Deep River, CT homes for sale & real estate

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92 Main St #214, Deep River, CT 06417
92 Main St #214, Deep River, CT 06417
92 Main St #214, Deep River, CT 06417
ABOUT THIS HOME
Deep River, CT Homes for Sale
Deep River's answer to Manhattan loft living! This 2 bedroom, 2 bath condominium is located in-town so you can walk to shops, library, restaurants and bank. This building was originally a piano factory which was converted to residential condominiums in 1985. Ample off street parking in the rear and the building entrance requires a key to unlock for added security. Once in the foyer it's just a few steps up to the elevators to access the second floor. There are card operated laundries on the first and third floors with numbered storage lockers for the units. Units have brick walls and 10' ceilings with heat and central air by heat pumps for each unit. This unit had the heat pump installed wi

$259,000

2 beds2 baths1,122 sq ft

92 Main St #214, Deep River, CT 06417

$473 HOA • Somewhat walkable

NEW CONSTRUCTION

Glen Grove Rd Rd, Deep River, CT 06417
Glen Grove Rd Rd, Deep River, CT 06417
Glen Grove Rd Rd, Deep River, CT 06417
ABOUT THIS HOME
Deep River, CT Homes for Sale
Introducing an opportunity to build your dream home on a secluded 3-acre interior lot in beautiful Deep River. Located off scenic Glen Grove Road, this custom-designed Modern Farmhouse offers over 3,300 sq ft of thoughtfully planned living space, blending timeless architecture with the flexibility to tailor finishes to your vision. This to-be-built home features 4 bedrooms, 2.5 bathrooms, and a smart, open-concept layout ideal for modern living. The main level boasts expansive gathering spaces filled with natural light, with seamless flow between the kitchen, dining, and living areas-perfect for everyday living or entertaining. The oversized primary suite is privately situated upstairs abov

$899,999

4 beds2.5 baths3,300 sq ft

Glen Grove Rd Rd, Deep River, CT 06417

3 acre lot • 2 garage spots • Car-dependent

538 Winthrop Rd #5, Deep River, CT 06417
538 Winthrop Rd #5, Deep River, CT 06417
538 Winthrop Rd #5, Deep River, CT 06417
ABOUT THIS HOME
Deep River, CT Homes for Sale
Welcome to 538 Winthrop Rd - a beautifully maintained and elegantly updated bungalow. This charming 1-bedroom, 1-bath home offers 786 sq ft of cozy living space, perfect for a weekend retreat or year-round residence. Step into the spacious kitchen featuring Italian marble countertops with a large island, solid wood white cabinetry, and a stainless steel French-door refrigerator. Just off the kitchen, the inviting dining room boasts serene views of nature and tranquil Star Lake. The open-concept living room flows seamlessly from the kitchen and offers generous space for relaxing or entertaining guests. The layout is thoughtfully designed to maximize comfort and connection. Enjoy the peaceful

$369,000

1 bed1 bath786 sq ft

538 Winthrop Rd #5, Deep River, CT 06417

0.23 acre lot • Car-dependent

156 Main St, Deep River, CT 06417
156 Main St, Deep River, CT 06417
156 Main St, Deep River, CT 06417
ABOUT THIS HOME
Deep River, 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,

$800,000

— 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
Deep River, 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

