104 Periwinkle Drive #104
Middlebury, Connecticut 06762
- Beds
- 2
- Baths
- 2 | 1
- SqFt
- 2,593
- Acres
- 1.00
- Year Built
- 2005
- 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
Welcome to Benson Woods, a desirable 55+ community! This beautiful freestanding Hopkins Model offers spacious rooms, soaring ceilings, and stylish features throughout. The spacious kitchen is a standout, featuring rich wood cabinetry, stainless steel appliances, abundant counter space, and an oversized center island with seating-perfect for casual dining and entertaining. The kitchen opens to the impressive Living and Dining Room, where soaring ceilings and beautiful hardwood floors create a bright, airy atmosphere. The first-floor primary suite offers two walk-in closets and a private bath with a double-sink vanity, large walk-in shower, and generous soaking tub. A second bedroom, convenient half bath, and laundry room complete the main level, providing comfortable one-floor living. Upstairs, a sun-filled loft overlooks the Living and Dining Room below. A second full bath and separate bonus room offer flexible space for a home office, hobby room, or guests. Additional highlights include hardwood floors in the Living Room, Dining Room, and hallway, a gas range, and a gas hookup on the back deck for convenient grilling-no propane tanks needed! With its inviting layout, spacious kitchen, and versatile living spaces, this lovely Hopkins Model offers the perfect opportunity to enjoy comfortable, low-maintenance living in Benson Woods. Come see all this wonderful home has to offer!
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 2005
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 2 full · 1 half
- Living Area
- 2,593 sq ft
- Lot Size
- 1.00 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $9,034 / Annually
- HOA Fee
- $600 / Monthly
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
25
20 under contract
Median List Price
$670,000
25 active listings
Median Closed Price
$574,900
79 sales
Median Days on Market
45
25 active listings
Median $ / Sq Ft
$280
25 active listings
Sale-to-List Ratio
100.0%
79 sales
How this home compares
List Price
$560,000
vs $670,000 median
16.4% below median
Price / Sq Ft
$216
vs $280 median
22.9% below median
Days on Market
0 days
vs 45 days median
45 days fresher than median
Based on 25 active and 79 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of October 15, 2026.
Location
104 Periwinkle Drive #104, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$3,102
- Property Taxes$753
- Insurance$187
- HOA$600
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlebury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 2005
- New Construction
- No/Resale
- Living Area
- 2,593 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasher
- Basement
- Full
Exterior & Lot
- Lot Size
- 1.00 acres
- Zoning
- PRD
- Garage / Parking
- 2 garage spacesAttached GarageUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Hardie Board
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
HOA / Association
- Fee
- $600 / Monthly
Listing & Financials
- Property Taxes
- $9,034 / Annually
- Days on Market
- 0
- MLS #
- 24214741
- 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 10/15/2026. 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 10/15/2026 at 9:10 PM UTC.