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Oregon, WI Houses for Sale

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  • /62

    $365,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    507 Janesville St, Oregon, WI 53575

    This beautifully updated home offers a fully remodeled main level with a modern kitchen featuring custom granite countertops, hickory cabinets, a stylish full bath with tiled shower, and a welcoming entry porch with cathedral ceiling. A expansive 33'6"x22'6" garage fully insulated and sheet rocked and painted. The garage and second floor were added in 2015, 2016 and includes two bedrooms and a

    Agent Photo

    Steve Evers

    Great Rock Realty LLC

    507 Janesville St, Oregon, WI 53575
  • /24

    $499,900

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    5794 Lincoln Rd, Oregon, WI 53575

    Opportunity awaits on this 5 acre property just south of Madison in the Town of Oregon. This classic foursquare farm house features spacious kitchen and dining room, four bedrooms and main level laundry. Several outbuildings on the property including the original barn, 3 car detached garage and two pole sheds provide multiple possibilities for storage, hobbies or animals. House and some

    Agent Photo

    Tommy Van Ess

    First Weber Inc

    5794 Lincoln Rd, Oregon, WI 53575
  • /44

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft

    690 US Highway 14, Oregon, WI 53575

    Rare opportunity with approximately 12 acres in Dane County! 2 tax parcels for sale 0510-191-9500-6 - 9.736 acres and 0510-202-9230-9 - 2.10 acres - both parcels to be sold together. The property includes eligibility for one potential land division/development right, which may be used on the property or transferred to another qualifying property, subject to all town and Dane County requirements

    Agent Photo

    Jon Vanden Brook

    First Weber Inc

    690 US Highway 14, Oregon, WI 53575
  • /32

    $439,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft

    1206 Tivoli Cir, Oregon, WI 53575

    Thoughtfully updated condo in a welcoming Oregon community! Condo Fees are $200/month. Vaulted ceilings and abundant natural light create an inviting main living space, complemented by upgraded lighting, new flooring, and a beautifully enhanced kitchen with added pantry cabinetry and butcher block counter. The main level offers easy everyday living, while the unfinished lower level is already

    Matt Winzenried Realty Executives Cooper Spransy

    1206 Tivoli Cir, Oregon, WI 53575
  • /2

    $749,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,057 Sq Ft

    1044 Autumn Blaze Ct, Oregon, WI 53575

    Under Construction. Get ready to fall in love with your brand-new home on Autumn Blaze Court. Arriving in December 2026 is a stunning new construction by Alterra Design Homes. It offers the perfect balance of peace and proximity. Nestled on a scenic hill overlooking the Village of Oregon, you're just 15 minutes from the heart of Madison but worlds away from the noise.

    Oscar Bennett Alterra Real Estate Group LLC

    1044 Autumn Blaze Ct, Oregon, WI 53575
  • /34

    $441,444

    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft

    1257 Tivoli Cir, Oregon, WI 53575

    The Villas are the ultimate in peace of mind living. Located within the Highlands of Netherwood, this unique neighborhood of Single Family homes brings all the conveniences of condo living (Fee: $200/mo) right to your door. Never mow your lawn or shovel your driveway again. Ideal for people that frequently travel or are in the area for part of the year. Walking path connects the neighborhood to a

    Joffre Pedretti Keller Williams Realty

    1257 Tivoli Cir, Oregon, WI 53575
  • /26

    $452,600

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    The Costello Plan at Greenview Preserve, Oregon, WI 53575

    WORK FROM HOME? NO PROBLEM HERE. With its spacious flex room, The Costello offers up the sanctuary you need to balance business with pleasure. Skip the fast food and prep your own gourmet lunch, because why wouldn’t you when you have a lovely kitchen pantry to hold all your meticulously organized spices and grains. When you’re ready to call it a day, retreat and recharge in your private oasis

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36450832, Oregon, WI 53575
  • /2

    $439,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    The Chelsea Plan at Greenview Preserve, Oregon, WI 53575

    Every home tells a story — and The Chelsea was designed to begin a beautiful one. This two-story carriage lane home strikes a beautiful balance between charm and contemporary living. Step inside to an open, airy main floor that invites connection. From simple weeknight dinners to lively gatherings, this inviting layout makes every moment feel natural. Graceful yet grounded, The Chelsea feels both

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 39223581, Oregon, WI 53575
  • /46

