Luxury homes for sale & real estate in Middlesex County, CT

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ABOUT THIS HOME
Luxury Home for sale in Middlesex County, CT:
The Well Maiden Estate is a rare architecturally significant waterfront estate where cascading waterfalls, winding streams, and Kroopa Pond converge across 3.5 private acres to create one of Connecticut's most extraordinary residential settings. Just minutes from the Connecticut shoreline, marinas, beaches, and fine dining, and ideally positioned between New York City and Boston, this private luxury retreat offers a rare opportunity to own a legacy estate equally suited for year-round living or a distinguished second-home escape. Originally a historic fishing shack, the restored wing blends seamlessly with a striking architectural residence designed to embrace its natural surroundings. Soar

$2,195,000

4 beds2.5 baths3,700 sq ft

18 Birch Mill Rd, Killingworth, CT 06419

Private acres • Waterfront estate • Winding streams

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ABOUT THIS HOME
Luxury Home for sale in Middlesex County, CT:
Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined living. Set on a . 45 private lot, this meticulously maintained antique residence spans approximately 3,769 square feet and captures serene water views from its beautifully landscaped grounds. Despite its central village location, just moments to shops, dining, and marinas, the home offers a

$3,595,000

5 beds4 baths3,769 sq ft

10 Scholes Ln, Essex, CT 06426

Waterfront estate • Private lot • Landscaped grounds

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ABOUT THIS HOME
Luxury Home for sale in Middlesex County, CT:
A rare combination of privacy, functionality, and sweeping water views distinguishes this exceptional year-round shoreline estate, ideally situated in one of Westbrook's most desirable coastal enclaves. Positioned on the quiet, exclusive end of Seaside Avenue just steps from a pristine private beach, the residence is set upon a rare double lot that offers an uncommon sense of openness, tranquility, and room to grow. Thoughtfully designed for effortless coastal living and grand-scale entertaining, the home is bathed in natural light and frames spectacular vistas of Long Island Sound from multiple viewing decks. The heart of the home features a bright, open-concept main level that seamlessly

$1,475,000

3 beds3.5 baths4,303 sq ft

449 Seaside Ave, Westbrook, CT 06498

Ensuite • Kitchenette • Private beach

ABOUT THIS HOME
Luxury Home for sale in Middlesex County, CT:
Three direct beachfront cottages located right on the sand of the Long Island Sound in Clinton, Connecticut offer a rare turnkey coastal investment opportunity. The property includes two well-appointed 2-bedroom cottages and one spacious 4-bedroom cottage, all fully furnished and recently updated for modern comfort. Each cottage provides unobstructed waterfront views, immediate beach access, and the charm of classic shoreline living. With a strong and proven rental history, this unique package is ideal for investors or buyers seeking a move-in ready, income-producing beachfront retreat along the Connecticut shoreline. Tax information provided is not based on the 2025 assessment.

$2,400,000

8 beds3 baths2,709 sq ft

127 Shore Rd, Clinton, CT 06413

Recently updated • 8,276 sq ft lot • 4 parking spots

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ABOUT THIS HOME
Luxury Home for sale in Middlesex County, CT:
Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring, ceiling fans throughout, and a dramatic two-sided fireplace that serves as a focal point for multiple living areas. German-engineered windows with roll shutters & premium German doors provide exceptional quality. Kitchen features new appliances & an open concept. 2 bedrooms with full bathroo

