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Highland Homes for Sale

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  • /27

    $225,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    5548 Century Ave Unit 4, Middleton, WI 53562

    Conveniently located in Middleton’s desirable Rolling Hills Condo Association, this bright & welcoming 2-bed, 2-bath condo offers a true escape from the daily grind. Sunlight streams into the spacious open-concept living area, which opens onto a private balcony overlooking rolling green lawns, mature trees, & the community pool. The well-designed galley kitchen provides ample cabinetry, counter

    Joe Shipley MHB Real Estate

    5548 Century Ave Unit 4, Middleton, WI 53562
  • /42

    $229,900

    Open Sun 12PM - 2PM $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,107 Sq Ft

    5522 Century Ave Unit 3, Middleton, WI 53562

    This 2-bed, 2-bath condo offers the perfect quiet park-like setting nestled near the Pheasant Branch Conservancy. This Garden style unit features plank flooring, a bright open concept with a private balcony overlooking the pool and gardens. The kitchen features natural wood cabinets, dedicated dining space as well as a smaller breakfast area. The primary suite includes an updated ensuite bath,

    Kelly Bakken Restaino & Associates

    5522 Century Ave Unit 3, Middleton, WI 53562
  • /29

    $249,500

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft

    5518 Century Ave Unit 2, Middleton, WI 53562

    Step into this bright and airy Middleton condo nestled in the desirable Rolling Hills neighborhood! Featuring beautiful wood flooring throughout, this inviting home offers a warm and seamless flow from room to room. Natural light pours into the living spaces, creating an open and welcoming atmosphere. Enjoy your morning coffee or unwind after a long day on the walkout patio, offering easy

    Marine Yoo Real Broker LLC

    5518 Century Ave Unit 2, Middleton, WI 53562
  • /25

    $300,000

    Open Sun 12PM - 2PM
    • 2 Beds
    • 2 Baths
    • 1,414 Sq Ft

    3108 Creekview Dr Unit 5, Middleton, WI 53562

    Middleton schools! This beautifully updated 2-bedroom, 2-bath condo features two recently remodeled bathrooms and a spacious, open layout. The large living room with a gas fireplace opens to a private patio, creating the perfect space to relax or entertain. The generously sized kitchen and dining room offer plenty of room for gatherings. Additional highlights include private in-unit laundry, a

    Joe Armentrout Pinnacle Real Estate Group LLC

    3108 Creekview Dr Unit 5, Middleton, WI 53562

Why Live in Highland

The Highland neighborhood in Middleton is a tranquil residential area surrounded by nature preserves and convenient amenities. With a mix of condos, apartments, and single-family homes, the neighborhood features Colonial Revival and split-level homes from the 1970s and 1980s, set on small lots with mature trees and sidewalks. The area is free from commercial developments, ensuring minimal through traffic on its winding streets. Highland is adjacent to the Pheasant Branch Conservancy, offering year-round hiking on paved trails, and the John C. Bock Community Forest, which provides miles of hiking and biking paths. Residents can also enjoy gardening at the Bock Community Garden or water activities at nearby Lake Mendota. Local dining options include Prairie Café and Bakery, Craftsman Table & Tap, and the upscale 1847 at the Stamm House. For groceries, residents have access to Willy Street Co-Op and Metro Market, while shopping needs can be met at Greenway Station, located about 4 miles away. The neighborhood falls within the highly rated Middleton-Cross Plains Area School District, with students attending Sauk Trail Elementary School, Kromrey Middle School, and Middleton High School, which is recognized as a top school in Wisconsin. While public transportation is limited to bus stops along Century Avenue, downtown Middleton is just minutes away, and downtown Madison is a 6-mile drive via University Avenue. The Dane County Regional Airport is approximately 12 miles away. Highland's crime rate is lower than the national average, contributing to its appeal as a safe residential area.

Frequently Asked Questions

Is Highland a good place to live?
Highland is a good place to live. Highland is considered car-dependent and very bikeable with some transit options. Highland is a suburban neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Highland has 8 parks for recreational activities. It is fairly sparse in population with 5.0 people per acre and a median age of 44. The average household income is $99,924 which is below the national average. College graduates make up 53.7% of residents. A majority of residents in Highland are home owners, with 44% of residents renting and 56% of residents owning their home. A local real estate agent serving Highland can help you decide if this neighborhood is the right one for you. Learn more on our Highland neighborhood guide.
Is Highland, WI a safe neighborhood?
Highland, WI is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Highland?
The median home price in Highland is $299,900. If you put a 20% down payment of $60,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $1,510 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $65K a year to afford the median home price in Highland. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Highland is $100K.
What are the best public schools in Highland?
The best public schools that serve Highland are:
What are the best private schools in Highland?
The best private schools that serve Highland are:
What are the most popular zip codes in Highland, Middleton, WI?
The most popular zip codes in Highland, Middleton, WI include 53562, 53597, 53703, 53705 and 53717.
What are the most popular neighborhoods near Highland, Middleton, WI?
The most popular neighborhoods near Highland, Middleton, WI are Middleton Coastline, Middleton Hills, Spring Harbor, Woodland Hills-The Highlands and Wexford Village.
Are home prices dropping in Highland?
Yes, home prices in Highland are down 24% in the last 12 months.

Highland Home Prices vs. Nearby Middleton, WI Neighborhoods

Highland Shorecrest Odana Hills Northeastern Sun Prairie
Median Home Price
$299,900
$350,000
$270,000
$379,000
Median Sale Price
$290,000
-21% YoY
$595,000
+65% YoY
$419,999
+91% YoY
$400,000
+9% YoY
Median Single Family Price
$286,000
$457,500
$475,000
$400,000
Total Active Listings
4
2
2
0
Market Conditions
7 Months
Buyer's Market
5 Months
Balanced Market
5 Months
Balanced Market
0 Months
Seller's Market
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