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$1,600,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,148 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 550 Rolling Hills Dr

General

  • Sold For: $1,600,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24126270
  • Added to Site: 158 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Laundry Room
  • Interior Features: Auto Garage Door Opener
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Remodeled, 9 ft+ Ceilings, Bedroom Suite, Full Bath, W, Upper
  • Bedroom 1: Bedroom - 9 ft+ Ceilings, Wall/Wall Carpet, Upper
  • Bedroom 2: Bedroom - 9 ft+ Ceilings, Wall/Wall Carpet, Upper
  • Bedroom 3: Bedroom - 9 ft+ Ceilings, Wall/Wall Carpet, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Hardwood Floor, Main
  • Family Room: Family Room - Vaulted Ceiling, Built-Ins, Gas Log Fireplace, Wall/Wall Carpet, Main
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, 9 ft+ Ceilings, Balcony/Deck, Hardwood Floor, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Built-Ins, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - 9 ft+ Ceilings, Patio/Terrace, Sliders, Wall/Wall Carpet, Lower
  • Rec Room: 9 ft+ Ceilings, Patio/Terrace, Sliders, Wall/Wall Carpet, Lower
  • Laundry: Main Level

Exterior

  • Exterior Features: Grill, Deck, Gutters, Lighting, Patio
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Greenfield Hill
  • Driving Directions: Black Rock Tpke to Congress to Morehouse Hwy to Rolling Hills Drive.

School Information

  • Elementary School: Burr
  • Middle School: Tomlinson
  • High School: Fairfield Warde

Community

  • Community Name: Greenfield Hill

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Heated, Cooled, Interior Access, Partially Finished, Walk-out, Liveable Space
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,148
  • Above Ground: 3,048 Sq. Ft.
  • Below Ground: 1,100 Sq. Ft.
  • Year Built: 1996

Lot Features

  • Lot Size (Acres): 2.38
  • Zoning: AAA
  • Lot Description: Fence - Full, Some Wetlands, Lightly Wooded

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $549,570
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 121202

Listed by Brown Harris Stevens, Marcia Lyman and Brown Harris Stevens, Annie Kruger
Sold by RE/MAX Heritage, Michael Traum

Listing agents

— 550 Rolling Hills Dr —

  • Marcia Lyman

    Brown Harris Stevens

  • Annie Kruger

    Brown Harris Stevens

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 550 Rolling Hills Dr

School District:Fairfield School District
NameGradesDistance
Burr Elementary School
1960 Burr Street, Fairfield, CT 06824
PK-51.8 mi
Tomlinson Middle School
200 Unquowa Road, Fairfield, CT 06824
6-85.6 mi
Fairfield Warde High School
755 Melville Avenue, Fairfield, CT 06825
9-123.4 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 550 Rolling Hills Dr

Date
Details
Price
Change
Source
11/14/2025
Sold
$1,600,000
-3.03%
MLS
9/17/2025
Listed
$1,650,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Brown Harris Stevens, Marcia Lyman and Brown Harris Stevens, Annie Kruger
Sold by RE/MAX Heritage, Michael Traum

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550 Rolling Hills Drive, Fairfield, CT 06824 (MLS# 24126270) is a Single Family property that was sold at $1,600,000 on November 14, 2025. Want to learn more about 550 Rolling Hills Drive? Do you have questions about finding other Single Family real estate for sale in Fairfield? You can browse all Fairfield real estate or contact a Coldwell Banker agent to request more information.