Homes with Basements for Sale in Chester, CT

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ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Steps to the Village! Vintage 1765 Cape with many updates but still true to the original charm of the Joseph Shipman House. Two staircases, 4 working firplaces, King's Board floors, wonderful floorplan and an up-to-date kitchen makes this home a step back in time but with the amenities of today. Quartz countertops and a complete kitchen renovation in 2017. New rear pressure treated deck in 2017. Renovated bath on first floor in 2018. Roof replaced in 2018 and gutters added. Complete second floor bath renovation off Primary Bedroom ( dual entrance ) in 2022. Invisible Fence. Brand new Post and Beam Barn with metal roof constructed in 2020 has a fantastic second floor space perfect for artist

$799,000

3 beds2 baths1,772 sq ft

35 Maple St, Chester, CT 06412

0.5 acre lot • 2 garage spots • Car-dependent

OPEN SAT, 12PM TO 3PM

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Charming 4-season cottage with views of Cedar Lake! Corner lot with deck, outdoor shower, and parking. Features an eat-in kitchen, open living area, 3 bedrooms, and hardwood floors.

$229,000

3 beds1 bath748 sq ft

15 Hazen St, Chester, CT 06412

Open living area • Cedar lake views • Outdoor shower

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
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 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, while the upper-level office is ready for ex

$499,000

2 beds1 bath1,470 sq ft

79 Middlesex Ave, Chester, CT 06412

0.82 acre lot • Built 1952 • Listed 22 days

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Enchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! Tucked away on 2 acres of picturesque land, this whimsical 3-bedroom, 2.5-bath Cape Cod home invites you to live among nature in style. Only a short distance from Cedar Lake and Chester Village, you'll have easy access to endless outdoor adventures and world-class restaurants and shopping just moments away. Inside, the home is a masterpiece of artisan post and beam craftsmanship, with a spacious great room featuring soaring ceilings, skylights that bathe the space in natural light, and exquisite woodwork that brings warmth and character to every corner. The thoughtful layout includes a generou

$795,000

3 beds2.5 baths2,139 sq ft

8 Butter Jones Rd, Chester, CT 06412

Exquisite woodwork • Spacious great room • Soaring ceilings

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Discover this waterfront delight in charming Chester, sure to reward with year-round views! Completely and thoughtfully renovated in 2012 from the ground up (including brand new septic system), this pristine Colonial offers 3 floors of living space and a smart L-shape open floor plan ensuring that you always have a gorgeous view. In addition to some hardworking 1st floor spaces (roomy mudroom, full bath and laundry room), the main living area serves up the ideal layout for dining, cooking and relaxing. The space enjoys loads of windows and natural light, oak HW flooring, white kitchen cabinetry w/ granite counters and marble tile backsplash, tiered island with breakfast bar, and stainless a

$549,000

3 beds2.5 baths1,664 sq ft

131 Middlesex Ave, Chester, CT 06412

0.72 acre lot • Garage • Built 1930

Property at 6 W Main St, Chester, CT 06412, 4 beds, 2 baths

$725,000

4 beds2 baths2,160 sq ft

6 W Main St, Chester, CT 06412

Property at 60 Goose Hill Rd, Chester, CT 06412, 7 beds, 2 baths

$849,900

7 beds2 baths2,402 sq ft

60 Goose Hill Rd, Chester, CT 06412

Property at 288 Middlesex Ave, Chester, CT 06412, 4 beds, 5 baths

$3,375,000

4 beds5 baths4,926 sq ft

288 Middlesex Ave, Chester, CT 06412

Property at 6 Spring St, Chester, CT 06412, 2 beds, 3 baths

$775,000

2 beds3 baths1,598 sq ft

6 Spring St, Chester, CT 06412

Property at 88 Winthrop Rd, Chester, CT 06412, 2 beds, 2.5 baths

$985,000

2 beds2.5 baths2,240 sq ft

88 Winthrop Rd, Chester, CT 06412

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VIDEO TOUR

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Experience the timeless beauty of New England living! This meticulously restored 1854 Colonial blends historic charm with modern comfort in the heart of Deep River. Every detail has been thoughtfully preserved or reimagined-from the gleaming pumpkin pine wide-plank floors and custom-milled woodwork to carefully selected reproduction hardware that speaks to its heritage. Six fireplaces grace the home, including a magnificent 12' natural stone Rumford. A carefully designed addition in 1987 doubled the home's size while maintaining its period character, offering multiple living and dining spaces with warmth and versatility for everyday living and entertaining. Seven bedrooms, each with its own

$1,199,999

9 beds9 baths4,982 sq ft

209 Main St, Deep River, CT 06417

0.45 acre lot • Somewhat walkable

OPEN SAT, 10:30AM TO 1PM

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Remodeled from the ground up this home is ready for new owners to move right in and enjoy! Centrally located to the village center & the CT River, gives you easy access to the town center where you find small shops, grocery store, pharmacy, library, town green & more. In the other direction you are close to the Connecticut River where there is boating, water skiing, kayaking & more. The exterior of the home has underground utilities, Everlast Siding, Thermopane windows, and a spacious front porch w/ wonderful views of the countryside. There is an attached 25.5' x29.5' oversized 2 car garage w/ outstanding HUGE IPE deck on top that feels like you're in your own tree house.

