Browse All Properties for Sale with Historic/Period Mlwk

5 Beds ⋅ 3 Baths ⋅ 12691511 MLS ⋅ ACTIVE Status

Opportunity awaits in this classic home that has been lovingly owned by the same family for over 40 years. While the home is ready for updating, it offers timeless architectural character, quality craftsmanship, and an unbeatable location, all the perfect ingredients to create your dream home. Step inside to discover striking natural-tone staircase millwork, beautiful transoms above the doorways, solid 5-panel wood doors, nearly 9-foot ceilings, built-in cabinetry, and two charming fireplaces (shared chimney has been capped). One of the five bedrooms is on the main level. Outside, enjoy barbecues on the deck overlooking the spacious yard that backs to a school field and playground, providing an open, park-like setting. The property has been maintained without pesticides and features an established collection of perennials and edible gardens, including hostas, strawberries, black raspberries, asparagus, irises, and a composting area. A detached two-car garage with a unique canoe bump-out offers additional storage for outdoor enthusiasts. Newer Roof and A/C in 2026. The location is truly exceptional-just minutes from vibrant downtown events, restaurants, shopping, the Metra station, schools, and the library. Whether you're looking to restore its original beauty or update it with your own style, this home offers incredible potential in one of the area's most desirable neighborhoods. Home is being sold As-is.

370 Lincoln Avenue, Woodstock

$350,000

3 Beds ⋅ 2 Baths ⋅ 12687963 MLS ⋅ CLOSED Status

Welcome to 805 Clay Street, located in the heart of historic Woodstock! This charming period home features three bedrooms, an office that can serve as a fourth bedroom, and one and a half bathrooms, all situated on a spacious three-quarter acre lot near Woodstock's historic square and the Metra train station. The floor plan includes a beautiful formal entry, a living room, a formal dining room, and an eat-in kitchen. You will appreciate the original woodwork, hardwood floors, and carpeting throughout the home. Modern conveniences include updated bathrooms, a newer furnace, air conditioning, a tankless water heater, 200 amp electrical service, and R-49 attic insulation. Outside, you'll find a front porch with PVC decking, fresh paint (done in 2022), a detached 20x30 garage with a drive-thru door, and a 20x12 storage shed.

805 Clay Street, Woodstock

$296,000

3 Beds ⋅ 3 Baths ⋅ 12558120 MLS ⋅ CLOSED Status

This grand home with a classic wraparound porch is in a prime location close to the Square, schools, and the train station. Inside, you'll appreciate hardwood floors and artistic trim. The inviting parlor showcases one of the home's original beveled glass windows. French doors lead into the formal dining room. The kitchen features vintage built-in cupboards. This home has a flexible floor plan. The main floor includes a bedroom or office. Upstairs, you'll find bedrooms plus a spacious sitting room that could easily be converted into an additional bedroom. A bonus room provides even more potential-ideal for a bedroom, office, or hobby space. There is a full bath on both the first and second floors. Laundry is conveniently located on the main floor. Additional features include a full basement and a two-car attached garage. The home needs TLC and is being sold as-is. The raised bed gardens are a treat, featuring your own herb garden, pollinator gardens, plus rhubarb, asparagus, elderberry, and a cascade of flowers throughout the season. Motivated Seller. Quick closing possible.

319 W South Street, Woodstock

$250,100

2 Beds ⋅ 2 Baths ⋅ 12540972 MLS ⋅ CLOSED Status

There's something easy about this house. It's the kind of place where the layout just makes sense, the details feel intentional, and the day-to-day routine flows without thinking about it. The main level gives you 1,080 square feet of comfortable, well-appointed living. Evenings in the living room settle naturally around the fireplace. Dinner in the dining room feels a little more special with the crown molding overhead-it's a small thing, but you notice it. The kitchen has more storage than you'd expect at this price point, with a butler pantry that takes the pressure off counter space. It's the kind of kitchen you actually want to cook in. Out back, the large deck is where this home earns its keep in the warmer months. Morning coffee, weekend cookouts, watching the seasons change-that deck becomes the extension of your living space from spring through fall. Downstairs, the full basement adds another 1,080 square feet of unfinished space with standard basement windows. It's quiet, functional, and ready for whatever you need-storage, a workshop, a future rec room. The attached 1-car garage connects directly to the basement level, so you're always coming in out of the weather. Two bedrooms and a full bath round out the main level, with a half bath for guests. The 0.16-acre corner lot means more yard, more breathing room, and more natural light coming into the home than you'd get tucked between two houses. Woodstock has a way of feeling like home quickly-and this house is a comfortable, livable place to start. Come see this dream home today!

