65 Hilltop Drive

Closed 4/25/25
Closed 4/25/25
Gallery Image 1
Sold
Last Sold Price
$1,375,000
4 beds3,100 sqft$444/sqft
65 Hilltop Dr, Fairfield, CT 06890
Single FamilyProperty Type
1.5 acresLot Size
1884Year Built
$444/sq ftPrice per sq ft
1 carParking Spaces

Description

Nestled on a picturesque 1.5-acre hillside on a cul-de-sac, this Southport residence offers a rare blend of historic craftsmanship and modern updates. Just a short walk to Southport Village and the train station, with easy access to all of Fairfield's amenities, this home checks all the boxes. Upon entering, enjoy 9ft+ ceilings, oversized windows and hardwood floors. Spanning three floors of finished living area and 3,100 sq. ft., the home features original craftsmanship moldings, custom built-in...Nestled on a picturesque 1.5-acre hillside on a cul-de-sac, this Southport residence offers a rare blend of historic craftsmanship and modern updates. Just a short walk to Southport Village and the train station, with easy access to all of Fairfield's amenities, this home checks all the boxes. Upon entering, enjoy 9ft+ ceilings, oversized windows and hardwood floors. Spanning three floors of finished living area and 3,100 sq. ft., the home features original craftsmanship moldings, custom built-in bookcases in the living room, a graceful curved staircase with rich wood accents, and two wood burning fireplaces. One fireplace is shared between the kitchen and dining room which is a very unique feature. The dining room has french doors which open to a bluestone patio off the front of the house which faces east-perfect for enjoying morning sun with your coffee. In 2023, the kitchen was fully redone with wide plank flooring, Quartz countertops, new GE appliances and a brand-new roof. The home seamlessly integrating modern convenience with timeless elegance. Surrounded by mature landscaping, rock outcroppings and classic stone walls, this rare find of a 1.5-acre property in Southport showcases classic architectural detail, timeless craftsmanship, and a setting that is truly one of a kind. A must see.

Listing Agents

  1. Tara Hawley

    Tara Hawley

    Listing Agent

    Coldwell Banker Realty

    P: (203) 254-7100

    M: (203) 331-5939

    CallText
  2. Doris J Rowe

    Doris J Rowe

    Alternative Listing Agent

    Coldwell Banker Realty

    P: (203) 254-7100

    M: (203) 767-0920

    CallText
Listing closed: 04/25/2025 12:00 AM • Source: SMARTMLS, MLS#: 24072040

Recent comparable sales

Median sold price

$1,428,000

Avg days on market

22

Sale-to-list ratio

104.7%

Fairfield, CT

9 comparable properties found

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$1,475,000 | 351 Hillside Road, Fairfield, CT 06824
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$1,375,000 | 139 High Meadow Road, Fairfield, CT 06890
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Location

Listing Courtesy of Coldwell Banker Realty, Tara Hawley; Coldwell Banker Realty, Doris J Rowe
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Property Information for 65 Hilltop Drive

