25 Holly Cir, Weston, MA 02493

• 5 beds |
• 9 baths |
• 7,766 sqft

Property Description

Privately sited on a cul-de-sac in Weston’s coveted South Side, this custom-built residence offers beautifully appointed living space across three finished levels, set on 1.38 acres. Designed by award-winning architect Bart O’Brien and built by Whitman Homes, the home brings together architectural distinction, exceptional craftsmanship, and professionally reimagined grounds to create a setting of impressive scale, privacy, and livability. A dramatic two-story foyer introduces formal living and dining rooms with custom millwork, hardwood floors, and multiple fireplaces. At the heart of the home, a light-filled family room with soaring ceilings and a commanding wall of windows opens seamlessly to a chef's kitchen with professional-grade appliances, center island, and two butler's pantries. A richly appointed library/home office and covered porch and bluestone patio complete a main level built for entertaining and everyday living. Five en-suite bedrooms include a luxurious primary suite with fireplace, custom walk-in closets, and beautifully appointed baths. The expansive walkout lower level extends directly to the backyard and features a great room with wet bar, media room, exercise room, and wine cellar. An attached three-car garage completes the residence. The grounds have undergone a significant professionally engineered, town-approved transformation — replacing formerly rocky terrain with an expansive, level, grassed backyard framed by mature trees and refreshed landscaping. The result is a rare combination of usable, private outdoor space for recreation, entertaining, and daily life, seldom found on estate lots of this scale. Ideally set on Weston's South Side bordering Wellesley — moments from Weston and Wellesley town centers, conservation trails, and the Weston public school district, with convenient commuter access to Boston. A distinguished offering in Weston, MA 02493 — where architecture, craftsmanship, and beautifully reimagined grounds come together.

Listing Status:

Active

Date Added:

September 8, 2026

Data Last Updated:

September 14, 2026 at 12:06AM

Listing Office:

Compass : 781-365-9954

Listing Agent:

Team Coyle : 978-289-0368

MLS ID:

73573009

Interior

• General: Beamed CeilingsCloset/Cabinets - Custom BuiltBathroom - 3/4Bathroom - Tiled With Shower StallWalk-In Closet(s)Open FloorplanCountertops - UpgradedWet barBathroom - HalfLibraryExercise RoomPlay RoomMedia RoomCentral Vacuum
• Appliances: Gas Water HeaterRangeOvenDishwasherMicrowaveRefrigeratorFreezerWasherDryerRange Hood
• Laundry: Flooring - Stone/Ceramic TileGas Dryer HookupFirst Floor
• Basement: Partially FinishedWalk-Out AccessGarage Access
• Flooring: TileHardwoodFlooring - HardwoodLaminate
• A/C: Central Air
• Heating: Forced AirNatural GasHydro Air
• Fireplace: Family RoomLiving RoomMaster BedroomFireplaceFireplaces: 3

Exterior

• General: PorchPatioRain GuttersProfessional LandscapingSprinkler SystemDecorative Lighting
• Style: ColonialCraftsman
• Parking: AttachedGarage Door OpenerOff StreetPavedParking spaces: 9

Construction

• Roofing: ShingleMetal
• Windows: Insulated Windows
• General: FrameConcrete Perimeter

Location

• Originating MLS: MLS Property Information Network
• County: Middlesex

Lot

• Zoning: A869559

Utilities

• Utilities: Generator ConnectionGenerator Connection
• Water: Public
• Sewer: Private Sewer

Financial

• Source: MLS Property Information Network
• Exclusions: See Inclusion And Exclusion List.