Winchester Homes with Colonial Style

Winchester Homes with Colonial Style

Welcome to Winchester, a charming subdivision nestled in the heart of the United States, where history and modern living intertwine seamlessly. This picturesque community is renowned for its stunning Colonial-style homes, which exude timeless elegance and a sense of warmth that makes every resident feel right at home.

As you stroll through the tree-lined streets of Winchester, you'll be captivated by the stately facades adorned with classic columns, intricate moldings, and inviting front porches that beckon you to sit and enjoy a cup of coffee while taking in the serene surroundings. These Colonial-style homes not only offer a glimpse into America's architectural heritage but also provide spacious interiors perfect for family gatherings and entertaining friends.

Winchester is more than just a collection of beautiful homes; it is a vibrant community that fosters a strong sense of belonging. With well-maintained parks, recreational facilities, and a variety of local shops and restaurants, residents have everything they need right at their fingertips. Families will appreciate the top-rated schools in the area, ensuring that children receive an excellent education while enjoying a safe and nurturing environment.

Whether you're searching for your first home or looking to settle down in a place that feels like a retreat from the hustle and bustle of everyday life, Winchester offers an idyllic setting that balances charm, comfort, and community spirit. Discover the beauty and warmth of Colonial-style living in this delightful subdivision, and make Winchester your next home sweet home!

Newest Winchester Homes with Colonial Style

3 Beds ⋅ 3 Baths

Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water heater, 2025 - new sewer line under driveway & from driveway to street, new LVP in kitchen, 2026 - replaced / leveled living room floor & subfloor, new LVP. Schedule your tour today!

117 E Pall Mall St, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com

3 Beds ⋅ 2 Baths

This beautifully renovated 3-bedroom, 2-bathroom rowhome is the perfect opportunity for a first-time homebuyer looking for style, comfort, and value. Step inside and enjoy a bright, modern interior featuring updated finishes, spacious living areas, and a thoughtfully designed layout that's ready for you to move right in. The updated kitchen offers contemporary cabinetry, sleek countertops, and plenty of space for cooking and entertaining. Both full bathrooms have been tastefully renovated with modern fixtures and finishes. The generous bedrooms provide comfort and flexibility for growing families, guests, or a home office. Located in a convenient Baltimore neighborhood with easy access to major commuter routes, shopping, dining, parks, and public transportation, this home combines affordability with modern living. Why rent when you can own? Don't miss your chance to make this fully renovated gem your new home. Schedule your private tour today!

1221 Ashburton St, Baltimore

Listing courtesy of Keller Williams Legacy. Contact: 4436609229

3 Beds ⋅ 1 Baths

NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Buyer to pay all transfer and recording fees Minimum $2,000 EMD. Excellent Opportunity ...use your imagination! Property can be rehabbed for a nice rental investment or homeowner. Property sold "as is". Home Inspections for informational purposes only. Seller will make no repairs. . In addition, this property qualifies for a special 5.75% mortgage program—a rare financing opportunity that makes this high-quality home even more affordable. Ask Listing Agent for details. Photos are old and new

2730 Winchester St, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

2 Beds ⋅ 1 Baths

MOVE IN READY TOWNHOME IN BALTIMORE!! END ROW TOWNHOME FRESHLY PAINTED THROUGH OUT, UPDATED LVP FLOORING...PREVIOUS RENTAL PROPERTY - WAS RENTED FOR $1660 PER MONTH!! Welcome to 1044 Ellicott Driveway in Baltimore, MD, a charming and inviting home offering a wonderful combination of comfort, character, and convenience. This well-maintained residence features spacious living areas filled with natural light, creating a warm and welcoming atmosphere throughout. The thoughtfully designed layout provides comfortable everyday living along with flexible spaces perfect for entertaining, working from home, or relaxing with family and friends. The kitchen offers ample cabinetry, quartz counters, gas cooking and workspace, flowing seamlessly into the dining and living areas for easy functionality. Generous bedrooms provide peaceful retreats, while the bathrooms are designed with both comfort and practicality in mind. Outside, enjoy private outdoor space ideal for relaxing, gardening, or entertaining guests. Conveniently located near shopping, dining, parks, commuter routes, and all that Baltimore has to offer, this home presents an exceptional opportunity for buyers seeking style, convenience, and value in a desirable location.

