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. 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, beautifully maintained homes, and a strong sense of community. Seller will review all offers on Tuesday, May 5th. Please submit all offers by 5:00 PM on Monday, May 4th. Seller reserves the right to accept an offer before this time." "Seller will review all offers on Tuesday, May 5th. Please submit all offers by 5:00 PM on Monday, May 4th. Seller reserves the right to accept an offer before this time."
Sold for $1,750,000
$1,750,000
264 Half Mile Road, Fairfield, CT 06890
4beds
2,642sqft
Single Family Residence
Built in 1973
1.03 Acres Lot
$1,722,900 Zestimate®
$662/sqft
$7,384 Estimated rent
Home value
$1,722,900
$1.64M - $1.81M
$7,384/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Katie O'Grady & Consultants Team,
Beth Mengel (203)610-3638,
Compass Connecticut, LLC 203-489-6499
Bought with:
Tara Hawley, RES.0796565
Coldwell Banker Realty
Source: Smart MLS,MLS#: 24162941
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Built-in Features, Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bathroom
- Features: Tile Floor
- Level: Main
Bathroom
- Features: Full Bath, Tub w/Shower, Tile Floor
- Level: Upper
Dining room
- Features: French Doors, Hardwood Floor
- Level: Main
Family room
- Features: Bookcases, Built-in Features, Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Granite Counters, Dry Bar, Kitchen Island, Pantry, Patio/Terrace, Hardwood Floor
- Level: Main
Living room
- Features: Built-in Features, Fireplace, Hardwood Floor
- Level: Main
Other
- Features: Built-in Features, Tile Floor
- Level: Main
Rec play room
- Features: Laminate Floor
- Level: Lower
Heating
- Forced Air, Zoned, Oil
Cooling
- Central Air
Appliances
- Included: Electric Cooktop, Oven, Convection Oven, Microwave, Range Hood, Refrigerator, Ice Maker, Dishwasher, Disposal, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Lower Level
Features
- Wired for Data
- Doors: Storm Door(s)
- Windows: Storm Window(s)
- Basement: Crawl Space,Full
- Attic: Walk-up
- Number of fireplaces: 2
Interior area
- Total structure area: 2,642
- Total interior livable area: 2,642 sqft
- Finished area above ground: 2,642
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 2
Features
- Patio & porch: Screened, Porch, Patio
- Spa features: Heated
- Waterfront features: Beach Access
Lot
- Size: 1.03 Acres
- Features: Sloped, Cul-De-Sac
Details
- Parcel number: 133395
- Zoning: AA
- Other equipment: Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1973
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities, Cable Available
Green energy
- Energy efficient items: Doors, Windows
Community & HOA
Community
- Subdivision: Southport
HOA
- Has HOA: No
Location
- Region: Southport
Financial & listing details
- Price per square foot: $662/sqft
- Tax assessed value: $625,030
- Annual tax amount: $17,745
- Date on market: 4/27/2026
Price history
| Date | Event | Price |
|---|---|---|
| 7/1/2026 | Sold | $1,750,000+9.7%$662/sqft |
Source:  Smart MLS #24162941 Report a problem | ||
| 5/11/2026 | Pending sale | $1,595,000$604/sqft |
Source: Smart MLS #24162941 Report a problem | ||
| 4/29/2026 | Listed for sale | $1,595,000+60.3%$604/sqft |
Source: Smart MLS #24162941 Report a problem | ||
| 6/1/2006 | Sold | $995,000+168.9%$377/sqft |
Source: Smart MLS #98275200 Report a problem | ||
| 11/5/1990 | Sold | $370,000-16.9%$140/sqft |
Source: Public Record Report a problem | ||
| 5/24/1989 | Sold | $445,000$168/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $17,745 +1.8% | $625,030 |
| 2024 | $17,438 +1.4% | $625,030 |
| 2023 | $17,195 +1% | $625,030 |
| 2022 | $17,026 +1% | $625,030 |
| 2021 | $16,863 -4.4% | $625,030 -5.1% |
| 2020 | $17,647 | $658,700 |
| 2019 | $17,647 +1.6% | $658,700 |
| 2018 | $17,363 +2.1% | $658,700 |
| 2017 | $17,008 +1.3% | $658,700 -2.7% |
| 2015 | $16,786 +1.6% | $677,110 |
| 2014 | $16,521 +2% | $677,110 |
| 2013 | $16,203 +6.5% | $677,110 |
| 2011 | $15,215 +8.9% | $677,110 -6.6% |
| 2010 | $13,968 +2% | $724,850 |
| 2009 | $13,700 +4.9% | $724,850 +3.2% |
| 2008 | $13,055 +6.7% | $702,660 |
| 2007 | $12,233 +4.4% | $702,660 |
| 2006 | $11,713 +7.1% | $702,660 +59.4% |
| 2005 | $10,935 +6% | $440,930 |
| 2004 | $10,318 +8.8% | $440,930 |
| 2003 | $9,480 +24% | $440,930 +68.5% |
| 2001 | $7,643 +85.3% | $261,730 |
| 2000 | $4,125 -41% | $261,730 |
| 1999 | $6,988 | $261,730 |
Find assessor info on the county website
Neighborhood: Southport
Nearby homes
- $1,506,5005 bd3 ba3.3k sqft230 Half Mile Rd, Southport, CT 06890Off Market
- $1,675,3004 bd2 ba2.7k sqft300 Half Mile Rd, Southport, CT 06890Off Market
- $1,330,8004 bd3 ba2.6k sqft243 Sturbridge Ln, Southport, CT 06890Off Market
- $1,589,7005 bd2 ba3.5k sqft207 Sturbridge Ln, Southport, CT 06890Off Market
- $1,401,0004 bd3 ba2k sqft235 Sturbridge Ln, Southport, CT 06890Off Market
- $2,307,7006 bd5 ba4.9k sqft255 Half Mile Rd, Southport, CT 06890Off Market
- $1,485,2004 bd3 ba3k sqft247 Sturbridge Ln, Southport, CT 06890Off Market
- $1,546,9004 bd3 ba2.4k sqft340 Half Mile Rd, Southport, CT 06890Off Market
Nearby schools
GreatSchools rating
- 10/10Dwight Elementary SchoolGrades: K-5Distance: 2.3 mi
- 8/10Roger Ludlowe Middle SchoolGrades: 6-8Distance: 1.6 mi
- 9/10Fairfield Ludlowe High SchoolGrades: 9-12Distance: 1.5 mi
Schools provided by the listing agent
- Elementary: Dwight
- Middle: Roger Ludlowe
- High: Fairfield Ludlowe
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Fairfield
- 06890
- Southport
- 264 Half Mile Road
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