34 houses for sale in Town of Oregon

A rare opportunity to own a luxury retreat on +/-13ac just outside Oregon, WI. This secluded estate is surrounded by mature forest and abundant wildlife, offering a peaceful country feel minutes from town. The home features a chef's kitchen with Wolf and Sub-Zero appliances, a grand entry, and refined living spaces with uninterrupted views of nature. The finished lower level includes its own kitchen, full bath, and walkout to a paver patio. This property is perfect for entertaining or escaping the hustle of daily life. Two impressive outbuildings, a 56x40 and a 30x24, provide exceptional versatility, including a batting cage and indoor basketball court. A one-of-a-kind property blending privacy, recreation and luxury. Schedule your private showing today. Open House. Sat and Sun!

Perched atop a scenic hill on 8+ beautiful acres, this property offers a rare opportunity to embrace country living just 15 minutes outside of Madison! Bring your animals and embrace the hobby-farm lifestyle with fenced pastures and a 32' x 24' pole barn complete with horse stables. The 3 bed/2 bath ranch home features a functional layout with two inviting living spaces, a spacious primary bedroom with en suite bath, and an unfinished lower level offering exciting potential for future living space. Whether you're dreaming of a hobby farm or a peaceful rural retreat for your family, this property offers the space, setting, and potential to make it your ownâall in the highly sought-after Oregon School District! Put down roots and enjoy the best of country living!

Tucked into the wooded Ravenoaks neighborhood, this spacious 4-bedroom, 2.5-bath contemporary style home offers privacy, mature trees, and a generous floor plan on a stunning 0.74 acre lot. The home features tall vaulted ceilings, a dramatic great room with an eye-catching wood burning fireplace, large bedrooms, primary suite with walk-in closet, loft, den/office, and finished lower level rec space. Enjoy the peaceful outdoors from the deck surrounded by mature hardwood trees, Raspberry bushes, an herb garden, and tons of wildflowers. The hardwoods provide a natural source of firewood for cozy evenings by the fireplace. A 3-car attached garage adds plenty of room for vehicles, hobbies, and storage. This tranquil setting remains conveniently close to Oregon's everyday necessities, including shopping, dining, schools, and more, with easy access to Madison

Inviting home on just under 4 acres within the top-rated Oregon School District, just 20 minutes from downtown Madison. The fantastic open layout creates an easy flow for entertaining, gathering with friends, and everyday living. Youâll love the character throughout, with original accents, exposed brick, gorgeous hardwood floors, and stylish finishes. Spend warm weather days on the patio taking in peaceful views of the surrounding landscape, then make the most of your 3.92 acres with a vegetable garden, apple orchard, chickens, or even your own hobby farm. The possibilities are wide open, whether you want room to roam, space for outdoor projects, or a place to create something all your own. The spacious 30x40â heated 4+ car garage offers plenty of room for vehicles, equipment, a boat, or your own workshop. A rare opportunity to enjoy country living with Madison just minutes away

Welcome to this beautifully updated Oregon ranch offering over 2,100 finished square feet and a long list of improvements inside and out! The main level features LVP and wood flooring throughout, updated trim and light fixtures, custom closets, and an updated kitchen with granite countertops, custom cabinetry, and a new stove. The main bath features a tiled tub, granite counters, and a custom dual vanity. The finished lower level adds incredible living space with a spacious family room, an amazing walk-in tiled shower, convenient backyard access, and a large storage closet. Outside, enjoy the large deck and beautiful views overlooking the adjacent park and green space. Major updates include new siding, driveway, gutters and downspouts, furnace under 2 years old, a new pressure tank in 2026, and a well pump approximately 3-4 years old. Located on a quiet dead-end street with plenty of space to relax, entertain, and enjoy everything Oregon has to offer!

