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Offering charm and character blended with modern conveniences in the heart of Winchester. Located in the lovely neighborhood of Whittier Acres, this home has been professionally redesigned with flexibility in mind... so you can call it "home" for years to come. Our main level is fitted with two bedrooms and two baths, in addition to a formal living room and an open concept kitchen/dining/family room - which presents the ideal one level living opportunity. The primary suite is a retreat, with a walk-in closet and well appointed ensuite and laundry. The secondary bedroom is sizeable and is served by the hall bath with plenty of storage. The kitchen/dining and family room areas have been thoughtfully designed to include Hickory floors, custom Kraftmaid cabinetry and plenty of lighting. The upper deck, outfitted with new Trex stairs to the pool, is accessed by the family room. It is the perfect spot for morning coffee or to contemplate a dip in the pool! Our Garden level is a light filled space where you will find two more bedrooms, full bath, laundry and a kitchen area. With access directly to the pool, this is your 'outdoor living' dream come true... luxury vinyl plank won't mind a little pool water and the convenience of a full bath is a must . This space is also ideal as a guest suite or perhaps an income opportunity. The back yard is fully fenced and the pool is open and waiting for you! This home has only had two owners in 54 years...come add your history to 329 Wood Avenue. Some nearby points of interest include, Historic Downtown Winchester, The Museum of the Shenandoah Valley with gardens and walking trails, Winchester Medical Center, Whittier Park and Handley Library. Shopping and dining options are also moments away. Please see attached document highlighting all the wonderful renovations. Floor plans are also in the document section. Furnishings are available for purchase.

4 Beds ⋅ 3 Baths

Offering charm and character blended with modern conveniences in the heart of Winchester. Located in the lovely neighborhood of Whittier Acres, this home has been professionally redesigned with flexibility in mind... so you can call it "home" for years to come. Our main level is fitted with two bedrooms and two baths, in addition to a formal living room and an open concept kitchen/dining/family room - which presents the ideal one level living opportunity. The primary suite is a retreat, with a walk-in closet and well appointed ensuite and laundry. The secondary bedroom is sizeable and is served by the hall bath with plenty of storage. The kitchen/dining and family room areas have been thoughtfully designed to include Hickory floors, custom Kraftmaid cabinetry and plenty of lighting. The upper deck, outfitted with new Trex stairs to the pool, is accessed by the family room. It is the perfect spot for morning coffee or to contemplate a dip in the pool! Our Garden level is a light filled space where you will find two more bedrooms, full bath, laundry and a kitchen area. With access directly to the pool, this is your 'outdoor living' dream come true... luxury vinyl plank won't mind a little pool water and the convenience of a full bath is a must . This space is also ideal as a guest suite or perhaps an income opportunity. The back yard is fully fenced and the pool is open and waiting for you! This home has only had two owners in 54 years...come add your history to 329 Wood Avenue. Some nearby points of interest include, Historic Downtown Winchester, The Museum of the Shenandoah Valley with gardens and walking trails, Winchester Medical Center, Whittier Park and Handley Library. Shopping and dining options are also moments away. Please see attached document highlighting all the wonderful renovations. Floor plans are also in the document section. Furnishings are available for purchase.

329 Wood Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Keller Williams Realty.

$535,000

Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a functional, flowing layout with spacious living and dining areas, an updated kitchen with stainless steel appliances, refreshed cabinetry, and a modern backsplash. A bright four-season sunroom overlooking the backyard is perfect for morning coffee, a home office, reading space, or an additional dining area. The lower level provides a large recreation area, half bath, and oversized laundry room (15' x 9') with exterior egress and excellent potential for conversion to a 4th bedroom or flex space by relocating the washer/dryer nearby. With full heating and cooling and 8-foot ceilings, the lower level offers a comfortable additional living space ideal for guests, hobbies, or everyday use. Major updates offer peace of mind, including a new roof, two heat pump HVAC systems, and water heater (all 2023), along with updated flooring, lighting, and refreshed interior finishes throughout. Outside, the property sits on a 0.36-acre lot with perennial landscaping, terraced natural stone outcroppings, and a large, established Basswood tree. An inviting front porch enhances curb appeal, while the true two-car side-entry garage and wide driveway provide excellent functionality and privacy. Enjoy the added benefit of being less than a block from Whittier Park, featuring a playground, soccer field, basketball court, and open green space. This home provides a rare opportunity to own a well-maintained, thoughtfully-updated home in one of Winchester’s most convenient neighborhoods.

