101 Oswego Rd, Pleasant Valley, NY 12569

Off Market Feb 2022 for $550K

$725,183

Est. refi paymentEst. refi $3,473/mo

•

2,140

sq ft

101 Oswego Rd, Pleasant Valley, NY 12569

About this home

Accepted Offer 12/3/2021...Showing for backup only. Do you love to entertain? With its new butler's pantry, wet bar, and additional kitchen space, this BEAUTIFUL, ONE-OF-A-KIND, 3 bedroom, 2.5 bath, country home near Millbrook is the perfect place to do so. Close to the TSP and the quaint Sky Acres Airport, providing easy access to NYC and many other places! NOTHING TO DO but MOVE in!! The circular drive leads to this beautifully, updated home, situated on TWO PRIVATE ACRES with mature landscaping. The custom Dutch door welcomes you into this lovely home with random width, 19th-century Barnwood floors, and custom moldings. New appliances, fresh paint, a new roof with GAF architectural shingles, new premium black Marvin windows and doors, and new cedar siding will give you peace of mind for many years to come. The stunning Butler's pantry with shiplap and radiant floor heat leads to the backyard and to the oversized front porch, perfect for entertaining or simply relaxing with its mountain and sunset views. An oversized, detached, heated garage with a workshop is located just up the driveway. Original owners. MUST SEE!!... TOO MANY CUSTOM FEATURES TO LIST! Close to the TSP, Rt 84, and the quaint village of Millbrook, its farmer's market, winery, and trails. Convenient to EVERYTHING the Hudson Valley has to offer! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:1 Car Detached,

Single-familyProperty Type

1996Year Built

2.1 acresLot Size

$339Est. Price/Sq.Ft.

1 car garageParking

Listing by Karen Rae • KW Hudson Valley North

Bought with Joan St. Aubyn • BHHS Hudson Valley Properties

Redfin checked: a few seconds ago

•Source:OneKey® MLS as Distributed by MLS Grid #H6128125

Redfin Estimate

$725,183

$175K since sold in February 2022$11K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.9% higher than the average sale price ($620K) of 6 comparable homes.

SOLD NOV 6, 2025
$550,000
A
3 beds2.5 baths1,980 sq ft
34 Grangevale Rd, Lagrangeville, NY 12540
Listing by eXp Realty
SOLD MAY 29, 2026
$687,000
B
3 beds2.5 baths2,594 sq ft
4 Theresa Ct, Lagrangeville, NY 12540
Listing by Corcoran Country Living
SOLD JUL 31, 2026
$750,000
C
3 beds2.5 baths2,344 sq ft
185 Verbank Village Rd, Millbrook, NY 12545
Listing by Compass Greater NY, LLC
SOLD DEC 30, 2025
$589,930
D
3 beds2.5 baths1,922 sq ft
264 Lauer Rd, Poughkeepsie, NY 12603
Listing by RE/MAX Town & Country
SOLD NOV 24, 2025
$580,000
E
3 beds2.5 baths2,100 sq ft
56 Hoof Print Rd, Millbrook, NY 12545
Listing by Four Seasons Sothebys Intl
SOLD NOV 24, 2025
$565,000
F
3 beds2.5 baths2,372 sq ft
30 Velie Rd, Lagrangeville, NY 12540
Listing by Houlihan Lawrence Inc.

