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103 Mayfair Ct, Winchester
$345,000
3 Beds ⋅ 2 Baths ⋅ 25501461 MLS
This well-maintained ranch offers 3 bedrooms, 2 full baths, and a 3-car garage that's insulated, heated, and wired with a — Looks good. The garage has a 100amp service, 3each. 220v 30amp breakers—ideal for hobbies or extra storage. The property sits on a great lot with a fenced-in backyard, perfect for both privacy and entertaining. Inside, the split-bedroom design separates the secondary bedrooms from the primary suite. You'll enjoy vinyl plank flooring throughout the main living areas, with carpet in the bedrooms for added comfort. The kitchen features granite countertops and stainless steel appliances, while the nine-foot smooth ceilings throughout create an open, airy feel. The unfinished walk-out basement is roughed in for a full bath, offering endless possibilities for future expansion. A blend of practicality and style, this Colby Ridge home is ready for its next owner!

103 Mayfair Ct, Winchester

168 Buckingham Ln, Winchester
$340,000
4 Beds ⋅ 3 Baths ⋅ 26006049 MLS
Tucked away on a quiet cul-de-sac, this well-maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and convenience. Featuring a 2-car garage plus an additional covered carport ideal for a boat, RV, or extra parking, this property is designed to fit a variety of lifestyles. Inside, you'll find a functional layout with a separate office and formal dining room, perfect for both everyday living and entertaining. The owner refreshed the home since purchasing with new paint and installed luxury vinyl plank flooring throughout the main living areas downstairs, giving it a clean, updated feel. Step outside to enjoy your own backyard retreat, complete with an above-ground pool featuring a new liner and updated decking, as well as raised garden beds ready for its next owners. Located just minutes from Kroger, Walmart, Downtown Winchester, and Boonesborough State Park—and only about 20 minutes to both Lexington and Richmond—this home offers peaceful living with unbeatable convenience. Don't miss your chance to make it yours!

168 Buckingham Ln, Winchester

305 Abbeywood Dr, Winchester
$310,000
3 Beds ⋅ 3 Baths ⋅ 26012645 MLS
Welcome to this updated home situated at the end of a cul de sac in desirable Colby Ridge. Updates include new flooring, appliances, paint & more! This adorable home features a first-floor primary suite, utilities on the first floor, a cozy gas fireplace, an eat-in kitchen, formal dining room & a large living room with a vaulted ceiling. Upstairs, you'll find 2 additional bedrooms, a full bath & a LARGE bonus room, perfect for a playroom, workout space or home office. Enjoy summer nights on your fresh-stained deck & enjoy your favorite hobby in the wooden backyard shed. Located just minutes to Kroger, Lowe's, Walmart & I-64, this home is a great value in a convenient location! Selling as is. Inspections welcome.

305 Abbeywood Dr, Winchester

202 Dubuy Dr, Winchester
$302,500
3 Beds ⋅ 3 Baths ⋅ 25506536 MLS
Step inside this meticulously maintained residence, essentially offering the rare opportunity to own a near-new home (2022) without the wait of new construction. This property has been thoughtfully designed for both sophisticated daily living and impressive entertaining. The open-concept main level centers around a custom-built kitchen that truly elevates the space. You'll find sleek, high-gloss cabinetry paired beautifully with carefully hand-selected granite countertops, providing a stunning visual and tactile experience. Durable, continuous LVP flooring flows throughout the main floor, combining style with absolute practicality. The main level also thoughtfully features a private, standalone office that overlooks the serene outdoors—ideal for remote work or a quiet reading retreat. The main floor primary suite is a true sanctuary, complete with a luxurious en-suite bathroom and a generously sized walk-in closet. The living space extends dramatically into the finished, walk-out basement, which provides extensive additional square footage. Here, you will find a comfortable second living room, two large additional bedrooms, and a full bathroom—perfect for guests, recreation, or extended family. Finally, enjoy the peace of mind offered by a fully fenced-in backyard, providing security and a private space for outdoor relaxation. This home delivers on every detail, from its impeccable finishes to its highly functional layout.

