590 Gulf Street
Milford, Connecticut 06460
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,430
- Acres
- 1.01
- Year Built
- 1936
- Neighborhood
- Gulf Beach
- Property Type
- Single Family

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About This Home
Perched high atop a scenic bluff, this extraordinary coastal retreat offers some of the most breathtaking water views in all of Milford, with sweeping, nearly 360-degree vistas of Long Island Sound and the neighboring bay. Set on over an acre of land, this is a truly rare opportunity to own one of the area's largest parcels with such expansive, unobstructed waterfront scenery. Originally built in 1936 and thoughtfully expanded in the early 2000s, this remarkable home blends timeless New England charm with modern design and functionality. Offering 4,430 square feet of finished living space across two levels, plus an additional 2,328 square feet of high-ceilinged unfinished basement, the possibilities here are endless-whether you envision a home theater, gym, or custom in-law suite. The residence features 5 spacious bedrooms and 4 full bathrooms, designed for both comfort and versatility. The open-concept kitchen flows seamlessly into a warm and inviting bar area, creating the perfect setting for entertaining, while the adjacent dining room provides an elegant space for gatherings and special occasions. Wake up to stunning sunrises, unwind with ocean breezes, and enjoy a lifestyle defined by tranquility and natural beauty. Located in one of Milford's most coveted coastal enclaves, this property is not just a home-it's a rare opportunity to create your dream waterfront retreat, all while being conveniently located near major highways, shopping, dining, and set within a highly
Key Facts
- City/Town
- Milford
- Neighborhood
- Gulf Beach
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1936
- Days on Market
- 153 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 4,430 sq ft
- Lot Size
- 1.01 acres
- Property Taxes
- $26,058 / Annually
Market Snapshot
The Milford Market
Single Family · trailing 12 months
Active Listings
77
93 under contract
Median List Price
$699,000
77 active listings
Median Closed Price
$555,000
443 sales
Median Days on Market
29
77 active listings
Median $ / Sq Ft
$363
77 active listings
Sale-to-List Ratio
100.0%
443 sales
How this home compares
List Price
$2.50M
vs $699,000 median
3.6× the median
Price / Sq Ft
$564
vs $363 median
55.4% above median
Days on Market
153 days
vs 29 days median
124 days longer than median
Based on 77 active and 443 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of August 18, 2026.
Location
590 Gulf Street, Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$12,861
- Property Taxes$2,172
- Insurance$833
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Milford
- Neighborhood
- Gulf Beach
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1936
- New Construction
- No/Resale
- Living Area
- 4,430 sq ft
Schools
- Elementary
- Calf Pen Meadow
- High
- Joseph A. Foran
Interior
- Heating
- Hydro Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Main Level
- Appliances
- Gas CooktopWall OvenMicrowaveFreezerSubzeroDishwasher
- Basement
- FullUnfinished
- In-Law Apartment
- PossibleFirst Floor
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 1.01 acres
- Zoning
- R18
- Waterfront
- Direct waterfront
- Waterfront Details
- L. I. Sound FrontageBeachWalk to WaterViewAccess
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Shingle
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyWrap Around Deck
- Lot Description
- Corner Lot
Listing & Financials
- Property Taxes
- $26,058 / Annually
- Days on Market
- 153
- MLS #
- 24158825
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/18/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 8/18/2026 at 6:51 AM UTC.