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Earn from this home

Sell

$279,473

Est. take-home

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Refinance

Est. cash available

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Rent

$3,273/mo

Redfin rental estimate

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Market trends in 12569, NY

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.5%

1.4% MoM

Median sale price

$485K

$108 MoM

Avg. days on market

84d

4 days MoM

Recently sold homes

2 MoM

New listings for sale

$675,000
4 beds2.5 baths3,078 sq ft
18 English Way, Pleasant Valley, NY 12569
Listing by Serhant LLC
OPEN SAT, 11AM TO 1PM
$549,900
4 beds2 baths3,346 sq ft
15 Rock Cut Ln, Pleasant Valley, NY 12569
Listing by eXp Realty
NEW 24 HRS AGO
$499,000
3 beds1.5 baths2,144 sq ft
10 Meadow Ln, Pleasant Valley, NY 12569
Listing by KW MidHudson
$304,900
3 beds1 bath904 sq ft
37 Shady Creek Rd, Pleasant Valley, NY 12569
Listing by BHHS Hudson Valley Properties
$650,000
3 beds2.5 baths2,232 sq ft
2800 Route 82, Pleasant Valley, NY 12569
Listing by Houlihan Lawrence Inc.
$449,900
3 beds1.5 baths1,640 sq ft
1078 Salt Point Tpke, Pleasant Valley, NY 12569
Listing by Century 21 Alliance Rlty Group
$649,000
3 beds2.5 baths2,264 sq ft
71 O'halloran Cir, Pleasant Valley, NY 12569
Listing by BERKSHIRE HATHAWAY
$175,000
3 beds1 bath1,120 sq ft
65 Water Loop, Pleasant Valley, NY 12569
Listing by VYLLA Home
See all

Provided by Redfin

Sale history for 101 Oswego Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,868 (+2.8%)

$73,900 + $308,500

$382,400

2024

$9,603 (−0.9%)

$73,900 + $308,500

$382,400

2023

$9,687

$73,900 + $308,500

$382,400

2022

$9,681 (+14.5%)

$73,900 + $308,500

$382,400

2021

$8,457 (+10.9%)

$73,900 + $277,000

$350,900

2020

$7,628 (+185.1%)

$73,900 + $277,000

$350,900

2019

$2,675 (−62.7%)

$73,900 + $277,000

$350,900

2018

$7,180 (+1.0%)

$73,900 + $277,000

$350,900

2017

$7,107 (+0.4%)

$73,900 + $260,300

$334,200

2016

$7,079 (−0.9%)

$73,900 + $260,300

$334,200

2015

$7,141 (+2.0%)

$73,900 + $260,300

$334,200

2014

$6,998

$73,900 + $260,300

$334,200

Tax history for 101 Oswego Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,868 (+2.8%)

$73,900 + $308,500

$382,400

2024

$9,603 (−0.9%)

$73,900 + $308,500

$382,400

2023

$9,687

$73,900 + $308,500

$382,400

2022

$9,681 (+14.5%)

$73,900 + $308,500

$382,400

2021

$8,457 (+10.9%)

$73,900 + $277,000

$350,900

2020

$7,628 (+185.1%)

$73,900 + $277,000

$350,900

2019

$2,675 (−62.7%)

$73,900 + $277,000

$350,900

2018

$7,180 (+1.0%)

$73,900 + $277,000

$350,900

2017

$7,107 (+0.4%)

$73,900 + $260,300

$334,200

2016

$7,079 (−0.9%)

$73,900 + $260,300

$334,200

2015

$7,141 (+2.0%)

$73,900 + $260,300

$334,200

2014

$6,998

$73,900 + $260,300

$334,200

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

2.1 Acres

Year renovated

2015

Sq. Ft.

2,084

Year built

1996

Style

Single Family Residential

County

Dutchess County

APN

135400A00666200001870370000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 31, 2026.

Property details

Parking

Parking Information
Parking Total: 1
Parking Features: Detached, Driveway, Garage, Off Street

Garage Information
Garage Spaces: 1

Interior

Virtual Tour Information

Heating & Cooling
Cooling: Wall/Window Unit(s)
Heating: Baseboard, Hot Water, Oil, Radiant

Interior Features
Interior Features: Ceiling Fan(s),Eat-in Kitchen,Entrance Foyer,Formal Dining,Granite Counters,Primary Bathroom,Pantry,Walk-In Closet(s),Wet Bar
Window Features: ENERGY STAR Qualified Windows, Screens, Storm Window(s)
Laundry Features: Inside
Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Oil Water Heater
Flooring: Hardwood
Patio And Porch Features: Deck, Porch

Room Information
Basement YN: Yes
Attic: Partial,Scuttle,Unfinished
Rooms Total: 8
Basement: Crawl Space, See Remarks, Unfinished

