Point Lookout
Exclusive Peninsula Living
Milford's most prestigious waterfront community with private beach association and stunning Long Island Sound views
About Point Lookout
Point Lookout stands as Milford's crown jewel of luxury waterfront living, representing the pinnacle of exclusive coastal real estate. This prestigious peninsula community, established as a private association, offers residents unparalleled access to Long Island Sound with deeded beach rights and extraordinary panoramic water views. The neighborhood has evolved into Connecticut's most coveted address for discerning buyers seeking the ultimate in waterfront luxury and privacy.
Location & Geography
Strategically positioned on a private peninsula overlooking Long Island Sound, Point Lookout encompasses approximately 200 acres of prime waterfront real estate. The elevated topography provides commanding views of Charles Island and the expansive Sound, while the 2.3 miles of pristine private coastline offer residents exclusive access to sandy beaches and deep-water docking facilities. The neighborhood's unique geography creates natural privacy and exclusivity unavailable elsewhere in the region.
Architectural Character
The architectural landscape of Point Lookout showcases magnificent waterfront estates ranging from classic New England colonials to contemporary masterpieces. Properties feature expansive windows to capture breathtaking water views, private docks, infinity pools, and luxury amenities befitting their premium locations. Many homes have been completely renovated or rebuilt to modern luxury standards while maintaining the timeless elegance that defines this exclusive enclave.
Community Profile
Point Lookout attracts Connecticut's most successful professionals, business executives, and affluent families seeking the ultimate waterfront lifestyle. The community commands some of Milford's highest property values, with residents typically holding advanced degrees and working in finance, healthcare, technology, and executive leadership roles. The neighborhood maintains an atmosphere of refined exclusivity while fostering a strong sense of community among its residents.
Point Lookout Real Estate Market Data
Market data as of January 2025
Property Profile in Point Lookout
Property Types
Property Sizes
Lot Information
What Makes Point Lookout Unique
Private peninsula location with 2.3 miles of exclusive beach access
Point Lookout Association membership with deeded beach rights
24/7 private security and gated community access
Community dock system with 45 private boat slips for residents
Panoramic views of Long Island Sound and historic Charles Island
Underground utilities and professionally landscaped common areas
Annual community regatta and exclusive member social events
Local Amenities & Attractions
Point Lookout Private Beach
Exclusive 2.3 miles of private sandy beach accessible only to Point Lookout Association members. Features pristine coastline, private boat docks, and unobstructed views of Long Island Sound and Charles Island.
Private Deep Water Marina
Community dock system with 45 boat slips available to residents, accommodating vessels up to 40 feet. Includes boat launch facilities, maintenance services, and direct Sound access.
Gulf Beach Public Access
Additional beach access with fishing pier, snack bar, and recreational facilities. Perfect for guests and extended family activities while maintaining private community exclusivity.
Downtown Milford Historic District
Charming downtown area featuring upscale restaurants, boutique shopping, art galleries, and the scenic Milford Green. Regular community events and farmers markets throughout the year.
School Information
Elementary School
Middle School
High School
Living in Point Lookout
Community Profile
Primary Appeal: Ultra-wealthy executives and established families seeking the pinnacle of waterfront luxury
Community Atmosphere: Exclusive, sophisticated, and privacy-focused with strong community traditions
Seasonal Dynamics: 70% year-round residents with notable increase during summer months
Social Scene: Private association events, yacht club gatherings, annual regatta, exclusive dinner parties, and sophisticated waterfront entertaining
Investment Insights
Rental Potential
Exceptional - Summer rentals $15,000-35,000/month for premium properties, annual rentals $8,000-18,000/month
Appreciation Outlook
Outstanding 8-12% annual appreciation expected due to ultra-limited inventory, private association exclusivity, and irreplaceable waterfront location
Tax Considerations
Mill rate 26.66, average annual property taxes $29,000-67,000 based on premium assessments
Future Development
Strictly controlled development with focus on luxury renovations and select teardown/rebuilds maintaining community character
Comparable Markets
Similar luxury neighborhoods include: Madison's Fence Creek, Old Saybrook's Fenwick, Westport's Compo Beach, Greenwich's Belle Haven
Commute & Transportation
To New York City
1 hour 35 minutes by car via I-95, 2 hours via Metro-North from Milford station
To New Haven
18 minutes via I-95, 25 minutes via scenic Route 1
To Hartford
42 minutes via Route 15 North to I-91
Public Transit
Milford Metro-North station 2.5 miles with Shore Line East service to Grand Central
Highway Access
I-95 Exit 39A (2 miles), Route 1 (1.5 miles), Route 146 direct access (0.5 miles)
Airports
Tweed New Haven Regional (20 minutes), Bradley International (50 minutes), Westchester County (65 minutes)
Frequently Asked Questions
What is the average home price in Point Lookout as of January 2025?
The median home price in Point Lookout is $1.1M as of January 2025, with luxury waterfront estates ranging from $700K for smaller properties to over $2.5M for premium penthouses with private docks, extensive grounds, and panoramic Sound views.
What makes Point Lookout unique compared to other Connecticut waterfront communities?
Point Lookout is Connecticut's most exclusive private waterfront association, featuring 2.3 miles of private beach, community dock system with 45 boat slips, 24/7 security, and spectacular views of Charles Island. The private association status ensures long-term exclusivity and premium property values.
Is Point Lookout suitable for families with children?
Absolutely. Point Lookout offers an exceptional family environment with private beaches, safe community atmosphere, access to top-rated Milford schools, and numerous family-oriented association activities. The private beach and dock facilities provide endless recreational opportunities for children.
How exclusive is the Point Lookout Association?
Extremely exclusive. Membership is limited to property owners within the association, providing access to private beaches, boat slips, and community facilities. The association maintains strict architectural standards and community guidelines to preserve the neighborhood's premium character and property values.
What is the rental market like in Point Lookout?
The rental market is exceptionally strong due to the exclusive nature and luxury amenities. Summer rentals for premium waterfront properties can command $15,000-35,000 per month, while year-round rentals typically range from $8,000-18,000 monthly depending on size, location, and amenities.
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