Oregon, WI Homes

• 

  

  

  /70

  $1,200,000

  • 5 Beds
  • 6 Baths
  • 5,729 Sq Ft

  670 Inverness St, Oregon, WI 53575

  Welcome to resort-style living in this stunning 5-bedroom, 6-bathroom custom home overlooking the 10th hole at The Legends at Bergamont. Designed for both everyday comfort and unforgettable entertaining, this home offers a perfect blend of elegance and function. Inside, you’ll find an updated chef’s kitchen, a spacious living room with a custom-built entertainment center, a dedicated home office,

  

  Sarah Gabrielse

  Devout Real Estate Group, LLC

  (608) 420-5980

  670 Inverness St, Oregon, WI 53575
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• 

  

  

  /32

  $2,040 - $2,405 per month

  Bergamont Townhomes

  2-3 Beds

  225 Bergamont Blvd, Oregon, WI 53575

  Townhomes with an open floor plan in scenic Oregon, WI. With a world-class golf course, exclusive clubhouse and swimming pool right down the road, you're just minutes from a lifestyle of luxury.

  225 Bergamont Blvd, Oregon, WI 53575
• 

  

  

  /20

  $236,000 Sold Jun 20, 2025

  • 1,142 Sq Ft
  • $207/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  496 Cledell St Unit 4, Oregon, WI 53575

  Spacious, Move-In-Ready Condo with 2 Bedrooms and 2 Full Bathrooms! Enjoy a large pantry in the kitchen, vaulted ceilings, and a cozy gas fireplace. Well-maintained and meticulously cared for. Features include a private balcony, attached private garage / storage, and in-unit laundry. Smoke-free property. Great location in quiet area ~ Just a short walk to parks, restaurants, and shopping. Easy

  Donald White First Weber Inc

  496 Cledell St Unit 4, Oregon, WI 53575
• 

  

  

  /30

  Est $382,304 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft

  474 Ithaca Ct, Oregon, WI 53575

  474 Ithaca Ct, Oregon, WI 53575
• 

  

  

  /20

  $2,550,000

  • 4 Beds
  • 1.5 Baths
  • 2,628 Sq Ft

  4890 County Road A, Oregon, WI 53575

  34 beautiful acres right outside of the Village of Oregon, hemmed in by parks and greenspace. With hardwood floors, the original mid-century styled kitchen and study, radiant heat, geothermal, and efficiency upgrades, add some cosmetic touches and the property will stand out! With mineral rights below the soil and the potential for alternate uses of the property in the future, this is one to

  

  Jean Armendariz-Kerr

  Mode Realty Network

  (608) 344-6238

  4890 County Road A, Oregon, WI 53575
• 

  

  /22

  $836 - $1,925 per month

  Prairie Brook

  Studio-3 Beds

  917 Janesville St, Oregon, WI 53575

  Nestled in the Village of Oregon, the Prairie Brook Apartments are in a great location for families, young professionals, retirees and more! There are many local parks nearby and the Jon Blanchard Dog Park is just minutes from your door. This new construction complex features many desirable amenities including on-site office, fitness center, community room, gazebo, grilling area and more. Each

  917 Janesville St, Oregon, WI 53575
• 

  

  /81

  $1,190,000 Sold Jun 20, 2025

  • 5,261 Sq Ft
  • $226/SF
  • 17 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1999

  6175 Oak Hollow Dr, Oregon, WI 53575

  Welcome to luxury living in the highly sought-after Hampton Hills neighborhood. This stunning home sits on a private 1-acre lot with breathtaking sunset views and a beautifully remodeled main level designed for both style and function. The open-concept layout features a dramatic two-story living room, chef’s kitchen with high-end appliances, and a serene main floor primary suite. Step into your

  Juliana Van Eck Sprinkman Real Estate

  6175 Oak Hollow Dr, Oregon, WI 53575
• 

  

  /32

  Est $425,739 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,051 Sq Ft

  494 Ithaca Ct, Oregon, WI 53575

  494 Ithaca Ct, Oregon, WI 53575
• 

  

  /50

  $849,900 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft

  1451 Storytown Rd, Oregon, WI 53575

  Incredible 20 acre horse farmette with 10 acres of pasture and 10 of woods. 5 stall horse barn and an 8,000 sq foot riding arena/outbuilding. This unique property was built in 1989 with aging in place in mind - first floor primary suite, walk in closet, barrier free entry from the garage, steel roof, and newer siding. The outbuildings are in incredible condition making for an easy move-in ready

  

  Jean Armendariz-Kerr

  Mode Realty Network

  (608) 546-9341

  1451 Storytown Rd, Oregon, WI 53575
• 

  

  /40

  $1,995 per month

  The Flats - 100 (Building 4)