Bathroom Information
Bathrooms Full: 2
Bathrooms Half: 1

Exterior

Exterior Features
Exterior Features: Speakers
Construction Materials: Cedar, Wood Siding
Other Structures: Outbuilding, Shed(s), Workshop
Security Features: Security System
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Near Public Transit, Near School, Near Shops, Stone/Brick Wall, Views

Property Information
Structure Type: Manufactured House
Living Area Source: Other
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2020
Tax Source: Other
Tax Annual Amount: $8,157

Financial Information
Buyer Financing: Conventional

Utilities

Utility Information
Electric Company: Central Hudson
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

HOA Information
Association Amenities: Park

School Information
Middle Or Junior School: Millbrook Middle School
High School: Millbrook High School
High School District: Millbrook

Location Information
Hamlet: Pleasant Valley
Directions: Route 55 East to Route 82 North. Right onto Cole Road, then Right onto Oswego. 101 Oswego is on the left.
County Or Parish: Dutchess County

Community Information
Community Features: Park

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,084
Stories: 2.0
Lot Size: 2.1 acres
Style: Single Family Residential
Year Built: 1996
Year Renovated: 2015
County: Dutchess County
APN: 135400A00666200001870370000

Home facts updated by county records on Jul 31, 2026

Around this home

Schools

Alden Place Elementary School

Public 3-5 • Assigned • 6.3mi

8/10

Millbrook Middle School

Public 6-8 • Assigned • 6.2mi

5/10

Millbrook High School

Public 9-12 • Assigned • 6.1mi

9/10

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

4/10 Wind Factor

15% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Pleasant Valley, NY • 12569

Average low and high temperatures (°F)

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 3.9 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

3.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$689,000 – $834,000

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New listings for sale in 12569

$675,000

4 beds2.5 baths3,078 sq ft

18 English Way, Pleasant Valley, NY 12569

Listing by Serhant LLC

OPEN SAT, 11AM TO 1PM

$549,900

4 beds2 baths3,346 sq ft

15 Rock Cut Ln, Pleasant Valley, NY 12569

Listing by eXp Realty

NEW 24 HRS AGO

$499,000

3 beds1.5 baths2,144 sq ft

10 Meadow Ln, Pleasant Valley, NY 12569

Listing by KW MidHudson

$304,900

3 beds1 bath904 sq ft

37 Shady Creek Rd, Pleasant Valley, NY 12569

Listing by BHHS Hudson Valley Properties

$650,000

3 beds2.5 baths2,232 sq ft

2800 Route 82, Pleasant Valley, NY 12569

Listing by Houlihan Lawrence Inc.

$449,900

3 beds1.5 baths1,640 sq ft

1078 Salt Point Tpke, Pleasant Valley, NY 12569

Listing by Century 21 Alliance Rlty Group

$649,000

3 beds2.5 baths2,264 sq ft

71 O'halloran Cir, Pleasant Valley, NY 12569

Listing by BERKSHIRE HATHAWAY

$175,000

3 beds1 bath1,120 sq ft

65 Water Loop, Pleasant Valley, NY 12569

Listing by VYLLA Home

Home values near 101 Oswego Rd

Data from public records.

Address	Redfin Estimate
90 Oswego Rd, Pleasant Valley, NY 3 Beds \| 1.5 Baths \| 1712 Sq. Ft.	$497,443
89 Oswego Rd, Pleasant Valley, NY 3 Beds \| 2 Baths \| 2200 Sq. Ft.	$566,294

Address	Redfin Estimate
136 Oswego Rd, Pleasant Valley, NY 3 Beds \| 2 Baths \| 2542 Sq. Ft.	$533,681
131 Oswego Rd, Pleasant Valley, NY 3 Beds \| 1 Baths \| 1080 Sq. Ft.	$333,940

Address	Redfin Estimate
151 Oswego Rd, Pleasant Valley, NY 4 Beds \| 2.5 Baths \| 3776 Sq. Ft.	$693,374
113 Oswego Rd, Pleasant Valley, NY 4 Beds \| 2.5 Baths \| 3074 Sq. Ft.	$557,718

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2021. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12569, NY

Sale history for 101 Oswego Rd

Tax history for 101 Oswego Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12569

Home values near 101 Oswego Rd

More real estate resources