    $589,900

    • 3 Beds
    • 2.5 Baths
    • 2,025 Sq Ft

    873 Peregrine Cir, Oregon, WI 53575

    Tucked away on a cul-de-sac with a quiet neighborhood setting, this inviting two-story home offers over 2,000 square feet of above-grade living space, blending timeless character with functional design. Located just two blocks from Anderson Farm Park, outdoor recreation is close at hand, with expansive green space and a large dog exercise area providing convenient opportunities to walk, explore,

    Heather Taylor MHB Real Estate

    873 Peregrine Cir, Oregon, WI 53575
  • /15

    $464,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,615 Sq Ft

    456 New Hampton Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    456 New Hampton Dr, Oregon, WI 53575
  • /2

    $429,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft

    456 Savannah Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    456 Savannah Dr, Oregon, WI 53575
  • /42

    $493,600

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    The Harlow Plan at Greenview Preserve, Oregon, WI 53575

    One look at the primary suite in The Harlow and you’ll feel your pulse quicken... an inviting retreat with a private bath and a closet spacious enough to dance in. The kitchen steals the show with a generous island perfect for entertaining, paired with a sunny set of patio doors that welcome in morning light for a quiet cup of coffee before the day begins. This thoughtfully designed single-level

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 40971249, Oregon, WI 53575
  • /2

    $539,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    1003 Merri-Hill Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1003 Merri-Hill Dr, Oregon, WI 53575
  • /64

    $569,900

    Open Sun 10AM - 12PM $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,558 Sq Ft

    422 Oakwood Dr, Oregon, WI 53575

    Freshly painted! Welcome to this beautifully maintained 4-bedroom, 3.5-bath home offering the perfect blend of space, comfort, and recreation. Filled with natural light, the main level features inviting living areas and easy access to the deck—ideal for grilling, entertaining, or simply relaxing outdoors. Upstairs, you'll find four spacious bedrooms, including a private primary suite with its own

    Sean Coffey First Weber Inc

    422 Oakwood Dr, Oregon, WI 53575
  • /37

    $696,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft

    534 Foxfield Rd, Oregon, WI 53575

    The one you have been waiting for. This Beautiful build with many owner upgrades is a 4 bedroom 3 full bath including the bed and bath in the gorgeous finished basement. The Open concept Ranch style home sits on a spacious over quarter acre lot with a fenced backyard. Move in ready.

    Robert Hanna Geneva Properties Real Estate Agency LLC

    534 Foxfield Rd, Oregon, WI 53575
  • /18

    $427,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,615 Sq Ft

    The Gramercy Plan at Greenview Preserve, Oregon, WI 53575

    Your takeout never tasted so good. No, it wasn’t that the food was any different, it was where it was eaten. That’s right, you ate at the best location around, at your brand new kitchen island. The experience that the Gramercy has to offer you is like it was made just for you (because it was!). With an open and airy first floor and three private retreats upstairs, you are exactly where you should

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36789044, Oregon, WI 53575
  • /28

    $525,600

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft

    The Everest Plan at Greenview Preserve, Oregon, WI 53575

    The Everest is one crafty home. Outside, it welcomes you like a cozy cottage. Step through the front door and it greets you more like a grand estate. To your right, a tucked-away den. Ahead, a massive great room. Off the garage, a laundry room to keep muddy boots and snowy coats at bay. The pleasant surprises continue with the four roomy bedrooms upstairs. And delighted smiles are pretty much

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36788956, Oregon, WI 53575
  • /77

    $1,275,000

    $125K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 6,638 Sq Ft

    1053 Winged Foot Dr, Oregon, WI 53575

    Perfectly positioned on the Bergamont Golf Course, this stunning home offers some of the most breathtaking views in the community—overlooking the 10th & 18th fairways as well as the spectacular clubhouse. The gourmet kitchen is a true showstopper, complete with a large center island, high-end appliances including Sub-Zero, Viking and Thermador-perfect for the culinary enthusiast. The main living

    Annette Tande Riemer First Weber Inc

    1053 Winged Foot Dr, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 36788946, Oregon, WI 53575

    $415,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft

    The Tribeca Plan at Greenview Preserve, Oregon, WI 53575

    Eggs sunny side up, at the sunniest breakfast nook around. Your breakfast nook. Yes, even the coffee tastes better while sipped slowly on the sofa that is anchoring your spacious great room. Why don’t you head on upstairs and grab the coziest robe you can find from your walk-in closet and then enjoy a quick read of the newspaper while out on your front porch. Because this really is all yours.

