550 Rolling Hills Dr

Fairfield, CT 06824

$1,600,000
Last Sold Price
4
Beds
4,148 Sq. Ft.
$386 / Sq. Ft.
4,148
Sq. Ft.
$386
per Sq. Ft.
Closed 11/14/25
Closed 11/14/25
a front view of house with yard and green space

Description

Welcome to this beautifully updated 4+ bedroom Colonial in a sought-after Greenfield Hill neighborhood, surrounded by rolling lawns and tree-lined streets. Offering over 3,000 sq. ft. of elegant living space plus 1,000+ sq. ft. in the spacious finished walk-out lower level, this home provides exceptional versatility and comfort. The grand entryway opens to a formal living and dining room with custom built-ins. The inviting family room, with vaulted ceilings and a natural stone fireplace, flows seamlessly...Welcome to this beautifully updated 4+ bedroom Colonial in a sought-after Greenfield Hill neighborhood, surrounded by rolling lawns and tree-lined streets. Offering over 3,000 sq. ft. of elegant living space plus 1,000+ sq. ft. in the spacious finished walk-out lower level, this home provides exceptional versatility and comfort. The grand entryway opens to a formal living and dining room with custom built-ins. The inviting family room, with vaulted ceilings and a natural stone fireplace, flows seamlessly into the impeccably updated eat-in kitchen. From here, sliding doors lead to an expansive Trex deck with a built-in gas grill, perfect for indoor/outdoor entertaining against the backdrop of a serene, private wooded yard. A mudroom, laundry area, and powder room complete the first floor. Upstairs, the tranquil primary suite features a walk-in closet and a spa-like bath with soaking tub, stall shower, and double vanity. Three additional bedrooms and a full bath complete the second level. The finished lower level includes a bedroom/office/potential au pair suite with full bath, ample storage, and walk-out access. Notable upgrades include fresh interior and exterior paint (2025), new roof (2024), remodeled kitchen and primary bath (2023), refinished hardwood floors (2023), and driveway sealing (2023). Meticulously maintained mechanicals and thoughtful updates make this home truly move-in ready.
  1. Listed by Marcia Lyman • Brown Harris Stevens
    P: (857)-492-1077 C: (857)-492-1077 MLyman@BHSUSA.com
  2. Listed by Annie Kruger • Brown Harris Stevens
    P: (203)-254-1500 C: (646)-712-4461 AKruger@BHSUSA.com

Property Details for 550 Rolling Hills Drive

Basement Description
Full, Heated, Cooled, Interior Access, Partially Finished, Walk-out, Liveable Space
Direct Waterfront
No
Expected Active Date
09-17-2025
Garages Number
2
Neighborhood
Greenfield Hill
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
No
LISTING UPDATED: 11/21/2025 01:05 PM

Property Details for 550 Rolling Hills Drive

StatusClosed
MLS #24126270
Days on Market7
Taxes$15,602 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1996
Lot Size2.38 AC / 103,672 SF
CountyFairfield County

Location

Listing Courtesy of Brown Harris Stevens, Marcia Lyman; Brown Harris Stevens, Annie Kruger

Sold By RE/MAX Heritage, Michael Traum

Add your commute

Building Information for 550 Rolling Hills Drive

Stories-Year Built1996Building Size-Lot Size2.38 AC / 103,672 SF

Payment Calculator

$9,206 per month

30 year fixed, 6.28% Interest

Principal and Interest

$7,906

Property Taxes

$1,300

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 550 Rolling Hills Drive

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Black Rock Tpke to Congress to Morehouse Hwy to Rolling Hills Drive.
  • Elementary School: Burr
  • Flood Zone: No
  • High School: Fairfield Warde
  • Latitude: 41.223569
  • Longitude: -73.276387
  • Middle Jr High School: Tomlinson
  • Neighborhood Amenities: Lake, Library, Park, Public Transportation
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $15,602
Interior and Exterior Features
Exterior Features
  • Exterior Features: Grill, Deck, Gutters, Lighting, Patio
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Disposal, Washer, Dryer
  • Attic Description: Storage Space, Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener
  • Laundry Room Info: Main Level
  • Rooms Additional: Laundry Room
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Built-Ins,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Vaulted Ceiling,Built-Ins,Gas Log Fireplace,Wall/Wall Carpet
  • Room Level: Main
  • Room Type: Family Room
Room 4
  • Room Entry Order: 4
  • Room Features: Remodeled,9 ft+ Ceilings,Balcony/Deck,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 5
  • Listing Key: 3E9D6E855DE21252E063E201100A6D4E
  • Room Entry Order: 5
  • Room Features: Remodeled,9 ft+ Ceilings,Bedroom Suite,Full Bath,Walk-In Closet,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 6
  • Room Entry Order: 6
  • Room Features: 9 ft+ Ceilings,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: 9 ft+ Ceilings,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Features: 9 ft+ Ceilings,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 3E9D6E855DE21252E063E201100A6D4E
  • Room Entry Order: 9
  • Room Features: 9 ft+ Ceilings,Patio/Terrace,Sliders,Wall/Wall Carpet
  • Room Level: Lower
  • Room Type: Rec/Play Room
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1996
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 1100
  • Living Area SQFT Per Public Records: 3048
Lot Information
  • Lot Description: Fence - Full, Some Wetlands, Lightly Wooded
  • Parcel Number: 121202
  • Sq Ft Est Heated Above Grade: 3048.0
  • Sq Ft Total: 4148.0
  • Zoning: AAA
Utilities
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 550 Rolling Hills Drive

DateEvent & SourcePriceAppreciation
Feb 17, 1999

Closed (Public Record)

Public Record #90960746

$660,000

+5.3% / yr

Sep 8, 1998

Closed (Public Record)

Public Record #90962304

$645,000

+21.6% / yr

Jun 23, 1998

Closed (Public Record)

Public Record #90961933

$619,000—
Jun 23, 1998

Closed (Public Record)

Public Record #90961933

$619,000

+58.5% / yr

Oct 18, 1995

Closed (Public Record)

Public Record #90966509

$180,000—
DateEvent & SourcePrice
02/17/1999

Closed (Public Record)

Public Record #90960746

$660,000

+5.3% / yr

09/08/1998

Closed (Public Record)

Public Record #90962304

$645,000

+21.6% / yr

06/23/1998

Closed (Public Record)

Public Record #90961933

$619,000
06/23/1998

Closed (Public Record)

Public Record #90961933

$619,000

+58.5% / yr

10/18/1995

Closed (Public Record)

Public Record #90966509

$180,000

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

Public Records for 550 Rolling Hills Drive

Taxable ValueLand$246,120Additions$303,450Total$549,570
Tax Record2024$15,602 ($1,300 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt3,048 SqFtAbove Grade Finished SqFt3,048 SqFtUnfinished Basement SqFt703 SqFtStories2Lot Size103,673 SqFtStyleSingle Family ResidenceYear Built1996ZoningAAACountyFAIRFIELDAPNFFLD M:67 B:15-NFireplace TypeHas Fireplace

Schools near 550 Rolling Hills Drive

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Burr Elementary School
Public - K to 5
Tomlinson Middle School
Public - 6 to 8
Fairfield Warde High School
Public - 9 to 12
Rating
School
Distance
Burr Elementary School
PublicK to 5

Tomlinson Middle School
Public6 to 8

Fairfield Warde High School
Public9 to 12

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.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Brown Harris Stevens, Marcia Lyman; Brown Harris Stevens, Annie Kruger

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.