$1,295,000

4 beds3.5 baths2,656 sq ft

1409 Millbrook Rd, Middletown, CT 06457

Custom log home • 39 acre estate • Panoramic views

Property at 47 E Kings Hwy, Chester, CT 06412, 4 beds, 3.5 baths

$1,900,000

4 beds3.5 baths3,957 sq ft

47 E Kings Hwy, Chester, CT 06412

Property at 89 River Rd, East Haddam, CT 06423, 4 beds, 3.5 baths

$5,775,000

4 beds3.5 baths9,852 sq ft

89 River Rd, East Haddam, CT 06423

Property at 81 Hartford Ave, Old Saybrook, CT 06475, 4 beds, 2 baths

$2,150,000

4 beds2 baths2,440 sq ft

81 Hartford Ave, Old Saybrook, CT 06475

Property at 1270 Saybrook Rd, Haddam, CT 06438, 3 beds, 3 baths

$1,400,000

3 beds3 baths3,375 sq ft

1270 Saybrook Rd, Haddam, CT 06438

Property at 53 Oakridge Dr, Westbrook, CT 06498, 4 beds, 4 baths

$1,295,000

4 beds4 baths4,937 sq ft

53 Oakridge Dr, Westbrook, CT 06498

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

$3,950,000

5 beds5.5 baths5,557 sq ft

323 River Rd, Deep River, CT 06417

Property at 11 Cambridge Ct E, Old Saybrook, CT 06475, 4 beds, 3 baths

$1,625,000

4 beds3 baths2,178 sq ft

11 Cambridge Ct E, Old Saybrook, CT 06475

Property at 26 Willard Ave, Old Saybrook, CT 06475, 3 beds, 2 baths

$1,175,000

3 beds2 baths2,904 sq ft

26 Willard Ave, Old Saybrook, CT 06475

Property at 175 River Rd, Essex, CT 06426, 3 beds, 4 baths

$6,595,000

3 beds4 baths4,664 sq ft

175 River Rd, Essex, CT 06426

Property at 21 Fenbrook Rd, Old Saybrook, CT 06475, 3 beds, 2.5 baths

$1,290,000

3 beds2.5 baths1,916 sq ft

21 Fenbrook Rd, Old Saybrook, CT 06475

Property at 6 Beechwood Dr, Ivoryton, CT 06442, 4 beds, 2.5 baths

$959,750

4 beds2.5 baths2,552 sq ft

6 Beechwood Dr, Ivoryton, CT 06442

Property at 18 Old South Cove Rd, Old Saybrook, CT 06475, 4 beds, 2 baths

$899,000

4 beds2 baths1,569 sq ft

18 Old South Cove Rd, Old Saybrook, CT 06475

Property at 87 Main St, Deep River, CT 06417, 8 beds, 6 baths

$1,150,000

8 beds6 baths7,300 sq ft

87 Main St, Deep River, CT 06417

Property at 5-7 Haddam Dock Rd, Haddam, CT 06438, 6 beds, 5.5 baths

$2,450,000

6 beds5.5 baths4,442 sq ft

5-7 Haddam Dock Rd, Haddam, CT 06438

Property at 11 River Edge Rd, Old Saybrook, CT 06475, 6 beds, 4 baths

$6,600,000

6 beds4 baths5,739 sq ft

11 River Edge Rd, Old Saybrook, CT 06475

Property at 2 Captains Ln, Old Saybrook, CT 06475, 5 beds, 4.5 baths

$2,899,900

5 beds4.5 baths5,062 sq ft

2 Captains Ln, Old Saybrook, CT 06475

Property at 209 Main St, Deep River, CT 06417, 9 beds, 9 baths

$1,199,999

9 beds9 baths4,982 sq ft

209 Main St, Deep River, CT 06417

Property at 480 Main St, Middletown, CT 06457, 8 beds, 9 baths

$1,300,000

8 beds9 baths13,837 sq ft

480 Main St, Middletown, CT 06457

Property at 30 Knowles Rd, East Hampton, CT 06424, 4 beds, 4 baths

$1,395,000

4 beds4 baths3,799 sq ft

30 Knowles Rd, East Hampton, CT 06424

Property at 1445 Boston Post Rd, Old Saybrook, CT 06475, 4 beds, 1 bath

$12,000,000

4 beds1 bath2,059 sq ft

1445 Boston Post Rd, Old Saybrook, CT 06475

Property at 12 Rocky Point Rd, Old Saybrook, CT 06475, 4 beds, 4 baths

$5,900,000

4 beds4 baths5,651 sq ft

12 Rocky Point Rd, Old Saybrook, CT 06475

