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$695,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,382 Sq. Ft.
  • 1 Car Garage
  • Updated 3 days ago
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Welcome to this charming Cape Cod-style home, offering an inviting entry into the quaint, historic village of Southport. Recently refreshed with a full interior repaint in a crisp, clean white palette, the home feels bright, open, and thoughtfully updated, with sparsely furnished spaces that highlight the light, flow, and flexibility. Recent improvements include a brand-new furnace, a new above-the-range microwave, and a Bosch dishwasher, while the roof carries a transferable warranty for added peace of mind. The home opens to a deck overlooking a naturally sloped backyard, creating a comfortable outdoor space for relaxing or entertaining without the burden of heavy yard maintenance. Set within an excellent school district, this property also offers exceptional walkability, just minutes to the harbor, train station, and charming village shops. A move-in-ready opportunity to enjoy classic New England charm, fresh updates, and one of Fairfield County's most desirable coastal communities.

Full Property Details for 53 Hilltop Dr

General

  • Price: $695,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24130595
  • Updated: 2/1/2026
  • Added to Site: 125 day(s) ago

Interior

  • Number of Rooms: 6
  • Appliances: Cook Top, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Hardwood Floor, Main
  • Bedroom 1: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 2: Bedroom - Vinyl Floor, Upper

Other Rooms

  • Kitchen: Kitchen - Tile Floor, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Laundry: Lower Level

Exterior

  • Exterior Features: Deck, Gutters
  • Color: Tan

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 1
  • Parking: Attached Garage, Under House Garage

Location

  • County: Fairfield
  • Neighborhood: Southport
  • Driving Directions: Bronson to Rockview to Hilltop.

School Information

  • Elementary School: Mill Hill
  • High School: Fairfield Ludlowe

Community

  • Community Name: Southport

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: 80 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Square Feet: 1,382
  • Above Ground: 1,382 Sq. Ft.
  • Year Built: 1949

Lot Features

  • Lot Size (Acres): 0.26
  • Zoning: AA
  • Lot Description: Sloping Lot, On Cul-De-Sac

Financial Considerations

  • Assessment Amount: $336,840
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 133824
Buyer's Brokerage Compensation: Contact Listing Agent
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— 53 Hilltop Dr —

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 53 Hilltop Dr

School District:Fairfield School District
NameGradesDistance
Mill Hill School
635 Mill Hill Terrace, Fairfield, CT 06890
K-50.2 mi
Roger Ludlowe Middle School
689 Unquowa Road, Fairfield, CT 06824
6-80.9 mi
Fairfield Ludlowe High School
785 Unquowa Road, Fairfield, CT 06824
9-120.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 53 Hilltop Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/25/2026
Price Reduced
$695,000
-0.71%
MLS
11/07/2025
Price Reduced
$699,999
-6.67%
MLS
10/09/2025
Listed
$750,000
316.67%
MLS
5/24/1993
Sold
$180,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 53 Hilltop Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,563
2%
$336,840
—
2023
$9,398
1%
$336,840
—
2023
$9,266
1%
$336,840
—
2022
$9,176
1%
$336,840
—
2021
$9,088
-1%
$336,840
-2%
2020
$9,165
—
$342,090
—
2019
$9,165
2%
$342,090
—
2018
$9,017
2%
$342,090
—
2017
$8,833
1%
$342,090
—
2016
$8,706
-1%
$342,090
-4%
2015
$8,831
2%
$356,230
—
2014
$8,692
2%
$356,230
—
2011
$8,525
—
$356,230
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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53 Hilltop Drive, Fairfield, CT 06890 (MLS# 24130595) is a Single Family property with 3 bedrooms and 2 full bathrooms. 53 Hilltop Drive is currently listed for $695,000 and was received on October 02, 2025. This property is listed by The Lewis Team at Coldwell Banker Realty from our Milford Office.Want to learn more about 53 Hilltop Drive? Do you have questions about finding other Single Family real estate for sale in Southport? You can browse all Southport real estate or contact a Coldwell Banker agent to request more information.

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