Woodstock

$275,000

4 Beds ⋅ 2 Baths ⋅ 12483383 MLS ⋅ CLOSED Status

Large home,(4-6 bedrooms possible depending upon reconfiguration) just blocks south of Woodstock's historic Square, on an extra-wide and deep lot with mature trees surrounding the house. The property has been a duplex for many years and can continue as such with over $2,000 in monthly income, or it is perfect for the buyer wanting to gain equity greatly by returning this Victorian to its original single-family splendor (suggested plans in the house that show possible floor plans based on the original layout). The downstairs ceiling height is 9 feet. So much space, plus a full walkout basement to the deep backyard, where a large cement patio is ready for the BBQ grill and fire pit. The basement has a high ceiling and can be finished to be used for additional living space. Several stained glass windows and leaded-cut windows, original woodwork, architectural roofing, tandem furnaces, water heaters, AC, and updated electrical service in two panels provide many circuits with room for more circuits. The upstairs bathroom has a separate bonus room that can be used as an office, playroom, or storage area. A metal shed in the backyard provides storage for yard and garden tools. Find your Woodstock dream and build immediate equity with your improvements, or claim your income from high-demand rentals. Because the home is currently configured as a duplex, a new owner could live in one half while rehabbing the other, or rent one unit while converting the other half. Sold "as is"(The home is realtor-owned).

601 S Jefferson Street, Woodstock

$383,000

3 Beds ⋅ 2 Baths ⋅ 12420794 MLS ⋅ CLOSED Status

OLD WORLD CHARM meets MODERN DAY CONVENIENCE in this beautifully reimagined home, just STEPS from Historic Woodstock Square! Step back in time while enjoying every modern update in this lovingly transformed gem. Enclosed porches to sip your morning coffee either at the front or the back - a perfect blend of character and comfort. Inside, fresh paint throughout and new flooring in every room give the entire home a clean, cohesive, and stylish feel. The heart of the home is a custom designed kitchen featuring quartz countertops, classic shaker cabinets, and a massive island-a true showstopper and the centerpiece for entertaining, gathering, and daily living. The main level offers two and potentially, 3 bedrooms, along with spacious living and dining rooms. Whether you're hosting guests or creating a home office, the layout offers flexibility and comfort. Upstairs, the primary suite includes its own private full bath and enough space for a workout room, desk space and/or a sitting room, creating a peaceful retreat fit for a queen. A portion of the yard is FENCED, but imagine fencing in the entire space for Fido, too! Lovingly brought to life by a renowned Woodstock contractor, this home is not just a renovation-it's a work of art. Come see it. Fall in LOVE. Make it yours! Just 2 blocks to the Historic Woodstock Square shops, restaurants and weekly celebrations. METRA Commuter Train to Chicago a mere 5 min walk.

310 S Tryon Street, Woodstock

$365,500

4 Beds ⋅ 2 Baths ⋅ 12407558 MLS ⋅ CLOSED Status

Multiple offers received, highest and best due 7/13 12pm. All the charm on this WRAPAROUND Front Porch! Sitting high & mighty, this home offers a view of the neighborhood and a newly paved road out front! Classic turn of the century home with all of today's conveniences. NEW Kitchen with Solid Surface Counters, Backsplash, 42" Custom cabinets, Soft Close Hinges & NEW appliances. NEW 1st Floor Full Bath & and First Floor Bedroom. Stone Patio, Deck & great gathering places indoors & out. Hardwood floors throughout the home, with inlaid wood design in the Eating Area. UPDATE list is extensive, 2024 updates include NEW Roof, NEW electrical panel, NEW Dishwasher & microwave. 2023 House Paint, 2023 Washer, 2025 Garage Roof & Paint, 2020 NEW HVAC & Central Air, Mostly new windows throughout. Copper Plumbing, too! Owners have loved this home and it shows from every angle. Close proximity to Dean Street Elementary School, Woodstock High School & Neighborhood Park. Hop, skip to the Historic Woodstock Square FUN and METRA Commuter Train!

