39 Vineyard Place
Guilford, Connecticut 06437
- Beds
- 6
- Baths
- 5 | 1
- SqFt
- 6,603
- Acres
- 2.00
- Year Built
- 1930
- 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
Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original "porthole" windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor "flex" space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches, an expansive patio for gatherings, and the rare luxury of a private boat house. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!
Key Facts
- City/Town
- Guilford
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1930
- Days on Market
- 136 days
- Beds
- 6
- Baths
- 5 full · 1 half
- Living Area
- 6,603 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $56,151 / Annually
- HOA Fee
- $900 / Annually
Market Snapshot
The Guilford Market
Single Family · trailing 12 months
Active Listings
38
39 under contract
Median List Price
$939,000
38 active listings
Median Closed Price
$650,000
225 sales
Median Days on Market
45
38 active listings
Median $ / Sq Ft
$359
38 active listings
Sale-to-List Ratio
100.8%
225 sales
How this home compares
List Price
$5.95M
vs $939,000 median
6.3× the median
Price / Sq Ft
$901
vs $359 median
2.5× the median
Days on Market
136 days
vs 45 days median
91 days longer than median
Based on 38 active and 225 closed sales (trailing 12 mo) of single family in Guilford. Source: SmartMLS · As of July 27, 2026.
Location
39 Vineyard Place, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$30,337
- Property Taxes$4,679
- Insurance$1,983
- HOA$75
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
- Subdivision
- Vineyard Place Associatio
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1930
- New Construction
- No/Resale
- Living Area
- 6,603 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot AirWall UnitZoned
- Heat Fuel
- Electric
- Cooling
- Ceiling FansCentral AirSplit System
- Fireplaces
- 3
- Laundry
- Main Level
- Laundry Location
- Main Floor off of kitchen
- Appliances
- Oven/RangeWall OvenRefrigeratorFreezerDishwasher
- Basement
- Crawl Space
- In-Law Apartment
- No
- Interior Features
- Audio SystemAuto Garage Door OpenerSecurity System
- Additional Rooms
- Bonus RoomFoyer
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- L. I. Sound FrontageBeachWalk to WaterView
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- ShingleStone
- Color
- Granite
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Porch-EnclosedUnderground UtilitiesTerraceTennis CourtPorchStone WallFrench DoorsUnderground SprinklerPatio
- Lot Description
- Level LotOn Cul-De-SacWater View
HOA / Association
- Fee
- $900 / Annually
Listing & Financials
- Property Taxes
- $56,151 / Annually
- Days on Market
- 136
- MLS #
- 24155090
- 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 7/27/2026. 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 7/27/2026 at 11:01 AM UTC.