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590 Gulf Street

Milford, Connecticut 06460

ACTIVE$2,499,000
Beds
5
Baths
4 | 1
SqFt
4,430
Acres
1.01
Year Built
1936
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$15,866

per 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

Similar Properties

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Listed By

Stacy Blake

(203) 927-9689

Stacy Blake Realty LLC

(203) 713-8090

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.