending4 beds 2 baths1,780 sq. ft.127 Shirley St, WINCHESTER, VA 22601
MLS# VAWI2009378Listed by: ERA OAKCREST REALTY, INC.
$430,000Active4 beds 2 baths2,100 sq. ft.17 E Leicester St, WINCHESTER, VA 22601
MLS# VAWI2009350Listed by: MARKETPLACE REALTY- New
$605,000Active7 beds -- baths4,396 sq. ft.540 Monticello St, WINCHESTER, VA 22601
MLS# VAWI2009974Listed by: MARKETPLACE REALTY 
$279,000Pending2 beds 1 baths1,176 sq. ft.239 Chestnut St, WINCHESTER, VA 22601
MLS# VAFV2037798Listed by: WILDHAWKS REALTY LLC
$469,999Active5 beds 3 baths2,080 sq. ft.419 Summit Ave, WINCHESTER, VA 22601
MLS# VAWI2009258Listed by: LIFESTYLE REALTY, LLC.
$371,990Active3 beds 4 baths1,784 sq. ft.210 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009246Listed by: DRB GROUP REALTY, LLC
$369,990Active4 beds 4 baths1,784 sq. ft.206 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009244Listed by: DRB GROUP REALTY, LLC
$469,900Pending3 beds 4 baths3,359 sq. ft.227 Miller St, WINCHESTER, VA 22601
MLS# VAWI2009194Listed by: REALTY ONE GROUP OLD TOWNE
$399,990Pending4 beds 4 baths1,889 sq. ft.1814 Blythe Way, WINCHESTER, VA 22601
MLS# VAWI2009220Listed by: D R HORTON REALTY OF VIRGINIA LLC
$429,990Active4 beds 4 baths1,889 sq. ft.1822 Blythe Way, WINCHESTER, VA 22601
MLS# VAWI2009206Listed by: D R HORTON REALTY OF VIRGINIA LLC
$279,900Active2 beds 1 baths870 sq. ft.1125 Conway St, WINCHESTER, VA 22601
MLS# VAWI2009200Listed by: ERA OAKCREST REALTY, INC.
$414,900Active3 beds 3 baths1,251 sq. ft.709 Ross St, WINCHESTER, VA 22601
MLS# VAFV2037236Listed by: SAMSON PROPERTIES
$414,900Active3 beds 3 baths1,251 sq. ft.713 Ross St, WINCHESTER, VA 22601
MLS# VAFV2037240Listed by: SAMSON PROPERTIES
$319,000Active3 beds 2 baths1,362 sq. ft.553 Highland Ave, WINCHESTER, VA 22601
MLS# VAWI2009182Listed by: CORCORAN MCENEARNEY
$300,000Pending3 beds 2 baths1,072 sq. ft.112 Star Fort Dr, WINCHESTER, VA 22601
MLS# VAFV2037188Listed by: LONG & FOSTER REAL ESTATE, INC.
$375,000Active3 beds 3 baths1,680 sq. ft.707 E Cork St, WINCHESTER, VA 22601
MLS# VAWI2009160Listed by: SAMSON PROPERTIES
$639,000Pending3 beds 3 baths3,153 sq. ft.147 Harvest Ridge Dr, WINCHESTER, VA 22601
MLS# VAFV2036978Listed by: ERA OAKCREST REALTY, INC.
$1,499,000Active2 Acres1625 Amherst St, WINCHESTER, VA 22601
MLS# VAWI2009110Listed by: COLONY REALTY
$654,000Active6 beds 4 baths3,511 sq. ft.1400 Valley Ave, WINCHESTER, VA 22601
MLS# VAWI2009108Listed by: REAL BROKER LLC
$654,000Active6 beds -- baths3,511 sq. ft.1400 Valley Ave, WINCHESTER, VA 22601
MLS# VAWI2008992Listed by: REAL BROKER LLC
$389,990Active3 beds 4 baths1,784 sq. ft.Tbb Monteith Dr #bedford Ii, WINCHESTER, VA 22601
MLS# VAWI2009636Listed by: DRB GROUP REALTY, LLC
$279,000Pending2 beds 1 baths950 sq. ft.20 E Hart St, WINCHESTER, VA 22601
MLS# VAWI2008932Listed by: LINK REALTY SERVICES LLC
$419,900Active5 beds -- baths2,376 sq. ft.510 N Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009826Listed by: RE/MAX ROOTS
$358,000Pending4 beds 2 baths1,534 sq. ft.323 Russelcroft Rd, WINCHESTER, VA 22601
MLS# VAWI2009662Listed by: SPRING HILL REAL ESTATE, LLC.
$225,000Pending3 beds 2 baths1,526 sq. ft.369 Charles St, WINCHESTER, VA 22601
MLS# VAWI2008716Listed by: ERA OAKCREST REALTY, INC.
$340,000Active3 beds 3 baths1,536 sq. ft.1004 S Cameron St, WINCHESTER, VA 22601
MLS# VAWI2007970Listed by: METAS REALTY GROUP, LLC
$899,000Active5 beds 5 baths4,438 sq. ft.769 Seldon Dr, WINCHESTER, VA 22601
MLS# VAWI2009972Listed by: KELLER WILLIAMS REALTY
$985,000Active7 beds 6 baths6,540 sq. ft.1020 Breckinridge Ln, WINCHESTER, VA 22601
MLS# VAWI2007912Listed by: RE/MAX ROOTS
$386,500Pending3 beds 2 baths1,416 sq. ft.31 W Whitlock Ave, WINCHESTER, VA 22601
MLS# VAWI2007870Listed by: LINK REALTY SERVICES LLC
$750,000Pending1.33 Acres903 N Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2007862Listed by: COLDWELL BANKER ELITE
$4,000,000Pending27.2 AcresNorth Frederick Pike, WINCHESTER, VA 22601
MLS# VAWI2007698Listed by: COLDWELL BANKER PREMIER
$4,500,000Pending11.43 Acres801 Fairmont Ave, WINCHESTER, VA 22601
MLS# VAWI2007696Listed by: COLDWELL BANKER PREMIER
$1,850,000Active12 beds -- baths7,190 sq. ft.908 Cedar Creek Grade, WINCHESTER, VA 22601
MLS# VAWI2007202Listed by: LINK REALTY SERVICES LLC
$499,000Active0.09 Acres1 N Braddock St, WINCHESTER, VA 22601
MLS# VAWI2005956Listed by: COLDWELL BANKER PREMIER
$685,000Active4 beds 3 baths3,108 sq. ft.1950 Melvor Ln, WINCHESTER, VA 22601
MLS# VAWI2007932Listed by: WASHINGTON DULLES REAL ESTATE GROUP
$500,000Active7 beds -- baths1,175 sq. ft.513 And 525 Monticello St, WINCHESTER, VA 22601
MLS# VAWI2000030Listed by: OAKCREST COMMERCIAL REAL ESTATE
$2,300,000Active3.51 Acres1721 Amherst St, WINCHESTER, VA 22601
MLS# VAWI2008980Listed by: OAKCREST COMMERCIAL REAL ESTATE
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.