241 Hoy Avenue, Woodstock

$200,000

5 Beds ⋅ 2 Baths ⋅ 12384240 MLS ⋅ CLOSED Status

Expansive 20' Covered FRONT porch and into a home full of character and OPPORTUNITY. The spacious Foyer welcomes you with beautiful natural light and original details. 10' ceilings and large windows create an airy, open feel throughout the main level. A formal dining room offers plenty of space for entertaining, while your kitchen redesign might include opening a wall, too! Upstairs, you'll find five generously sized bedrooms, each filled with sunlight and timeless charm. WALKUP Attic offers additional storage and expansion, too! 3 Car Garage. This home OFFERS the kind of space and architectural charm you can't find on the market at this price. Whether you're an investor, DIY enthusiast, or simply looking for a home to make your own, this property is brimming with POTENTIAL. Located just moments from METRA train access, shopping, culture, and all the charm of downtown Woodstock. Home is being sold AS IS.

645 E Calhoun Street, Woodstock

$760,000

6 Beds ⋅ 5 Baths ⋅ 12397553 MLS ⋅ CLOSED Status

The Details are in the Design. Too many amazing architectural design features to completely list out- reclaimed hardwood throughout, 200 year old Vintage beam for the mantel, mahogany entertainment center cabinets, circa 1880s antique store counter with marble, Tasmanian Green granite, a full dog wash station, 2 laundry rooms for convenience the list goes on and on. 4 bedrooms upstairs with 3 full bathrooms, all en-suite. Owners suite has an semi private step up entrance from the hallway with one of the 5 fireplaces, full finished walkout basement with 2 additional bedrooms and a full bathroom. Media Room with walkout private patio, Workout room, lots of storage. Less than 5 minutes to Metra and the Historic Woodstock Square with nightlife and cute shops. Walking path to elementary school. Surrounded by a wooded area with creek owned by HOA.

1415 Oakview Terrace, Woodstock

$452,000

4 Beds ⋅ 3 Baths ⋅ 12363033 MLS ⋅ CLOSED Status

OLD World CHARM meets MODERN Day Convenience in this TRANSFORMATION just steps from the Historic Woodstock Square! Step back in time when you could greet your neighbors from the covered Front Porch and take in the views from the ENCLOSED Porch, as well. Every inch of this home has been tended to with fresh paint, refinished Hardwood Flooring, Carpet runner and carpeting. NEW Custom Kitchen Cabinetry, Quartz Counters, Pantry Cabinet and the Butler's Pantry you've dreamed of! 1st Floor Laundry and Bedroom or Flex Space, too! Of course, the home features a GRAND Foyer, the quintessential "water closet" and Generous Living and Dining Rooms. Master Sweet features it's own attached FULL Bathroom, fit for a Queen. Another piece of REAL ESTATE ARTWORK from a fabulous Woodstock Contractor. NEW Driveway, too! Come see and fall in LOVE!

319 W Judd Street, Woodstock

$305,000

3 Beds ⋅ 2 Baths ⋅ 12364430 MLS ⋅ CLOSED Status

Welcome to a home where history lives and memories are waiting to be made. Built in 1922 and rich with timeless detail, this 3-bedroom, 2-bath treasure in Woodstock invites you to step into a space filled with warmth, charm, and room to grow. As you enter through the spacious enclosed front porch, you're welcomed into a home where character takes center stage. Step through the double glass doors to the heart of the home. An expansive great room, filled with sunlight and warmth from beamed ceilings above, hardwood floors below, and custom built-ins surrounding a cozy fireplace-the perfect place to gather, relax, and make new memories. Just beyond, the separate dining room invites family dinners and celebrations under the original wood beams that carry whispers of the past. The kitchen, full of vintage charm, opens to a dedicated pantry room complete with built-in cupboards-ideal for organizing all your essentials. On the main floor, you'll find two comfortable bedrooms with hardwood floors, including the primary bedroom, and a full bath just steps away. Upstairs, a private third bedroom offers a peaceful retreat, alongside a quaint loft, and dressing room -great for a home office, playroom, or quiet nook. There is also another full bath. Tucked in behind the second floor dressing room is an oversized attic that could easily be transformed into an additional room. There are two additional attic areas, full of possibility for storage, creativity, or future expansion. Downstairs, the basement houses a laundry area and even more space for hobbies or storage. Outside, the magic continues with not only a generous backyard-ideal for gatherings, gardening, or relaxing under the trees-but also a second large enclosed porch at the back of the home, perfect for summer evenings or peaceful mornings with coffee in hand. A detached 2-car garage sits at the end of a long driveway that provides parking for five or more cars, so there's always room for visitors. Located next to Woodstock's vibrant downtown square, you'll be seconds away from charming shops, cozy cafes, community festivals, and a true small-town spirit that makes every season special. The library is two doors away. With timeless details like hardwood floors, beamed ceilings, built-ins, and unique spaces full of history and heart, this home is so much more than a place to live-it's a place to belong. Set on a deep lot along a tree-lined street with sidewalks, this storybook home is ready for your next chapter. Come see the charm, feel the history, and imagine the memories waiting to be made. With a little imagination and some updating this home will sparkle for you like it has for its owners. Truly a solidly built home.