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36788946, Oregon, WI 53575
  • /14

    $404,900

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    1087 Tundra Ave, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1087 Tundra Ave, Oregon, WI 53575
  • /5

    $799,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,719 Sq Ft

    480 Foxfield Rd, Oregon, WI 53575

    Completion date: September 30, 2026. Exceptional custom built 4-bedroom home offering the perfect blend of comfort and thoughtful design! This well appointed home offers an incredible gourmet kitchen with custom cabinets, quartz counters, stainless appliances, hidden walk-in pantry and center island with snack bar. Enjoy the sun filled great room with gas fireplace, large dinette with access to

    Jordan Armentrout Pinnacle Real Estate Group LLC

    480 Foxfield Rd, Oregon, WI 53575
  • /34

    $434,900

    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft

    1232 Tivoli Cir, Oregon, WI 53575

    The Villas are the ultimate in peace of mind living. Located within the Highlands of Netherwood, this unique neighborhood of Single Family homes brings all the conveniences of condo living (Fee: $200/mo) right to your door. Never mow your lawn or shovel your driveway again. Ideal for people that frequently travel or are in the area for part of the year. Walking path connects the neighborhood to a

    Joffre Pedretti Keller Williams Realty

    1232 Tivoli Cir, Oregon, WI 53575
  • /2

    $579,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    1083 Merri-Hill Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1083 Merri-Hill Dr, Oregon, WI 53575
  • /2

    $449,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    462 New Hampton Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    462 New Hampton Dr, Oregon, WI 53575
  • /54

    $450,000

    $15K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,547 Sq Ft

    855 Clover Ln, Oregon, WI 53575

    Looking for a well-maintained ranch home in a great neighborhood? This 3 bed/3 bath home on 1/3 acre lot in the Oregon School District is it! The main level boasts an updated eat-in kitchen with granite counters and SS appliances, LVP flooring throughout much of the home, and newer carpet in the sizable living room and bedrooms. A substantial primary suite with a private full bath w/skylight,

    Jason Holtman RE/MAX Preferred

    855 Clover Ln, Oregon, WI 53575
  • /37

    $415,000

    • 3 Beds
    • 3 Baths
    • 1,855 Sq Ft

    746 Thompson Dr, Oregon, WI 53575

    Showings 8/7. Exceptionally maintained 3 BR/ 3BA ranch situated on a quaint pond in Oregon! Step inside to discover a main level featuring a convenient mudroom with washer/dryer and access to 2 car garage. Kitchen has a breakfast bar and stainless steel appliances, and lot of pantry space. Cozy living room with a stone encased gas fireplace. Enjoy the deck overlooking pond and and large yard. The

    Liz Slaby Real Broker LLC

    746 Thompson Dr, Oregon, WI 53575
  • /12

    $1,375,500

    • 4 Beds
    • 1.5 Baths
    • 1 Sq Ft

    6050 County Highway M, Oregon, WI 53575

    Rare opportunity to own a piece of local history. Anchored by a farmhouse dating back to approximately 1880, this Farm 88 property offers endless possibilities for a private country retreat, hobby farm, recreational getaway, or future homestead. Several existing outbuildings provide functional space for storage, workshops, livestock, equipment, or creative repurposing. The land features a

    Kristine Jaeger Sprinkman Real Estate

    6050 County Highway M, Oregon, WI 53575
  • /30

    $379,900

    Open Sat 11AM - 12PM
    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    530 Lexington Dr Unit 8, Oregon, WI 53575

    Here we have a beautifully updated stand alone unit where you will receive a level of independence rare for condos. The newly finished basement creates an additional bonus room(theater) and flex room(workout room), custom tiled bathroom adding plenty of additional living space to enjoy. The stamped concrete Patio backs up to the Hawthorne breeze(Green space) and wooded city owned property you

    Robin St Clair EXIT Realty HGM

    530 Lexington Dr Unit 8, Oregon, WI 53575
  • /90

    $6,000,000

    • 4 Beds
    • 3.5 Baths
    • 4,515 Sq Ft

    2797 Lalor Rd, Oregon, WI 53575

    Rarely does an estate of this magnitude and architectural significance come to market. Set against the rolling, pastoral beauty just outside Madison, Five Bridges Farm is an extraordinary 80-acre self-contained sanctuary designed for the equestrian, the outdoor enthusiast, and the architectural purist. This pristine landscape weaves together spring-fed creeks, ancient hardwood canopies, and

