Chester Center, CT homes for sale & real estate

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6 Spring St, Chester, CT 06412
6 Spring St, Chester, CT 06412
6 Spring St, Chester, CT 06412
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Welcome to 6 Spring Street, a residence that transcends the ordinary. Known affectionately as "The Recycle House, " this home is a testament to over a decade of meticulous craftsmanship, with the majority of its structure composed of upcycled materials. Its acclaim extends beyond its eco-friendly design, having been rated as one of the top 70 Airbnbs near NYC by the online magazine "Curbed" and featured on EarthxTV's "House of What" series. The main unit of this unique property boasts a cozy yet spacious layout, complete with an eclectic living room with floor to ceiling windows, kitchen, one bedroom, and two well-appointed baths. The lower level houses a separ

$790,000

2 beds3 baths1,598 sq ft

6 Spring St, Chester, CT 06412

0.34 acre lot • Somewhat walkable

28 S Wig Hill Rd, Chester, CT 06412
28 S Wig Hill Rd, Chester, CT 06412
28 S Wig Hill Rd, Chester, CT 06412
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Step into history with this 1770 Cape, part of "Old Homes of Chester. " Nestled on beautiful grounds featuring rolling hills, gardens, and stunning stone walls, the property abuts 8 acres of serene land trust, offering unparalleled privacy and a park-like setting. The main house spans 1303 square feet and includes 2 bedrooms and 2 full baths. Recent upgrades include a new furnace (2023), electric hot water heater, oil tank (2022), and a whole-house generator, ensuring modern comfort while maintaining historic charm. A delightful patio with a gazebo, adorned with wine grapes, provides a perfect spot to relax and enjoy the picturesque surroundings. Additionally, the property feature

$645,000

2 beds3 baths3,091 sq ft

28 S Wig Hill Rd, Chester, CT 06412

2.34 acre lot • Garage • Car-dependent

25 Spring St, Chester, CT 06412
25 Spring St, Chester, CT 06412
25 Spring St, Chester, CT 06412
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Tucked away on Spring Street in the heart of Chester village, this stately two-story residence gracefully combines classic farmhouse tradition with all the amenities of modern living. As you enter the home through the foyer, sunlight pours through generous windows, illuminating the living room anchored by an elegant fireplace. Recessed lighting and gleaming wide-plank wood floors lend an understated sophistication, while the open layout flows effortlessly into the dining room and a cozy den. The den boasts tranquil views of the lush backyard and patio, with direct access for seamless indoor-outdoor living. French doors in the dining room flood the space with natural light and provide anothe

$895,000

3 beds2.5 baths2,344 sq ft

25 Spring St, Chester, CT 06412

0.62 acre lot • Garage • Car-dependent

43 N Main St, Chester, CT 06412
43 N Main St, Chester, CT 06412
43 N Main St, Chester, CT 06412
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Fantastic home in wonderful private setting with views of Chester Creek and sounds of the waterfall across the street. Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Beautiful farm porch, detached two car garage, the "glass house" at the edge of Chester Creek to relax and watch nature. 3 bedrooms, 1 1/2 baths, beautiful propane fireplace, updated yet all the original charm and character remain. Sidewalk to Chester Village with restaurants, shops, art galleries, and the incredible (in season) farmers market.

$749,900

3 beds1.5 baths1,538 sq ft

43 N Main St, Chester, CT 06412

0.76 acre lot • 2 garage spots • Car-dependent

FOR SALE BY OWNER

32 Gilbert Hill Rd, Chester, CT 06412
32 Gilbert Hill Rd, Chester, CT 06412
32 Gilbert Hill Rd, Chester, CT 06412
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Step into history with this one-of-a-kind converted barn home with a story to tell. Note: The listed price on Zillow is a placeholder. This is a genuine off-market opportunity for those who find it first! Seller is thoughtfully inviting offers rather than setting a fixed asking price. Willing to work directly with buyers, and with buyer & rsquo; s agents. Text Stephen @ 860-214-9077 to be invited to an exclusive viewing the week of April 28th before this property is publicly listed on the MLS. Check out the full story and details at this website: www. thebarnhomesale.com (more photos coming soon!)

$1,111,111

3 beds3 baths3,788 sq ft

32 Gilbert Hill Rd, Chester, CT 06412

5.31 acre lot • Car-dependent

Property at 7 Old Depot Rd, Chester, CT 06412, 4 beds, 2.5 baths

$1,150,000

4 beds2.5 baths3,149 sq ft

7 Old Depot Rd, Chester, CT 06412

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28 Hoop Pole Hill Rd, Chester, CT 06412
28 Hoop Pole Hill Rd, Chester, CT 06412
28 Hoop Pole Hill Rd, Chester, CT 06412
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm, the main level is thoughtfully designed with your comfort in mind. It features a primary bedroom suite with a spa-like full bath for ease of living, a cozy living room with built-ins provides a tranquil space to unwind, while the formal dining room is ideal for hosting gatherings. The heart of the

$774,000

4 beds3.5 baths3,396 sq ft

28 Hoop Pole Hill Rd, Chester, CT 06412

2.01 acre lot • 2 garage spots • Car-dependent

92 Main St Apt 102, Deep River, CT 06417
92 Main St Apt 102, Deep River, CT 06417
92 Main St Apt 102, Deep River, CT 06417
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Small Studio Condo in Piano Works. Central Air and High Ceilings. Association Common Room. Gym. Walk to town & CT River.