$985,000

3 beds2 baths4,184 sq ft

163-165 Main St, Deep River, CT 06417

3,049 sq ft lot • Somewhat walkable

Property at 139 Kirtland St, Deep River, CT 06417, 7 beds, 2 baths

$795,000

7 beds2 baths3,157 sq ft

139 Kirtland St, Deep River, CT 06417

Property at 138 River Rd, Deep River, CT 06417, 5 beds, 5.5 baths

$2,250,000

5 beds5.5 baths5,698 sq ft

138 River Rd, Deep River, CT 06417

Property at 323 River Rd, Deep River, CT 06417, 5 beds, 5.5 baths

$4,495,000

5 beds5.5 baths5,557 sq ft

323 River Rd, Deep River, CT 06417

Property at 134 Meadow Woods Rd, Deep River, CT 06417

$2,000,000

— beds— baths— sq ft

134 Meadow Woods Rd, Deep River, CT 06417

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109 Elys Ferry Rd, Lyme, CT 06371
109 Elys Ferry Rd, Lyme, CT 06371
109 Elys Ferry Rd, Lyme, CT 06371
ABOUT THIS HOME
Deep River, CT Homes for Sale
A timeless aesthetic and a sensibility respecting nature have resulted in an eminently livable, grand and gracious waterfront country house overlooking spectacular views of Hamburg Cove in sylvan Lyme, Connecticut. The skillful fusion of top quality materials and distinctive details of this offering are without parallel. Designed by the architectural firm Di Biase Filkoff whose guiding philosophy is effortless elegance, built by renowned housewright Skip Broom and landscaped with specimen trees by Peter Cummin and Christopher Thorp, this secluded, gated estate on more than twelve park-like, manicured acres is perfect for those seeking privacy and relaxation while immersed in nature. Boaters

$11,750,000

5 beds6.5 baths9,489 sq ft

109 Elys Ferry Rd, Lyme, CT 06371

12.4 acre lot • 5 garage spots • Pool

OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH

80 W Main St, Chester, CT 06412
80 W Main St, Chester, CT 06412
80 W Main St, Chester, CT 06412
ABOUT THIS HOME
Deep River, CT Homes for Sale
Nestled in the storybook town of Chester, Connecticut-renowned for its vibrant arts scene, scenic countryside, and charming village center-this one-of-a-kind historic home lovingly maintained by its current steward, offers a truly inspiring lifestyle. Set on lush, idyllic grounds framed by mature trees, gardens, & stone walls, the property exudes timeless New England beauty. A collection of intriguing outbuildings and workshop adds versatility & character-ideal for hobbyists, inventors, writers or anyone seeking a creative escape. Inside, the home blends historic charm with modern functionality. Wide-plank floors, original architectural details including elliptical window plus taste

$699,000

3 beds2 baths2,389 sq ft

80 W Main St, Chester, CT 06412

1.4 acre lot • 2 garage spots • Car-dependent

102 Pritchett Dr, Westbrook, CT 06498
102 Pritchett Dr, Westbrook, CT 06498
102 Pritchett Dr, Westbrook, CT 06498
ABOUT THIS HOME
Deep River, CT Homes for Sale
This beautiful home sits quietly at the end of a cul-de-sac. Yet an easy commute location. Well laid out for entertaining in and out. An open front porch greets you as you arrive. The large living room steps out to a screened porch, then to a deck. Both overlooking the nicely landscaped grounds. A 15x24 Eat-in kitchen with Granite counters. Two additional living areas offer home office/ hobby areas/playroom opportunities or a potential in-law option. Upstairs you have the primary suite with walk-in closet and full bath, 2 additional bedrooms and the main bathroom. Central Air conditioning. Full unfinished basement.

$675,000

3 beds3 baths2,621 sq ft

102 Pritchett Dr, Westbrook, CT 06498

2.56 acre lot • 2 garage spots • Car-dependent

Undisclosed address, Lyme, CT 06371
Undisclosed address, Lyme, CT 06371
Undisclosed address, Lyme, CT 06371
ABOUT THIS HOME
Deep River, CT Homes for Sale
Perched on a stunning rise overlooking the Connecticut River, this remarkable residence, appropriately named "River Knoll", incorporates an 18th Century Cape with dramatic additions that blend seamlessly with the original construction. Beautiful old beams, paneled walls and wide board flooring creates a feeling of warmth and historical integrity while the house has every imaginable functionality. .. from a Chef's kitchen with pantry, updated bathrooms throughout, and an incredible primary suite with French doors leading to a private terrace overlooking the River. The pool complex with separate pavilion makes outdoor gatherings a part of the easy summer entertaining life of the res

$7,700,000

5 beds5.5 baths5,015 sq ft

Undisclosed address, Lyme, CT 06371

9.43 acre lot • $67 HOA • 5 garage spots

44 Main St, Essex, CT 06409
ABOUT THIS HOME
Deep River, CT Homes for Sale
Rare opportunity in the heart of charming Ivoryton Village! This prime piece of land offers endless potential for those ready to tear down and build anew. Situated in a sought-after location just steps from Ivoryton Playhouse, shops, restaurants, Essex village amenities, and close to Falls river, this property provides an ideal setting for your next project. The existing structure on site is in need of complete demolition - bring your vision and create something spectacular. Whether you're a builder, entrepreneur, or investor, this is your chance to capitalize on one of the few available parcels in this desirable area. Do not enter the property-structure is unsafe. Location, potential, and

