188 Settlers Hill Road
Southbury, Connecticut 06488
Reduced from $990,000
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,473
- Acres
- 3.89
- Year Built
- 1978
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Versatility, and multi-generational living opportunities available with this exceptionally beautiful colonial offering endless living possibilities with its ample space! Located on a secluded cul-de-sac. The main house boasts three spacious bedrooms, complemented by a separate, two-bedroom, two-level in-law suite. Beautiful professionally landscaped grounds, featuring a paved driveway and a three-car garage. The outdoor amenities are exceptional, including a heated in-ground saltwater pool with pool house, a wooded walking trail, storage shed and firepit. Entire perimeter of the property is fenced. The main primary kitchen is masterfully designed to accommodate sizeable gatherings, equipped with dual Frigidaire Gallery refrigerators, a gas cooktop, double wall ovens, luxurious granite countertops, and a large center island. Windows frame picturesque views of the private backyard and pool, providing access to an expansive deck. Adjacent to the kitchen is the formal dining room. The upper level of the main house comprises a grand primary bedroom, a secondary bedroom, and additional bedroom or office. Plus, two full baths. The main level also contains a living/den accented by a paneled wood-burning fireplace, and a half bath. The in-law suite features a dramatic two-story stone fireplace in the family room, elegant primary and gorgeous marble ensuite bath. Includes 2nd floor bedroom or office and a full bath. A must see!
Key Facts
- City/Town
- Southbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1978
- Days on Market
- 84 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 4,473 sq ft
- Lot Size
- 3.89 acres
- Garage / Parking
- 3 garage · 6 total
- Property Taxes
- $13,853 / Annually
Market Snapshot
The Southbury Market
Single Family · trailing 12 months
Active Listings
33
35 under contract
Median List Price
$645,000
33 active listings
Median Closed Price
$632,500
164 sales
Median Days on Market
27
33 active listings
Median $ / Sq Ft
$287
33 active listings
Sale-to-List Ratio
100.0%
164 sales
How this home compares
List Price
$965,000
vs $645,000 median
49.6% above median
Price / Sq Ft
$216
vs $287 median
24.7% below median
Days on Market
84 days
vs 27 days median
57 days longer than median
Based on 33 active and 164 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of July 28, 2026.
Location
188 Settlers Hill Road, Southbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,920
- Property Taxes$1,154
- Insurance$322
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Southbury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1978
- New Construction
- No/Resale
- Living Area
- 4,473 sq ft
Schools
- Elementary
- Longmeadow Elementary School
- High
- Pomperaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Attic FanCentral AirSplit System
- Fireplaces
- 2
- Laundry
- Lower Level
- Appliances
- Electric CooktopGas CooktopWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- Full
- In-Law Apartment
- YesOver GarageSeparate Entry
- Interior Features
- Auto Garage Door Opener
- Additional Rooms
- Laundry RoomWorkshop
Exterior & Lot
- Lot Size
- 3.89 acres
- Zoning
- R-60
- Garage / Parking
- 3 garage spaces6 total parking spacesUnder House GarageDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- HeatedPool HouseSalt WaterIn Ground Pool
- Construction
- Clapboard
- Color
- Light Green
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedAwningsDeckGarden Area
- Lot Description
- SecludedLightly WoodedSloping LotOn Cul-De-SacProfessionally LandscapedRolling
Listing & Financials
- Property Taxes
- $13,853 / Annually
- Days on Market
- 84
- MLS #
- 24165581
- 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 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.