328 W Judd Street, Woodstock

$415,500

4 Beds ⋅ 3 Baths ⋅ 12271540 MLS ⋅ CLOSED Status

Beautifully UPDATED, this picturesque HISTORIC George Burger Queen Anne move-in-ready home perfectly blends VICTORIAN charm with MODERN living - all just two blocks from the Woodstock Square and the METRA. The home design is a unique combination of a SQUARE BAY and OCTOGON steeple that stands out, giving the home an unmistakable presence. Inside, the home continues to impress with high ceilings, BRIGHT light from seven crystalline lead glass windows, a beautiful OAK staircase, original wide-plank pine flooring, pocket privacy doors, ORIGINAL entry doors, and a unique double-wide folding divider door - all with original hardware. The updated LARGE kitchen (2022) is a standout, featuring sleek GRANITE countertops, custom cabinetry, and MODERN touches, including a stainless steel Bosch dishwasher (2024), stainless steel GE Advantage microwave convection oven (2019), and can and pendant lighting. The fully remodeled primary bath (2021) is a true retreat, with luxurious marble flooring, a spacious walk-in spa-like shower, dual sinks, and high-end fixtures, including heated towel racks. Additional updates include an elegant first-floor powder room (2022), upstairs bath (2018), dual-level Trane HVAC forced air heat furnaces and A/C units, cedar closet, and custom-made cedar wrap-around front and back porches (2021). Enjoy the professional landscaping while relaxing on the WRAP AROUND front porch and a private patio.

524 Clay Street, Woodstock

$417,000

4 Beds ⋅ 3 Baths ⋅ 12192828 MLS ⋅ CLOSED Status

Welcome to this stunning Victorian home, where classic elegance meets modern convenience. Nestled in the heart of downtown Woodstock, this architectural beauty boasts a wraparound front porch, leaded glass windows, intricate period details, high ceilings and spacious living areas that invite warmth and character. As you step inside, you'll be greeted by original hardwood floors and carved staircase and large windows that fill the space with natural light. The inviting living room flows seamlessly into a formal dining area, perfect for entertaining or cozy family gatherings. The updated kitchen features modern appliances while preserving the home's historic charm. The main level study could also be used as a bedroom and has a powder room attached. Upstairs, you will find a spacious primary suite with a sitting room and deep closet. Three additional lovely bedrooms with closets that boast built-in dressers and hardwood floors. The full house length bonus room in the attic features a full bath and a beverage sink in the petite bar area. The fenced in yard is a gardener's delight filled with perennials, hydrangeas, groundcover and serene privacy. Just minutes from the historic Woodstock Square, where you can explore charming shops, dine at local restaurants, visit the Farmers Market, and enjoy performances at the Opera House along with year-round community events. Don't miss the opportunity to own this unique and beautiful home in an unbeatable location!

327 S Jefferson Street, Woodstock

$317,000

4 Beds ⋅ 2 Baths ⋅ 12138948 MLS ⋅ CLOSED Status

This historic home has been recently remodeled and is located across from the Woodstock Public Library. It is conveniently located just a few blocks away from the Woodstock Square and train station. With four bedrooms and two bathrooms, it also features a first floor bedroom. The house boasts refinished hardwood floors, a new roof, a newly paved asphalt driveway, re-insulated attic and a brand new two-car garage. Additionally, the HVAC system, electric panel, bathrooms and kitchen have all been updated. The interior has been freshly painted along with new light fixtures & a few classics. Take advantage of the beautiful refreshed front porch and enjoy all that Woodstock has to offer.