$114,900

3 beds— baths1,066 sq ft

44 Main St, Essex, CT 06409

0.24 acre lot • Somewhat walkable

OPEN TODAY, 1PM TO 3PM

19 W Hills Rd, Essex, CT 06442
19 W Hills Rd, Essex, CT 06442
19 W Hills Rd, Essex, CT 06442
ABOUT THIS HOME
Deep River, CT Homes for Sale
Welcome to 19 W Hills Rd, a meticulously updated 3-bedroom, 2.5-bath Colonial offering modern comfort in the desirable Falls River neighborhood of Ivoryton. Built in 1966, this move in-ready home blends classic charm with contemporary upgrades, perfect for those seeking a blend of suburban tranquility and convenince. This home features a bright, open layout with 3 bedrooms and 2.5 bathrooms. Upstairs has a large primary suite w private bath, room for office space, workout area or create a relaxing retreat area. Two additional bedrooms share a full bath. The recently renovated kitchen shines with sleek quarts countertops and stainless appliances. Panoramic views of the great outdoors from th

$620,000

3 beds2.5 baths2,648 sq ft

19 W Hills Rd, Essex, CT 06442

0.99 acre lot • 2 garage spots • Car-dependent

Property at 7 Hanna Ln, Essex, CT 06426, 3 beds, 3.5 baths

$4,495,000

3 beds3.5 baths4,383 sq ft

7 Hanna Ln, Essex, CT 06426

Property at Undisclosed address, Essex, CT 06426, 6 beds, 4 baths

$4,495,000

6 beds4 baths4,951 sq ft

Undisclosed address, Essex, CT 06426

Property at 9 Stonebrook Dr, Essex, CT 06442, 3 beds, 2.5 baths

$829,000

3 beds2.5 baths2,804 sq ft

9 Stonebrook Dr, Essex, CT 06442

Property at 20 Hemlock Dr, Essex, CT 06426, 4 beds, 3.5 baths

$2,200,000

4 beds3.5 baths4,162 sq ft

20 Hemlock Dr, Essex, CT 06426

Property at 755 W Pond Meadow Rd, Westbrook, CT 06498, 3 beds, 2.5 baths

$649,000

3 beds2.5 baths2,312 sq ft

755 W Pond Meadow Rd, Westbrook, CT 06498

Property at 15 Westwood Rd, Essex, CT 06442, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths2,597 sq ft

15 Westwood Rd, Essex, CT 06442

Property at 34 West Ave, Essex, CT 06426, 3 beds, 3 baths

$995,000

3 beds3 baths3,467 sq ft

34 West Ave, Essex, CT 06426

Property at 15 Sunset Ter #10, Essex, CT 06426, 1 bath

$189,900

— beds1 bath540 sq ft

15 Sunset Ter #10, Essex, CT 06426

Property at 86 Lynn Rd, Essex, CT 06442, 2 beds, 2.5 baths

$599,000

2 beds2.5 baths2,484 sq ft

86 Lynn Rd, Essex, CT 06442

Property at 16 N Main St, Essex, CT 06426, 2 beds, 2 baths

$739,000

2 beds2 baths1,076 sq ft

16 N Main St, Essex, CT 06426

Property at 43 N Main St, Chester, CT 06412, 3 beds, 1.5 baths

$764,900

3 beds1.5 baths1,538 sq ft

43 N Main St, Chester, CT 06412

Property at 101 N Main St, Essex, CT 06426, 4 beds, 3.5 baths

$2,345,000

4 beds3.5 baths3,724 sq ft

101 N Main St, Essex, CT 06426

Property at 41 Woodland Dr, Essex, CT 06409, 3 beds, 1.5 baths

$525,000

3 beds1.5 baths1,742 sq ft

41 Woodland Dr, Essex, CT 06409

Property at 7 Foxboro Rd, Essex, CT 06426

$2,900,000

— beds— baths— sq ft

7 Foxboro Rd, Essex, CT 06426

Average home prices near Deep River, CT

Cities

Zip Codes
Minor Civil Divisions

Deep River, CT real estate trends

$408K

Sale price

-18.9%
since last year

$288

Sale $/sq ft

+15.9%
since last year

Under list price

0.2%

Days on market

Down payment

—

Total homes sold

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