Connecticut Luxury Real Estate Market Overviews

Discover Connecticut's most prestigious coastal communities through comprehensive neighborhood guides, market insights, and luxury property analysis.

4
Premium Towns
67
Neighborhoods
$2M+
Average Luxury

Explore Connecticut's Premier Markets

Each town offers distinct character, amenities, and investment opportunities. Click to explore detailed neighborhood analyses.

Guilford Connecticut luxury real estate

Guilford, Connecticut

Quintessential New England town with historic green, excellent schools, and three distinct luxury market segments

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Luxury Market Segments:

Waterfront Prestige

Flagship neighborhoods for Guilford's luxury shoreline market

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Sachem Head – premier peninsula, yacht club lifestyle
Mulberry Point – exclusive peninsula, direct waterfront
Money Island – intimate peninsula with water views
Old Quarry – dramatic shoreline with unique topography
Indian Cove – private cove with beach access
Jacobs Beach – smaller, walkable beachfront community
Grass Island – marshland waterfront enclave
Historic Charm & Walkable Prestige

Luxury with New England heritage, centered on history and amenities

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Guilford Center – historic town hub, walkability to shops/green
Whitfield Street – historic residential street with prestige homes
Countryside Estates

Space, privacy, and rural elegance for luxury buyers

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North Guilford (select parts) – equestrian estates, large acreage, farm-style luxury
Madison Connecticut luxury real estate

Madison, Connecticut

Affluent shoreline community known for excellent schools, beautiful beaches, and upscale residential neighborhoods

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Luxury Market Segments:

Waterfront Prestige

Madison's crown jewels with direct Long Island Sound access, private beaches, and yacht club lifestyle

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Madison Beach – premier beachfront, exclusive access
Middle Beach – central beachfront with community association
East Wharf – marina district with boating & dining
West Wharf – marina and waterfront lifestyle
Surf Club – private beach club amenities
Fence Creek – exclusive enclave with private beach
Grove Beach – beachfront, more seasonal but charming
Historic & Town-Center Prestige

Luxury with heritage, walkability, and traditional New England vibe

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Madison Center – historic hub, shops, dining, walkability
Rockland – historic area with stone walls, colonial charm
Countryside & Estate Living

For buyers seeking privacy, space, and elevated views inland

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Green Hill – scenic estates with elevated views
Opening Hill – panoramic water views from hillside
North Madison – rural estates, larger lots, equestrian lifestyle
Summer Hill – hillside enclave, history as summer residences

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