Browse All Cottage Style Properties for Sale

Discover exceptional one-level living in one of Winchester’s premier communities, where homes rarely become available! This exquisite all-brick home combines timeless ele...

3 Beds
2 Baths
The Downs At Meadowbranch SubDv.
22601 Zip Code
COMING SOON Status

3 S Euclid Ave, Winchester $305,500

Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently locat...

3 Beds
2 Baths
City Of Winchester SubDv.
22601 Zip Code
ACTIVE Status

2519 Hockman Ave, Winchester $299,900 ▼

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detache...

2 Beds
2 Baths
City Of Winchester SubDv.
22601 Zip Code
ACTIVE Status

1306 Vanceright Cir, Winchester $480,000

Filled with storybook charm and timeless character, this enchanting cottage-style home is much larger than it appears! Newly refinished hardwood floors flow throughout th...

4 Beds
2 Baths
Himelright/Vanceright SubDv.
22601 Zip Code
CLOSED Status

159 Lauck Dr, Winchester $410,000 ▼

Imagine... a BRAND-NEW CUSTOM HOME (not a townhouse) for your family at just $410,000 AND a BUILDER-PAID 2-1 buydown for FHA loans giving you a starting lender rate of 5...

3 Beds
3 Baths
None Available SubDv.
22603 Zip Code
ACTIVE Status

151 Lauck Dr, Winchester $410,000

Imagine... a BRAND-NEW CUSTOM HOME (not a townhouse) for your family at just $415,000! This custom home is in an established neighborhood just minutes from downtown Win...

3 Beds
3 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

110 Red Fox Trl, Winchester $275,000

3-bedroom cottage in Shawneeland offering great potential to make it your own. Recent updates include new kitchen cabinets, countertops, updated bathroom vanities, modern...

3 Beds
2 Baths
Shawneeland SubDv.
22602 Zip Code
CLOSED Status

980 Adams Rd, Winchester $418,500

Brand NEW Roof installed June 2026! Discover your own 25.54-acre private retreat in the scenic rolling hills of the northern Shenandoah Valley with three contiguous parce...

2 Beds
1 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

1063 Foreman Ln, Winchester $200,000

This is the perfect starter Home completely remodeled in 2024. The home has brand new HVAC, new flooring, a new kitchen, a new bathroom, all new stainless steel applianc...

2 Beds
1 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

123 Doonbeg Ct, Winchester $429,900

Brand New one level Cottage Style homes in Charming Cottage Glen an Age 55 and Better Community. Two Bedrooms and Two Full Baths. Bright Kitchen with Stainless Steel Appl...

2 Beds
2 Baths
Cottage Glen SubDv.
22602 Zip Code
CLOSED Status

1860 Rosser Ln, Winchester $328,900

Charming 2-bed, 1-bath cottage nestled within the Willow Lawn community. Enjoy modern comforts with a new roof and updated appliances. The open floor plan invites a cozy ...

2 Beds
1 Baths
Willow Lawn Cottages SubDv.
22601 Zip Code
CLOSED Status

246 Jeb Dr, Winchester $830,000

Don’t miss this opportunity to own this Custom-Built Cape Cod home located on 5.98 acres in the upscale Brookneill Subdivision. Secluded yet close to the Winchester, this...

5 Beds
4 Baths
Brookneill SubDv.
22602 Zip Code
CLOSED Status

147 Doonbeg Ct, Winchester $494,000

Welcome to your cozy retreat nestled in the heart of a Winchester! This delightful 3 bedroom, 2.5 bathroom home exudes warmth and comfort from the moment you step inside....

3 Beds
3 Baths
Cottage Glen SubDv.
22602 Zip Code
CLOSED Status

107 Apache Trl, Winchester $217,106

2 YEAR HOME WARRANTY OFFERED!! Welcome to your new sanctuary at Shawneeland! Step into your adorable brand-new build home by RG Homes. This cottage-like abode offers the ...

2 Beds
1 Baths
Shawneeland SubDv.
22602 Zip Code
CLOSED Status

103 Cranberry Ct, Winchester $379,900

This charming 2-bed/2-bath brick front home is situated in the desirable Cross Creek community, exclusively for individuals aged 55 and above. Conveniently located just m...

2 Beds
2 Baths
Cross Creek Village SubDv.
22602 Zip Code
CLOSED Status

1803 Melvor Ln, Winchester $359,900

Move in ready in this quiet 55+ community in the heart of Winchester with swift access to walking trails, hospital, and conveniences. Open floor plan with handicapped do...

2 Beds
2 Baths
Willow Lawn SubDv.
22601 Zip Code
CLOSED Status

102 Hickory Ln, Winchester $330,000

Check out this Charming 4 bedroom, 1 bath home is a great find with several recent upgrades! The new windows and siding provide a fresh and modern look to the exterior. T...

4 Beds
1 Baths
J P Darlington SubDv.
22603 Zip Code
CLOSED Status

1854 Kershaw Ln, Winchester $369,900

Freshly painted and ready for new owners right away! 1854 Kershaw has all the space you need! Featuring a wonderful, open concept floorplan with vaulted ceiling in the ki...

