28 Walden Hill Road
Guilford, Connecticut 06437
- Beds
- 5
- Baths
- 5 | 2
- SqFt
- 5,185
- Acres
- 1.96
- Year Built
- 1960
- Neighborhood
- Sachems Head
- Property Type
- Single Family
Matt Caiola
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About This Home
A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.
Key Facts
- City/Town
- Guilford
- Neighborhood
- Sachems Head
- Property / Style
- Single Family · Colonial
- Year Built
- 1960
- Days on Market
- 17 days
- Beds
- 5
- Baths
- 5 full · 2 half
- Living Area
- 5,185 sq ft
- Lot Size
- 1.96 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $29,112 / Annually
- HOA Fee
- $1,685 / Annually
Market Snapshot
The Guilford Market
Single Family · trailing 12 months
Active Listings
37
39 under contract
Median List Price
$929,000
37 active listings
Median Closed Price
$657,500
224 sales
Median Days on Market
47
37 active listings
Median $ / Sq Ft
$352
37 active listings
Sale-to-List Ratio
100.8%
224 sales
How this home compares
List Price
$3.75M
vs $929,000 median
4.0× the median
Price / Sq Ft
$723
vs $352 median
2.1× the median
Days on Market
17 days
vs 47 days median
30 days fresher than median
Based on 37 active and 224 closed sales (trailing 12 mo) of single family in Guilford. Source: SmartMLS · As of July 28, 2026.
Location
28 Walden Hill Road, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$19,120
- Property Taxes$2,426
- Insurance$1,250
- HOA$140
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Guilford
- Neighborhood
- Sachems Head
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1960
- New Construction
- No/Resale
- Living Area
- 5,185 sq ft
Schools
- Elementary
- A. W. Cox
- Middle
- Baldwin
- High
- Guilford
Interior
- Heating
- Hot Air
- Heat Fuel
- ElectricOilPropane
- Cooling
- Central AirSplit System
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorDishwasher
- Basement
- PartialUnfinishedStorageInterior Access
- In-Law Apartment
- PossibleFirst FloorSecond Floor
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - Pre-wiredOpen Floor PlanSecurity System
- Additional Rooms
- BreezewayFoyerLaundry RoomMud RoomWorkshop
Exterior & Lot
- Lot Size
- 1.96 acres
- Zoning
- A
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Walk to WaterBeach RightsWater CommunityView
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- ClapboardWood
- Color
- grey
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BreezewayGuttersGarden AreaLightingStone WallFrench DoorsPatio
- Lot Description
- Level LotOn Cul-De-SacWater ViewOpen Lot
HOA / Association
- Fee
- $1,685 / Annually
- Amenities
- ParkTennis Courts
Listing & Financials
- Property Taxes
- $29,112 / Annually
- Days on Market
- 17
- MLS #
- 24190774
- 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 7/28/2026. 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 7/28/2026 at 4:31 AM UTC.