Enjoy room to spread out inside and out! Set on approximately 2.7 acres, this 4-bedroom, 2-bath bi-level offers over 2,200 square feet of finished living space surrounded by your own peaceful retreat. Wonderful walking paths create a serene setting with plenty of room to explore and enjoy the outdoors. Inside, the versatile layout features three bedrooms on the main level, convenient main-floor laundry and additional finished living space below, including a fourth bedroom. A unique spiral staircase adds a fun architectural touch and provides a second connection between levels in addition to the homeâs main staircase. With comfortable living spaces on both levels, an attached 2-car garage and nearly three acres to call your own, this property offers a wonderful combination of space, character and tranquility, all just minutes from Brooklyn and Oregon!

Priced below assessed value! This spacious ranch invites you to relax on 4.21 acres located on a peaceful cul de sac in a rural subdivision. A large open great room invites you to just come inside, sit by the fireplace, and look out the massive windows. Others might want to relax on the screened porch for a quick dip in the hot tub while overlooking the woods. The kitchen includes tons of cabinets surrounding the functional island, bright new tile, and updated fixtures. The primary suite feels like a relaxing spa with a large soaking tub, new tile shower, and stylish updates around the double vanity. The lower level makes entertaining easy around the large basement bar, relaxing by the pellet stove, or walk directly outside private deck. Thereâs room for a home office or workout area. The two legal bedrooms include large windows to bring in natural light. I could ramble on, but this rambling ranch speaks for itself. Schedule your showing today!

Built in 2020, this accessible ranch duplex in the Village of Oregon is within walking distance of the library and shopping and across the street from walking/biking trails. The main floor features a zero entry/no step in from the garage, an open concept floor plan with vaulted ceilings, and 2 bedrooms. The spacious lower level offers a large rec room, a 3rd bedroom, and plenty of storage. Catch the sunrise on the large east facing deck or enjoy the shade on a summer afternoon, overlooking the adjacent green space. Showings Start 9/11

Show 8/21. Beautifully updated 5-bedroom, 3-full-bath home in Oregon, WI! The main level features vaulted ceilings, new LVP flooring, a spacious kitchen with stainless steel appliances, granite counters, and island with breakfast bar, plus a formal dining room and convenient mudroom/laundry. The primary suite offers tray ceilings, dual walk-in closets, a tiled walk-in shower, and dual vanity. Finished lower level includes a rec room, wet bar, 2 bedrooms, and full bath. Enjoy the Trex deck, spacious yard, and attached oversized 2-car garage (30X25) with epoxy flooring! Conveniently located near downtown Oregon, Oregon Public Library, and multiple parks and walking trails!

Custom feel + thoughtful updates + meticulous maintenance define this exceptional ranch home. Thoughtfully designed + ready to move in, this 4-bedroom split-design, 3-bath home features 9' ceilings, abundant natural light + a spacious finished lower level. The inviting kitchen offers granite countertops, center island, pantry + new appliances, opening to the great room with newly refinished hardwood floors, cozy carpet insert + gas fireplace. The primary suite offers a large walk-in closet, double vanity + tiled walk-in shower. Lower level highlights a generous family room, 4th bedroom, full bath, wet bar with custom walnut countertops + ample storage. Enjoy the upgraded low-maintenance deckâperfect for relaxing + entertaining without the upkeep while the 3-car garage features an epoxy floor. Updates include roof, water heater, garage doors/motors, washer/dryer + refinished flooring. Meticulously maintained with custom touches throughout, this home is ready to move in + enjoy!

Beautiful ranch home offering the perfect blend of comfort, convenience, and outdoor enjoyment. Stunning hardwood floors welcome you inside, while the remodeled kitchen is ready for everyday living and entertaining alike. Unwind in the spa-like bathroom, designed to feel like your own private retreat. Outside, enjoy a generous lot featuring cherry trees, apple trees, plum tree, raspberry bush, and plenty of room to garden, play, or relax. The new maintenance-free deck is perfect for summer gatherings and quiet mornings alike. A dedicated theater room, complete with all equipment included, provides the ultimate movie-night experience. The oversized 3-car garage offers ample storage and workspace. Conveniently located near shopping, restaurants, parks, and everyday amenities, this home combines thoughtful updates, beautiful outdoor spaces, and exceptional value. Roof'20/'21, Water Heater'21, Kitchen Appliances'22, Furnace & A/C'23!

