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42 Straits Rd, Chester
$460,000
3 Beds ⋅ 3 Baths ⋅ 24192544 MLS
Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths, including a beautifully glass tiled hall bath that adds beachy vibes. The spacious primary suite offers both a walk-in closet and an additional traditional closet, with ample room for a king-sized bed and your favorite furnishings. The bright, functional kitchen boasts an abundance of cabinetry, stainless steel appliances, and the convenience of a first-floor laundry room just steps away, between the kitchen and the powder room. The finished lower level provides valuable additional living space, ideal for a family room, recreation area, home gym, or hobby room, with direct access to the oversized two-car garage. With fresh paint and your personal decorating touches, this home can truly shine. Best of all, you're just a short walk from Chester's picturesque town center, where you'll enjoy charming shops, restaurants, galleries, and community events. Experience firsthand why Chester is consistently celebrated as one of Connecticut's most beloved small towns.

42 Straits Rd, Chester

25 Goose Hill Rd, Chester
$430,000
2 Beds ⋅ 2 Baths ⋅ 24185639 MLS
Multiple offers - Seller requests highest and best, Monday, 7/27 by 5PM. No escalation clauses. Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural light overlooking a private 2.39 acre lot. The partially finished, walk-out lower level offers excellent flexible living space, complete with a half bath (with room to expand to a full shower) and a small kitchenette - ideal for an in-law or guest suite. Key features include: New oil-fired furnace; public water; central air; generator; freshly painted interior, one car garage and storage shed. Bring your updates and vision to life! With fabulous expansion possibilities, this property is ready for its next chapter. Enjoy being just steps away from Chester's vibrant village center, known for its boutiques, acclaimed restaurants, art galleries, theater and the historic Chester Ferry crossing the Connecticut River.

25 Goose Hill Rd, Chester

79 Middlesex Ave, Chester
$410,000
2 Beds ⋅ 1 Baths ⋅ 24131519 MLS
Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm newly refinished hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the aspiring chef! The cheerful & sunny dining room opens to a huge back deck overlooking a private yard that backs up to North Quarter Park-perfect for entertaining, walking trails or relaxing outdoors. Two first floor bedrooms and a full bath offer easy one-floor living. The light & bright upper-level multipurpose room is perfect for a home office, hobby room, studio or den. The updated electrical service is equipped with a generator transfer switch & the generator conveys. Plenty of storage in the full basement. Enjoy peaceful surroundings with mature trees and a park-like backyard, yet just a short stroll to restaurants, galleries, coffee shops, and the Sunday Farmers' Market in the heart of Chester. Convenient to Route 9, the Connecticut River, the Chester Ferry and the scenic shoreline. A truly special property offering charm, flexibility, and the lifestyle of one of Connecticut's most beloved villages-welcome home to 79 Middlesex Avenue, Chester CT.

79 Middlesex Ave, Chester

50 Bokum Rd, Chester
$375,000
2 Beds ⋅ 2 Baths ⋅ 24124299 MLS
Welcome to this delightful 2-bedroom, 1.5 bath home tucked in the heart of historic Chester, CT. Brimming with character, this cozy home blends modern updates with small-town New England charm. Step inside to find a bright and inviting living space, an updated kitchen, and thoughtful touches throughout. Perfectly sized for easy living, the property offers a low-maintenance yard ideal for gardening, relaxing, or entertaining. Just a short stroll from Chester's vibrant village center, you'll enjoy boutique shops, acclaimed restaurants, art galleries, and the scenic Connecticut River-all just minutes from your doorstep. Whether you're looking for a weekend retreat, starter home, or a downsize with style, this Chester gem is ready to welcome you. 2hours +/- to New York or Boston.

50 Bokum Rd, Chester

11 Kings Hwy, Chester
$225,000
170533629 MLS
1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line available at the street. Well-engineered and installed driveway roughed in with stone base from street level to elevation at top; highly engineered drainage system adjacent to driveway from top to bottom connected to town road storm drain. No wetlands, no water crossings, no shared access, no intrusive noise. Less than a mile walking via country roads to downtown Chester, and to historic Chester-Hadlyme Ferry. Not a development; no covenants or restrictions specific to lot. Drone footage available https://youtu.be/Ks6ut-XOkng

11 Kings Hwy, Chester

15 Hazen St, Chester
$220,000
3 Beds ⋅ 1 Baths ⋅ 24155554 MLS
**FINAL AND BEST OFFERS DUE BY WEDNESDAY 3/4/26 BY 5PM** Fantastic condo alternative with year-round charm and lake lifestyle appeal! Enjoy scenic views of Cedar Lake and take advantage of the easy walk to nearby beaches from this inviting 4-season cottage. Situated on a large corner lot framed by classic New England stone walls, this property offers privacy, character, and outdoor enjoyment. Relax or entertain on the spacious wooden rear deck, rinse off after a swim in the outdoor shower, and enjoy the convenience of off-street parking. Inside, you'll find six well-proportioned rooms including an eat-in kitchen, a bright and open living room perfect for gathering, three upstairs bedrooms, and a full bath on the first floor. Hardwood floors upstairs add warmth and character, while carpeting and linoleum downstairs offer comfort and functionality. The home is serviced by two wells (one regular and one pump) and includes a washer and dryer in the basement for added convenience. Whether you're looking for a full-time residence, a weekend retreat, or a summer escape, this Cedar Lake cottage offers flexibility, charm, and lifestyle value - all without condo fees. Optional private beach association membership available for just $120/year.

15 Hazen St, Chester

19 Castle View Dr, Chester
$214,000
3 Beds ⋅ 1 Baths ⋅ 24142850 MLS
Investor/Builder Opportunity! Discover a rare opportunity in charming Chester, Connecticut! Minutes from Chester's vibrant village center known for its restaurants, boutiques, galleries, theater and farmer's market. This property offers tremendous potential for the right buyer. The existing structure is not currently habitable! This property require significant renovation/demolition due its current condition. This is ideally suited for contractor or investors seeking a project Chester is one of the Connecticut River Valley's most sought-after small towns, blending natural beauty with a walkable downtown. Bring your vision and transform this into a beautiful home! Property being sold "as is" Not Currently Habitable!

19 Castle View Dr, Chester

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