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104 Periwinkle Drive #104

Middlebury, Connecticut 06762

ACTIVE - NEW$560,000
Beds
2
Baths
2 | 1
SqFt
2,593
Acres
1.00
Year Built
2005
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,642

per 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

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Listed By

Heather Crabtree

(203) 558-7720

RE/MAX RISE

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.