$179,900

— beds1 bath474 sq ft

92 Main St Apt 102, Deep River, CT 06417

$473 HOA • Somewhat walkable

156 Main St, Deep River, CT 06417
156 Main St, Deep River, CT 06417
156 Main St, Deep River, CT 06417
ABOUT THIS HOME
Chester Center, CT Homes for Sale
This is a rare opportunity to acquire a fully stabilized retail asset in Downtown Deep River. Additional income generation is possible by monetizing 800sqft of unrented commercial space. Inside the past 5 years the owner has replaced the entire roof, upgraded the electrical service and replaced all of the furnaces. Upon leasing up the existing units along with the 800sqft space in the rear of the building, this property will appraise north of $1.2M. What this means for a potential buyer, is that through an all cash or bridge acquisition, they will be able to pull out 100% of their investment upon refinancing during the 12-24 month lease up period. The income analysis, location, walkability,

$750,000

— beds1 bath5,460 sq ft

156 Main St, Deep River, CT 06417

8,712 sq ft lot • Somewhat walkable

3D WALKTHROUGH

163-165 Main St, Deep River, CT 06417
163-165 Main St, Deep River, CT 06417
163-165 Main St, Deep River, CT 06417
ABOUT THIS HOME
Chester Center, CT Homes for Sale
EXCITING NEWS, ARV has increased to $1.7 MILLION!!! We met with the town's building inspector and fire marshal for an on-site assessment, and they have expressed interest in seeing the 3rd Floor "Penthouse" get developed into rentable living space. The town needs about 30 days from application and submission of site plans to review the addition for approval. Pre-existing zoning regulations have been adjusted allowing the semi-finished third floor to be converted into a livable penthouse suite, and these revisions took effect on April 17, 2025. What's so great about this, is that we can now broker bridge financing that cuts the required down payment in HALF, for a total estimated C

$935,000

3 beds2 baths4,184 sq ft

163-165 Main St, Deep River, CT 06417

3,049 sq ft lot • Somewhat walkable

138 River Rd, Deep River, CT 06417
138 River Rd, Deep River, CT 06417
138 River Rd, Deep River, CT 06417
ABOUT THIS HOME
Chester Center, CT Homes for Sale
"Broad View" Privately sited on 3+ acres atop Architects Hill, the epitome of coastal living awaits from this extraordinary residence with expansive views of the Connecticut River, Lyme Hills, Hamburg Cove and beyond. Custom built and thoughtfully designed, the timeless and versatile floor plan features the perfect blend of traditional architecture with modern home design. A welcoming courtyard with three bay-garage leads to a gracious entry and spacious well-proportioned rooms that blend seamlessly with the natural surroundings. Ideal for special occasions, the living room & dining room feature the perfect balance of relaxed and refined; a well-appointed kitchen with a priv

$2,250,000

5 beds5.5 baths5,698 sq ft

138 River Rd, Deep River, CT 06417

3.34 acre lot • $333 HOA • 3 garage spots

45 Castle Hts, Deep River, CT 06417
45 Castle Hts, Deep River, CT 06417
45 Castle Hts, Deep River, CT 06417
ABOUT THIS HOME
Chester Center, CT Homes for Sale
Discover this wooded 0.83-acre lot located just minutes from Deep River Landing and all the charm of downtown Deep River. With no HOA restrictions, this property offers flexibility and privacy. A newly installed 300'+ driveway is already in place, and engineering for a 4-bedroom home and septic system is on file-saving you time and money. Enjoy convenient access to shopping, restaurants, and local amenities while building your dream home in a peaceful, natural setting.

$52,999

— beds— baths— sq ft

45 Castle Hts, Deep River, CT 06417

0.83 acre lot • Car-dependent

Property at 11 Kings Hwy, Chester, CT 06412

$232,500

— beds— baths— sq ft

11 Kings Hwy, Chester, CT 06412

Average home prices near Chester Center, CT

Cities

Zip Codes
Minor Civil Divisions

06417 homes for sale
$645,000
06412 homes for sale
$790,000

Chester Center, CT real estate trends

$1.07M

Sale price

+128.3%
since last year

$332

Sale $/sq ft

+23.4%
since last year

Over list price

3.2%

Days on market

Down payment

—

Total homes sold

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