1044 Ellicott Driveway, Baltimore

Listing courtesy of Winning Edge. Contact: 4434636009

3 Beds ⋅ 2 Baths

NOT AN AUCTION, NOT A SHORT SALE, NOT A BANK OWNED, NOT A FORECLOSURE, NOT WHOLESALING---QUICK AND EASY. Ask me about 5.75% financing program.

2813 Riggs Ave, Baltimore

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

3 Beds ⋅ 2 Baths

Welcome to 2737 Riggs Avenue in Baltimore, Maryland — a beautifully renovated home where classic charm meets modern comfort. As you approach the property, you’ll be greeted by a brand-new front porch with durable Trex flooring, the perfect spot to enjoy your morning coffee or greet neighbors passing by. Step through the new front door, and you’ll immediately notice the attention to detail and high-quality craftsmanship throughout. The main level welcomes you with fresh paint, elegant crown molding, recessed lighting, and beautiful luxury vinyl plank flooring that flows seamlessly from the living room through the dining area and into the kitchen. This open-concept space feels bright, spacious, and inviting — perfect for entertaining or relaxing at the end of the day. The kitchen has been fully updated with new cabinetry, sleek countertops, and brand-new stainless steel appliances, giving it both style and functionality. A rear entrance from the kitchen leads out to a fenced backyard overlooking a nearby playground — an ideal setup for children, pets, or simply enjoying a private outdoor retreat. Upstairs, you’ll find three comfortable bedrooms, each offering new flooring, fresh paint, modern light fixtures, and plenty of natural light through the updated windows. One of the bedrooms features a charming barn door, adding a touch of character and style. The full bath on this level has been completely renovated, showcasing designer tile, a quality vanity, and modern brushed-nickel fixtures for a spa-like feel. The unfinished basement offers extra space for storage and a half bath. Beyond its beautiful interior, this home offers peace of mind with all the major systems recently upgraded: New roof (Sept 2025) New heat and AC system (Sept 2025) New front and back doors (Sept–Oct 2025) New exterior front steps and porch floor (Oct 2025) New kitchen cabinets and appliances (Fall 2025) Located in a convenient Baltimore neighborhood, you’ll enjoy close proximity to Gwynns Falls/Leakin Park, Mondawmin Mall, Coppin State University, and just minutes to downtown Baltimore for shopping, dining, and entertainment. Nearby schools, playgrounds, and public transit make this home ideal for both families and commuters. This properties qualifies for Baltimore City grant program, where it offers $10k-$20k down payment & closing costs for eligible buyers! This home is truly a move-in ready home. Come see what 2737 Riggs Avenue has to offer.

2737 Riggs Ave, Baltimore

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000

3 Beds ⋅ 1 Baths

Interior Rowhome with updated flooring and bathroom that is in need of finishing. The property is near completion and ready for a new owner. Large front porch for those summer evenings, unfinished basement. Come and get it! The property is sold As-Is, Cash/ Hard Money.

2730 Riggs Ave, Baltimore

Listing courtesy of Marathon Real Estate. Contact:

Start Your Search

Joseph Ciganek

As an Eastern Shore Realtor, I know that a real estate transaction is built on trust. I pride myself on my honesty and integrity in providing the highest quality representation for my clients. I have spent my entire life in Chestertown and on the Chesapeake Bay and have a deep respect and understanding for why life here is so special. You can rely on my deep knowledge of the eastern shore and its waterways when buying a home. As an Eastern Shore native, full-time Realtor and licensed Attorney, I have the skill set to help you navigate any real estate transaction; waterfront, farms, commercial, you name it. Buying or selling real estate requires an experienced and trustworthy advocate. Let me be your guide. Growing up on the banks of the Chester River, I was fortunate enough to enjoy everything the Chesapeake Bay has to offer, whether crabbing, fishing or just about every water-sport you can think of. After graduating from Washington College with a B.A. in Economics and Finance, I attended University of Baltimore School of Law. Working full time and going to school at night, I graduated cum laude and proceeded to clerk for the Honorable Harris P. Murphy, Circuit Court of Kent County, Md. That’s when I decided to make a drastic career shift to practicing full time as a Realtor in 2021. Since then I have enjoyed showing others why life on the shore really is the land of pleasant living. Outside of real estate, I enjoy getting exercise with my black lab, playing pickleball, soccer and racing the historic log canoe sail boats up and down the Chesapeake Bay.

Learn More

Browse Winchester Homes by Lot features