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66 High Street #17

Guilford, Connecticut 06437

PENDING$2,990,000
Beds
3
Baths
2 | 1
SqFt
3,348
Year Built
2016
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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ElevatorPool2-Car Garage1 FireplaceVirtual Tour

About This Home

Welcome to a truly exceptional living experience at The Residences at 66 High Street! This stunning three-bedroom, two-and-a-half-bathroom condo presents a rare opportunity for those seeking luxury and convenience in one of Guilford's most desirable locations. Spanning an impressive 3,148 square feet, this custom single-level home offers elegant design and modern amenities, ensuring comfort and style at every turn. Step inside to discover an exquisite open floor plan highlighted by two-inch marble and black walnut countertops, complemented by high-end finishes from Waterworks and custom built-ins throughout. Enjoy the culinary delight of a gourmet kitchen equipped with Subzero appliances, a 48" Wolf range, and two spacious walk-in pantries. The inviting living area features a gas fireplace for cozy evenings and a state-of-the-art Full Swing sports simulator that also serves as a perfect media room. This smart home boasts temperature-controlled fresh air and is easily managed via iPad. Step outside to your covered private terrace and be captivated by stunning marsh and Long Island Sound views, accompanied by refreshing salty breezes. The vibrant community offers a heated pool, fitness center, fire pit, dog park, and more, making it an ideal setting for relaxation and recreation. With easy access to the marina, beach, dining, shopping, and cultural experiences in downtown Guilford, this property epitomizes Connecticut shoreline living at its finest.

Key Facts

City/Town
Guilford
Neighborhood
N/A
Property / Style
Condo · Ranch
Year Built
2016
Days on Market
94 days
Beds
3
Baths
2 full · 1 half
Living Area
3,348 sq ft
Garage / Parking
2 garage
Property Taxes
$33,212 / Annually
HOA Fee
$1,877 / Monthly

Market Snapshot

The Guilford Market

Condo · trailing 12 months

Median Days on Market

158

19 active listings

Median $ / Sq Ft

$276

19 active listings

Sale-to-List Ratio

100.0%

55 sales

How this home compares

List Price

$2.99M

vs $259,995 median

11.5× the median

Price / Sq Ft

$893

vs $276 median

3.2× the median

Days on Market

94 days

vs 158 days median

64 days fresher than median

Based on 19 active and 55 closed sales (trailing 12 mo) of condo in Guilford. Source: SmartMLS · As of August 28, 2026.

Location

66 High Street #17, Guilford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$21,014

per month

  • Principal & Interest$15,372
  • Property Taxes$2,768
  • Insurance$997
  • HOA$1,877

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
Condo
Subtype
Condominium
Style
Ranch
Year Built
2016
New Construction
No/Resale
Living Area
3,348 sq ft

Schools

Elementary
Per Board of Ed
Middle
Baldwin
High
Guilford

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Appliances
Gas RangeRange HoodRefrigeratorDishwasherWasherDryerWine Chiller
Basement
None
In-Law Apartment
No
Interior Features
Audio SystemCable - Pre-wiredElevatorOpen Floor Plan
Additional Rooms
FoyerLaundry Room

Exterior & Lot

Zoning
I-1
Garage / Parking
2 garage spacesParking Garage
Waterfront Details
Walk to WaterView
Water Source
Public Water Connected
Sewer
Shared Septic
Flood Zone
Yes
Pool
Ramp EntrancePool HouseSafety FenceIn Ground Pool
Construction
Hardie Board
Color
white
Exterior Features
Underground UtilitiesSidewalkDeckGuttersGarden AreaLightingFrench DoorsUnderground Sprinkler
Lot Description
Level LotOn Cul-De-SacWater View

HOA / Association

Fee
$1,877 / Monthly
Amenities
ElevatorExercise Room/Health ClubGardening AreaGuest ParkingPool

Listing & Financials

Property Taxes
$33,212 / Annually
Days on Market
94
MLS #
24167886
MLS Status
Under Contract - Continue to Show

Similar Properties

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

Listed By

Barbara Goetsch

(203) 927-7146

William Pitt Sotheby's Int'l

(203) 453-2533

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/28/2026. 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 8/28/2026 at 8:55 PM UTC.