  2 Beds

  100-180 Peterson Trail, Oregon, WI 53575

  Brand new one and two bedroom apartments located in Oregon. Each unit is equipped with stainless steel appliances, granite countertops and your own washer and dryer. The units have large open floor plans, walk in closets, 9 foot ceilings (2nd floor offers vaulted ceilings), and many more upgrades. Units also include a private entrance and a one car garage.Pet friendly, Pet fee and

  100-180 Peterson Trail, Oregon, WI 53575
• 

  

  /43

  $415,000 Sold Jun 20, 2025

  • 1,951 Sq Ft
  • $213/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1910

  159 State St, Oregon, WI 53575

  Showings begin 4/18 @ 5pm. Stylish home, just blocks away from Oregon’s charming downtown area, with restaurants, shopping, coffee shops, parks, and Oregon Community Pool. The fantastic layout provides a great flow for entertaining and socializing. Relax at the end of the day on your spacious deck overlooking the backyard, perfect for summer BBQs and friendly outdoor gatherings. You’ll love this

  Dan Chin Homes Team Real Broker LLC

  159 State St, Oregon, WI 53575
• 

  

  /8

  Est $358,677 Not Listed For Sale

  312 Kassander Way, Oregon, WI 53575

  312 Kassander Way, Oregon, WI 53575
• 

  

  /67

  $875,000

  • 5 Beds
  • 3.5 Baths
  • 3,366 Sq Ft

  963 Brynhill Dr, Oregon, WI 53575

  Beautifully maintained Alterra Design Home in The Legend at Bergamont! This spacious 2-story offers an open main level with a gourmet kitchen, walk-in pantry, and high-end KitchenAid SS appliances. The informal dining area flows into a 2-story great room with a gas fireplace and custom built-ins. A flex room, screened porch, mudroom with custom lockers, and half bath complete the main floor.

  Ryan Oliversen Bunbury & Assoc, REALTORS

  963 Brynhill Dr, Oregon, WI 53575
• 

  

  /37

  $1,395 per month

  880 N Main

  1 Bed

  880 N Main St, Oregon, WI 53575

  Available now! These thoughtfully designed apartments have a lot to offer including key fob entry, full kitchens with stove, refrigerator, dishwasher, and microwave, private balcony, full bathrooms, and in-unit washer and dryer. No need to worry about parking, as off-street parking is available for your convenience.

  880 N Main St, Oregon, WI 53575
• 

  

  /75

  $1,249,000 Sold Jun 19, 2025

  • 4,133 Sq Ft
  • $302/SF
  • 76 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 2015

  659 Rinpoche Ln, Oregon, WI 53575

  Luxury golf course living close to Madison, nestled on the 13th tee box, this exquisite home offers unparalleled blend of luxury, comfort & smart living. Thoughtfully upgraded w/ high-end finishes, the home boasts tall ceilings & expansive windows, filling the freshly painted interior with natural light. Enjoy the warmth of two fireplaces or unwind in the custom traditional sauna. The screened

  Sandy Joudrey NextHome Midwest

  659 Rinpoche Ln, Oregon, WI 53575
• 

  

  /8

  Est $449,213 Not Listed For Sale

  306 Kassander Way, Oregon, WI 53575

  306 Kassander Way, Oregon, WI 53575
• 

  

  /55

  $1,149,000

  • 4 Beds
  • 4.5 Baths
  • 4,504 Sq Ft

  863 Augusta Dr, Oregon, WI 53575

  Welcome to this exquisite 2-story home boasting over 4500 square feet of thoughtfully designed living space. With 4 spacious bedrooms and 4.5 baths, this home offers an ideal blend of elegance, comfort, and functionality. Soaring vaulted ceilings and an open floor plan creates a grand atmosphere. The second-floor catwalk adds a dramatic touch, overlooking the main living area. Gourmet kitchen

  Julie Larson First Weber Inc

  863 Augusta Dr, Oregon, WI 53575
• 

  

  /33

  $1,150 - $1,850 per month

  The Commons of Foxboro

  Studio-3 Beds

  218 Wolfe St, Oregon, WI 53575

  **$1,000 OFF OF FIRST MONTHS RENT WITH A 12 MONHT LEASE!**Tenant pays for gas, electric, internet & cable.Dogs (up to 40lbs) and cats are welcome for $40/month per pet and a $250 refundable pet deposit.**The appearance of the unit may vary slightly. We strongly encourage viewing the unit in person before signing any lease agreement. Opting to skip a showing is entirely at

  218 Wolfe St, Oregon, WI 53575
• 

  /2

  $397,900 Sold Jun 16, 2025

  • 1,480 Sq Ft
  • $269/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  1081 Tundra Ave, Oregon, WI 53575

