29 Drake Rd

















































Description
Perched gracefully on the banks of the shimmering waters of Upton Lake, this distinguished compound residence by Lake Flato presents a rare opportunity to own a residence of architectural distinction, refined craftsmanship and immersive nature. Both the primary residence and guest house as well as the pool are custom, site-specific and sustainably built designs that seamlessly merge expansive indoor living with the surrounding landscape for a lifestyle of...Exquisitely Designed Compound on Upton Lake
Perched gracefully on the banks of the shimmering waters of Upton Lake, this distinguished compound residence by Lake Flato presents a rare opportunity to own a residence of architectural distinction, refined craftsmanship and immersive nature. Both the primary residence and guest house as well as the pool are custom, site-specific and sustainably built designs that seamlessly merge expansive indoor living with the surrounding landscape for a lifestyle of ease, elegance and discovery.
Drawing on Lake Flato’s celebrated “Porch House” methodology, the residence is defined by three gabled volumes, two of which are connected by a glass-pavilion, clad in warm western red cedar and capped by metal standing-seam roofs, a respectful nod to farmhouse vernacular reinterpreted for modern sensibility. Heavy timber-glulam white oak framing expands the great room to dramatic effect, while triple-glazed windows and super-insulated SIP panels (R35 walls, R55 roof) ensure comfort, performance and efficiency.
Inside, soaring vaulted ceilings and exposed beams combine with radiant heated, polished concrete floors and finely slated woodwork to create a refined and elemental material palette. A board-formed concrete hearth anchors the great room and frames a panoramic view of the lake beyond - engaging the landscape as a continuous extension of the interior.
The main living wing features an open chef’s kitchen, dining and living area fronted by full-height sliding glass doors that disappear to unite deck, lawn and lake in one seamless experience. Outdoors become indoors and every room feels connected to the forest, shore and sky. A retractable screened porch extends living into summer breezes, while overlooking the grounds, pool and guest house.
The sleeping wing offers a media room and first-floor primary suite with a spa inspired wet-room bath, deep soaking tub and floating dual vanity - an intimate sanctuary of light and calm. Upstairs, two ensuite bedrooms provide serene and separated sleeping spaces. A free standing guest house on the property features two private bedrooms with en-suites and creates a true compound feel.
Set on approximately two lush acres of manicured grounds, the property winds through a gravel pathway to the guest house, and beyond to the entertainment amenities. A heated 40' x 16' gunite pool edged in bluestone patio is surrounded by woodland and morning light, while adjacent recreation includes a bocce court, basketball court, treehouse, private dock and direct water access. The lakes peninsula offers a large outdoor area for community members to gather, swim, kayak, paddle-board or row.
The site’s layout, designed with sensitivity to privacy and views, allows forested seclusion even as the lake lies just steps away. The architecture responds to the terrain and the waterfront in equal measure - integrated, grounded and elegant.
This remarkable compound offers the best of both worlds: quiet, natural retreat and access to vibrant Hudson Valley culture. Just 14 minutes from the village of Millbrook and under 20 minutes from destinations such as Stissing House, Black Snake Brewing, and several acclaimed wineries, it remains proximate to the region’s finest dining and leisure. Within a 30-minute radius are the towns of Rhinebeck, Red Hook, Millerton, and access to both the Wassaic and Poughkeepsie train stations - making both local exploration and regional connection effortless.
Rarely does a home arrive that so completely fulfills the promise of design, nature and lifestyle. Here is a compound that invites both lively gatherings and serene solitude, built by visionary architects and sited with impeccable care. For the buyer seeking something beyond the ordinary - an exceptional retreat rooted in place, architecture and waterside living - this is the one.
