N4272 Sleepy Hollow Rd

Oakland, WI 53523

$1,450,000
Price
4
Beds
4,590 Sq. Ft.
$316 / Sq. Ft.
4,590
Sq. Ft.
$316
per Sq. Ft.
56
38 (1)
36 (1)
39 (1)
43 (1)
37 (1)
42 (1)
47 (1)
46 (1)
50
51
40 (1)
52
53
62
66
71
70
65
59
73
75
95
96
77
80
91
92
84
90
79
82
55
57
06 (2)
27 (1)
22 (2)
IMG_1979-preview copy
23 (2)
IMG_7883
04 (2)
02 (1)
10 (2)
09 (2)
12 (1)
20 (2)
16 (3)
28 (2)
30 (2)
33 (1)

Description

Spectacular estate on 7 acres with 300 feet of frontage on Spring fed Lake Ripley. Custom built log home overlooking tranquil marshland with stunning views. Take in the sounds of nature as you walk along the board walk to your private pier. Open floor plan with vaulted ceilings & wide plank flooring, 4 bedrooms, 4 baths, 3 season room, screened porch, floor to ceiling stone fireplace in great room to keep you warm & cozy on cooler days, nice main level deck with tiki bar, walkout lower level, inground...Spectacular estate on 7 acres with 300 feet of frontage on Spring fed Lake Ripley. Custom built log home overlooking tranquil marshland with stunning views. Take in the sounds of nature as you walk along the board walk to your private pier. Open floor plan with vaulted ceilings & wide plank flooring, 4 bedrooms, 4 baths, 3 season room, screened porch, floor to ceiling stone fireplace in great room to keep you warm & cozy on cooler days, nice main level deck with tiki bar, walkout lower level, inground pool, pickleball court, & an extra garage with 3+ stalls for all those lake & pool toys. Spacious kitchen with two large islands, beautiful knotty cherry cabinets, granite/quarts counters, walk-in pantry, and SS appliances. This property has so much to offer its like a private resort!
  1. Listed by Linda L Jeffers • Brokerage DRE #700654-91 • RE/MAX Community Realty • lindajeffers@remax.net

Property Details for N4272 Sleepy Hollow Road

Architectural Style
Log Home
Water Body Name
Ripley
Waterfront Features
Pier
Waterfront
Yes
LISTING UPDATED: 12/16/2025 09:36 AM

Property Details for N4272 Sleepy Hollow Road

StatusActive
MLS #1944317
Days on Market17
Taxes$16,763 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle-Family
Year Built2005
Lot Size6.99 AC / 304,484 SF
CountyJefferson County

Location

Listing Courtesy of RE/MAX Community Realty
Add your commute

Building Information for N4272 Sleepy Hollow Road

Stories-Year Built2005Building Size-Lot Size6.99 AC / 304,484 SF

Payment Calculator

$8,562 per month

30 year fixed, 6.28% Interest

Principal and Interest

$7,165

Property Taxes

$1,397

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for N4272 Sleepy Hollow Road