  This Emerson home features a smart, open layout and checks off all your boxes. 3 bedrooms, 2.5 baths with locally crafted cabinetry, and painted trim and doors throughout. Gourmet kitchen w/ island and stainless appliances, plus a large pantry for added storage. Owner’s Suite has a private bath, walk-in closet, and tray ceiling. 2-car garage. Retreat to your patio for some R&R. To top it off,

  trey Recknor Stark Company, REALTORS

  1081 Tundra Ave, Oregon, WI 53575
• 

  

  /56

  Est $690,772 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  366 Kassander Way, Oregon, WI 53575

  366 Kassander Way, Oregon, WI 53575
• 

  

  /27

  $666,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,907 Sq Ft

  Raleigh, Oregon, WI 53575

  A foyer leads directly into the double-height living and dining room of this two-story residence, while the family room, kitchen and breakfast area share a spacious open floorplan toward the back of the home. Ideal for at-home work is a quiet study. The top level hosts all four bedrooms, including the sprawling owner’s suite with a private full-sized bathroom and two walk-in closets for ample

  Lennar

  Raleigh, Oregon, WI 53575
• 

  

  /19

  $1,225 per month

  Twin Peaks

  1 Bed

  881-889 Janesville St, Oregon, WI 53575

  Beautiful townhomes located in Oregon WI. Easy access to the HWY, yet in a quiet area. All units come with attached 1.5 car (Shotgun Style) garage.No pets.**The appearance of the unit may vary slightly. We strongly encourage viewing the unit in person before signing any lease agreement. Opting to skip a showing is entirely at the renter's discretion.**

  881-889 Janesville St, Oregon, WI 53575
• 

  

  /83

  $600,000 Sold Jun 13, 2025

  • 1,770 Sq Ft
  • $339/SF
  • 17 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1960

  4287 Oak Hill Rd, Oregon, WI 53575

  Fantastic horse farm! Mid-century ranch-style house w/ fireplace, 3-season room, front & rear decks, expansive views overlooking the pastures and backs to woods. Farm has two barns and outbuilding. Barn #1, built 1973, 51x72, 10 box stalls, 50x60 indoor riding arena, water, tack room, grooming area, workroom, and tack room/lounge which is being used as small living quarters. Barn #2, built 1971,

  Kari Manson Hvam Sprinkman Real Estate

  4287 Oak Hill Rd, Oregon, WI 53575
• 

  

  /7

  Est $760,504 Not Listed For Sale

  426 Kassander Way, Oregon, WI 53575

  426 Kassander Way, Oregon, WI 53575
• 

  

  /17

  $609,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft

  Ridgefield, Oregon, WI 53575

  This single-story home is designed to offer low-maintenance living and great space to grow. A modern open layout is situated among the large family room, kitchen and breakfast room, with an attached covered patio to offer seamless indoor-outdoor living. Found off the foyer are two secondary bedrooms, while tucked away in the back corner for maximum privacy is the sprawling owner’s suite with a

  Lennar

  Ridgefield, Oregon, WI 53575
• 

  

  /29

  $1,975 per month

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft
  • Townhouse for Rent

  833 Peace Unit 833, Oregon, WI 53575

  Luxury 3-bedroom, 2 1/2 bath townhomes for rent. 1,400 sq. ft. of living space, a two car garage, laundry hookups and storage on ground floor. Like-new apartment! Main floor has 9 foot ceilings, a huge living-dining room with gas fireplace, balcony, and fully appointed kitchen with breakfast bar, and a half bath. The second floor has a master suite with full bath and walk-in closet, and two more

  833 Peace Unit 833, Oregon, WI 53575
• 

  

  /23

  $340,000 Sold Jun 12, 2025

  • 1,911 Sq Ft
  • $178/SF
  • 4 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1949

  512 Jefferson St, Oregon, WI 53575

  Charming Cape Cod in an ideal location! Walking distance to the new Oregon Public Library, new post office, Keller Alpine Meadows Park, and just 5 short blocks from downtown Oregon's restaurants, shops and Kwik Trip! This three bedroom home has newer windows, roof, siding and a new water heater in 2025. Large two-car detached garage and fenced in back yard. Showings start at 10:00AM on Thursday

  Jeffrey Roberts JB Roberts Jr & Company

  512 Jefferson St, Oregon, WI 53575
• 

  

  /7

  Est $317,000 Not Listed For Sale

  449 Kassander Way, Oregon, WI 53575

  449 Kassander Way, Oregon, WI 53575
• 

  

  /23

  $562,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  Siena II, Oregon, WI 53575

  Designed for low-maintenance living, this single-story home showcases an open-concept kitchen that overlooks the family room and dining room in an ideal set-up for seamless transitions between spaces. At the front of the home are two secondary bedrooms to provide restful retreats, while in a back corner is the private owner’s suite with a full-sized bathroom. A two-car garage offers versatile

  Lennar

  Siena II, Oregon, WI 53575
• 

  

