Oregon Homes under $750,000

Welcome to Oregon, Wisconsin – a charming village nestled in the heart of Dane County, where small-town charm meets modern convenience. With its picturesque landscapes and vibrant community, Oregon offers an inviting atmosphere that makes it an ideal place to call home.

Oregon is renowned for its friendly residents and a strong sense of community. The village boasts a rich history, with beautifully preserved architecture and a variety of local shops and eateries that create a warm, welcoming vibe. Residents enjoy access to an array of parks and recreational facilities, making it easy to embrace the great outdoors. Whether you’re hiking along the scenic trails or enjoying a picnic in one of the many parks, there’s always something to do in this delightful village.

For those seeking a home in Oregon, you’ll be pleased to find a diverse selection of properties available under $750,000. From charming single-family homes to spacious townhouses, there’s a perfect fit for every lifestyle and budget. Many of these homes feature modern amenities, beautiful gardens, and are located within close proximity to top-rated schools, shopping, and dining options.

Oregon’s strong sense of community is complemented by its excellent educational institutions, making it a fantastic place for families. With a blend of urban conveniences and rural tranquility, Oregon, Wisconsin, is not just a place to live; it’s a place to thrive. Discover your dream home in this idyllic village and experience the warmth and charm of Oregon for yourself!

Newest Oregon Homes under $750,000

$449,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status

Welcome to this 4 bed/3 bath ranch home located on a quiet cul-de-sac just minutes to everything Oregon has to offer & only 15 minutes to Madison! The open-concept main level features updated flooring & seamless flow between the kitchen, dining & living rm w/easy access to the backyard through a patio door. Updated kitchen offers white cabinetry, granite counters, tile backsplash, stainless steel appliance & large island w/breakfast bar. Spacious primary bedroom includes a large walk-in closet & private bath w/new flooring & extended vanity. Two additional bedrooms & a full bath complete the main level. The expansive lower level offers a large rec room with projector, 4th bedroom, full bath & two generous storage areas. Outside, enjoy a spacious backyard with an included hot tub, two storage sheds & pergola?ideal for relaxing & entertaining. Two-car attached garage adds convenience & storage. Great location and move-in ready!

431 Thomas Court, Oregon

Listing courtesy of Collective Real Estate Group.

$250,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

This 2-bed/2-bath condo is the best deal on the market in the Village of Oregon! 1st floor, zero-step entry from the garage and main entrance makes this condo accessibility-friendly. Laminate floors throughout most of the condo. New flooring in the bathrooms. Spacious primary bedroom features a walk-in closet and a walk-in shower in the attached bathroom. Huge pantry off the kitchen. Patio that backs up to a lovely, private green space. Move-in ready, yet room for your touches, if you're looking to put your personal stamp on your new home. 1-car attached garage. Hot water and water/sewer is included in the condo fee! Great location right off Highway 14 makes access to Madison so easy. Important amenities like schools, the senior center, a dog park, and Kwik Trip and Culver's are within walking distance. Homeownership is in reach with this great condo!

883 Park Street Unit 102, Oregon

Listing courtesy of Realty Executives Cooper Spransy.

$269,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Bright and spacious end unit condo offering the perfect balance of warmth and style! Private entry sets the tone for the feeling of home as you step into the open concept living/dining/kitchen areas that flow seamlessly together. 9-ft. ceilings and many windows for an abundance of natural light. Freshly painted and new carpet throughout. Kitchen features island with breakfast bar and has been thoughtfully updated with new countertops, sink and stainless appliances. Living area with cozy fireplace and walkout to private patio facing a backdrop of trees. Primary bedroom features en suite full bath and walk in closet. Additional bedroom and full bath. Convenient in-unit laundry. Attached 1-car garage that has direct entrance into condo. (New garage door-2026). Well-managed condo association, low monthly condo fees and healthy reserve fund. UHP home warranty for added peace of mind. Located in the sought-after Village of Oregon, move-in ready and waiting for you!

748 Dunn Avenue, Oregon

Listing courtesy of Stark Company, REALTORS.

