Welcome to 169 Milton Road, a once-in-a-lifetime opportunity to own one of Rye’s most iconic properties once known as the sea captain's house. This home offers an unparalleled lifestyle in a sought after, walk-to-all location. The elegant 7-bedroom home is set on a sprawling one-acre lot, offering both historical charm and modern sophistication. The property underwent a significant transformation in 2016 to create outdoor living space designed by renowned Sean Jancski Landscape Architects. The outdoor resort space features a stunning 20x44 swimming pool, a luxurious hot tub, and a meticulously designed entertainment area with two handsome fireplaces, a built-in BBQ, bar, and pergola. Enjoy the tranquil sound of fountains amid lush new plantings, all enhanced by state-of-the-art outdoor lighting and sound systems. In 2021, the original four-car garage was reimagined into a versatile two-car garage with an adjoining pool house. This sanctuary includes a lounge area with a built-in bar and fireplace, a full bath, and flexible space for fitness pursuits—perfect for retreating and relaxing in a resort-like setting and great for guest. Inside, the home exudes elegance with its high ceilings, built-in cabinetry, and beautifully scaled rooms, ideal for both grand entertaining and intimate gatherings. The sophisticated dining area features a charming fireplace, complemented by a butler's pantry for seamless hosting. The kitchen boasts modern upgrades while maintaining its classic appeal. Additional enhancements include new flooring throughout, updated bathrooms, and essential infrastructure upgrades such as new A/C units, a new boiler, and a new roof. The exterior has been refreshed with new paint, shutters, and shingles, ensuring this home is as striking outside as it is within. This residence offers a harmonious blend of retreat and convenience, situated in the heart of Rye less than minutes to the vibrant, quaint town of Rye, schools and beach. Walk to all schools, nursery schools, town, train and beach.
Single-familyProperty Type
1884Year Built
0.98 acresLot Size
$1,324Est. Price/Sq.Ft.
2 car garageParking
Listing by Kimberly Arenas• Compass Greater NY, LLC
Bought with Non Non Member-MLS• Buyer Representation Office
Source:OneKey® MLS as Distributed by MLS Grid #821114
Redfin Estimate
$7,695,650
$701K since sold in November 2025$19K since October
Recently sold homes
Estimate history
Homes for sale
This home's estimate is 69.8% higher than the average sale price ($4.53M) of 6 comparable homes.
Welcome to 169 Milton Road, a once-in-a-lifetime opportunity to own one of Rye’s most iconic properties once known as the sea captain's house. This home offers an unparalleled lifestyle in a sought after, walk-to-all location. The elegant 7-bedroom home is set on a sprawling one-acre lot, offering both historical charm and modern sophistication. The property underwent a significant transformation in 2016 to create outdoor living space designed by renowned Sean Jancski Landscape Architects. The outdoor resort space features a stunning 20x44 swimming pool, a luxurious hot tub, and a meticulously designed entertainment area with two handsome fireplaces, a built-in BBQ, bar, and pergola. Enjoy the tranquil sound of fountains amid lush new plantings, all enhanced by state-of-the-art outdoor lighting and sound systems. In 2021, the original four-car garage was reimagined into a versatile two-car garage with an adjoining pool house. This sanctuary includes a lounge area with a built-in bar and fireplace, a full bath, and flexible space for fitness pursuits—perfect for retreating and relaxing in a resort-like setting and great for guest. Inside, the home exudes elegance with its high ceilings, built-in cabinetry, and beautifully scaled rooms, ideal for both grand entertaining and intimate gatherings. The sophisticated dining area features a charming fireplace, complemented by a butler's pantry for seamless hosting. The kitchen boasts modern upgrades while maintaining its classic appeal. Additional enhancements include new flooring throughout, updated bathrooms, and essential infrastructure upgrades such as new A/C units, a new boiler, and a new roof. The exterior has been refreshed with new paint, shutters, and shingles, ensuring this home is as striking outside as it is within. This residence offers a harmonious blend of retreat and convenience, situated in the heart of Rye less than minutes to the vibrant, quaint town of Rye, schools and beach. Walk to all schools, nursery schools, town, train and beach.
HGMLS #4401915
Aug 4, 2014
Price Changed
$4,840,000
$833/sq ft
Aug 4, 2014
Sold
$4,840,000
$833/sq ft
May 15, 2014
Contingent
—
May 15, 2014
Price Changed
$5,295,000
$911/sq ft
Apr 3, 2014
Listed
$5,295,000
$911/sq ft
This unique property has it all! Situated in the heart of Rye, this 1884 classic combines the character of yesteryear with the conveniences of today. It boasts 7 BR's, including the Master Suite w/ 1.5 baths & his/her closets. State of the art gourmet kitchen & butler's pantry w/ high- end appliances. The manicured grounds feature flagstone patios w/ tranquil fountains, in- ground spa/ wading pool and built-in gas grill. Walking distance to all Rye has to offer! Not just a home- a lifestyle!
