550 Rolling Hills Drive, Fairfield, Connecticut

$1,650,000

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4

Beds

4

Baths

4,148

Square feet

2.38

Acres

About 550 Rolling Hills Drive

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.

Features of 550 Rolling Hills Drive

MLS® # 24126270
Price $1,650,000
Bedrooms 4
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 4,148
Acres 2.38
Type Single Family For Sale
Style Colonial
Status Under Contract

Community Information

Address 550 Rolling Hills Drive
Area Greenfield Hill
City Fairfield
County Fairfield
State Connecticut
Zip Code 06824

Amenities

Parking Attached Garage
# of Garages 2
Is Waterfront No
Waterfront Beach Rights
Has Pool No

Interior

Interior Features Auto Garage Door Opener
Appliances Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Disposal, Washer, Dryer
Heating Hot Air, Natural Gas
Cooling Central Air
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Heated, Cooled, Interior Access, Partially Finished, Walk-out, Liveable Space

Exterior

Exterior Clapboard
Exterior Features Grill, Deck, Gutters, Lighting, Patio
Lot Description Fence - Full, Some Wetlands, Lightly Wooded
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Burr
Middle Tomlinson
High Fairfield Warde

Additional Information

Date Listed September 15th, 2025
Days on Market 16
Zoning AAA
RE / Bank Owned No

Listing Details

OfficeBrown Harris Stevens

Listing Map

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Listing information last updated on October 19th, 2025 at 11:34am EDT.