Property Details
  • Taxes: $18,425 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Full, Storage, Garage Access, Interior Access, Partially Finished, Concrete Floor, Full With Walk-Out
  • Direct Waterfront: No
  • Expected Active Date: 03-06-2025
  • Garages Number: 1
  • Neighborhood: Southport
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
  • Expected On Market Date: 03-06-2025
Building Information
  • Year Built: 1884
  • Lot Size: 1.50 AC / 65,340 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Bronson Road to Hilltop Drive in Southport
  • Elementary School: Mill Hill
  • Flood Zone: No
  • High School: Fairfield Ludlowe
  • Latitude: 41.144465
  • Longitude: -73.277529
  • Middle Jr High School: Roger Ludlowe
  • Neighborhood Amenities: Golf Course, Health Club, Library, Private School(s), Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $18,425
Interior and Exterior Features
Exterior Features
  • Exterior Features: Gutters, Lighting, Patio
  • Waterfront Description: Water Community
Interior Features
  • Appliances Included: Cook Top, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Heated, Storage Space, Floored, Walk-up
  • Cooling System: Attic Fan, Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Auto Garage Door Opener, Cable - Available, Security System
  • Laundry Room Info: Lower Level
  • Laundry Room Location: Lower Level
  • Rooms Additional: Foyer, Mud Room
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Book Shelves,Built-Ins,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: On 3rd Floor
  • Room Level: Other
  • Room Type: Office
Room 3
  • Room Entry Order: 11
  • Room Features: On 3rd Floor
  • Room Level: Other
  • Room Type: Full Bath
Room 4
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 5
  • Listing Key: 2D05F6D4C617BE45E063D501100AFC64
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Quartz Counters,Dining Area,Fireplace,Island,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 6
  • Room Entry Order: 4
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Half Bath
Room 7
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 8
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 2D05F6D4C617BE45E063D501100AFC64
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 8
  • Room Level: Upper
  • Room Type: Full Bath
Room 11
  • Room Entry Order: 9
  • Room Features: On 3rd Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame, Concrete
  • Exclusions: See separate list
  • Exterior Siding: Shingle, Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1884
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: Based off floor plans
  • Living Area SQFT Per Public Records: 2948
Lot Information
  • Lot Description: Lightly Wooded, Sloping Lot, On Cul-De-Sac
  • Parcel Number: 133822
  • Sq Ft Est Heated Above Grade: 3100.0
  • Sq Ft Total: 3100.0
  • Zoning: AA & Partial on A
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Electric, Tank Size Unknown
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 65 Hilltop Drive

DateEvent & SourcePriceAppreciation
Apr 24, 2025

Closed (Public Record)

Public Record #1556720236

$1,375,000

+5.2% / yr

Jun 16, 2014

Closed (Public Record)

Public Record #418608038

$795,000

+2.0% / yr

May 23, 2001

Closed (Public Record)

Public Record #90997150

$615,000

+10.1% / yr

DateEvent & SourcePrice
04/24/2025

Closed (Public Record)

Public Record #1556720236

$1,375,000

+5.2% / yr

06/16/2014

Closed (Public Record)

Public Record #418608038

$795,000

+2.0% / yr

05/23/2001

Closed (Public Record)

Public Record #90997150

$615,000

+10.1% / yr

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 65 Hilltop Drive

Taxable ValueLand$472,150Additions$188,230Total$660,380
Tax Record2025$18,748 ($1,562 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt2,948 SqFtAbove Grade Finished SqFt2,948 SqFtUnfinished Basement SqFt682 SqFtStories2Lot Size65,340 SqFtStyleSingle Family ResidenceYear Built1884Year Renovated1884ZoningAACountyGREATER BRIDGEPORTAPNFFLD M:229 B:226

Schools near 65 Hilltop Drive

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Mill Hill School
Public - K to 5
Roger Ludlowe Middle School
Public - 6 to 8
Fairfield Ludlowe High School
Public - 9 to 12
The Southport School
Private - 2 to 8
Rating
School
Distance
Mill Hill School
PublicK to 5

Roger Ludlowe Middle School
Public6 to 8

Fairfield Ludlowe High School
Public9 to 12

The Southport School
Private2 to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Fairfield & Southport
Fairfield & Southport
Bustling small city amenities meet outstanding Connecticut natural beauty. Fairfield is a charming coastal New England town spanning 30 square miles along the Long Island Sound, just 50 miles from NYC. Here, 62,000 residents enjoy the vibrant energy and sophisticated air of a small city combined...
Fairfield & Southport Guide

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 65 Hilltop Drive, Fairfield, CT 06890
$1,375,000
4
3,100
65,340
66 Hilltop Drive, Fairfield, CT 06890
$890,000
4
3,100
14,810
335 Bronson Road, Fairfield, CT 06890
$960,000
4
3,112
50,094
37 Hilltop Drive, Fairfield, CT 06890
$430,000
3
1,420
11,325
52 Rockview Road, Southport, CT 06890
$479,000
4
2.5
2,100
9,375
23 Hilltop Drive, Southport, CT 06890
–
3
2.5
1,279
47,500

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty, Tara Hawley; Coldwell Banker Realty, Doris J Rowe

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.