Set in Autumn Ridge. Oregon Subdivision this newer two-story has the light and flow buyers keep asking for. The open main level moves from a STUNNING granite kitchen with work island, breakfast bar and large pantry into a dining room crowned by a three-tier French vintage chandelier enhance by cathedral-ceiling + wrapped with sun-filled five windows leading to the patio and private fenced backyard. Settle in by the stone gas fireplace, pour a nightcap in the cocktail lounge/flex room, and drop everything in the custom rear-foyer mudroom area. Crisp white cabinetry and trim plus east and west-facing windows keep the whole house bright from morning to evening. Upstairs holds four bedrooms, two granite-topped full bathrooms and second-floor laundry + the GORGEOUS primary suite offers two walk-in closets & a private full bath w/tile walk-in shower! The lower level is ready to finish with 8'+ ceilings, two egress windows, and a bathroom stub-in

Showings to begin 10/1/26. If youâve been waiting for a lovely ½ acre home, with updates & a yard you'll want to spend all your time in, AND itâs on a quiet street 5 minutes from the beltline, this is the one! Lovingly maintained by the same owners for almost 40 years and it's time for new owners! Kitchen, both upstairs baths, all upstairs doors & flooring all new in the last 4 years â basement windows, well pump and whole house water filter new in 2026! On top of all that, the old septic drain field is still there and easily switchable with the current one if needed. Itâs a worry-free private oasis thatâs close to everything. Donât wait!

One Owner 3 bedroom 2 bath ranch in an established neighborhood that has been lovingly taken care of. Beautiful landscaping with outside patio that looks at mature trees. Sip your drink on the covered front porch and look at a sitting area under the trees and plantings that make you smile. Primary bedroom has its own bathroom and if new buyer wants to add on can purchase the parcel next door which belongs to this owner. Basement is unfinished and has amble room to make it your own. Home lives much larger than you think and you need to look at it to truly appreciate it

Country Living at it's very best! This 5+Acre Farmette is a dream come true. Whether you're a horse person, have prize cows, love to garden, or yearn for privacy and an incredible location, this is it! The open flow of the main level, is complimented by a full wrap around deck offering incredible views and privacy all in one! Cozy, comfortable, welcoming, are all adjectives that describe this beautiful property. You are adjacent to 200 Acres owned by the DNR, the Ice Age Walking Trails, pheasants, deer, and more. The outbuildings are immense (42'x100' & 26'x90'). Concrete (lg bldg) or dirt flooring. There are two (2) year round cattle waterers, three (3) fire hydrants (1 per outbuilding & 1 outside), two (2) private drives, a lean to for equipment storage and 2 stanchions within the smaller barn for horses and more. A covered awning area for farm animals exists on both buildings. Close to everything. 20 min. To Oregon/Verona or Madison. A rare opportunity. Don't miss it!

Well-maintained multi-story home in the Village of Oregon offering 3 bedrooms, 1.5 baths, and plenty of flexible living space. The inviting sunroom is a great place to relax, enjoy your morning coffee, or take in the changing seasons. A finished basement provides additional room for a rec area, home office, workout space, or hobbies. Numerous updates throughout the home add comfort and convenience while still leaving room to make it your own. Conveniently located near Oregon schools, parks, and community amenities, with easy access to downtown Oregon and the surrounding Madison area. A comfortable and functional home in a great village location

Welcome home to rural Brooklyn, where country charm meets small-town living just minutes from Oregon and an easy commute to Madison! Enjoy morning coffee on your private patio or evenings around the fire pit overlooking the neighboring cornfield for added privacy. The main level features 3 bedrooms, a full bath, an open kitchen with backyard access, and a spacious living room filled with natural light. The finished lower level offers a large rec room, 2 additional bedrooms, a second full bath, and plenty of storage. Located across the wayt from the elementary school, this home offers space, comfort, and a peaceful setting? Don't miss your chance to make it yours! UHP warranty included