202 Dubuy Dr, Winchester

110 Buckingham Ln, Winchester
$290,000
3 Beds ⋅ 2 Baths ⋅ 26014133 MLS
The original buyer's plans changed, and their loss may be your second chance. This beautiful Winchester ranch is the kind of home buyers walk into and immediately feel good about. From the vaulted ceilings and incredibly beautiful luxury vinyl plank flooring to the updated bathrooms, well-maintained systems, epoxied garage floor, and easy one-level layout, this home is truly move-in ready and built to be enjoyed for years to come. The charm continues outside with a covered front porch, a beautiful back wood deck, a relaxing pergola area, and a nice-sized backyard with a well-maintained vegetable garden ready for its next owner to enjoy. It has that rare "cute house" feeling that is hard to fake and even harder to find. In fact, agents who showed it the first time around said it best: "Wow, that was a cute house. We really enjoyed it." Homes like this do not come around often. This one hit the market a month and a half ago, received multiple offers, and now it is unexpectedly available again. Everything about this home feels like a little fairy tale that came true. Now is your chance. Do not miss out this time. Schedule your private showing today.

110 Buckingham Ln, Winchester

207 Abbeywood Dr, Winchester
$287,000
3 Beds ⋅ 3 Baths ⋅ 26011852 MLS
This 3 bedroom, 2.5 bath home offers an incredible chance to build equity in a fantastic Winchester location close to shopping, dining, schools, and everyday conveniences. Big-ticket updates are already handled, including a new roof (2025), new water heater (2025), HVAC replaced in 2016, and updated doors/windows (2018)—giving buyers peace of mind where it matters most. Inside, the home is priced to reflect cosmetic updates needed, including paint and flooring, making this the perfect opportunity for buyers who want to personalize a home and gain instant value rather than pay premium pricing for cosmetic finishes they may change anyway. Whether you're a first-time buyer, investor, or someone looking for a smart opportunity in a desirable neighborhood, this one is worth a look.

207 Abbeywood Dr, Winchester

136 Sturbridge Ln, Winchester
$274,900
3 Beds ⋅ 3 Baths ⋅ 26015181 MLS
Good things absolutely do come in affordable packages! This well maintained 3 bed 2.5 bath home on the Lexington side of Winchester has a beautiful back yard with a deck and built-in porch swing. It is privacy fenced and ready for you to enjoy, but not at the expense of access to town! With shopping right around the corner, and access to the highway not far off, this home would be great for someone who already loves Winchester, or a commuter from Lexington who is looking for more bang for their buck. This home is competitively priced per square foot and boasts a young roof, fault free systems, and easy to manage layout. The generous primary bedroom has an oversized walk in closet, and one of the additional bedrooms has a walk in closet, assuring storage is no issue. Enjoy your peace and quiet, or bring the kids and dogs- this set up is turnkey for everyone!

136 Sturbridge Ln, Winchester

164 Buckingham Ln, Winchester
$263,000
3 Beds ⋅ 2 Baths ⋅ 26009383 MLS
Welcome home to easy, one-level living in this inviting 3-bedroom, 2-bath ranch! From the moment you step inside, the foyer opens to a spacious living room with a vaulted ceiling, creating a bright and open feel. The desirable split-bedroom layout offers privacy, with the primary suite tucked away on one side of the home featuring a large walk-in closet and full bath. Two additional bedrooms and a second full bath are located on the opposite side, making the floor plan both functional and comfortable. The spacious eat-in kitchen provides plenty of room for gathering and opens to a screened-in patio, the perfect spot for morning coffee, relaxing evenings, or enjoying the backyard view. Outside, the large backyard offers room to garden, play, or entertain, plus a unique two-level storage shed for extra space and organization. Conveniently located near restaurants, shopping, and everyday amenities. Home being sold AS-IS. Inspections welcome.

164 Buckingham Ln, Winchester

410 Wellington Way, Winchester
$262,500
3 Beds ⋅ 2 Baths ⋅ 25506265 MLS
Discover 410 Wellington Way, a beautifully updated property in a convenient Winchester location! This fully updated, move-in-ready home delivers style, comfort, and convenience from the moment you walk in. Enjoy a bright eat-in kitchen equipped with brand-new, warrantied appliances, plus modern finishes throughout—including all-new paint, new flooring, new light fixtures, new doors, updated vanities, faucets, hardware, and ceiling fans in every bedroom. The spacious primary suite offers the privacy buyers want, complete with an ensuite bath and walk-in closet. Outside, the fenced backyard is perfect for pets, play, or entertaining. A one-car garage adds to the practicality that today's buyers are seeking. With fresh updates in every room and large windows for lots of light, this cozy home is truly move-in ready.

