5 Rolling Hills Drive
Seymour, Connecticut 06483
Reduced from $699,999
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,564
- Acres
- 0.45
- Year Built
- 2009
- Neighborhood
- Skokorat
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to 5 Rolling Hills Drive, a beautifully maintained home located in one of Seymour's most sought-after neighborhoods. Set on a spacious 1/2-acre lot, this property offers the ideal combination of comfort, space, privacy, and convenience. From the moment you walk in, you'll appreciate the freshly painted interior and beautiful hardwood floors, creating a bright and welcoming atmosphere. OPEN LAYOUT floor plan and a spacious family room, complete with soaring cathedral ceilings, provides the perfect setting to relax, entertain, and create lasting memories. A brand-new roof, installed just weeks ago, means one of the most important home improvements has already been taken care of-giving you added confidence and peace of mind from day one. Outside, the generous 1/2-acre property gives you the space to enjoy your own private outdoor retreat, whether you're hosting family and friends, gardening, or simply enjoying a quiet afternoon at home. And the location truly sets this home apart. Situated in a highly desirable Seymour neighborhood, you'll enjoy convenient access to schools, parks, major highways, shopping, dining, and everyday essentials while coming home to a peaceful and welcoming community. Owner Agent.
Key Facts
- City/Town
- Seymour
- Neighborhood
- Skokorat
- Property / Style
- Single Family · Colonial
- Year Built
- 2009
- Days on Market
- 50 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,564 sq ft
- Lot Size
- 0.45 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $12,019 / Annually
Market Snapshot
The Seymour Market
Single Family · trailing 12 months
Active Listings
22
20 under contract
Median List Price
$472,500
22 active listings
Median Closed Price
$426,000
140 sales
Median Days on Market
34
22 active listings
Median $ / Sq Ft
$236
22 active listings
Sale-to-List Ratio
100.9%
140 sales
How this home compares
List Price
$684,900
vs $472,500 median
45.0% above median
Price / Sq Ft
$267
vs $236 median
13.1% above median
Days on Market
50 days
vs 34 days median
16 days longer than median
Based on 22 active and 140 closed sales (trailing 12 mo) of single family in Seymour. Source: SmartMLS · As of September 28, 2026.
Location
5 Rolling Hills Drive, Seymour, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$3,656
- Property Taxes$1,002
- Insurance$228
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Seymour
- Neighborhood
- Skokorat
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2009
- New Construction
- No/Resale
- Living Area
- 2,564 sq ft
Schools
- Elementary
- Chatfield - LoPresti
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Gas RangeMicrowaveRefrigeratorDishwasherDisposalWasherElectric Dryer
- Basement
- FullPartially Finished
- In-Law Apartment
- No
- Interior Features
- Cable - AvailableOpen Floor Plan
- Additional Rooms
- Mud Room
Exterior & Lot
- Lot Size
- 0.45 acres
- Zoning
- MF
- Garage / Parking
- 2 garage spacesUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Vinyl Siding
- Color
- Brown
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-EnclosedUnderground UtilitiesSidewalkPorchDeckLightingStone Wall
- Lot Description
- In SubdivisionProfessionally Landscaped
Listing & Financials
- Property Taxes
- $12,019 / Annually
- Days on Market
- 50
- MLS #
- 24197872
- MLS Status
- Under Contract - Continue to Show
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/28/2026 at 7:15 PM UTC.