Middleton Homes with Wooded Lot features

Middleton Homes with Wooded Lot features

Welcome to Middleton, Wisconsin—a hidden gem nestled in the heart of Dane County, where natural beauty meets a vibrant community spirit. Known for its picturesque landscapes and friendly atmosphere, Middleton offers residents a unique blend of suburban tranquility and urban convenience. With its charming downtown area filled with local shops, delightful eateries, and a thriving arts scene, you’ll find that this city truly has something for everyone.

One of the most appealing aspects of Middleton is its commitment to preserving nature, which is reflected in the abundance of wooded lots available for homebuyers. Imagine waking up to the soothing sounds of chirping birds and rustling leaves, all from the comfort of your own home. Properties with wooded lots not only provide a serene backdrop but also offer a sense of privacy and connection to nature that is hard to find elsewhere.

These homes often feature spacious yards, perfect for outdoor gatherings, gardening, or simply enjoying the beauty of the changing seasons. Whether you’re looking for a cozy retreat or a modern family home, Middleton’s real estate market boasts a diverse array of options that cater to all lifestyles.

With excellent schools, numerous parks, and a strong sense of community, Middleton is not just a place to live; it’s a place to thrive. Discover your dream home among the trees in this enchanting city, where every day feels like a breath of fresh air. Come experience the charm of Middleton, where your ideal lifestyle awaits!

Newest Middleton Homes with Wooded Lot features

$1,799,000
5 Beds ⋅ 7 Baths ⋅ 2027557 MLS ⋅ ACTIVE UNDER CONTRACT Status
Custom home w/ classic beauty + timeless elegance, perfectly suited on over 1.4 landscaped acres w/waling trails connecting to green space. Grand in scale + design, this thoughtfully crafted residence offers sweeping views, floor-to-ceiling windows, & open yet refined floor plan. Chef's kitchen offers Wolf appliances, Sub-Zero refrigeration, custom cabinetry, + exceptional workspace. Rich woodwork, crown molding, tray ceilings, nine-foot doors, + three stone gas fireplaces showcase impeccable craftsmanship. Luxurious primary features a spa-inspired bath w/ steam shower, body sprays, soaking tub, + expansive walk-in closet. 4 addtl ensuite bedrooms each include private baths + walk-in closets. Walkout LL w/ a spacious family room, Tuscan-inspired brickwork, wet bar + wine cellar. Amenities include exercise room, sunroom, patios, 4-car garage, central vac, programmable irrigation system + much more! A truly remarkable home offering luxury + exceptional attention to detail.

3952 Caribou Rd, Middleton
$249,000
2 Beds ⋅ 1 Baths ⋅ 2027352 MLS ⋅ ACTIVE Status
Conveniently located near shopping, restaurants, and the bus line, this beautifully updated end-unit condo offers comfort, convenience, and investment potential. Featuring 2 bedrooms, 1 full bath, an open layout, in-unit washer and dryer, and a spacious private balcony, this home is move-in ready. Enjoy the convenience of heated underground parking with one assigned space, elevator access, and secure building amenities. Currently operating as a successful short-term rental, this property offers rental income potential through the remainder of the year. The established short-term rental business and all furnishings are available for purchase separately, providing a turnkey investment opportunity or a fully furnished personal retreat. Don't miss this versatile property in an exceptional location!

2051 Allen Blvd Unit 201, Middleton
$1,750,000
5 Beds ⋅ 6 Baths ⋅ 2027081 MLS ⋅ ACTIVE Status
Exceptional custom home offering timeless design, luxurious amenities, & exceptional living spaces throughout. The grand foyer opens to elegant formal living & dining rooms, while the dramatic two-story great room showcases a floor-to-ceiling stone fireplace, custom built-ins, & a wall of windows overlooking the private backyard. The chef's kitchen features a Wolf induction range, Sub-Zero refrigerator, Bosch dishwasher, granite island, & walk-in pantry, w/adjoining dinette leading to the screened porch & maintenance-free deck. The luxurious primary suite offers a lighted tray ceiling, 3-sided fireplace, sitting area w/private balcony, spa-like bath, & dual walk-in closets. The finished walkout LL includes a spacious family room w/fireplace, theater room, exercise room, & guest suite. Additional highlights include a bonus room, central vacuum, Hunter Douglas automatic blinds, 2 new zoned Lennox furnaces (2025), & an exceptional floor plan designed for everyday living & entertaining.

