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Discover timeless charm and modern comfort in this exquisite brick ranch home, perfectly situated on a spacious corner lot in the West End Allentown. The classic brick exterior, complemented by a neatly manicured lawn and mature landscaping, creates an inviting first impression. Step inside to a welcoming living space adorned with refinished hardwood floors and a generously sized bay window, bathing the room in natural light. Architectural archways gracefully connect the living area to the naturally illuminated dining space, which also features rich hardwood flooring, leading seamlessly into a functional corner kitchen. This kitchen boasts ample cabinetry, practical counter space, and durable tile flooring, ready for culinary adventures. Comfort continues throughout the tranquil bedrooms, all featuring warm hardwood flooring and ample natural light. Ceiling fans provide a cooling comfortable atmosphere, while baseboard heating ensures warmth during cooler months. The bathrooms offer a unique retro charm with distinctive black and pink tile work, creating a vibrant aesthetic. The mostly finished basement offers versatile space, including a full bathroom area and a corner soaking tub, presenting endless possibilities for customization. Daylight windows and walk-out access further enhance this versatile area, providing an inviting side entrance with a decorative glass front door. Outside, a spacious wood deck overlooks a pristine, level lawn, bordered by mature landscaping and privacy fencing. A lower deck provides a great entertaining area or the possibility of an expansive relaxation area. A charming backyard shed provides additional storage, completing this verdant oasis. This residence truly blends enduring appeal with modern living, offering an exceptional lifestyle.

2 Beds ⋅ 2 Baths

Discover timeless charm and modern comfort in this exquisite brick ranch home, perfectly situated on a spacious corner lot in the West End Allentown. The classic brick exterior, complemented by a neatly manicured lawn and mature landscaping, creates an inviting first impression. Step inside to a welcoming living space adorned with refinished hardwood floors and a generously sized bay window, bathing the room in natural light. Architectural archways gracefully connect the living area to the naturally illuminated dining space, which also features rich hardwood flooring, leading seamlessly into a functional corner kitchen. This kitchen boasts ample cabinetry, practical counter space, and durable tile flooring, ready for culinary adventures. Comfort continues throughout the tranquil bedrooms, all featuring warm hardwood flooring and ample natural light. Ceiling fans provide a cooling comfortable atmosphere, while baseboard heating ensures warmth during cooler months. The bathrooms offer a unique retro charm with distinctive black and pink tile work, creating a vibrant aesthetic. The mostly finished basement offers versatile space, including a full bathroom area and a corner soaking tub, presenting endless possibilities for customization. Daylight windows and walk-out access further enhance this versatile area, providing an inviting side entrance with a decorative glass front door. Outside, a spacious wood deck overlooks a pristine, level lawn, bordered by mature landscaping and privacy fencing. A lower deck provides a great entertaining area or the possibility of an expansive relaxation area. A charming backyard shed provides additional storage, completing this verdant oasis. This residence truly blends enduring appeal with modern living, offering an exceptional lifestyle.

2901 W Washington St, Allentown

Listing courtesy of RE/MAX Real Estate-Allentown. Contact:

Selling Office: Non Subscribing Office.

$325,000

3 Beds ⋅ 1 Baths

202 Valley Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$318,000

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind that sells itself: leave the car in the driveway and run the day on foot, from morning coffee downtown to an evening stroll after the festivals. Inside, the sun-filled sunroom anchors the home with year-round natural light and a flexible layout that adapts to how you actually live. Use it as a quiet reading nook, a bright home office, an art studio, or simply a place to begin and end each day. The three-bedroom, single-level floor plan delivers true main-level living with no stairs and no wasted square footage, an increasingly rare find in historic Chestertown. The HVAC has been recently updated, providing year-round comfort, modern efficiency, and predictable utility costs for new owners. Step outside to a generous, tree-shaded yard offering a level of privacy and outdoor space uncommon to a home this close to downtown. There's room to garden, host family dinners, let pets roam, or simply enjoy a quiet afternoon in the shade. The setting feels tucked away while the rest of the town is just a short walk from your front door. For weekend owners, the home offers true lock-and-leave simplicity. For full-time residents, it offers the daily rhythm of a small college town with a real cultural calendar, a thriving farmers market, and a walkable downtown filled with independent shops and restaurants. Fiber optic internet is available at the property, supporting fast, reliable connectivity for remote work, streaming, and study without compromise. Single-level, move-in ready, and walkable to it all — a rare combination in this small, storybook college town. The home suits a wide range of buyers, from first-time homeowners and downsizers to weekend retreat owners and anyone seeking a quieter life with genuine connection to community. Schedule your private tour today!

