Winchester, VA Homes for Sale

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  /76

  $400,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  /36

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  224 Lauck Dr, Winchester, VA 22603

  Custom Home in Historic Star Fort: Timeless Charm Meets modern Comfort for Discerning Buyers.This impeccably designed 3-bedroom, 2.5-bath home is a harmonious blend of classic elegance and contemporary convenience. Boasting cherry wood flooring throughout the main living areas, high-quality tile in the kitchen and bathrooms, and carpeted bedrooms, this home is as stylish as it is practical. Be

  Gidget Smallwood Coldwell Banker Premier

  224 Lauck Dr, Winchester, VA 22603
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  /73

  $525,000

  • 3 Beds
  • 1.5 Baths
  • 2,964 Sq Ft

  306 Burnt Church Rd, Winchester, VA 22603

  Welcome to this charming Circa 1801-Farmette, nestled on approximately 7.5 unrestricted acres just outside the City of Winchester. This property offers the perfect blend of historic character and rural tranquility, with convenient access to shopping, dining, and major commuter routes, including Rt. 37 and I-81. Enjoy the open space for gardening, raising poultry, or embracing a country

  Sue Goodwin Long & Foster Real Estate, Inc.

  306 Burnt Church Rd, Winchester, VA 22603
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  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  Bedford II, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /2

  $452,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  Homesite 20 Monteith Dr, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage & Gourmet Kitchen! This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, and a box bay window in the rear of the home for extra lighting located in the kitchen. You are

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /2

  $429,340 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  Homesite 114 Monteith Dr, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished Sq Ft & 1 Car Garage! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door opener.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /12

  $249,999

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  311 Ash Hollow Dr, Winchester, VA 22602

  Opportunity awaits in Ash Hollow Estates! This 3-bedroom, 2-bath townhouse is full of potential—solid bones, a smart layout, and endless possibilities for transformation. Whether you're an investor or a first-time buyer ready to create something special, this home is the perfect canvas. With a little TLC, a fresh new look is on the horizon!Located just off Route 7, this property offers easy

  Josh Medina ERA Oakcrest Realty, Inc.

  311 Ash Hollow Dr, Winchester, VA 22602
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  /12

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  Welcome home to 711 E. Cork Street! Centrally located in Winchester, VA. Enjoy the ease of access to downtown Winchester, Jim Barnett Park, shopping, and commuter routes. This 2 bedroom 1 1/2 bath detached home with brand new exterior update(new vinyl siding). Deeded right away provides access to rear of the property. Call today for your private showing!

  Jim Stafford ERA Oakcrest Realty, Inc.

  711 E Cork St, Winchester, VA 22601
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  /30

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  223 Monticello Square, Winchester, VA 22602

  Welcome to this stunning, move-in-ready townhome in the desirable Brookland Manor Subdivision in Winchester, VA! This 3-bedroom, 2.5-bath home boasts an open floor plan, perfect for modern living and entertaining. Interior Features: Hardwood floors grace the main level and staircase, adding warmth and elegance. High ceilings and large daylight windows create a bright, airy atmosphere. Groumet

  Minhkhoa Tran Fairfax Realty Premier

  223 Monticello Square, Winchester, VA 22602
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  /81

  $1,224,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  Step into refined elegance and exceptional quality in this beautifully upgraded residence, located in one of Winchester’s most desirable and walkable neighborhoods. This stately home offers the perfect blend of timeless architecture, sophisticated updates, and a lifestyle of convenience—just minutes from charming downtown shops, acclaimed restaurants, picturesque parks, and Winchester Medical

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  801 Armistead St, Winchester, VA 22601
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  /20

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  102 Winnepeg Place, Winchester, VA 22603

  This beautiful home located on a quiet cul-de-sac has been completely renovated in the past few years. It features a great interior space with a wonderful open floor plan. Updates include a new HVAC system, hot water heater, bathrooms, flooring, countertops, and more! Outside it backs to the preserved 3rd battlefield of Winchester woods providing both privacy and immediate access to miles of

  Jacob Taylor Blue Valley Real Estate

  102 Winnepeg Place, Winchester, VA 22603
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  /18

  $449,900

  • 3 Beds
  • 3 Baths
  • 1,924 Sq Ft

  275 Greenwood Rd, Winchester, VA 22602

  Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access to Routes 7 and 81. The main level boasts neutral-toned walls and a distinctive dual-sided fireplace, seamlessly connecting the living and dining areas. The dining room and well-appointed kitchen feature elegant hardwood flooring and an abundance of natural light, enhanced by a full-size window and sliding