Summary
Location and General Information
  • Accessibility Features: Level Drive, Ramped or Level Entrance, Open Floor Plan, Full Bath on Main Level, Laundry on Main Level, Bedroom on Main Level
  • Directions: Hwy 12 just east of downtown Cambridge, turn left onto Sleepy Hollow Road, first property on the left. Or I94 west , south on Hwy 26 , HWY 18 west, to Park St. left on Hwy 12, to Sleepy Hollow Road
  • Latitude: 42.997792
  • Location: OAKLAND - T
  • Longitude: -89.000097
  • Postal Code: 53523
  • Postal Code Plus4: 9758
  • Zoning: residential
  • Zoning Description: residential
Parking
  • Attached Garage: No
  • Garage Spaces: 5.0
  • Garage Type: Attached
  • Garage: Yes
  • Parking Features: Electric Door Opener, Paved
Taxes and HOA
  • Additional Parcels Description: 022-0613-0742-051
  • Parcel Number: 02206130742050
  • Tax Annual Amount: $16,763
  • Tax Year: 2025
School Information
  • Elementary School: Cambridge
  • High School: Cambridge
  • High School District: Cambridge
  • Middle Or Junior School: Nikolay
Property
Lot Information
  • Building Area Source: Other
  • Building Area Total: 4590.0
  • Lot Features: Corner Lot, Rural, Wooded, View of Water, Wetlands
  • Lot Size Acres: 6.99
  • Lot Size Area: 6.99
  • Lot Size Source: Appraiser
  • Lot Size Square Feet: 304484.4
  • Lot Size Units: Acres
Property and Assessments
  • Exclusions: Garage & basement fridge, statuary in yard including bench, 4 post car lift in detached garage, wall phone in LL, and seller's personal property.
  • Inclusions: Range, oven, microwave, refrigerator, dishwasher, disposal, wine fridge, washer, dryer, water softener, bar fridge in tiki bar, gas firepit on screen porch, wall clock by dining room, ship window mirror on sauna door, fountain in front yard, and all window treatments.
  • Year Built: 2005
Utilites
  • Sewer: Municipal Sewer
Interior and Exterior Features
Exterior Features
  • Exterior: Log
  • Patio And Porch Features: Deck, Patio
  • Pool Features: Inground Pool
Interior Features
  • Appliances: Oven, Range, Refrigerator, Disposal, Dishwasher, Microwave, Washer, Dryer
  • Basement: Full, Walk Out/Outer Door, Shower, 8+ Ceiling, Partially Finished
  • Bathrooms Full: 4
  • Bathrooms Half: 0
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 4
  • Construction Materials: Log
  • Cooling: Central Air
  • Cooling: Yes
  • Fireplace Features: Free Standing Stove, Gas Fireplace
  • Fireplace: Yes
  • Flooring: Wood Floors
  • Heating: Natural Gas, Forced Air
  • Heating: Yes
  • Interior Features: Pantry, Sauna, Hot Tub, Kitchen Island, Split Bedrooms, Walk-In Closet(s), Vaulted Ceiling(s), High Speed Internet
  • Levels: 1 Story
  • Other Structures: Additional Garage(s)
  • Property sp Information co Est sp Total sp Sq sp Ft: 4590.0
  • Property sp Information co Est sp Unfin sp Below sp Gr sp Sq sp Ft: 594.0
  • Rooms Total: 12
Room Information
Room 1
  • Room Dimensions: 29 x 25
  • Room Length: 29.0
  • Room Level: Main
  • Room Type: Living/Great Room
  • Room Width: 25.0
Room 2
  • Room Dimensions: 17 x 12
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 12.0
Room 3
  • Room Dimensions: 18 x 12
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 12.0
Room 4
  • Room Dimensions: 20 x 16
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 16.0
Room 5
  • Room Dimensions: 26 x 29
  • Room Length: 26.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 29.0
Room 6
  • Room Dimensions: 11 x 12
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Bedroom 2
  • Room Width: 12.0
Room 7
  • Room Dimensions: 19 x 12
  • Room Length: 19.0
  • Room Level: Lower
  • Room Type: Bedroom 3
  • Room Width: 12.0
Room 8
  • Room Dimensions: 14 x 13
  • Room Length: 14.0
  • Room Level: Lower
  • Room Type: Bedroom 4
  • Room Width: 13.0
Room 9
  • Room Dimensions: 10 x 12
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Laundry
  • Room Width: 12.0
Room 10
  • Room Dimensions: 24 x 12
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Three Season Room
  • Room Width: 12.0
Room 11
  • Room Dimensions: 23 x 12
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Screened Porch
  • Room Width: 12.0
Room 12
  • Room Dimensions: 8 x 7
  • Room Length: 8.0
  • Room Level: Lower
  • Room Type: Other Room
  • Room Width: 7.0

