Browse All Winslow Acres Properties for Sale

3 Beds ⋅ 2 Baths ⋅ 12724682 MLS ⋅ CONTINGENT Status

This beautifully updated 1,750-square-foot one-story ranch home offers perfect modern living. The spacious three-bedroom layout features a private master suite complete with a beautifully updated master bathroom. Step inside to find fresh interior paint and stunning hardwood flooring stretching through the main living areas. Cozy new carpet adds warmth to all of the bedrooms. The heart of the home shines with a updated kitchen boasting sleek new countertops. Both bathrooms have been modernized with stylish, fixtures. Brand-new window blinds are installed throughout the home, offering immediate privacy and light control. Every detail has been meticulously refreshed, meaning you can move right in without the stress of remodeling. Combining classic ranch-style charm with entirely new finishes, this turnkey property is ready to welcome you home.

1020 Winslow Avenue, Woodstock

$399,900

4 Beds ⋅ 4 Baths ⋅ 12463231 MLS ⋅ CLOSED Status

Welcome to this beautiful 4-bedroom, 3.5-bathroom home located in the highly desirable Winslow Acres neighborhood! Enjoy serene mornings with stunning sunrise views through the wooded backyard, best enjoyed from the brand-new deck surrounded by vibrant, seasonal blooms. Inside, this spacious home features a thoughtful layout with dual staircases-including one off the kitchen-and a full, partially finished basement with rough-in plumbing for a future bathroom and over 1,200 sq ft of additional living space. The kitchen boasts warm oak cabinetry, stainless steel appliances, and an adjoining dining area overlooking the peaceful backyard garden. Original hardwood floors complement the kitchen and hallway, while brand-new laminate and vinyl flooring have been installed throughout the rest of the home (2025). A separate formal dining room, gas fireplace, and solid six-panel doors add both function and charm. Upstairs, you'll find four generously sized bedrooms and a bright, spacious second-floor laundry room for added convenience. Recent updates include: New roof (2024) New deck (2023) Entire exterior painted (2023) Entire interior painted (2022) Updated lighting in bathrooms and living room (2025) New sump pump (2022) New kitchen appliances and laundry (2022) Garbage disposal (2025) Gardeners will love the established berry patch with raspberries, strawberries, blueberries, currants, grapes, and herbs-plus a ready-to-plant vegetable garden. Location highlights: Just 5 minutes to Historic Woodstock Square, the Opera House, Emricson Park, Water Works Pool, farmers market, top-rated schools, and local conservation areas. This lovingly maintained home offers the perfect blend of nature, neighborhood charm, and modern updates-move-in ready and waiting for you!

1317 Winslow Circle, Woodstock

$525,000

5 Beds ⋅ 3 Baths ⋅ 12204211 MLS ⋅ CLOSED Status

1234 Gerry Street, Woodstock

$370,000

4 Beds ⋅ 4 Baths ⋅ 12074048 MLS ⋅ CLOSED Status

#HotHomeSummer! Welcome home to this spacious, custom 2-story gem spanning over 2700 SF in the sought-after Winslow Acres neighborhood! This charmer is not just a house; it's a haven for the adventurous family who is ready to embrace every minute! The moment you step into the foyer, you're embraced by an aura of warmth and hospitality. Picture-perfect living room with a crackling wood-burning fireplace, offers a picturesque view of the professionally landscaped fenced yard and sets the stage for cozy family gatherings. Indulge in culinary delights in the spacious kitchen featuring gleaming stainless steel appliances, ample cabinets and counter space, complemented by a charming eat-in area. Open the doors to the deck and reveal your own private oasis, ideal for alfresco dining or simply basking in the sunshine! The luxurious first-floor master suite beckons with its abundant natural light, a giant walk-in closet, and a spa-like master bath boasting a rejuvenating whirlpool tub and a walk-in shower. Discover an impressive office space adorned with double doors, ensuring productivity in this quiet, private space. Ascend to the second floor, where a sprawling 26 x 14 great room awaits, perfect for a man cave, home theater, or study sessions for the kiddos. Two generously sized bedrooms connected by a Jack & Jill bath, each boasts their own private walk-in closet and offer comfort and privacy for all. Venture to the lower level where an English Basement awaits, transformed into a killer spot for recreation and relaxation. With an additional full bath, utility room, and walkout access through the three-car garage, you'll have ample storage for your cars, tools, and toys. Don't forget to check out the fully fenced yard, which offers enough space for a garden, shed, or even a swimming pool- The choice is yours! Nestled in the heart of the Woodstock community, this residence is just a stone's throw away from a neighborhood park with a playground, great schools, parks, the vibrant Woodstock Square, and the Metra train station. Don't let this opportunity slip away; seize the chance to turn this exquisite house into your forever home!

