Moving to Chester CT | real estate for sale in Chester Connecticut | Property Statistics of living in Chester
Chester is one of Middlesex County's most desirable small-town real estate markets, known for its quintessential New England village center, strong preservation ethic, and limited development. Housing consists primarily of single-family homes, historic properties, and rural estates situated on larger lots. The town's walkable downtown and scenic setting contribute significantly to its appeal. Real estate values in Chester are supported by constrained inventory, strong buyer demand, and a reputation for quality of life. The market attracts professionals, retirees, and second-home buyers seeking a charming small-town environment with convenient access to the Connecticut shoreline and regional employment centers.
88 Winthrop Road
Chester, Connecticut 06412
$650,000 | Active
3 Beds | 3 Baths | 2240 Sqft | 33.97 Acres | 103 Days on Market
Property Type: Single Family For Sale
Set on 33.97 private acres in beautiful Chester, CT, this inviting home offers space, privacy, and scenic views. The main level features a primary bedroom with a full bath, while upstairs youll find 3 additional bedrooms with 2 full baths. The bright, open living room features so...
11 Castle View Drive
Chester, Connecticut 06412
$496,900 | Active
3 Beds | 2 Baths | 2103 Sqft | 0.47 Acres | 4 Days on Market
Property Type: Single Family For Sale
Offered for sale for the very first time, this lovingly cared-for home is a rare opportunity in the welcoming Castle View Drive neighborhood, just moments from Chester Center. While the manicured lawn, mature gardens, and meticulous exterior maintenance create an excellent first ...
136 Goose Hill Road
Chester, Connecticut 06412
$825,000 | Active
4 Beds | 3 Baths | 3343 Sqft | 2.05 Acres | 96 Days on Market
Property Type: Single Family For Sale
Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood floorin...
25 Goose Hill Road
Chester, Connecticut 06412
$385,000 | Under Contract - Continue
2 Beds | 2 Baths | 1454 Sqft | 2.39 Acres | 6 Days on Market
Property Type: Single Family For Sale
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 hi...
1 Kirtland Avenue
Chester, Connecticut 06412
$439,900 | Under Contract - Continue
3 Beds | 2 Baths | 1198 Sqft | 0.43 Acres | 19 Days on Market
Property Type: Single Family For Sale
One floor living in this well maintained Ranch. 1 Full Bath & One 1/2 Bathroom. Hardwood floors. Fireplace in Living Room. Large Eat-in kitchen with Stainless Steel appliances. Recent upgrades include: New HVAC, New 200 AMP electric panel, new roof, new pellet stove, and remodele...
22 Goose Hill Road
Chester, Connecticut 06412
$450,000 | Under Contract - Continue
3 Beds | 3 Baths | 1714 Sqft | 1.96 Acres | 15 Days on Market
Property Type: Single Family For Sale
Welcome to this inviting 3-bedroom split-level ranch, ideally situated within walking distance to the heart of Chester Village. Designed for comfortable living and entertaining, the home features a spacious family room with sliders leading to a large deck overlooking the inground...
135 Middlesex Avenue
Chester, Connecticut 06412
$499,000 | Active
3 Beds | 2 Baths | 1188 Sqft | 0.68 Acres | 44 Days on Market
Property Type: Single Family For Sale
NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first fl...
47 Kings Highway
Chester, Connecticut 06412
$2,200,000 | Active
4 Beds | 4 Baths | 3957 Sqft | 3.2 Acres | 61 Days on Market
Property Type: Single Family For Sale
A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valleys most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, an...
6 Jagger Lane
Chester, Connecticut 06412
$805,000 | Under Contract - Continue
2 Beds | 3 Baths | 2428 Sqft | 0.83 Acres | 57 Days on Market
Property Type: Single Family For Sale
Step into timeless New England charm with this beautifully updated 1901 Colonial, where classic character meets modern comfort just moments from the heart of Chester. Thoughtfully renovated between 2008 and 2023, this inviting home offers warm, sun-filled spaces designed for both...
288 Middlesex Avenue
Chester, Connecticut 06412
$3,150,000 | Active
4 Beds | 6 Baths | 4926 Sqft | 2.65 Acres | 129 Days on Market
Property Type: Single Family For Sale
Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct rive...