410 Wellington Way, Winchester

414 Wellington Way, Winchester
$259,000
3 Beds ⋅ 2 Baths ⋅ 26002092 MLS
Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance package in the kitchen—so the big-ticket items are already done for you. The home features durable vinyl plank flooring throughout, providing a clean, modern look and easy maintenance. An attached one-car garage adds everyday convenience, while the fully fenced backyard is perfect for pets, play, or relaxing outdoors. Whether you're a first-time buyer, downsizing, or looking for a turnkey investment, this home checks all the boxes: updated, affordable, and truly move-in ready. Don't miss this one!

414 Wellington Way, Winchester

319 Essex Ct, Winchester
$195,000
3 Beds ⋅ 3 Baths ⋅ 26003610 MLS
This Colby Ridge neighborhood townhome location is hard to beat as it is just minutes from Kroger, Walmart, the Bypass, interstate access, and a wide variety of restaurants and everyday conveniences. The main floor offers a convenient half bath, a welcoming living room that opens naturally into the dining area and kitchen, and a laundry room tucked just inside the one-car garage entry. Off the dining area, step out onto the back deck (built in 2023) overlooking a fully fenced yard which is a great spot to relax or let pets play. The unfinished walkout basement adds plenty of storage space with room to expand in the future. Upstairs, you'll find three bedrooms and a full bath, including a primary suite with double closets and a private bath with a shower. With a practical layout, inviting outdoor space, and an unbeatable location, this townhome is ready for its next owner.

319 Essex Ct, Winchester

325 Essex Ct, Winchester
$190,000
2 Beds ⋅ 2 Baths ⋅ 26022515 MLS
FRESHLY PAINTED BRAND NEW APPLIANCES HUGE FENCED BACKYARD NEWER PRIVACY FENCE FIRST TIME BUYER OPPORTUNITY INVESTMENT OPPORTUNITY $1,000 BUYER CREDIT Welcome to 325 Essex Ct in Winchester! This charming 2 bedroom, 1.5 bath home offers an excellent opportunity for a first time homebuyer or investor looking for an affordable property with great potential. Inside, you'll find fresh paint and brand new appliances, giving the home a clean and refreshed feel. The spacious backyard is a standout feature, offering plenty of room for pets, entertaining, gardening, or simply enjoying your own private outdoor space, with a newer privacy fence already in place. With a functional layout, desirable updates, and a large fenced in yard, this home is ready for its next owner. Whether you're looking to stop renting and make homeownership a reality or add another property to your investment portfolio, this one is worth a look! Plus, the lender I work with is offering a $1,000 buyer credit to qualified buyers. Don't miss your opportunity to make 325 Essex Ct your next home or investment!

325 Essex Ct, Winchester

310 Essex Ct, Winchester
$185,000
2 Beds ⋅ 3 Baths ⋅ 26009036 MLS
Welcome home to this charming and spacious 2-bedroom, 2.5-bath townhome perfectly situated on a quiet cul-de-sac. Offering both comfort and privacy, this home backs up to a peaceful open field—providing serene views and no rear neighbors. Step inside to find a bright and inviting living space featuring an elegant electric fireplace, perfect for cozy evenings. The open layout flows seamlessly into an eat-in kitchen designed for both functionality and style, complete with a center island, ample cabinetry, and plenty of room for casual dining or entertaining. Upstairs, you'll find two generously sized bedrooms, each offering comfort and privacy, along with well-appointed bathrooms to accommodate family or guests. The additional half-bath on the main level adds extra convenience. Whether you're enjoying quiet mornings overlooking the field or hosting friends in your open-concept living area, this townhome offers the perfect blend of comfort, space, and location. Don't miss your opportunity to own this beautifully positioned home in a desirable setting!

310 Essex Ct, Winchester

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