2 Beds
2 Baths
Willow Lawn Cottages SubDv.
22601 Zip Code
CLOSED Status

229 Glaize Orchard Rd, Winchester $347,000

This is a great opportunity for someone looking to own a Farmette with an existing home. The updated two-bedroom house has a third bedroom that has been converted to a la...

2 Beds
1 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

106 Blackfeet Trl, Winchester $176,000

*****GREAT OPPORTUNITY TO OWN A WEEKEND GET AWAY CABIN - OR FULL TIME HOME IN HISTORIC SHAWNEELAND. ITS WITHIN WALKING DISTANCE OF THE LAKE, JUST TWO STREETS UP THE MO...

1 Beds
1 Baths
Shawneeland SubDv.
22602 Zip Code
CLOSED Status

2161 Northwestern Pike, Winchester $289,900

Charming three bedroom, home conveniently located near, Winchester Medical Center, Walmart and Route 37. Lots of wood flooring. Living room with wood burning fireplace...

3 Beds
1 Baths
Stonewall Orchard SubDv.
22603 Zip Code
CLOSED Status

105 Apache Trl, Winchester $280,000

**Back on market — buyer financing fell through after a successful contract process. Second chance for buyers who may have missed this opportunity the first time around.*...

3 Beds
1 Baths
Shawneeland SubDv.
22602 Zip Code
CLOSED Status

939 Woodland Ave, Winchester $277,000

This Winchester City charmer is the perfect starter home, downsizing option, or investment opportunity. Thoughtfully updated with all the heavy lifting complete at the...

2 Beds
2 Baths
Harris Addition SubDv.
22601 Zip Code
CLOSED Status

200 & 210 W Fairfax Ln, Winchester image

200 & 210 W Fairfax Ln, Winchester $675,000

Nestled in the heart of Winchester's cherished historic district, this enchanting circa 1928 cottage blends timeless charm with exceptional opportunity. Rich in character...

5 Beds
4 Baths
Historic District SubDv.
22601 Zip Code
CLOSED Status

424 Highland Ave, Winchester $279,000

CUTE AS A BUTTON! This updated Cottage Rambler perched on a quiet tree lined street sits in the heart of booming Winchester, just minutes from Old Towne. Newly renovated ...

2 Beds
1 Baths
None Available SubDv.
22601 Zip Code
CLOSED Status

627 Watson Ave, Winchester $294,990

CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences...

3 Beds
1 Baths
Orchard Terr/Plumly SubDv.
22601 Zip Code
CLOSED Status

309 Raccoon Dr, Winchester — Wapoa $252,900

Move in ready 3 bedroom 2 full baths home nestled in the woods that comes with additional lots(2) that can be built on or kept as a privacy buffer and equates to an acr...

3 Beds
2 Baths
Wilde Acres SubDv.
22602 Zip Code
CLOSED Status

27 Jackson Ave, Winchester $181,000

Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a leve...

2 Beds
1 Baths
Winchester City SubDv.
22601 Zip Code
CLOSED Status

1033 Sunnyside Dr, Winchester $215,000

Price Reduced - Come check out this charming bungalow cottage, easy to show, freshly painted, located just off Rt. 522 North, outside the northern border of the City of...

2 Beds
1 Baths
Sunnyside SubDv.
22603 Zip Code
CLOSED Status

242 Footstone Ln, Winchester $268,000

Peaceful Country Retreat on 4.7 Acres – Minutes from Winchester This private country home combines solid craftsmanship with serene mountain views. Located on a quiet grav...

1 Beds
1 Baths
Nain SubDv.
22603 Zip Code
CLOSED Status

208 Opossum Trl, Winchester $240,000

Welcome to this charming two-story home nestled in a peaceful country setting, surrounded by mature trees, vibrant flower beds, and a majestic weeping willow that graces ...

3 Beds
1 Baths
Wilde Acres SubDv.
22602 Zip Code
CLOSED Status

1182 Greenwood Rd, Winchester $260,000

INVESTMENT OPPORTUNITY! Two dwellings on 2.25 UNRESTRICTED acres! Discover the potential of this unique property located on the east side of Frederick County! Whether yo...

2 Beds
2 Baths
None Available SubDv.
22602 Zip Code
CLOSED Status

428 Canyon Rd, Winchester $700,000

Live and entertain with pride at this stunning home in a 9-acre lake community, where comfort meets sophistication. From soaring 10’ ceilings and engineered hardwood floo...

4 Beds
3 Baths
Twin Lakes Overlook SubDv.
22602 Zip Code
CLOSED Status

121 Doonbeg Ct, Winchester $439,900

Brand New one level Cottage Style homes in Charming Cottage Glen an Age 55 and Better Community. Two Bedrooms and Two Full Baths. Bright Kitchen with Stainless Steel Appl...

2 Beds
2 Baths
Cottage Glen SubDv.
22602 Zip Code
CLOSED Status

508 Highland Ave, Winchester $290,000

This beautifully maintained 3-bedroom, 2-bath detached home, built in 2007, is a true gem in downtown Winchester! Upgraded LVP flooring greets you into the spacious livin...