Property at 180 Green Hill Rd, Killingworth, CT 06419, 4 beds, 4 baths

$1,299,900

4 beds4 baths4,154 sq ft

180 Green Hill Rd, Killingworth, CT 06419

Property at 134 Meadow Woods Rd, Deep River, CT 06417, 3 beds, 2 baths

$2,200,000

3 beds2 baths1,591 sq ft

134 Meadow Woods Rd, Deep River, CT 06417

Property at 82 Main St, East Hampton, CT 06424, 27 beds, 19.5 baths

$3,650,000

27 beds19.5 baths16,973 sq ft

82 Main St, East Hampton, CT 06424

Property at 85 Salem Rd, Colchester, CT 06415, 4 beds, 4 baths

$1,224,999

4 beds4 baths5,452 sq ft

85 Salem Rd, Colchester, CT 06415

Property at 130 Mares Hill Rd, Ivoryton, CT 06442, 4 beds, 3 baths

$979,860

4 beds3 baths2,246 sq ft

130 Mares Hill Rd, Ivoryton, CT 06442

Property at Portland St, Middletown, CT 06457, 8 beds, 4 baths

$900,000

8 beds4 baths5,176 sq ft

Portland St, Middletown, CT 06457

Property at 31 N Main St, Essex, CT 06426, 4.5 baths

$2,195,000

— beds4.5 baths12,155 sq ft

31 N Main St, Essex, CT 06426

Property at 25 Silver Springs Dr, Higganum, CT 06441, 5 beds, 3.5 baths

$1,250,000

5 beds3.5 baths3,689 sq ft

25 Silver Springs Dr, Higganum, CT 06441

Property at 702 Fox Hopyard Rd, East Haddam, CT 06423, 3 beds, 2.5 baths

$1,550,000

3 beds2.5 baths2,500 sq ft

702 Fox Hopyard Rd, East Haddam, CT 06423

Property at 153 Wallingford Rd, Durham, CT 06422, 15 beds, 7.5 baths

$2,800,000

15 beds7.5 baths10,623 sq ft

153 Wallingford Rd, Durham, CT 06422

Property at 148 Wallingford Rd, Durham, CT 06422, 7 beds, 2.5 baths

$1,999,000

7 beds2.5 baths3,308 sq ft

148 Wallingford Rd, Durham, CT 06422

Property at 48A Ironworks Rd, Clinton, CT 06413, 3 beds, 3.5 baths

$899,900

3 beds3.5 baths2,164 sq ft

48A Ironworks Rd, Clinton, CT 06413

Property at 53 Shanaghans Rd, East Haddam, CT 06423, 5 beds, 4.5 baths

$1,895,000

5 beds4.5 baths6,517 sq ft

53 Shanaghans Rd, East Haddam, CT 06423

Property at Westbrook Rd, Essex, CT 06426

$3,400,000

Land33.02 acres (lot)

Westbrook Rd, Essex, CT 06426

Property at 1 Ballahack Rd, East Haddam, CT 06423

$1,300,000

Land63.74 acres (lot)

1 Ballahack Rd, East Haddam, CT 06423

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Luxury Homes for Sale in Middlesex County

There are currently 87 luxury homes for sale in Middlesex County at a median listing price of $500K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middlesex County stay on the market for 47 days and receive 4 offers. This map is refreshed with the newest listings in Middlesex County every 15 minutes.

In the past month, 185 homes have been sold in Middlesex County. In addition to houses in Middlesex County, there were also 100 condos, 0 townhouses, and 29 multi-family units for sale in Middlesex County last month. Find your dream home in Middlesex County 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 Middlesex County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middlesex County. If you're looking to sell your home in the Middlesex County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middlesex County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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