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244 Pine Orchard Road

Branford, Connecticut 06405

PENDING$2,899,000
Beds
5
Baths
5 | 2
SqFt
6,075
Acres
0.93
Year Built
2019
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Guest HouseWine CellarPool3-Car Garage2 Fireplaces

About This Home

A hand-laid stone wall greets you at the entrance to this stately Pine Orchard residence, setting the tone for everything that lies beyond. Nestled within one of Branford's most coveted coastal enclaves, this architectural masterpiece redefines luxury living. Exquisitely crafted and recently built, the 6,075-square-foot custom home offers five-bedrooms and five full baths - each space thoughtfully designed with both beauty and function in mind. At the heart of the home, a kitchen of sleek, refined sophistication features high-end appliances and a generous island that anchors the space beautifully. It opens seamlessly to a dedicated dining area and expansive living spaces, creating a natural flow that is as inviting as it is elegant. Distinctive enclosed porches and multiple balconies extend the living areas outward, framing views of lush grounds and the gentle breezes of Long Island Sound - perfect for outdoor dining and quiet moments alike. Also on the main level, the primary bedroom suite is a luxurious retreat unto itself, offering a serene escape with a beautifully appointed private bath and gas fireplace. Above the the 3 car garage, a private apartment with its own separate entrance provides a haven for guests or extended family, a thoughtful touch that speaks to the home's exceptional versatility. The grounds, just shy of an acre features a beautiful inground pool and manicured landscapes.

Key Facts

City/Town
Branford
Neighborhood
Pine Orchard
Property / Style
Single Family · Contemporary
Year Built
2019
Days on Market
30 days
Beds
5
Baths
5 full · 2 half
Living Area
6,075 sq ft
Lot Size
0.93 acres
Garage / Parking
3 garage · 6 total
Property Taxes
$46,523 / Annually
HOA Fee
$185 / Annually

Market Snapshot

The Branford Market

Single Family · trailing 12 months

Median Days on Market

45

40 active listings

Median $ / Sq Ft

$382

40 active listings

Sale-to-List Ratio

100.0%

171 sales

How this home compares

List Price

$2.90M

vs $747,000 median

3.9× the median

Price / Sq Ft

$477

vs $382 median

24.9% above median

Days on Market

30 days

vs 45 days median

15 days fresher than median

Based on 40 active and 171 closed sales (trailing 12 mo) of single family in Branford. Source: SmartMLS · As of July 27, 2026.

Location

244 Pine Orchard Road, Branford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$19,639

per month

  • Principal & Interest$14,781
  • Property Taxes$3,877
  • Insurance$966
  • HOA$15

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Branford
Neighborhood
Pine Orchard
County
New Haven

Residence

Property Type
Single Family
Style
Contemporary
Year Built
2019
New Construction
No/Resale
Living Area
6,075 sq ft

Schools

Elementary
Mary R. Tisko
High
Branford

Interior

Heating
Radiant
Heat Fuel
Gas In Street
Cooling
Central AirDuctlessSplit SystemZoned
Fireplaces
2
Laundry Location
1st Floor Centralized
Appliances
Gas CooktopConvection OvenMicrowaveRange HoodSubzeroDishwasherDisposalInstant Hot Water TapWasherDryerWine Chiller
Basement
FullHeatedSump PumpStorageFully FinishedCooledInterior Access
In-Law Apartment
YesOver GarageSeparate Entry
Interior Features
Audio SystemCentral VacuumOpen Floor PlanSecurity System
Additional Rooms
Bonus RoomLaundry RoomWine Cellar
Accessibility
Accessible Bath,Bath Grab Bars

Exterior & Lot

Lot Size
0.93 acres
Zoning
AA1
Garage / Parking
3 garage spaces6 total parking spacesAttached GarageDrivewayPrivateCircularCrushed Stone
Waterfront Details
Walk to WaterBeach RightsAssociation RequiredView
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Pool
GuniteIn Ground Pool
Construction
Hardie Board
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Porch-Wrap AroundPorch-EnclosedWrap Around DeckGuest HouseFrench DoorsPatioBalconyPorchGarden AreaStone WallUnderground Sprinkler
Lot Description
Level LotProfessionally Landscaped

HOA / Association

Fee
$185 / Annually

Listing & Financials

Property Taxes
$46,523 / Annually
Days on Market
30
MLS #
24187111
MLS Status
Under Contract

Similar Properties

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

Listed By

Vicky Welch

(203) 215-4990

William Raveis Real Estate

(203) 433-4387

Co-Listed By

Steve Sinapis

William Raveis Real Estate

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 6:10 PM UTC.