3 Beds ⋅ 3 Baths

Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a functional, flowing layout with spacious living and dining areas, an updated kitchen with stainless steel appliances, refreshed cabinetry, and a modern backsplash. A bright four-season sunroom overlooking the backyard is perfect for morning coffee, a home office, reading space, or an additional dining area. The lower level provides a large recreation area, half bath, and oversized laundry room (15' x 9') with exterior egress and excellent potential for conversion to a 4th bedroom or flex space by relocating the washer/dryer nearby. With full heating and cooling and 8-foot ceilings, the lower level offers a comfortable additional living space ideal for guests, hobbies, or everyday use. Major updates offer peace of mind, including a new roof, two heat pump HVAC systems, and water heater (all 2023), along with updated flooring, lighting, and refreshed interior finishes throughout. Outside, the property sits on a 0.36-acre lot with perennial landscaping, terraced natural stone outcroppings, and a large, established Basswood tree. An inviting front porch enhances curb appeal, while the true two-car side-entry garage and wide driveway provide excellent functionality and privacy. Enjoy the added benefit of being less than a block from Whittier Park, featuring a playground, soccer field, basketball court, and open green space. This home provides a rare opportunity to own a well-maintained, thoughtfully-updated home in one of Winchester’s most convenient neighborhoods.

315 Walker St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Colony Realty.

$487,500

Conveniently located in the heart of Winchester, this spacious brick ranch offers the perfect combination of timeless character, thoughtful updates, and flexible living space. Situated on a nearly half-acre corner lot, the property provides room to spread out while remaining just minutes from Winchester Medical Center, shopping, dining, and major commuter routes. Inside, you'll find beautiful hardwood flooring throughout much of the main level and an abundance of natural light pouring through oversized windows. The updated kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, butcher block countertops, tile backsplash, and a large peninsula that creates additional seating and workspace. The adjoining dining area opens to a charming sunroom that can be enjoyed year-round. Exposed brick accents, a wood-burning stove, and easy access to the kitchen make this a favorite gathering space for relaxing with family and friends. The main level offers four generously sized bedrooms, including a private primary suite with an updated bath featuring a walk-in glass shower and modern finishes. A conveniently located laundry area adds everyday practicality. One secondary bedroom showcases its own wood-burning fireplace, creating a cozy retreat ideal for guests, a home office, or hobby space. A second updated full bathroom serves the additional bedrooms and features stylish finishes, a double vanity, and a tiled tub/shower combination. Downstairs, the partially finished basement expands the home's living potential with a large recreation area centered around a striking brick fireplace. Whether used as a family room, game room, home gym, or media space, the possibilities are endless. An unfinished section provides ample storage space for seasonal items and equipment. Outside, mature trees frame the backyard, creating a peaceful setting for outdoor enjoyment. A rear patio, charming brick walkway, pergola, storage shed, oversized attached two-car garage, and expansive driveway complete the property, offering both functionality and outdoor appeal. With generous living space, desirable updates, and an exceptional Winchester location, this home is ready to welcome its next owners. Some photos have been virtually staged to illustrate potential furniture placement and room design

