66 High Street #38
Guilford, Connecticut 06437
Reduced from $3,200,000
- Beds
- 3
- Baths
- 3
- SqFt
- 2,983
- Year Built
- 2016
- Property Type
- Condo
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Exquisitely reimagined with uncompromising attention to detail, this exceptional upper-level residence at The Residences at 66 High Street presents refined luxury in a premier in-town setting. Originally created by seamlessly merging two units, the owner collaborated with an interior designer, contractor, and master craftspeople to conceive a truly one-of-a-kind, fully customized home. The result is an expansive and impeccably executed "double" residence in the Leete Building offering approximately 3,000 square feet of meticulously maintained, sophisticated living space designed for both grand entertaining and effortless everyday comfort. A gracious living room anchored by a gas fireplace and a mounted 150-year old half hull ship model, flows seamlessly into a dining area with access to a private balcony; creating the perfect backdrop for intimate evenings or lively gatherings. The chef's kitchen and custom millwork throughout showcase superior craftsmanship, bespoke built-ins, and curated finishes of the highest caliber. The master bedroom suite is a private sanctuary, complete with its own fireplace, a dedicated office with built-in shelves, file drawers and cabinets for remote work, private balcony, a spa-inspired bath appointed with luxury fittings and steam shower, and two walk-in closets. Two additional bedrooms and beautifully designed full baths provide comfort and flexibility for guests.
Key Facts
- City/Town
- Guilford
- Neighborhood
- N/A
- Property / Style
- Condo · Ranch
- Year Built
- 2016
- Days on Market
- 164 days
- Beds
- 3
- Baths
- 3 full
- Living Area
- 2,983 sq ft
- Garage / Parking
- 3 garage · 5 total
- Property Taxes
- $33,158 / Annually
- HOA Fee
- $1,800 / Monthly
Market Snapshot
The Guilford Market
Condo · trailing 12 months
Active Listings
19
10 under contract
Median List Price
$259,995
19 active listings
Median Closed Price
$475,000
55 sales
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
$3.00M
vs $259,995 median
11.5× the median
Price / Sq Ft
$1,004
vs $276 median
3.6× the median
Days on Market
164 days
vs 158 days median
In line with 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 #38, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$15,397
- Property Taxes$2,763
- Insurance$998
- HOA$1,800
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
- 2,983 sq ft
Schools
- Elementary
- Calvin Leete
- Middle
- Baldwin
- High
- Guilford
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Laundry Room with washer/dryer & sink
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorDishwasherWasherDryerWine Chiller
- Basement
- None
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - AvailableElevatorOpen Floor Plan
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Zoning
- R-3
- Garage / Parking
- 3 garage spaces5 total parking spacesDetached GarageCovered GaragePavedParking LotAssigned Parking
- Waterfront
- Direct waterfront
- Waterfront Details
- RiverAssociation RequiredWater CommunityView
- Water Source
- Public Water Connected
- Sewer
- Shared Septic
- Flood Zone
- Yes
- Construction
- Hardie Board
- Color
- Blue Gray
- Exterior Features
- GrillSidewalkGarden AreaLightingCovered Deck
- Lot Description
- Level LotHistoric DistrictWater View
HOA / Association
- Fee
- $1,800 / Monthly
- Amenities
- ElevatorExercise Room/Health ClubGardening AreaPool
Listing & Financials
- Property Taxes
- $33,158 / Annually
- Days on Market
- 164
- MLS #
- 24155789
- MLS Status
- Active
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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 8:00 PM UTC.