  Jose Ugaz Gates Smart Realty, LLC

  275 Greenwood Rd, Winchester, VA 22602
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  /36

  $449,900

  • 3 Beds
  • 3 Baths
  • 1,830 Sq Ft

  325 W Tevis St, Winchester, VA 22601

  Welcome to 325 Tevis St! This charming home is filled with natural light and offers a spacious layout perfect for modern living. The open-concept living and dining areas flow seamlessly, creating an inviting space for both everyday living and entertaining. The generous eat-in kitchen boasts ample cabinet space and is bathed in natural light. Step directly from the kitchen onto the back

  Danielle Carter Redfin Corporation

  325 W Tevis St, Winchester, VA 22601
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  /28

  $499,000

  • Studio
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  ATTENTION INVESTORS!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester, just minutes from Valley Health Campus, shopping, restaurants and Rt. 37, may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not offered separately, and all for

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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  /52

  $300,000

  • 2 Beds
  • 4 Baths
  • 2,438 Sq Ft

  102 Duwamish Trail, Winchester, VA 22602

  If you are looking for a home with privacy and a peaceful rural feel but only 15 minutes to Winchester then this home is for you! Set in a natural habitat, 102 Duwamish Trail has a vintage feel and could be a weekend getaway or your primary residence away from the city. There is an open feel to the main level which has a versatile floor plan. There is a sunroom, a family room & a kitchen with

  Dorothy Beach Samson Properties

  102 Duwamish Trail, Winchester, VA 22602
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  /30

  $309,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  305 Winchester Dr, Winchester, VA 22602

  Welcome to 305 Winchester Dr — This stone-front beauty features wood laminate flooring throughout the main level and a freshly painted interior. The inviting covered front porch sets the tone for relaxed living, while the fully fenced backyard offers privacy and serenity, backing up to peaceful trees.The kitchen is complete with a cooktop, wall oven, breakfast bar, and newer refrigerator and

  Katie Landi Jordan Samson Properties

  305 Winchester Dr, Winchester, VA 22602
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  /60

  $359,990

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  1005 Pennsylvania Ave, Winchester, VA 22601

  This charming classic brick ranch in Winchester, VA, features 3 bedrooms and 2 full bathrooms, with easy access to downtown Winchester. As you approach, the covered front porch sets a welcoming tone. The basement has a separate entrance and additional space for bedrooms, a laundry area, and a full bathroom. Recent updates include an HVAC system, a washer and dryer, and complete renovations of

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  /45

  $475,000 Open Sun 11AM - 2PM

  • 5 Beds
  • 3 Baths
  • 2,974 Sq Ft

  2620 Stonegate Dr, Winchester, VA 22601

  Contemporary 5-Bedroom Rancher - Prime Winchester LocationDiscover one of Winchester's most coveted addresses – where urban convenience meets serene privacy in this meticulously maintained contemporary rancher. This exceptional 5-bedroom, 3-full-bath home sits on a premium lot backing to Frederick Douglass Elementary School and beautiful parkland, offering privacy with breathtaking sunrise and

  Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
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  /31

  $305,000

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  7 E Hart St, Winchester, VA 22601

  Beautifully Maintained and Ideally Located!Nestled within city limits and just minutes from shopping, local dining, and the vibrant downtown walking mall, this home offers the perfect blend of comfort and convenience. Recent updates include fresh paint on all interior levels (2025), new carpet (2025), upgraded granite countertops (2019), a 30-year Timberline American Harvest roof (2017), HVAC

  Jennifer Sacco RE/MAX Roots

  7 E Hart St, Winchester, VA 22601
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  /62

  $780,000

  • 4 Beds
  • 4.5 Baths
  • 5,183 Sq Ft

  1877 Clayton Ridge Dr, Winchester, VA 22601

  Nestled at the end of a quiet cul-de-sac and backing to serene wetlands and a protected preserve, this expansive colonial offers over 5,000 square feet of refined living space on nearly half an acre—providing both privacy and picturesque views. Boasting 4 generously sized bedrooms and 4.5 bathrooms, this home features a comfortable and functional main level layout perfect for everyday living and

  Dave Spence RE/MAX Roots

  1877 Clayton Ridge Dr, Winchester, VA 22601
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  /17

  $429,990 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,664 Sq Ft

  111 Cheshire Ct, Winchester, VA 22602

  Immaculate End-Unit Townhome on in Winchester. Welcome to this beautifully maintained end-unit townhome located in one of Winchester’s most sought-after communities. Designed for both comfort and convenience, this home offers a thoughtful blend of style, functionality, and modern living. Step inside to discover gleaming hardwood floors that create a warm and inviting entry. The open-concept

  Anthony Howard Real Broker, LLC

  111 Cheshire Ct, Winchester, VA 22602
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  /22

  $269,900

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  213 Little River Dr, Winchester, VA 22602