7534 Summit Ridge Rd, Middleton
$399,999
2 Beds ⋅ 2 Baths ⋅ 2026790 MLS ⋅ ACTIVE Status
Light, bright & spacious 2BR/1.5BA condo in desirable Woodridge Condo Community with vaulted ceilings, 2 stories of windows, beautiful wood floors, skylights, tranquil back deck overlooking Pheasant Branch Conservancy and an open plan ideal for everyday living. Gas Fireplace. Some updates include refrigerator, Microwave and Oven/Range-2024, Garbage Disposal-2020, New Window in loft- 2023, New Toilets in both baths-2026, New Water Heater--aprox. 2023. Enjoy green space and bordering Pheasant Branch Conservancy for walking, biking, wildlife & serenity. Convenient Middleton location close to shopping, restaurants and quick access to the Beltline. Beautifully maintained, move-in ready — a rare find!

7305 Donna Dr, Middleton
$450,000
4 Beds ⋅ 2 Baths ⋅ 2026834 MLS ⋅ ACTIVE UNDER CONTRACT Status
Town of Middleton country living with all the conveniences! Nestled on a partially wooded 1.13-acre lot in desirable Enchanted Valley Estates, this charming one-owner 4-bedroom, 2-bath home offers privacy, character, and endless possibilities. The great room features stunning beamed ceilings and a beautiful fireplace and hearth. French doors in the kitchen open to a deck overlooking the picturesque yard, creating the perfect space for relaxing or entertaining. Each bedroom includes custom built-in cabinetry and shelving. The walkout lower level offers a spacious family/rec room, laundry area, and dedicated craft or hobby room. Outside, a concrete slab with electrical service is ready for a future outbuilding, workshop, or outdoor gathering space. Enjoy the serenity of country living just minutes from Middleton, Madison's west side, shopping, dining, and everyday amenities.

7807 Big Timber Trl, Middleton
$190,000
2 Beds ⋅ 1 Baths ⋅ 2026336 MLS ⋅ ACTIVE Status
Cozy first floor 2bd/1bth garden condo features a easy access to downtown Middleton, beautiful cottonwood filled green space, and a patio view of Lake Mendota! Complex just had all roofs replaced! Condo fee includes heat, water/sewer, and hot water! Affordable and convenient, this cute condo is waiting for you.

2134 Allen Blvd Unit 2, Middleton
$1,174,900
4 Beds ⋅ 3 Baths ⋅ 2026028 MLS ⋅ ACTIVE Status
What sets this incredible property apart is clear before you even step inside. This contemporary home is surrounded by carefully tended prairie and woods, a thriving habitat for birds, pollinators, and wildlife. Architect Bruce Nichols designed this home with one intention: to bring the outside in. Floor to ceiling windows and skylights draw natural light deep into the heart of the home. The open kitchen w/pantry and lg island flows easily into the family room and sunny bfast nook, w/hardwood floors throughout. Guest bed + bath on main level w/primary suite + 2 beds/bath up. Glass railing overlooks the 2-story great room w/gas FP. Primary suite is a sanctuary of its own w/gas FP, oversized WIC, and bath w/shower and whirlpool tub. Solar panels, whole house fan, and updated mechanicals. Middleton schools w/low Town of Middleton taxes and nearly 2 acres of seclusion combine to create a package that rarely comes to market. If you’ve been waiting for something truly different, this is it.

8685 Airport Rd, Middleton
$669,000
3 Beds ⋅ 2 Baths ⋅ 2025170 MLS ⋅ ACTIVE Status
Price drop 6/23/26. Charming raised ranch in Woodside Heights enclave, just one block from Stricker's Pond, on tree-lined, quiet, well-kept and in-demand neighborhood with downtown Middleton and schools within walking distance. In-ground pool has new liner and heater (2023), slide & stone paved decking. New carpet & paint throughout. Extensive work on landscape. Expansive Great Room has tongue & groove wood vaulted ceiling with recessed lighting, elegant wood floor, gas fireplace and extensive wood shelving & cabinetry, open to bright kitchen with cooktop island and barstool (3 incl with sale) counter for in-kitchen dining and ceramic floor. Generous window views to fully fenced pool/backyard that makes for great entertaining space! AC(07), Roof/gutters (06), H2O Htr (13), Boiler (16), spray foam insulation in attic. New Bosch DW; disposal. Thermador electric cooktop, stainless wall microwave & oven pair.

