A rare legal two-family just steps from the Rhinecliff Amtrak station and minutes to Rhinebeck village. Currently configured with a 2-bedroom apartment on the first floor and a 3-bedroom apartment above, this home offers immediate income potential, flexible multi-generational living, or the option to convert to a single-family residence. Envision transforming the upstairs kitchen into a large ensuite primary bathroom with access to a private rear deck overlooking the backyard. Set on nearly an acre across two parcels, recent upgrades include a brand new roof (2026), new HVAC system (2026), hot water heater (2022), and sump pump (2022). A detached garage on the adjacent parcel has a new roof and offers conversion potential for studio, guest house, or workspace, subject to town approval. Space, flexibility, and village-level convenience in one of the Hudson Valley's most sought-after locations. Sellers are open to negotiation for a turnkey/furnished sale.
Single-familyProperty Type
1860Year Built
0.84 acresLot Size
$206Price/Sq.Ft.
1 car garageParking
Listing by Juliana Botta• Four Seasons Sothebys Intl
A rare legal two-family just steps from the Rhinecliff Amtrak station and minutes to Rhinebeck village. Currently configured with a 2-bedroom apartment on the first floor and a 3-bedroom apartment above, this home offers immediate income potential or flexible multi-generational living. Or, envision converting the upstairs kitchen into a large ensuite primary bathroom with access to a private rear deck overlooking the backyard. Set on nearly an acre across two parcels, recent upgrades include a brand new roof (2026), new HVAC system (2026), hot water heater (2022), and sump pump (2022). A detached garage on the adjacent parcel has a new roof and offers conversion potential for studio, guest house, or workspace, subject to town approval. Space, flexibility, and village-level convenience in one of the Hudson Valley's most sought-after locations. Sellers are open to negotiation for a turnkey/furnished sale.
OneKey® MLS as Distributed by MLS Grid #1030248
Sep 30, 2026
Price Changed
$599,000
$206/sq ft
Aug 26, 2026
Price Changed
$669,000
$230/sq ft
Jul 27, 2026
Listed
$705,000
$243/sq ft
HVCRMLS #20264256
Sep 29, 2026
Price Changed
$599,000
$206/sq ft
Aug 26, 2026
Price Changed
$669,000
$230/sq ft
Jul 27, 2026
Listed
$705,000
$243/sq ft
+33
A rare legal two-family just steps from the Rhinecliff Amtrak station and minutes to Rhinebeck village, where mornings can start with a walk for coffee and end with a seamless trip back from the city. Currently configured with a 2-bedroom apartment on the first floor and a 3-bedroom apartment above, the home offers immediate income potential, flexible multi-generational living, or the chance to reimagine it as a single-family residence. The first floor moves comfortably from a formal dining room to a welcoming family room, with a mudroom and rear porch opening to a fenced yard. Upstairs, three bedrooms create room for extended stays or a simple investment setup. Set on approximately 0.84 acres across two parcels, the property feels unexpectedly expansive for such a convenient location. The adjacent parcel (formerly 410 Rhinecliff Rd) is included in the sale, adding a detached garage with a new roof and conversion potential for studio, guest house, or workspace, subject to town approval. Recent upgrades bring peace of mind: brand new roof (2026), new HVAC system (2026), hot water heater (2022), and sump pump (2022). Sellers are open to negotiation for a turnkey/furnished sale. Space, flexibility, and village-level convenience in one of the Hudson Valley's most sought-after settings. And though you're not on the water, the river breeze reminds you it's never far.
HVCRMLS #20264257
Sep 29, 2026
Price Changed
$599,000
$206/sq ft
Aug 26, 2026
Price Changed
$669,000
$230/sq ft
Jul 27, 2026
Listed
$705,000
$243/sq ft
OneKey® MLS as Distributed by MLS Grid #964881
Jul 25, 2026
Listing Removed
—
Jun 11, 2026
Price Changed
$745,000
$256/sq ft
May 1, 2026
Listed
$790,000
$272/sq ft
OneKey® MLS as Distributed by MLS Grid #967819
Jul 25, 2026
Listing Removed
—
Jun 11, 2026
Price Changed
$745,000
$256/sq ft
May 1, 2026
Listed
$790,000
$272/sq ft
HVCRMLS #20262016
Jun 11, 2026
Price Changed
$745,000
$256/sq ft
May 1, 2026
Listed
$790,000
$272/sq ft
HVCRMLS #20262018
Jun 11, 2026
Price Changed
$745,000
$256/sq ft
May 1, 2026
Listed
$790,000
$272/sq ft
OneKey® MLS as Distributed by MLS Grid #M375128
Nov 30, 2018
Sold
$307,000
$106/sq ft
Sep 13, 2018
Listed
$315,000
$108/sq ft
HVCRMLS #123073
Sep 13, 2018
Listed
$315,000
$108/sq ft
OneKey® MLS as Distributed by MLS Grid #H4800654
Sep 17, 2018
Listing Removed
—
Jun 5, 2018
Price Changed
$319,500
$110/sq ft
May 17, 2018
Price Changed
$329,000
$113/sq ft
Apr 29, 2018
Price Changed
$339,900
$117/sq ft
Mar 19, 2018
Price Changed
$359,900
$124/sq ft
Feb 4, 2018
Price Changed
$379,900
$131/sq ft
Jan 6, 2018
Listed
$389,900
$134/sq ft
Public Records
Dec 3, 2001
Sold
$118,000
$41/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$9,368
$77,900 + $580,700
$658,600
2025
$9,368 (+12.2%)
$77,900 + $580,700
$658,600
2024
$8,348 (+9.6%)
$74,900 + $514,900
$589,800
2023
$7,614 (−1.0%)
$74,900 + $442,400
$517,300
2022
$7,688 (−0.8%)
$65,100 + $404,100
$469,200
2021
$7,750 (+11.3%)
$65,100 + $344,200
$409,300
2020
$6,960 (−7.1%)
$65,100 + $287,100
$352,200
2019
$7,494 (+3.2%)
$48,500 + $261,200
$309,700
2018
$7,259 (+25.8%)
$48,500 + $261,200
$309,700
2017
$5,770 (+2.7%)
$48,500 + $261,200
$309,700
2016
$5,620 (+15.0%)
$48,500 + $235,300
$283,800
2015
$4,885 (+1.9%)
$48,500 + $235,300
$283,800
2014
$4,792
$48,500 + $235,300
$283,800
Public record
Beds
5
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
0.84 Acres
Year renovated
1975
Finished Sq. Ft.
2,906
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,906
Year built
1860
Style
Multi-Family (2-4 Unit)
County
Dutchess County
APN
135089A00607000184580930000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 5, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 99° expected this year, 15 days in 30 years
4/10 Wind Factor
10% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Rhinebeck, NY • 12572
Average low and high temperatures (°F)
32
19
36
20
53
32
63
42
70
51
82
61
85
66
81
59
76
54
65
44
52
35
37
23
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
94/ 100
Exceptional sunlight
Sunscore
This home receives average direct sun exposure in Rhinebeck. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.9 hrs
6.4 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 420 Rhinecliff Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $412,000 and $800,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $412K to $800K.