  Welcome to this freshly painted 2-bedroom end-unit townhouse. This home offers an unbeatable location—just minutes from Route 7 and I-81Enjoy added privacy and space with an extra-large lot and a low-maintenance, mulched backyard surrounded by a privacy fence—ideal for relaxing or entertaining. As an end unit, you'll love the extra natural light.Conveniently close to shopping, dining, and

  Meghan Pachas Realty ONE Group Old Towne

  213 Little River Dr, Winchester, VA 22602
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  /28

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 2,281 Sq Ft

  154 Solara Dr, Winchester, VA 22602

  Charming Townhome with Solar Savings in a Prime Location!Welcome to this beautifully updated townhome nestled in a highly sought-after neighborhood just minutes from Rt 7! This move-in ready home boasts paid-off solar panels, keeping your electric bills at an incredible $20/month on average—a rare and valuable find.Inside, you'll find fresh paint throughout, new luxury vinyl plank flooring, and

  Kandi Ross Realty ONE Group Old Towne

  154 Solara Dr, Winchester, VA 22602
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  /35

  $875,000

  • 4 Beds
  • 3 Baths
  • 2,566 Sq Ft

  103 Derrynan Ct, Winchester, VA 22601

  Welcome to 103 Derrynan Ct! This exceptional 4-bedroom, 3-bath home offers the perfect blend of luxury, quality, and location—set on a premium oversized cul-de-sac lot just minutes from everything Winchester has to offer. With over $100K in high-end upgrades, this home is built for comfort, efficiency, and timeless style. Soaring 9-foot ceilings, elegant trim work, and a stunning coffered ceiling

  Jason Beaton Burch Real Estate Group, LLC

  103 Derrynan Ct, Winchester, VA 22601
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  /49

  $599,000

  • 5 Beds
  • 3 Baths
  • 3,200 Sq Ft

  1019 Berryville Ave, Winchester, VA 22601

  1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full kitchens, and separate electric. Middle unit may be used for commercial space. Units have been

  Pamela Debnam Houwzer, LLC

  1019 Berryville Ave, Winchester, VA 22601
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  /22

  $329,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft

  102 Zephyr Ln, Winchester, VA 22602

  Motivated Sellers! Don’t miss this opportunity for a Beautifully Updated 3-Bedroom Town home in Prime Location!Welcome to this charming 3-bedroom, 1.5-bath town home located in a highly sought-after neighborhood. Featuring a cozy fireplace in the living room and a stylishly remodeled kitchen with modern finishes, this home combines comfort and convenience. Enjoy quiet evenings or entertain guests

  Kandi Ross Realty ONE Group Old Towne

  102 Zephyr Ln, Winchester, VA 22602
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  /67

  $699,000

  • 5 Beds
  • 3.5 Baths
  • 3,426 Sq Ft

  960 Laurel Grove Rd, Winchester, VA 22602

  Interior photos to come!Welcome to 960 Laurel Grove Road — a peaceful retreat nestled in the scenic countryside of Winchester, VA. This charming property offers the perfect blend of comfort, space, and privacy, making it an ideal home for those seeking a quiet lifestyle without sacrificing convenience.Set on a generous lot surrounded by mature trees and natural beauty, this home features a

  Matt Leiva Keller Williams Realty

  960 Laurel Grove Rd, Winchester, VA 22602
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  /37

  $268,000

  • 2 Beds
  • 1.5 Baths
  • 1,214 Sq Ft

  104 Braeburn Dr, Winchester, VA 22601

  Turnkey and full of charm, this brick-front townhome offers an ideal location near Route 7 and I-81. Inside, enjoy an open flow, warm natural light, and fresh updates throughout. The family room features hardwood floors and a bay window, while the kitchen boasts ceramic tile and gas cooking. A laundry room with washer and dryer on the main level adds convenience. Upstairs, the spacious primary

  Steph Mitchell Realty ONE Group Old Towne

  104 Braeburn Dr, Winchester, VA 22601
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  /48

  $349,900

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  128 Fox Dr, Winchester, VA 22601

  Welcome to 128 Fox Dr — a spacious, move-in ready home nestled in the heart of Winchester, offering three levels spanning over 2,600 square feet of flexible living space, with 4 bedrooms, 3 bathrooms, and unbeatable convenience! This Cape Cod-style home features a thoughtful layout with at least one bedroom and a full bathroom on every level. Step into the main level to discover hardwood floors

  Robert Salehi Real Broker, LLC

  128 Fox Dr, Winchester, VA 22601
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  /18

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  221 Boyd Ave, Winchester, VA 22601

  CHARMING HOME LOCATED CLOSE TO I-81 AND RT.7 HOME HAS 3 BEDROOMS WITH FULL BATH ON SECOND FLOOR AND HALF BATH ON FIRST. ADD YOUR PERSONAL TOUCHES AND MAKE THISA CUTE AND INVITING HOME. FRONT PORCH HAS BEEN GLASSED IN. PERFECT SPOT FOR YOUR MORNING COFFEE. **HOME BEING SOLD AS IS**

  Mary Hammond Jim Barb Realty Inc.