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 living spaces offer a flexible floor plan and room for everyone to find their favorite spot in the home. Upstairs, a truly spectacular primary bedroom addition shines with vaulted ceilings, incredible natural light & and a large walk-in closet. If you love outdoor spaces, there are so many great options. A welcoming, lemonade-sipping front porch; a large, sunny deck; and a beautifully landscaped, fully fenced yard. Numerous updates, including windows, HVAC, and a newer garage! Incredible location. Walking distance to parks, schools, and downtown Oregon

Terrific 3 bedroom 2 bath home with a unique floorplan and new windows in 2022; eat-in kitchen with stainless steel appliances opens to great room with vaulted ceiling and new sliding glass doors leading to a patio overlooking the large backyard which is fully fenced and includes a storage shed; Lower level has a generous second family room with home office or 4th bedroom option; An extra level offers ample storage space; attached 2-car garage with attic; walk into town from this convenient location!

Calling all investors and owner occupants! Great opportunity to own a ranch-style side-by-side duplex in the heart of downtown Oregon. The 259 side has been gutted and completely redone, featuring new flooring and carpet, fresh paint, new doors and trim, new appliances and moreâmove-in ready for a new tenant or the perfect opportunity to live in one side while renting out the other! Major update with a new roof in 2024, plus one unit features a private, fenced-in backyard. Fantastic location just steps from schools, parks, pickleball courts, coffee shops, restaurants and everything downtown Oregon has to offer. Whether you're looking to add to your investment portfolio or offset your mortgage with rental income, this one is ready to go!

Privacy, nature & space right outside your front door! Nestled on a quiet dead-end street with private wooded park land & walking trails adjoining the property, this 4-bedroom, 3.5-bath home offers room to spread out in a beautiful, private setting. An inviting wraparound front porch welcomes you inside, where gleaming refinished hardwood floors run throughout the main level. The spacious layout features a bright front living room, formal dining room & kitchen with solid-surface counters, stainless steel appliances plus new double oven, fridge, dishwasher & microwave in 2022. The kitchen opens to a large family room with brick gas fireplace, while the four-season sunroom offers hardwood floors, vaulted ceilings & peaceful views. You'll love the tree-filled backyard that is peaceful and quiet. Major updates include a new roof in 2025, new insulated garage doors & furnace/A/C replaced in 2023. Desirable 3-car garage provides plenty of room for vehicles, toys, storage & more!

Charming 3-bedroom, 1-bath Brooklyn home with 1,276 sq ft, a 2-car detached garage, and a spacious village lot. Recent improvements include a professionally completed basement with a concrete floor and block work, an updated bathroom, newer flooring, a garage roof, and many replacement windows. The home also features updated electrical, municipal water and sewer, natural gas heat, a first-floor bedroom and full bath, and a level lot. Gas stove, refrigerator, washer, and gas dryer are included. A one-year home warranty is offered for added peace of mind

Beautifully updated ranch on nearly half an acre just minutes south of Oregon! Enjoy the feel of country living while still being close to everything Oregon has to offer. This 2-bedroom, 1-bath home has seen extensive recent updates, including a brand-new kitchen and bathroom, new siding (2026), and a new roof (2025). Inside, you'll find two nicely sized bedrooms and a comfortable, functional layout that's truly move-in ready. Outside, the. 449-acre lot offers plenty of space to relax, entertain, garden, or simply enjoy the scenic farm field views in both the front and back. A rare opportunity to enjoy an updated home, extra space, and a peaceful country setting. All just minutes from Oregon and an easy drive to Madison!

Inviting home in the heart of Brooklyn, WI, less than a 30 minute drive from downtown Madison. The fantastic open layout provides a great flow for entertaining and socializing. Relax at the end of the day on the patio overlooking the spacious, beautifully landscaped backyard, perfect for summer BBQs, outdoor dining, and crisp fall evenings around the fire roasting marshmallows. Spend your morning on the front porch sipping coffee and taking in the sights and sounds of the neighborhood. Stainless appliances, 1 car attached garage, tons of character throughout. Unparalleled opportunity and value!