4 Beds ⋅ 2 Baths

Conveniently located in the heart of Winchester, this spacious brick ranch offers the perfect combination of timeless character, thoughtful updates, and flexible living space. Situated on a nearly half-acre corner lot, the property provides room to spread out while remaining just minutes from Winchester Medical Center, shopping, dining, and major commuter routes. Inside, you'll find beautiful hardwood flooring throughout much of the main level and an abundance of natural light pouring through oversized windows. The updated kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, butcher block countertops, tile backsplash, and a large peninsula that creates additional seating and workspace. The adjoining dining area opens to a charming sunroom that can be enjoyed year-round. Exposed brick accents, a wood-burning stove, and easy access to the kitchen make this a favorite gathering space for relaxing with family and friends. The main level offers four generously sized bedrooms, including a private primary suite with an updated bath featuring a walk-in glass shower and modern finishes. A conveniently located laundry area adds everyday practicality. One secondary bedroom showcases its own wood-burning fireplace, creating a cozy retreat ideal for guests, a home office, or hobby space. A second updated full bathroom serves the additional bedrooms and features stylish finishes, a double vanity, and a tiled tub/shower combination. Downstairs, the partially finished basement expands the home's living potential with a large recreation area centered around a striking brick fireplace. Whether used as a family room, game room, home gym, or media space, the possibilities are endless. An unfinished section provides ample storage space for seasonal items and equipment. Outside, mature trees frame the backyard, creating a peaceful setting for outdoor enjoyment. A rear patio, charming brick walkway, pergola, storage shed, oversized attached two-car garage, and expansive driveway complete the property, offering both functionality and outdoor appeal. With generous living space, desirable updates, and an exceptional Winchester location, this home is ready to welcome its next owners. Some photos have been virtually staged to illustrate potential furniture placement and room design

1317 Caroline St, Winchester

Listing courtesy of Weichert Realtors - Blue Ribbon. Contact:

Selling Office: RE/MAX Roots.

$480,000

Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry room. the finished lower level expands the living space with a second fireplace, a wet bar, and a large recreation area ideal for a pool table, ping-pong, or game nights with family and friends. Additional features include a one-and-a-half-car garage, providing excellent storage and parking options, along with additional off-street parking. Enjoy outdoor living on the rear deck overlooking a great backyard—perfect for relaxing or entertaining. Located on a quiet street within walking distance to downtown and convenient to the hospital, this home offers both privacy and accessibility in a desirable setting.

3 Beds ⋅ 3 Baths

Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry room. the finished lower level expands the living space with a second fireplace, a wet bar, and a large recreation area ideal for a pool table, ping-pong, or game nights with family and friends. Additional features include a one-and-a-half-car garage, providing excellent storage and parking options, along with additional off-street parking. Enjoy outdoor living on the rear deck overlooking a great backyard—perfect for relaxing or entertaining. Located on a quiet street within walking distance to downtown and convenient to the hospital, this home offers both privacy and accessibility in a desirable setting.

308 Ridge Ave, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Samson Properties.

$430,000

Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

3 Beds ⋅ 2 Baths

Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

338 Lanny Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Pearson Smith Realty, LLC.

$425,000

Location, Location. Brick Rancher offers Walkout Basement, 4 Bedrooms, Two Full Baths. Hardwood Floors throughout. Front Entry Ceramic Tiled. Kitchen Luxury Vinyl Floor, New Dishwasher,Disposal, Refrigerator with Ice-maker( Not Hooked Up) and Electric Range. Basement Partially Finished with Brick Fireplace with Timberline Wood Stove Insert, Fourth Bedroom, Laundry and Storage Area. Rear 15x12 Concrete Patio of Garage. Large Back Yard with Chain-link Fencing. Two Outbuildings for Storage. One Car Garage with Concrete Driveway.

3 Beds ⋅ 2 Baths

Location, Location. Brick Rancher offers Walkout Basement, 4 Bedrooms, Two Full Baths. Hardwood Floors throughout. Front Entry Ceramic Tiled. Kitchen Luxury Vinyl Floor, New Dishwasher,Disposal, Refrigerator with Ice-maker( Not Hooked Up) and Electric Range. Basement Partially Finished with Brick Fireplace with Timberline Wood Stove Insert, Fourth Bedroom, Laundry and Storage Area. Rear 15x12 Concrete Patio of Garage. Large Back Yard with Chain-link Fencing. Two Outbuildings for Storage. One Car Garage with Concrete Driveway.

341 Wood Ave, Winchester

Listing courtesy of Jim Barb Realty Inc.. Contact:

Selling Office: MarketPlace REALTY.

How much is your home worth?

How much is your home worth?