Property History for N4272 Sleepy Hollow Road

DateEvent & SourcePriceAppreciation
Dec 8, 2025

Listed (Active)

MetroMLS #1944317

$1,450,000—
Dec 8, 2025

Listed (Active)

SCWMLS #2013258

$1,450,000—
Jul 21, 2017

Sold

MRED #08953514

—
Jul 21, 2017

Sold

SCWMLS #1749560

—
May 31, 2017

Off Market

SCWMLS #1778155

—
Apr 8, 2017

Pending

MRED #08953514

—
Apr 8, 2017

Pending

SCWMLS #1749560

—
Jan 31, 2017

Off Market

MetroMLS #1483320

$849,000—
Jun 23, 2016

Listed (Active)

MetroMLS #1483320

$925,000—
Jun 7, 2016

Listed (Active)

SCWMLS #1778155

$849,000—
Jun 14, 2015

Listed (Active)

MRED #08953514

$849,000—
Jun 14, 2015

Listed (Active)

SCWMLS #1749560

$650,000—
DateEvent & SourcePrice
12/08/2025

Listed (Active)

MetroMLS #1944317

$1,450,000
12/08/2025

Listed (Active)

SCWMLS #2013258

$1,450,000
07/21/2017

Sold

MRED #08953514

—
07/21/2017

Sold

SCWMLS #1749560

—
05/31/2017

Off Market

SCWMLS #1778155

—
04/08/2017

Pending

MRED #08953514

—
04/08/2017

Pending

SCWMLS #1749560

—
01/31/2017

Off Market

MetroMLS #1483320

$849,000
06/23/2016

Listed (Active)

MetroMLS #1483320

$925,000
06/07/2016

Listed (Active)

SCWMLS #1778155

$849,000
06/14/2015

Listed (Active)

MRED #08953514

$849,000
06/14/2015

Listed (Active)

SCWMLS #1749560

$650,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for N4272 Sleepy Hollow Road

Taxable ValueLand$225,000Additions$1,034,400Total$1,259,400
Tax Record2024$16,793 ($1,399 / month)
Home Facts
Beds0Lot Size304,484 SqFtStyleSingle Family ResidenceCountyJEFFERSONAPN022-0613-0742-050

Schools near N4272 Sleepy Hollow Road

This home is within Cambridge School District.
Rating
School
Type
Grades
Distance
Cambridge Elementary School
Public - PK to 5
Nikolay Middle School
Public - 6 to 8
Cambridge High School
Public - 9 to 12
Koshkonong Trails School
Charter - 7 to 12
Rating
School
Distance
Cambridge Elementary School
PublicPK to 5

Nikolay Middle School
Public6 to 8

Cambridge High School
Public9 to 12

Koshkonong Trails School
Charter7 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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More information about N4272 Sleepy Hollow Road, Oakland, WI 53523

N4272 Sleepy Hollow Road is a single family home for sale in Oakland, WI 53523. This property was listed for sale on December 8, 2025 by RE/MAX Community Realty, it's currently listed at $1,450,000. It has been on the market for a total of 17 days and was last sold on July 21, 2017. This listing's school district is Cambridge School District. Nearby schools include Cambridge Elementary School, Nikolay Middle School and Cambridge High School. N4272 Sleepy Hollow Road is a 4-bed, 4-bath, 4,590 sqft single family home built in 2005.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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.

Listing Courtesy of RE/MAX Community Realty

Based on information from one of the following Multiple Listing Services: Metro Multiple Listing Service (Metro MLS), REALTORS Association of Northeast Wisconsin. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Metro Multiple Listing Service (Metro MLS), REALTORS Association of Northeast Wisconsin is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Data last updated on 12/16/2025 09:36 AM Listing presented by Compass RE WI-Tosa. Information is supplied by seller and other third parties and has not been verified. Copyright 2025 – WiREx. – All Rights Reserved