3 Beds
2 Baths
Winchester SubDv.
22601 Zip Code
CLOSED Status

1860 Melvor Ln, Winchester $341,500

Welcome to the sought after 55+ community of Willow Lawn Cottages. This corner lot home offers ample light throughout and plenty of parking surrounding this 2 bedroom, 2 ...

2 Beds
2 Baths
Willow Lawn Cottages SubDv.
22601 Zip Code
CLOSED Status

537 Hillman Dr, Winchester $95,000

Welcome to 537 Hillman Drive! This adorable home is conveniently located just off Valley Avenue in Winchester, close to W Jubal Early Drive and Weems Lane. It features on...

1 Beds
1 Baths
Orchard Hill SubDv.
22601 Zip Code
CLOSED Status

1840 Rosser Ln, Winchester $332,500

This charming 2 bedroom, 1 bath detached home is located in the 55+ Willow Lawn Cottages HOA. Located in Winchester close to shopping, Valley Health and medical offices....

2 Beds
1 Baths
Willow Lawn Cottages SubDv.
22601 Zip Code
CLOSED Status

1819 Melvor Ln, Winchester $359,900

This lovely home has had only one owner. It was purchased directly from the builder and the floor plan is available. Spacious one level home located in Willow Lawn Cotta...

2 Beds
2 Baths
Willow Lawn Cottages SubDv.
22601 Zip Code
CLOSED Status

443 West Ln, Winchester $229,000

Deadline for offers, Monday, 9/16 at Noon. Charming cottage in the heart of Winchester. Just blocks from the walking mall, this home offers three bedrooms and one and a h...

3 Beds
2 Baths
Liberty Heights SubDv.
22601 Zip Code
CLOSED Status

2518 Hockman Ave, Winchester $240,000

Ready to step into homeownership or make a smart investment? This charming cottage, located in a peaceful neighborhood just off Route 11, is the perfect opportunity. Fe...

2 Beds
1 Baths
None Available SubDv.
22601 Zip Code
CLOSED Status

205 Shawnee Ave, Winchester $379,000

This charming fully renovated cottage is adorable. Minutes to central downtown Winchester. Total renovation by skilled craftsmen completed in late May 2024. Everything...

3 Beds
2 Baths
Shawnee Heights SubDv.
22601 Zip Code
CLOSED Status

1910 Harvest Dr, Winchester $655,000

SELLER OFFERING 1% TOWARDS CLOSING COSTS WITH FULL PRICE OFFER**Welcome Home in High Demand Meadow Branch neighborhood in Winchester! Brand new construction by a great lo...

5 Beds
4 Baths
Meadow Branch South SubDv.
22601 Zip Code
CLOSED Status

231 Millwood Ave, Winchester $390,000

Welcome to your charming 1930s cottage nestled in the heart of Winchester! This recently renovated gem boasts over 1600 square feet of living space, including 4 cozy bedr...

4 Beds
2 Baths
None Available SubDv.
22601 Zip Code
CLOSED Status

3247 Front Royal Pike, Winchester $265,000

Welcome to a rare gem on the market—this charming home, nestled on around .75 acres across two lots, is a must-see for anyone looking for open layout and modern amenities...

2 Beds
1 Baths
Brown SubDv.
22602 Zip Code
CLOSED Status

106 Nevermore Dr, Winchester $525,000

Why wait for new construction when you can have this gorgeous home now! Located within a quiet culdesac in the fantastic Raven Oaks neighborhood, this like-new home was b...

3 Beds
2 Baths
Raven Oaks SubDv.
22602 Zip Code
CLOSED Status

99 Dixie Belle Dr, Winchester $342,500

"This lovely ranch home has been beautifully updated and is ready for its new owners. Completely move-in ready, with a modern remodeled kitchen, new stainless appliances...

4 Beds
1 Baths
Burning Knolls SubDv.
22602 Zip Code
CLOSED Status

108 Dunbar Ln, Winchester $275,950

Located in Frederick County, just on the outskirts of Winchester City, this adorable bungalow begs you to pull up a chair and enjoy a cool drink on the porch. Mature Norw...

3 Beds
3 Baths
None Available SubDv.
22603 Zip Code
CLOSED Status

145 Doonbeg Ct, Winchester $405,000

Welcome to 145 Doonbeg, located in desirable Cottage Glen, a 55+ community. This well maintained home has recently been painted and offers several upgrades. This one-lev...

2 Beds
2 Baths
Cottage Glen SubDv.
22602 Zip Code
CLOSED Status

125 Doonbeg Ct, Winchester $429,900

Brand New one level Cottage Style homes in Charming Cottage Glen an Age 55 and Better Community. Two Bedrooms and Two Full Baths. Bright Kitchen with Stainless Steel Appl...

2 Beds
2 Baths
Cottage Glen SubDv.
22602 Zip Code
CLOSED Status

Winchester Cottage Style Real Estate & Homes

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