  221 Boyd Ave, Winchester, VA 22601
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  /10

  $58,900

  • Land
  • 0.69 Acre
  • $85,362 per Acre

  Lots 6 & 7 Glen Ridge Rd, Winchester, VA 22602

  Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have

  Bradley Comstock ERA Oakcrest Realty, Inc.

  Lots 6 & 7 Glen Ridge Rd, Winchester, VA 22602
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  /10

  $48,900

  • Land
  • 0.34 Acre
  • $143,824 per Acre

  LOT 8 Glen Ridge Rd, Winchester, VA 22602

  Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have

  Bradley Comstock ERA Oakcrest Realty, Inc.

  LOT 8 Glen Ridge Rd, Winchester, VA 22602
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  /10

  $58,900

  • Land
  • 0.69 Acre
  • $85,362 per Acre

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602

  Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have

  Bradley Comstock ERA Oakcrest Realty, Inc.

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602
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  /28

  $319,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  946 Franklin St, Winchester, VA 22601

  Relax on the back decks overlooking a treed canopy yard. Cape code with fresh paint, laminate flooring , large walk-in closets on upper lever with sitting room and 1 bedroom plus attic storage. Main level has 2 bedrooms, bathroom, living room and kitchen with door to back decks and yard. Unfinished basement with plenty of room to expand and for storage. Home has NEW windows 2024, NEW roof 2022

  Stan Dull The Wiley Companies, Inc.

  946 Franklin St, Winchester, VA 22601
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  /14

  $339,900

  • 3 Beds
  • 1.5 Baths
  • 1,704 Sq Ft

  10 Richards Ave, Winchester, VA 22601

  Back on the market with updated baths and brand-new flooring in the enclosed porch! Welcome to this charming classic home located in the City of Winchester. Built in 1940, this home offers timeless appeal and craftsmanship. Inside, you'll find 3 bedrooms, 1.5 baths, and a versatile fourth room—ideal for a home office, guest room, or creative space. The main level greets you with a welcoming

  Lindsey Richardson ERA Oakcrest Realty, Inc.

  10 Richards Ave, Winchester, VA 22601
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  /26

  $245,000

  • Land
  • 23 Acres
  • $10,452 per Acre

  0 Mockingbird Lot 7 Ln Unit VAFV2034380, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. There are potential building sites located throughout the

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Mockingbird Lot 7 Ln Unit VAFV2034380, Winchester, VA 22603
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  /49

  $280,000

  • Land
  • 25 Acres
  • $11,129 per Acre

  0 Mockingbird Lot 7a Ln Unit VAFV2034376, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin wired for a generator hook up with propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters in an attached

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Mockingbird Lot 7a Ln Unit VAFV2034376, Winchester, VA 22603
• 

  

  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  0 Mockingbird Lot 8 Ln Unit VAFV2034374, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Mockingbird Lot 8 Ln Unit VAFV2034374, Winchester, VA 22603
• 

  

  /49

  $600,000

  • 4 Beds
  • 3 Baths
  • 2,203 Sq Ft

  167 Morning Glory Dr, Winchester, VA 22602

  Welcome to the beautiful Twin Lakes Community! This charming ranch-style residence offers the ease of one-level living with a spacious and thoughtfully designed floor plan. The main level features a welcoming front den—perfect for a home office or reading nook—an updated kitchen with a large pantry area, a dining room filled with natural light, and a cozy family room complete with a gas

  Lisa Behr Coldwell Banker Premier

  167 Morning Glory Dr, Winchester, VA 22602
• 

  

  /63

  $349,900

  • 2 Beds
  • 2 Baths
  • 1,333 Sq Ft

  151 Mccormick Cir Unit 200, Winchester, VA 22602

  Welcome to Winchester Landing, a thoughtfully designed 55+ condo community offering comfort, convenience, and modern living—unlike anything else available in a 55+ setting. There truly are no other condos like these!This condo features an updated, open floor plan where the kitchen flows seamlessly into the spacious great room—perfect for both daily living and entertaining. The kitchen is

  Rhonda Shade ERA Oakcrest Realty, Inc.

  151 Mccormick Cir Unit 200, Winchester, VA 22602

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