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$325,000
4 Beds ⋅ 3 Baths
Price Improved and Move-In Ready! Welcome to 112 Chatham Square in desirable Huntington Meadows, where comfort, convenience, and recent updates come together in a fantastic Winchester location. Freshly painted throughout, this well-maintained 4-bedroom, 2.5-bath townhome offers a functional layout with generous living space designed to accommodate a variety of lifestyles. The updated kitchen features stainless steel appliances, while the remodeled second-floor bathroom provides a fresh, modern touch. A finished basement adds valuable flexibility and can easily serve as a recreation room, home office, fitness area, guest space, or additional living room. A full-size washer and dryer convey, making everyday living even more convenient. Step outside to enjoy one of the home’s standout features—an impressive fenced backyard offering plenty of space for entertaining, relaxing, gardening, pets, or outdoor gatherings. A deck has creates an ideal setting for enjoying morning coffee, evening meals, or time with family and friends. Conveniently located just minutes from Route 7, I-81, shopping, dining, schools, and everyday amenities, this home offers easy access to commuter routes while maintaining the feel of a quiet neighborhood setting. With a recent price adjustment, fresh paint, thoughtful updates, and exceptional outdoor space, this home presents an outstanding opportunity for buyers seeking value, flexibility, and convenience in Winchester. Schedule your showing today and experience everything this home has to offer.

112 Chatham Sq, Winchester

Listing courtesy of HoneyWay. Contact:

Selling Office: Re/Max Roots.

$310,000
3 Beds ⋅ 2 Baths
Updated brick townhome featuring 3 bedrooms and 1.5 baths with numerous recent improvements. Updates include HVAC (2025), water heater (2024), roof (2023), granite countertops and kitchen sink (2026), stove and microwave (2026), fresh paint (2026), updated lighting (2026), new carpet and pad (2026), updated bath and laundry flooring (2026), and new door hardware throughout (2026). Convenient location close to shopping, dining, and commuter routes. Move-in ready with major updates already completed! Window shades as-is. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

218 Stratford Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Samson Properties.

$250,000
2 Beds ⋅ 1 Baths
Welcome to this well-maintained home just outside city limits, offering easy access to Route 7 and I-81 while still feeling tucked away from noise and traffic. Enjoy being close to community tot lots, tennis courts, restaurants, Winchester Medical Center, and shopping. Step inside to find beautiful hardwood floors throughout and a bright, welcoming feel. The main living area features charming built-in wall details, creating a cozy space to relax or gather. The kitchen offers plenty of cabinet space, a new backsplash, convenience of a washer/dryer and built-in shelving for everyday needs. Upstairs, the spacious primary bedroom is filled with natural light and includes a built-in office area—perfect for working from home or a quiet retreat. Enjoy soft morning sunlight that makes the space feel warm and inviting year-round. Outside, the fully fenced backyard offers privacy along with recent landscaping, a newly finished deck floor—perfect for relaxing or entertaining—and an oversized shed for extra storage. With thoughtful updates including kitchen countertops, appliances, fencing, decking, and landscaping, this move-in ready home is a wonderful opportunity to settle into a comfortable space under $250,000!

207 Stratford Dr, Winchester

Listing courtesy of RE/MAX Real Estate Connections. Contact:

Selling Office: Samson Properties.

$200,000
2 Beds ⋅ 3 Baths
Welcome to 301 Braeburn Drive, a spacious brick end-unit townhouse conveniently located in Winchester City. This home features 2 bedrooms, 2.5 baths, and a finished walk-out basement offering additional living space plus a separate storage area. Enjoy the added privacy and natural light of an end unit, along with two personal parking spaces. Major updates include a new roof and a new HVAC system, both 3 years old, providing added peace of mind. Conveniently located near shopping, dining, commuter routes, and all that Winchester has to offer. A great opportunity to make this well-maintained townhouse your new home!

301 Braeburn Dr, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.