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188 Settlers Hill Road

Southbury, Connecticut 06488

PENDING$965,000

Reduced from $990,000

Beds
5
Baths
4 | 1
SqFt
4,473
Acres
3.89
Year Built
1978
Matt Caiola

Matt Caiola

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Pool3-Car Garage2 FireplacesPrice Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,396

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Michele Pierce

(203) 312-3509

Coldwell Banker Realty

(203) 263-3003

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.