$595,000

3 beds2.5 baths2,018 sq ft

21 River Ln, Deep River, CT 06417

0.7 acre lot • 2 garage spots • Car-dependent

3D WALKTHROUGH

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
The walkability and quintessential New England charm of downtown Deep River is a big draw for buyers seeking a trophy property or a dream location for their small business. Built in 1850, this mixed-use gem has much to offer including two commercial tenants (Hally Jo's Corner Restaurant and the Anchor and Compass clothing store), three residential units on the second floor, and 1,200 square feet of semi-finished attic space. EXCITING NEWS, 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 additional living space. An amendment to mixed-use zoning code took eff

$899,000

6 beds3 baths4,184 sq ft

163 Main St, Deep River, CT 06417

3,049 sq ft lot • Somewhat walkable

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Step into history with this charming circa 1780 Mill House combined with a historic chapel converted to a modern AUD. Located in the Hadlyme area of East Haddam, this unique property boasts many upgrades. Just under two miles from the Historic Hadlyme Ferry and Gillette's Castle State Park. This enchanting home spans 1,786 sf and beautifully balances antique elegance with modern amenities. Bedrooms: Two second floor primary bedrooms, plus two cozy attic rooms for flexible living arrangements. First-Floor Suite: A welcoming suite features a fireplace and private entrance, offering stunning views of the historic spring fed pond. Original Hardwood Floors: Original hardwood floors flow througho

$999,999

4 beds3 baths2,641 sq ft

11 Phelps Rd, East Haddam, CT 06423

2.03 acre lot • Car-dependent

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
Welcome to your dream home at 112 Cedar Swamp Road, Deep River, CT! This charming Cape Cod-style residence, originally built in 1940, has been beautifully renovated to blend classic charm with modern efficiency. With 4 spacious bedrooms and 3 full bathrooms, this home has +/- 2,900 square feet of living space, providing ample room for all your lifestyle needs. Step inside to discover a bright and airy family room complete with a wood stove, perfect for chilly nights. There is a mini split as well & French doors for privacy. The modern kitchen is a chef's delight, outfitted with stainless steel appliances, a large center island, and a wine fridge, making it a hub for entertaining and c

$625,000

4 beds3 baths2,969 sq ft

112 Cedar Swamp Rd, Deep River, CT 06417

2.45 acre lot • Garage • Car-dependent

ABOUT THIS HOME
Home with Basement for sale in Chester, CT:
A RARE GEM, WELCOME TO THIS RESTORED VICTORIAN TWO FAMILY HOME DESIGNED FOR EASY LIVING. COMPLETELY REMODELED, EACH UNIT HAS TWO BEDROOMS AND 1 BATH AS WELL NEW KITCHEN AND APPLIANCES. THE HOME ALSO OFFERS CITY WATER AND CITY SEWERS. DON'T MISS THIS OPPORTUNITY, THE HOME IS PERFECT FOR MULTIGENERATIONAL LIVING, OR AN INVESTMENT PROPERTY. New roof, siding, sheetrock, kitchen, plus kit hen appliances, baths, driveway. interior design by cristian chacon

$799,000

4 beds2 baths1,970 sq ft

62 RIVER St, Deep River, CT 06417

0.93 acre lot • Somewhat walkable

Property at 153 Ferry Rd, Lyme, CT 06439, 5 beds, 6 baths

$10,000,000

5 beds6 baths7,021 sq ft

153 Ferry Rd, Lyme, CT 06439

Property at 170 Main St, Deep River, CT 06417, 7 beds, 5 baths

$1,700,000

7 beds5 baths3,461 sq ft

170 Main St, Deep River, CT 06417

Property at 168 Main St, Deep River, CT 06417, 5 beds, 3 baths

$1,700,000

5 beds3 baths4,180 sq ft

168 Main St, Deep River, CT 06417

Property at 46 Hemlock Dr, Deep River, CT 06417, 4 beds, 1.5 baths

$419,900

4 beds1.5 baths1,688 sq ft

46 Hemlock Dr, Deep River, CT 06417

Property at 8 Route 148, Killingworth, CT 06419, 4 beds, 3 baths

$699,000

4 beds3 baths3,864 sq ft

8 Route 148, Killingworth, CT 06419

Property at 53 Selden Road Rd, Lyme, CT 06371, 5 beds, 5 baths

$3,600,000

5 beds5 baths4,734 sq ft

53 Selden Road Rd, Lyme, CT 06371

Property at 7 Shelter Rock Rd, East Haddam, CT 06423, 4 beds, 3.5 baths

$1,100,000

4 beds3.5 baths3,494 sq ft

7 Shelter Rock Rd, East Haddam, CT 06423

Property at 156 Main St, Deep River, CT 06417, 1 bath

$695,000

— beds1 bath5,460 sq ft

156 Main St, Deep River, CT 06417

Homes with Basements for Sale in Chester

There are currently 10 homes with basements for sale in Chester at a median listing price of $750K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 54 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 3 homes have been sold in Chester. In addition to houses in Chester, there were also 0 condos, 0 townhouses, and 3 multi-family units for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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