    Tim Vitense Keeps. Real Estate

    2797 Lalor Rd, Oregon, WI 53575
  • /80

    $1,599,999

    • 4 Beds
    • 4.5 Baths
    • 5,263 Sq Ft

    2395 White Oak Trail, Oregon, WI 53575

    In delayed, coming soon! 8/6

    Imani Jones EXIT Realty HGM

    2395 White Oak Trail, Oregon, WI 53575
  • /55

    $619,500

    • 4 Beds
    • 5 Baths
    • 3,664 Sq Ft

    396 Robinson Rd, Oregon, WI 53575

    This spacious side-by-side duplex presents a flexible layout with two distinct residences. The larger unit lives much like a single-family home, with a vaulted living room, generous kitchen and dining spaces, screened porch, private primary bath and a finished lower level for additional living space. The adjoining unit has comfortable living and dining areas, along with an unfinished basement for

    Gerardo Jimenez Sprinkman Real Estate

    396 Robinson Rd, Oregon, WI 53575
  • /40

    $469,900

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,718 Sq Ft

    137 Lynne Trail, Oregon, WI 53575

    Tucked into a quiet Oregon neighborhood, this home offers green space views and thoughtful updates throughout. This 3BR, 2.5BA home features a cozy sunken family room with fireplace, generous natural light, and an easy-flowing layout for daily living and entertaining. Updates include a new roof in 2025, high quality composite windows throughout, new carpeting and fresh paint on the main level.

    Heather Taylor MHB Real Estate

    137 Lynne Trail, Oregon, WI 53575
  • /63

    $435,000

    • 4 Beds
    • 2 Baths
    • 2,410 Sq Ft

    145 Dewey St, Oregon, WI 53575

    If you're looking for a beautiful blend of yesteryear charm & modern updates, don't miss this Oregon charmer! Gorgeous woodwork, stained glass, exposed brick and hardwood floors create a warm, memorable space. An updated kitchen is the true heart of the home and is as functional as it is inviting - with room to gather, tons of counter space & storage (don't miss the huge pantry!). Two large

    Andrea Bolan Relish Realty

    145 Dewey St, Oregon, WI 53575
  • /15

    $424,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft

    1035 Merri-Hill Dr, Oregon, WI 53575

    The Pilot Home (504 Greenview Preserve) features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and

    Todd Pierce Stark Company, REALTORS

    1035 Merri-Hill Dr, Oregon, WI 53575
  • /39

    $488,000

    • 3 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    425 Landover Dr, Oregon, WI 53575

    Step inside this beautifully updated and excellently maintained home featuring a vaulted, open-concept main level designed for comfortable living and effortless entertaining. The remodeled kitchen showcases rich cherry cabinetry, quartz countertops, a spacious island, and a stylish tile backsplash, while luxury vinyl plank flooring flows throughout the main living areas. A striking stone gas

    Heather Taylor MHB Real Estate

    425 Landover Dr, Oregon, WI 53575
  • /17

    $399,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,481 Sq Ft

    1043 Merri Hill Dr, Oregon, WI 53575

    This Emerson home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable

    Veronica Isham Stark Company, REALTORS

    1043 Merri Hill Dr, Oregon, WI 53575
  • /2

    $439,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    457 Savannah Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    457 Savannah Dr, Oregon, WI 53575

Why Live in Oregon

Oregon, Wisconsin, is a small city located 11 miles south of downtown Madison, offering suburban comforts with a small-town feel. Surrounded by farmland, Oregon features a historic Main Street with charming brick buildings and local businesses. Residents can enjoy a variety of dining options, such as Firefly Coffeehouse for pastries and coffee, Sonny’s Kitchen for homestyle meals, and the Wine Reserve for evening drinks. The city is home to highly rated schools in the Oregon School District, including Prairie View Elementary, Rome Corners Intermediate, and Oregon High. Housing in Oregon ranges from established ranch-style homes and large Foursquares near Main Street to contemporary homes in new subdivisions with spacious lots. Oregon is safer than the national average, providing a secure environment for families. For outdoor activities, Lerner Conservation Park offers a scenic 2-mile paved path, while Kiser Fireman’s Park features sports facilities including baseball diamonds and tennis courts. Golf enthusiasts can visit the Legend at Bergamont, and pet owners can take their dogs to Jon Blanchard Dog Park. Despite limited biking infrastructure, residents can easily commute to Madison in about 20 minutes, making Oregon a convenient location for those working in the city.

Single Family Home Price Trends

Median Home Price
$486,500
Median 3-Bedroom Home Price
$442,450
Median 4-Bedroom Home Price
$625,790
Median 5-Bedroom Home Price
$824,500
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