Set along one of Southport's most picturesque residential cul-de-sac's, 264 Half Mile Road embodies the quiet sophistication and understated elegance that define this coveted coastal enclave. Privately sited on just over an acre, this classic Colonial residence offers a rare blend of space, serenity, and enduring charm in a setting known for its natural beauty and refined lifestyle. With approximately 2,900 square feet of living space, the home is thoughtfully scaled with four bedrooms and two and a half baths, creating a layout that is both functional and inviting. Built in the early 1970s, its architecture reflects timeless New England character-graceful proportions, warm wood elements, and a sense of quiet permanence-while offering the opportunity for a discerning buyer to reimagine or elevate the interiors to today's luxury standards. Mature trees, open lawn, and the gentle rhythm of the surrounding landscape create a private, park-like atmosphere-ideal for outdoor entertaining, future enhancements, or simply enjoying the tranquility that defines life on Half Mile Road. Located just minutes from Southport Village, residents enjoy effortless access to shopping, harbor views, beaches, and the Metro-North Railroad for a seamless connection to Manhattan. The neighborhood itself is celebrated for its peaceful, established feel, where a tree lined street, beautifully maintained homes, and a strong sense of community create an exceptional quality of life.
Listed by Beth Mengel
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Compass Connecticut, LLC
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(203) 610-3638
Last updated April 30, 2026
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Source: SmartMLS #24162941
Listing Facts
TypeSingle-family
NeighborhoodFairfield
Bedrooms4
Bathrooms3
Days on Prevu5
Taxes$17,745/year
Size2,642 sqft
Price per sqft$604
Location
Mortgage Calculator
Listing History
04/30/2026
Status changed to Active
$1,595,000
04/29/2026
Status changed to Removed from Feed
$1,595,000
04/27/2026
Listed by Compass Connecticut, LLC
$1,595,000
Property Details for 264 Half Mile Road
Exterior
Construction
New Construction: No/Resale
Roof: Asphalt Shingle
Year Built: 1973
Year Built Details: Public Records
Architectural Style: Colonial
Construction Materials: Frame
Exterior Features: Porch-Screened, Underground Utilities, Porch, Hot Tub, Patio
Features
Waterfront Features: Beach Rights
Measurements
Lot Features: Sloping Lot, On Cul-De-Sac
Lot Size Acres: 1.03
Financial
Taxes
Parcel Number: 133395
Tax Annual Amount: $17,745.00
Tax Year: 25
Interior
Features
Appliances: Electric Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Icemaker, Dishwasher, Disposal, Washer, Electric Dryer, Wine Chiller
Fireplaces Total: 2
Interior Features: DROPEN, CABLE, PREWIRED
Measurements
Living Area: 2,642
Rooms
Basement: Crawl Space, Full
Bathrooms Full: 2
Bathrooms Half: 1
Bathrooms Total Integer: 3
Bedrooms Total: 4
Rooms Total: 10
Parking
Parking
Attached Garage: Attached Garage
Garage Spaces: 2
Schools
Elementary School
Elementary School: Dwight
High School
High School: Fairfield Ludlowe
Middle or Junior School
Middle Or Junior School: Roger Ludlowe
Utilities
Equipment
Cooling: Central Air
Heating: Hot Air, Zoned
Laundry Features: Lower Level
Sewer: Septic
Water Source: Public Water Connected
Frequently Asked Questions
How many bedrooms and bathrooms does this single-family home have?
There are 4 bedrooms and 3 bathrooms in this single-family home at 264 Half Mile Road.
What schools are nearby to 264 Half Mile Road?
Nearby schools include the Dwight Elementary School, Roger Ludlowe Middle School, and Fairfield Ludlowe High School.
Does this single-family home have parking?
Yes, there are 2 parking spaces available for 264 Half Mile Road.
What are the annual taxes for 264 Half Mile Road?
Annual taxes for this single-family home are estimated at $17,745.
How does 264 Half Mile Road compare to other single-family homes in Fairfield?
This single-family home is listed 2% above the average price for single-family homes in Fairfield and has been on the market for 53 less days than the typical home in this area.
What is the square footage on this single-family home?
According to the MLS, this listing is 2,642 sqft.
264 Half Mile Road is a 4-bedroom, 3-bath single-family home for sale in Fairfield CT 06890. On Prevu for 5 days at $1,595,000. This residence features 2,642 square feet of living space, located in Fairfield. The median listing price for single-family homes in this area is $1,100,000. Nearby schools include Dwight Elementary School, Roger Ludlowe Middle School, and Fairfield Ludlowe High School. View other single-family home listings in Fairfield County.
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