Better than new, this 2023 Oregon ranch has been thoughtfully finished and upgraded since the day it was built. Step inside to an open, airy main level with wood floors that flow throughout and a great room made for gathering. The kitchen is a standout, featuring a large island, pantry, and quartz countertops, all opening naturally into the living and dining spaces. The primary suite is a true retreat with a walk-in closet and spa-like bathroom with walk-in shower. The main level laundry brings everyday convenience, and two additional bedrooms and a second full bath round out the level. Downstairs, the newly finished lower level adds serious value! The entire space is flooded with natural light, and features a rec room w/ wet bar, a fourth bedroom, a full bath, and an office. Out back, the patio with remote-control screened enclosure makes outdoor entertaining effortless, with easy access to patio and fenced yard. All this, with walking distance to library, parks and more!

Country beauty on a on 2.26 acres with a hidden pond! Well maintained home with hardwood flooring, newer kitchen appliances, new carpet in LL, updated Anderson windows, New Roof. 2026 & newer mechanicals. The large windows in the living room give the house a mid century vibe with volumes of natural light. The light woodwork and custom features add to the modern feel. 3 good-sized bedrooms & full bath on the main level. In the LL you will find a large exposed family room with a wood burning fireplace, full bath and a large screen porch opening to the back yard with a trail to a secluded pond and plenty of room for gardens, chickens, perennials! Large walk in laundry mud room/storage room. If you are looking for privacy and a country setting close to Madison, do not miss this move-in-ready home! Property is on the edge of the T-Oregon and Rutland

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 fireplace with a Heat & Glo insert creates a warm and inviting focal point. The spacious 19x17 addition offers flexible use as a sunroom, family room, or gathering space, complete with skylights that fill the room with natural light. Just beyond, the screened porch features versatile gel windows and is structurally designed to support an eight-person hot tub. All three BR and two full BA are conveniently located on the main level, along with main-floor laundry. The primary suite includes dual closets, an additional linen closet, and a private bathroom with a walk-in shower. New roof 2021

Showings start Sunday, August 16th. Two homes on 4 private acres just minutes to the Beltline and downtown Madison! Beautiful open and bright 4 bedroom, 3 bathroom home with an oversized 4 car attached garage nestled partially in the woods located far off the road. Plenty of room for your horses and guests! Enjoy the four season pool house that was built in 2023, which features 2 full bathrooms, 1 bedroom, large living/recreation area, kitchenette with a full size refrigerator, washer and dryer. Ample space for all of your toys and storage needs in the detached 48 x 30 five car garage/shed. Truly a one of a kind property that doesn't come available very often! Home needs some minor cosmetic updates and the in-ground pool would need repair if you choose to keep it. Easy to show

Discover this stunning new home, designed with both comfort and style in mind. Boasting 1968 square feet of living space, this modern residence offers a spacious and open floor plan. The interior features three bedrooms, three bathrooms, and luxurious low-maintenance LVP flooring throughout. The brand new kitchen is a dream, complete with sleek stainless steel appliances, custom cabinetry with soft-close, with a large center island. Cozy up by the gas-burning fireplace on chilly evenings. Located on a peaceful street, this home is great for families with children, offering easy access to nearby schools. Don't miss this opportunity to make this beautiful new home your own!

Showing Start Sat 7/25 at noon. This stunning ranch home delivers spacious, high-quality living with an excellent open floor plan. The home features 6 bedrooms and 4 full bathrooms. A highlight is the massive six plus car heated garage measuring over 1,500 square feet, providing exceptional space for vehicles, storage, and hobbies while remaining comfortable in all seasons. The main level includes a private suite in its own separate wing, along with a dedicated home office and workout room. The lower level boasts a large, sunny walkout basement complete with a custom home theaterâideal for entertaining and enjoyment. This property offers the privacy and presence of a gated-style home without the added taxes or ongoing fees. It is also barrier-free design directly from the garage. Set on beautifully landscaped grounds, the home is move-in ready and includes a 2-year UHP home warranty for added peace of mind. Combining thoughtful design, generous living space, and practical luxury