7 Bailey Drive
Guilford, Connecticut 06437
Reduced from $725,000
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 3,342
- Acres
- 1.40
- Year Built
- 1988
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Back on the market through no fault of the home the previous buyers' financing fell through. A full inspection was completed with no requests made. Their loss is your second chance.Tucked at the end of a quiet cul-de-sac on 1.4 private acres, this one-owner Guilford Colonial has been waiting 38 years for its second chapter and it's ready to tell a new story. Start your mornings on the covered back porch, coffee in hand, ceiling fans turning, watching the yard wake up and end summer nights out there too, because this porch is where this house does its living. Inside, the open-concept kitchen anchors it all: granite island, stainless appliances, and a sightline that runs straight to the brick fireplace in the family room, so whoever's cooking never misses a moment. When the weather turns, this is a cozy-nights-by-the-fire kind of home. The flexible main level keeps up with real life a bonus room off the dining area ready to become a walk-in pantry or office, and a den with half bath that could be a second office, opening to a 675 sq ft studio that's begging to be a home gym, workshop, creative space, or garage once again. Upstairs, the freshly painted primary suite with brand-new carpet stretches nearly 40 feet sitting room, walk-in closet, private laundry, full bath, and French doors to your own balcony over the treetops. Two additional bedrooms serviced by an updated full bath, a floored walk-up attic, central air (2025), and 3,300+ sq ft of room to grow.
Key Facts
- City/Town
- Guilford
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1988
- Days on Market
- 99 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 3,342 sq ft
- Lot Size
- 1.40 acres
- Garage / Parking
- 5 total
- Property Taxes
- $12,334 / Annually
Market Snapshot
The Guilford Market
Single Family · trailing 12 months
Active Listings
44
34 under contract
Median List Price
$839,500
44 active listings
Median Closed Price
$674,500
207 sales
Median Days on Market
39
44 active listings
Median $ / Sq Ft
$336
44 active listings
Sale-to-List Ratio
100.9%
207 sales
How this home compares
List Price
$699,000
vs $839,500 median
16.7% below median
Price / Sq Ft
$209
vs $336 median
37.8% below median
Days on Market
99 days
vs 39 days median
60 days longer than median
Based on 44 active and 207 closed sales (trailing 12 mo) of single family in Guilford. Source: SmartMLS · As of October 28, 2026.
Location
7 Bailey Drive, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$3,841
- Property Taxes$1,028
- Insurance$233
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Guilford
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1988
- New Construction
- No/Resale
- Living Area
- 3,342 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Upper Level
- Laundry Location
- in primary bedroom
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullStorageFull With Hatchway
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 1.40 acres
- Zoning
- R-5
- Garage / Parking
- 5 total parking spacesPavedDrivewayPrivateShared
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- blue
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyShedDeckCovered DeckFrench Doors
- Lot Description
- Fence - FullIn SubdivisionLightly WoodedOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $12,334 / Annually
- Days on Market
- 99
- MLS #
- 24193021
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/28/2026. 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 10/28/2026 at 10:10 PM UTC.