  /33

  $555,000 Sold Jun 11, 2025

  • 2,320 Sq Ft
  • $239/SF
  • 12 Days On Market

  • 3 Beds
  • 1.5 Baths

  2024 Sand Hill Rd, Oregon, WI 53575

  Showings begin Friday, 4/18. Tucked back on a quiet road on 10.39 Acres is this charming farmhouse. Views of Grass lake across to the west and Government land behind the property to the East. Hardwood floors, Pocket Door. Large Family room, 1st fl. Laundry, walk-up attic could be finished off. Outbuildings (old dairy barn, loafing shed, machine shed, det. 2 c. garage. *See list of updated in

  Julie Bollig RE/MAX Preferred

  2024 Sand Hill Rd, Oregon, WI 53575
• 

  

  /7

  Est $269,006 Not Listed For Sale

  437 Kassander Way, Oregon, WI 53575

  437 Kassander Way, Oregon, WI 53575
• 

  

  /27

  $611,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,607 Sq Ft

  Wren, Oregon, WI 53575

  This two-story home combines modern comfort with convenience. Found off the foyer is a flex room for versatile needs, followed by a cohesive open main living area with direct access to the backyard for indoor-outdoor activities. In a private corner of the first floor is a study ideal for at-home work. Upstairs are three secondary bedrooms and the spacious owner’s suite with a full-sized bathroom.

  Lennar

  Wren, Oregon, WI 53575
• 

  

  /83

  $724,000 Sold Jun 10, 2025

  • 3,376 Sq Ft
  • $214/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2016

  956 Brynhill Dr, Oregon, WI 53575

  Well-appointed ranch w/quality finishes, custom details, + thoughtful layout perfect for everyday living & entertaining. Gorgeous hrdwd floors thru-out open-concept ML, highlighted by coffered ceiling + stylish tiled fireplace surround in spacious great room. Kitchen seamlessly connects to living space, featuring quality cabinetry, granite counters + eat-in area-access to Trex deck. ML Primary

  Jennifer Evenson Sprinkman Real Estate

  956 Brynhill Dr, Oregon, WI 53575
• 

  

  /18

  Est $899,361 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,465 Sq Ft

  427 Kassander Way, Oregon, WI 53575

  427 Kassander Way, Oregon, WI 53575
• 

  

  /20

  $559,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft

  Rutherford II, Oregon, WI 53575

  This new single-story home provides the convenience of having everything laid out on one level. It features an open design among the living room, dining room and kitchen, which has a large center island. The covered front porch and back patio enhance outdoor enjoyment. Included are two secondary bedrooms and an owner’s suite tucked in a back corner of the home for privacy.

  Lennar

  Rutherford II, Oregon, WI 53575
• 

  

  /79

  $1,230,000 Sold Jun 10, 2025

  • 4,914 Sq Ft
  • $250/SF
  • 11 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2013

  935 Carnoustie Way, Oregon, WI 53575

  This exquisite ranch home is a true blend of luxury and comfort offering breathtaking sunset views overlooking the scenic Bergamont Golf Course. Immaculately maintained & thoughtfully designed w/ tasteful, timeless, luxurious touches: 3 Car heated garage + 4th for golf cart/workshop, kitchen features top-of-the-line Sub-Zero and Wolf appliances, Amish Cabinetry & Granite countertops w/a seamless

  Juli Stinson Restaino & Associates

  935 Carnoustie Way, Oregon, WI 53575
• 

  

  /48

  Est $834,406 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,183 Sq Ft

  419 Kassander Way, Oregon, WI 53575

  419 Kassander Way, Oregon, WI 53575
• 

  

  /24

  $601,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft

  Townsend, Oregon, WI 53575

  This two-story home combines comfort with convenience. Off the foyer is a versatile flex room well-suited for hosting guests, while down the hallway is a cohesive open layout among the kitchen, dining room and family room. The second level is occupied by all four bedrooms to provide restful retreats, including the spacious owner’s suite with a private full-sized bathroom. Completing the home is a

  Lennar

  Townsend, Oregon, WI 53575
• 

  

  /42

  $535,000 Sold Jun 06, 2025

  • 2,725 Sq Ft
  • $196/SF
  • 8 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1996

  465 Landover Dr, Oregon, WI 53575

  This well maintained updated ranch with split bedroom layout is looking for a new family to call it Home. Ideal layout includes large sunny eat-in kitchen with cherry cabinets, hardwood maple floors, solid surface countertops, pantry, island w/ seating & newer stainless appliances (2021), vaulted living room with vaulted ceiling and gas fireplace with stone surround overlooking full fenced

  Teresa Duerst Haufle Stark Company, REALTORS

  465 Landover Dr, Oregon, WI 53575
• 

  

  /20

  Not Listed For Sale

  L511 Leeward Ln, Oregon, WI 53575

  L511 Leeward Ln, Oregon, WI 53575

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