Property Details for 29 Drake Road
Property Details for 29 Drake Road
| Status | Pending |
|---|---|
| MLS # | 928684 |
| Days on Market | 17 |
| Taxes | $30,209 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Compass Type | Single Family |
| MLS Type | Single Family |
| Year Built | 2016 |
| Lot Size | 2.00 AC / 87,120 SF |
| County | Dutchess County |
Location
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Building Information for 29 Drake Road
Payment Calculator
$14,130 per month
30 year fixed, 6.28% Interest
$11,612
$2,517
$0
Property Information for 29 Drake Road
- Senior Community YN: No
- Year Built Effective: 2017
- Property Attached: No
- Structure Type: false
- Levels: Two
- State Or Province: NY
- Water Access YN: Yes
- School District: Millbrook
- Elementary School District: Millbrook
- Elementary School: Elm Drive Elementary School
- Middle Or Junior School District: Millbrook
- Middle Or Junior School: Millbrook Middle School
- High School District: Millbrook
- High School: Millbrook High School
- Lease Considered: No
- Building Units Total: 1
- Parcel Number: 135200-6567-16-912424-0000
- Tax Assessed Value: $1,875,100.00
- Association: No
- Amenities: 1st Floor Bedrm, Basketball Court, Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral/Vaulted/High Ceiling, Chandelier, Chefs Kitchen, Concrete, Contemporary, Deck, Dock, Double Vanity, Drapes, Entrance Foyer, Family Room, Fire Pit, First Floor Full Bath, Floor to Ceiling Windows, Garden, Guest House, Hardwood Floors As Seen, High Ceilings, His and Hers Closets, In Basement, In Ground, Kitchen Island, Lake Views, Lakefront, Lighting, Modern, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Oversized Windows, Pantry, Patio, Pool Cover, Porch, Primary Bathroom, Privacy, Screened, Screens, Shed(s), Soaking Tub, Storage, Trees/Woods, Triple Pane Windows, Wall of Windows, Washer/Dryer Hookup, Water Access, Water View, Waterfront, Well, Wood, Wood Burning
- Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral Ceiling(s), Chandelier, Chefs Kitchen, Double Vanity, Entrance Foyer, High Ceilings, His and Hers Closets, Kitchen Island, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Pantry, Primary Bathroom, 1st Fl Master Bedroom, Soaking Tub, Storage, Washer/Dryer Hookup
- Appliances: Cooktop, Dishwasher, Freezer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
- Total Rooms: 10
- Primary on Main: Yes
- Basement: Partially Finished
- Attic Description: None
- Fireplace: Yes
- Fireplaces Total: 1
- Fireplace Features: Family Room, Wood Burning
- Location Amenities: Stainless Steel Appliances, Basketball Court, Dock/Mooring, Hardwood Floors As Seen, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Chef's Kitchen, Dual Sinks, Entry Foyer, Foyer, High Ceilings, Island Kitchen, Open Kitchen, Original Details, Pantry, Soacking Tub, Storage, WD Hookup, Deck, Patio, Porch, In Ground Pool, Lake Views, Water View, Lakefront, Water Access, Oversized Windows, Triple Thermo Windows, Wall of Windows
- Laundry Features: In Basement
- Spa: No
- Window Features: Drapes,Floor to Ceiling Windows,Oversized Windows,Screens,Triple Pane Windows,Wall of Windows
- Flooring: Concrete, Hardwood, Wood
- Living Area: 3,540.00
- Foundation Details: Concrete Perimeter
- Basement: Yes
- Exterior Features: Basketball Court, Dock, Fire Pit, Garden, Lighting
- Exterior Property Features: Basketball Court, Dock, Fire Pit, Garden, Lighting, In Ground, Pool Cover, Deck, Patio, Porch, Screened, Carport, Covered, Driveway, Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Triple Pane Windows, Wall of Windows
- Elevation Certificate: No
- Patio And Porch Features: Deck,Patio,Porch,Screened
- Construction Materials: Wood Siding
- Other Structures: Guest House,Shed(s)
- Waterfront Features: Lake Front, Water Access, Waterfront
- Horse: No
- Pool Private: Yes
- Pool Features: In Ground,Pool Cover
- Pool Details: In Ground,Pool Cover
- Building Area Units: Square Feet
- Parking Features: Carport, Covered, Driveway
- Garage: No
- Carport: Yes
- Carport Spaces: 2.0
- Cooling: Central Air
- Heating: Electric, Forced Air, Propane, Radiant, Radiant Floor
- Heat Fuel Type: Electric, Forced Air, Propane, Radiant, Radiant Floor
- Sewer: Septic Tank
- Water Source: Well, Private
- Utilities: Cable Available, Electricity Connected, Phone Connected, Propane, Sewer Connected, Trash Collection Private, Water Connected
- Green Features: Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Triple Pane Windows, Wall of Windows, Cooktop, Dishwasher, Freezer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer, Electric, Forced Air, Propane, Radiant, Radiant Floor, Basketball Court, Dock, Fire Pit, Garden, Lighting, In Ground, Pool Cover
- Down Payment Resource: No
Property History for 29 Drake Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Dec 5, 2014 | Sold (Public Record) Public Record #552922775 | $530,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 12/05/2014 | Sold (Public Record) Public Record #552922775 | $530,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 29 Drake Road
Schools near 29 Drake Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 2 | |||
| Public - | 3 to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Elm Drive Elementary School PublicPK to 2 | ||
Alden Place Elementary School Public3 to 5 | ||
Millbrook Middle School Public6 to 8 | ||
Millbrook High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/05/2025 02:15 AM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.

















