$550,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status

WELCOME HOME! This spacious 5-bedroom, 3-bath ranch offers over 3000 square feet of finished living space & a wonderfully versatile floor plan. The main level features an inviting layout with a gas fireplace, convenient main-level laundry & plenty of room for everyday comfort and entertaining. The finished walk-out lower level offers a separate living space, offering a family room, second kitchen, full bathroom, 2-bedrooms & an office, along with its own private exterior entrance. This flexible arrangement is ideal for extended family, guests, multigenerational households, a private work from home setup or simply extra room to spread out. Outside, enjoy the fenced backyard and peaceful setting. An attached 2 car garage adds everyday convenience. With generous room throughout, an exceptionally versatile lower level and a desirable Oregon location, this home offers possibilities that are hard to find. ONE YEAR, ULTIMATE HOME WARRANTY INCLUDED

875 Merri-Hill Drive, Oregon

Listing courtesy of First Weber Inc.

$449,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Showings Begin 10-15-2026 - Welcome home to this beautiful 3-bedroom, 2-bath property in the desirable Hickory Estates neighborhood. The spacious kitchen and dinette area offer plenty of room for everyday living and feature a walkout to the deck, perfect for outdoor dining and entertaining. Enjoy the large fenced backyard with ample space for recreation, gardening, or relaxing. The inviting living room provides plenty of natural light and easy access to outdoor living areas, while the cozy family room features a wood-burning fireplace, creating the perfect gathering space for family and friends. The spacious primary bedroom offers a comfortable retreat at the end of the day. Ideally located directly across from a park and just minutes from downtown Oregon, this home also provides convenient access to the community's extensive paved walking trails. Combining comfort, space, and a fantastic location, this home is ready for its next owner to enjoy. New Roof & Siding 2025, New A/C 2026

381 Cherry Wood Drive, Oregon

Listing courtesy of Bunbury & Assoc, REALTORS.

$297,500

3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

Welcome home to this well-maintained condo in the desirable community of Oregon! This inviting property offers comfortable living with the convenience of an attached one-car garage and a practical layout with plenty of natural light and comfortable everyday living areas. Enjoy the ease of condo living while still having the benefits of your own private garage and additional basement space. Conveniently located in Oregon with easy access to local shopping, dining, parks, schools, and nearby Madison. A great opportunity for anyone looking for a move-in-ready home with room to make it their own!

118 Elliott Lane, Oregon

Listing courtesy of EXIT Realty HGM.

$395,000

3 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status

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.

607 Hillcrest Drive, Oregon

Listing courtesy of RE/MAX Preferred.

$699,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status

Bring all offers and your vision, creativity, and TLC to transform this spacious home into one that reflects your own style. The setting and space are here-the home is ready for your updates and personal touches. A rare 5-acre retreat in an incredibly convenient location?just 6 miles from Oregon, Verona and the Beltline! The home is on 3 levels and offers 3400 sq ft. Two fireplaces and plenty of entertaining area. Once a Christmas tree farm, this unique property offers mature trees and a park-like setting. Two large outbuildings provide exceptional space for hobbies,storage,vehicles or a workshop. Inside, the expansive family room features an Endless pool, perfect for swimming exercise at home, plus additional exercise space and plenty of room to gather. relax and watch the big game. See the Drone view of land on the video tour link.

5981 Purcell Road, Oregon

Listing courtesy of Sue Pederson & Assoc., REALTORS LLC.

$434,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

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 large park. Open-concept, ranch style homes have spacious living rms w/ direct deck access. Basements can be finished for extra living space & 3rd bed & bath. The majority of lots have half or full exposure in the basement. Multiple finish options & upgrades available. Builder is offering lots 1-30, see association docs.

1232 Tivoli Circle, Oregon

Listing courtesy of Keller Williams Realty Signature.

$475,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

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. You?ll 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 30x40? 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.

749 County Road Mm, Oregon

Listing courtesy of Real Broker LLC.

$429,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

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.

145 Dewey Street, Oregon

Listing courtesy of Relish Realty.

$299,900

2 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

This inviting townhome offers spacious bedrooms, a generously sized primary suite, and the comfort of a full primary bath. The home has recently been refreshed with all-new flooring, giving the interior a clean, updated feel.The two oversized bedrooms provide plenty of room for furniture, guests, a home office, or additional living space, while the large primary suite offers a comfortable retreat with its own full bath. With its combination of generous room sizes, low price point and recent updates, this property offers a wonderful opportunity for buyers looking for space and move-in-ready appeal in Oregon.

326 Alpine Meadows Circle, Oregon

Listing courtesy of Barnes & Associates Realty Group.

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