1349 Winslow Circle, Woodstock

$475,000

5 Beds ⋅ 4 Baths ⋅ 11901770 MLS ⋅ CLOSED Status

"HONEY STOP THE CAR NOW!" That's right- you've just found your forever home! Nestled on an extra large 3/4 acre lot in highly desired Winslow Acres, this country style charmer offers a rural feel near all of the modern conveniences that Woodstock has to offer! Stunning curb appeal welcomes you to a home surrounded by lush mature trees, shrubs & vibrant, fragrant flowers. Once inside, you'll be in awe of all of the luxury touches & upgrades that all three floors of this home has to offer! Gleaming hardwood floors (freshly sanded & stained), custom fixtures, neutral colors, and closet space galore! Truly an entertainer's dream both inside out, your tour begins in the Formal Living Room, where you'll find a giant bay window to let the sun shine in, customs touches such as chair rail, crown molding, even an art ledge above the bay window! French doors lead you right into the Family Room, which offers glorious views of nature, cozy wood burning fireplace w/gas starter, opening right into the Kitchen for ease of entertaining. A fully remodeled Gourmet Kitchen is ready to impress the Family Chef with its endless granite counters (NEW just installed!), crisp white 42" showcase cabinets, sub zero refrigerator, double oven (go ahead and commit to making TWO turkeys this Thanksgiving! lol), recessed lighting, extended breakfast bar, and French doors to the expansive heated 4 Season Room. This gorgeous space is perfect for lounging on breezy summer days, dining al fresco on balmy nights, & snuggling under blankets during crisp Fall sunsets! You'll love the serene views of the wetlands & the Donato Conservation Area from every angle. Back inside, you'll find that the Formal Dining Room is also conveniently right off of the Kitchen, making parties & holidays a breeze! Be the "Hostess with the Mostest" in this dazzling room, featuring another bay window, tray ceilings, & custom chair rail. Venture upstairs where you will find 3 ample guest bedrooms w/large windows, oodles of closet space, the Laundry area, & a huge guest Bathroom with dual vanities so the kiddos won't fight over the sink ;) The Primary Ensuite Retreat is a relaxing oasis, with vaulted ceilings, a fan for comfort all year long, & enough room for the largest of furniture! Do you dream of falling asleep to National Geographic on an 80" flat screen at night? Now is your chance to buy that TV, because this bedroom has the space for it! The massive walk in closet will impress even the most voracious shoe lover & the Master Bathroom is like having your own personal spa right at home! Bathed in natural light from the skylight, the Master Bathroom offers a deep whirlpool tub, separate tiled shower, and an extended vanity with dual sinks. If all of this isn't impressive enough, there's still more to explore! The professionally finished, FULL WALKOUT basement is huge boasting a rec room, gaming area, home gym, storage space, full bathroom, & a private bedroom. This would be a great space for an in-law arrangement, roommate, home office(s), and so much more! Now that you've toured the inside, I've saved the best for last- The yard! The entire home is surrounded by fabulous professional landscaping, & dual decks that are beckoning the Grill Master of the house to get their apron and spatula ready! There's so much space for you to add more to the garden, add a she-shed, swing set, hot tub- The choice is yours! Such an amazing home, ideally located in beautiful Woodstock, recently voted one of the best places to live in Illinois (famous for being featured in shows like Prison Break & one of my fave movies of all time- Plaines, Trains, and Automobiles!) Super close to the Metra, schools, multiple parks, dining, shopping, cafes, nature trails, conservation areas, walking distance to the Woodstock Square Historic District, and only 30 minutes to action-packed Lake Geneva, WI! YES, PLEASE. Drive up, go in, and fall in love today! (New photos of kitchen coming soon!)

1214 Gerry Street, Woodstock

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