OneKey® MLS as Distributed by MLS Grid #H4401915
Aug 4, 2014
Sold
$4,840,000
$833/sq ft
Apr 3, 2014
Listed
$5,295,000
$911/sq ft
Public Records
Sep 5, 2000
Sold
$2,750,000
$473/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$89,120 (+2.5%)
$9,450 + $60,850
$70,300
2025
$86,908 (+3.3%)
$9,450 + $60,850
$70,300
2024
$84,100 (+7.5%)
$9,450 + $60,850
$70,300
2023
$78,249 (+1.3%)
$9,450 + $60,850
$70,300
2022
$77,251 (+0.3%)
$9,450 + $60,850
$70,300
2021
$77,022 (+1.2%)
$9,450 + $60,850
$70,300
2020
$76,082 (+146.1%)
$9,450 + $60,850
$70,300
2019
$30,918
$9,450 + $60,850
$70,300
2018
$9,450 + $60,850
$70,300
2017
$9,450 + $60,850
$70,300
2016
$9,450 + $60,850
$70,300
2014
$9,450 + $57,350
$66,800
2013
$9,450 + $57,350
$66,800
2012
$9,450 + $57,350
$66,800
2011
$9,450 + $57,350
$66,800
2010
$9,450 + $57,350
$66,800
2009
$9,450 + $57,350
$66,800
2008
$9,450 + $57,350
$66,800
Tax history for 169 Milton Rd
Year
Property tax
Land + Additions
Assessment*
2026
$89,120 (+2.5%)
$9,450 + $60,850
$70,300
2025
$86,908 (+3.3%)
$9,450 + $60,850
$70,300
2024
$84,100 (+7.5%)
$9,450 + $60,850
$70,300
2023
$78,249 (+1.3%)
$9,450 + $60,850
$70,300
2022
$77,251 (+0.3%)
$9,450 + $60,850
$70,300
2021
$77,022 (+1.2%)
$9,450 + $60,850
$70,300
2020
$76,082 (+146.1%)
$9,450 + $60,850
$70,300
2019
$30,918
$9,450 + $60,850
$70,300
2018
$9,450 + $60,850
$70,300
2017
$9,450 + $60,850
$70,300
2016
$9,450 + $60,850
$70,300
2014
$9,450 + $57,350
$66,800
2013
$9,450 + $57,350
$66,800
2012
$9,450 + $57,350
$66,800
2011
$9,450 + $57,350
$66,800
2010
$9,450 + $57,350
$66,800
2009
$9,450 + $57,350
$66,800
2008
$9,450 + $57,350
$66,800
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Property details
Interior
Bathroom Information
# of Full Baths: 5
Fireplace Information
# of Fireplaces: 5
Has Fireplace
Exterior
Exterior Information
Building Style Type: Colonial
Exterior Wall: Frame Wood
Property Information
Subdivision Name: SECTION 14616
Living Sq. Ft: 5,813
Ground Floor Sq. Ft: 2,835
Building Sq. Ft: 5,813
Lot Information
# of Buildings: 1
Land Sq. Ft: 42,732
Legal Lot Number: 9
Legal Block Number: 1
School Tax District: RYE
Municipality Name: RYE CITY
Acres: 0.981
Zoning Code: R1
State Use Description: SINGLE FAMILY RESID
Financial
Assessor Information
Assessment Year: 2025
Public facts
Beds: 7
Baths: 5.0
Sq. Ft.: 5,813
Stories: —
Lot Size: 0.98 acres
Style: Single Family Residential
Year Built: 1884
Year Renovated: —
County: Westchester County
APN: 551400A14601500010090000000
Home facts updated by county records on Sep 25, 2026
Around this home
Schools
K - 12
Preschool & daycare
Midland School
Public K-5 • Assigned • 0.4mi
9/10
Rye Middle School
Public 6-8 • Assigned • 0.1mi
7/10
Rye High School
Public 9-12 • Assigned • 0.1mi
10/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
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
6/10 Heat Factor
7 days above 98° expected this year, 16 days in 30 years
6/10 Wind Factor
27% chance of strong winds in next 30 years
4/10 Air Factor
5 unhealthy days expected this year, 7 days in 30 years
Provided by First Street
Historical weather
Rye, NY • 10580
Average low and high temperatures (°F)
36
23
38
25
53
35
62
44
69
53
81
64
85
69
80
63
76
60
65
49
55
40
41
28
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.7 hours in
June and 4.4 hours in December, placing it below the
U.S. average for solar exposure.
8.7 hrs
4.4 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$7.31M – $8.85M
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