3 Beds ⋅ 3 Baths

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind that sells itself: leave the car in the driveway and run the day on foot, from morning coffee downtown to an evening stroll after the festivals. Inside, the sun-filled sunroom anchors the home with year-round natural light and a flexible layout that adapts to how you actually live. Use it as a quiet reading nook, a bright home office, an art studio, or simply a place to begin and end each day. The three-bedroom, single-level floor plan delivers true main-level living with no stairs and no wasted square footage, an increasingly rare find in historic Chestertown. The HVAC has been recently updated, providing year-round comfort, modern efficiency, and predictable utility costs for new owners. Step outside to a generous, tree-shaded yard offering a level of privacy and outdoor space uncommon to a home this close to downtown. There's room to garden, host family dinners, let pets roam, or simply enjoy a quiet afternoon in the shade. The setting feels tucked away while the rest of the town is just a short walk from your front door. For weekend owners, the home offers true lock-and-leave simplicity. For full-time residents, it offers the daily rhythm of a small college town with a real cultural calendar, a thriving farmers market, and a walkable downtown filled with independent shops and restaurants. Fiber optic internet is available at the property, supporting fast, reliable connectivity for remote work, streaming, and study without compromise. Single-level, move-in ready, and walkable to it all — a rare combination in this small, storybook college town. The home suits a wide range of buyers, from first-time homeowners and downsizers to weekend retreat owners and anyone seeking a quieter life with genuine connection to community. Schedule your private tour today!

109 Cedar St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$249,000

Sought after location in College Heights. Short walk to downtown Chestertown and Parks. This cozy rancher is a diamond in the rough and is ready for new owners! located on a safe and quiet street, with public water and sewer with municipal pickups. Don't miss your opportunity to live in a great location! Being sold as is and priced accordingly.

3 Beds ⋅ 1 Baths

Sought after location in College Heights. Short walk to downtown Chestertown and Parks. This cozy rancher is a diamond in the rough and is ready for new owners! located on a safe and quiet street, with public water and sewer with municipal pickups. Don't miss your opportunity to live in a great location! Being sold as is and priced accordingly.

112 Elm St, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Bayside Realty.

$222,000

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights.A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

3 Beds ⋅ 1 Baths

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights.A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

202 Pine St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Taylor Properties.

$85,000

Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+, comparable renovated properties in this location are selling for $275K-$300K, creating potential equity of $80K-$125K for buyers with vision and capability. Close proximity to Washington College creates built-in rental demand from students, faculty, and staff. Plus easy access to Downtown Chestertown shops, restaurants, and waterfront parks are minutes away on foot. Starbucks and grocery stores are easily accessible. This is a prime location renovation opportunity where comparable updated homes command premium pricing. The renovation reality. This property requires full renovation and is priced accordingly. Systems, finishes, and layout will need comprehensive updating. Estimated investment ranges from $60,000 to $80,000+ depending on finish level and scope decisions. This is a project for experienced investors, renovation contractors, or buyers with construction capability who understand forced appreciation through strategic improvements. The opportunity math works. Purchase at $115,000. Invest $60K-$80K in renovations. All-in cost: $175K-$195K. Recent comparable sales for fully renovated 3-bedroom homes in walkable Chestertown locations are selling in the $275K-$300K range. Your potential equity position: $80,000 to $125,000 upon completion. Multiple exit strategies. Flip after renovation for immediate profit. Hold as rental property serving Washington College market with strong rental history in the area. Owner-occupy and build instant equity while creating your ideal home. The location flexibility supports whatever investment strategy fits your goals. Property sold AS-IS. Serious buyers should conduct thorough inspections and due diligence. This is a renovation project, not a cosmetic update - price reflects condition and opportunity. Act quickly on clear value plays. Properties offering this equity spread in prime walkable locations move fast when priced correctly.

3 Beds ⋅ 1 Baths

Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+, comparable renovated properties in this location are selling for $275K-$300K, creating potential equity of $80K-$125K for buyers with vision and capability. Close proximity to Washington College creates built-in rental demand from students, faculty, and staff. Plus easy access to Downtown Chestertown shops, restaurants, and waterfront parks are minutes away on foot. Starbucks and grocery stores are easily accessible. This is a prime location renovation opportunity where comparable updated homes command premium pricing. The renovation reality. This property requires full renovation and is priced accordingly. Systems, finishes, and layout will need comprehensive updating. Estimated investment ranges from $60,000 to $80,000+ depending on finish level and scope decisions. This is a project for experienced investors, renovation contractors, or buyers with construction capability who understand forced appreciation through strategic improvements. The opportunity math works. Purchase at $115,000. Invest $60K-$80K in renovations. All-in cost: $175K-$195K. Recent comparable sales for fully renovated 3-bedroom homes in walkable Chestertown locations are selling in the $275K-$300K range. Your potential equity position: $80,000 to $125,000 upon completion. Multiple exit strategies. Flip after renovation for immediate profit. Hold as rental property serving Washington College market with strong rental history in the area. Owner-occupy and build instant equity while creating your ideal home. The location flexibility supports whatever investment strategy fits your goals. Property sold AS-IS. Serious buyers should conduct thorough inspections and due diligence. This is a renovation project, not a cosmetic update - price reflects condition and opportunity. Act quickly on clear value plays. Properties offering this equity spread in prime walkable locations move fast when priced correctly.

108 Pine St, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

Selling Office: Rosendale Realty.