1308 Shirley St, Middleton
$695,000
3 Beds ⋅ 4 Baths ⋅ 2025413 MLS ⋅ ACTIVE Status
Enjoy this Town of Middleton Stonebrook Estates 3 bedroom propertunity nestled on nearly .5 acres next to a 5-acre park setting. Look no further if you are looking for privacy, room to roam with the 66-acre walking trails/land or crave the active opportunities riding your bike to Settlers Park overlooking the local prairie/savanna. The backyard is perfect to practice your World Cup skills or work on your 9-iron aim over your vegetable/flower gardens. Soak in nature as you relax on the deck or patio while you fire up the smoker for your favorite BBQ. The inside layout is ideal for quality time together with enough space to focus on your work/projects with privacy. The inviting cooks kitchen has abundant counter space to cook together or meal prep for the week. Abundant storage not only in the kitchen but throughout the home. After a fun day in the neighborhood enjoy a relaxing soak in the tub or retreat to the exposed lower level for game or a movie night. New roof, AC, furnace, deck.

8600 Ellington Way, Middleton
$1,175,000
2 Beds ⋅ 2 Baths ⋅ 2024463 MLS ⋅ ACTIVE UNDER CONTRACT Status
The perfect Lake Mendota getaway! Welcome to this gorgeous, stylish and easy to maintain LAKE MENDOTA home. With 50 feet of frontage, land mounted dock, expansive shaded yard w/pergola & patio, this is the best of lake living. Newer, quality craftsman-style home, huge windows for light and lake views, open floor plan, skylights, floor-to-ceiling gas fireplace, in-floor radiant heat on main level, efficient and chic kitchen w/quartz counters, stainless appliances and lovely center island. 2 bedrooms up and 2 full bathrooms. Generous garage w/extra storage. This is the perfect spot for gathering after boating, fishing and enjoying all that Middleton, Madison and Lake Mendota has to offer. Special spot for entertaining all year round. THIS IS THE BEST DEAL ON THE LAKE BY FAR!

2830 Tomahawk Ct, Middleton
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 2023900 MLS ⋅ ACTIVE Status
Welcome to a home where style and design converge to create a truly curated luxury living experience. Privately positioned with sweeping views of Pheasant Branch Conservancy, this residence offers a sense of serenity that will leave you in awe. This thoughtfully updated 3-bedroom, 3-bath home maximizes every inch of its private setting, blending high-end finishes with effortless comfort throughout. From the moment you step inside, the intentional design and refined details are unmistakable, creating an immediate sense of sophistication and warmth. Three distinct outdoor living spaces—each offering exceptional privacy—invite you to fully embrace Wisconsin’s seasons, whether entertaining, relaxing, or simply taking in the natural surroundings. This home feels like a secluded retreat, yet remains just 20 minutes from Capitol Square. An extraordinary opportunity to own a one-of-a-kind property where luxury, privacy, and design come together seamlessly.

3702 Pheasant Branch Rd, Middleton
$875,000
4 Beds ⋅ 4 Baths ⋅ 2024287 MLS ⋅ ACTIVE UNDER CONTRACT Status
GREAT LOCATION! Keewatin Trail sits in one of Dane County's higher-elevation residential areas, offering a country feel just minutes from Middleton and Madison's West Side. Timeless architecture on a mature wooded 1.4-acre lot near the end of a quiet dead-end road in the exclusive Nature's Cove subdivision within the highly rated Middleton-Cross Plains School District. This sanctuary-like property features a 4-bedroom, 3,700 sq ft home with a huge bonus room above the garage. Enjoy spectacular sunset views from the main living room with custom wood floors crafted from trees harvested from previously owned adjacent land. Spacious primary suite offers cathedral ceilings, floor-to-ceiling stonework, and peaceful nature views. Finished walk-out lower level includes private bedroom, half bath, family room with wood-burning fireplace, laundry/workshop area, root/wine cellar, and access to a newly rebuilt deck. Exceptional built-in storage throughout plus brand-new carpet. Showings begin 5/30

4105 Keewatin Trl, Middleton
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