431 W Judd Street, Woodstock

$425,000

4 Beds ⋅ 2 Baths ⋅ 12088056 MLS ⋅ CLOSED Status

This Wonderful 5.26 Acre Farmstead is an exceptional location in the Woodstock School District, just minutes from town. The 4 bedroom 2 bath home is perfect for a growing family, especially if they would love participating in 4H programs and have that wonderful experience and life style on their own hobby farm. Several upgrades and improvements have been made to this lovely Farmhouse, all freshly painted inside and out, a new front sidewalk, new FA Gas Furnace, hot water tank, new windows, new roof, plumbing, updated electric, new Kitchen cabinets, and flooring, Huge Country Kitchen w/ eating area, Laundry area in Kitchen, natural gas, and the list goes on. the house is still work in progress and will be definitely be in move-in condition by closing. There are several outbuildings such as a 8 stall barn 30 x 67 with a partial new roof, a Cattle Shed 28 x 50, a 24 x 12 Chicken coop and other outbuildings as well as two 44' long trailers, and a lean twos, etc. This is such a picturesque setting with great views of the countryside and the most beautiful sunrises and sunsets....

3813 Franklinville Road, Woodstock

$485,000

4 Beds ⋅ 2 Baths ⋅ 12009524 MLS ⋅ CLOSED Status

Experience the beauty and tranquility of rural living with this charming one-of-a-kind property that exudes character and sophistication. Escape at home on this 3 acre property, A-1 zoning, where you can enjoy al fresco dining on the decks or embrace the simple pleasures of nature in the vast backyard. This welcoming 1846 home seamlessly blends historic charm and contemporary comforts. Exposed brick, some original leaded glass windows, hand-hewn wood posts and the inclusion of vintage architectural millwork add additional character throughout. Whether preparing a casual meal or hosting a lavish dinner party, the bright kitchen space is as functional as it is stylish. High-end appliances include Stainless Subzero glass door double wide side-by-side refrigerator, Viking Oven, Cook-top and Microwave surround the central island hub with its granite counters and breakfast bar seating. A checkerboard floor and rich wood ceiling flow seamlessly into the adjoining dining room and mud/laundry room. The large living room is home to the centrally located gas fireplace that is faced with a curated vintage mantel. The first floor has a great flex room that would make an inviting family room or even a delightful main floor bedroom. It adjoins the sunroom that overlooks the back of the three acre property. Striking large first floor full bath is finished in white marble subway tile and hexagon mosaic porcelain floor tile with a pedestal sink and full shower/bath. Vaulted ceiling and three walls of windows are highlights in the private office alcove. Head upstairs to find three bedrooms and a den that currently has floor-to-ceiling shelving, which could be used as another bedroom. The largest upstairs bedroom is currently used as a primary bedroom and has a full wall of built-in closets. Storage upstairs is abundant and includes a large walk-in closet and an attic accessed by pull down stairs. The updated second floor bathroom also features clean white subway tile finishes with glass shower enclosure and marble floor tile that create a fresh atmosphere. The basement has space used as a rustic rec room/hangout/game room with exterior access and a separate mechanical/storage room. The three car detached garage has an adjoining barn space with sliding rear door access and a separate garden shed provides more space for all your yard goodies. All of this plus A-1 zoning provides you the option to bring your horses, small animals and/or chickens! This property represents a rare opportunity to own a piece of history in a coveted location offering both privacy and convenience. The property is conveniently located within easy reach of local shopping, dining, entertainment and Metra. Chicago and Milwaukee are approx. 60 miles and Lake Geneva fun is only twenty minutes away. Cinch Home Warranty included for buyer's peace of mind. Don't miss your chance to make this timeless treasure your own - schedule a showing today!

11516 Country Club Road, Woodstock

$160,000

4 Beds ⋅ 2 Baths ⋅ 12012308 MLS ⋅ CLOSED Status

Multiple offers received, Highest and best due 4/26 9AM. Make it your very own! QUIET street, just off the beaten path, this home features a 20' COVERED FRONT PORCH. Beautiful old world FOYER, perfect for greeting guests and the double glass doors to the living room. Spacious Dining Room and 10' Ceilings. Kitchen is loaded with cabinet space and access to the AMPLE back yard. A very convenient half bath just off the kitchen. The upper level has 4 generous sized rooms that offer tons of LIGHT. This home has the potential of GREATNESS just waiting for you to bring your ideas to life. Home comes with some work already completed, newer WINDOWS. Hop, skip and jump to all the amenities the charming town of Woodstock has to offer! METRA Train access, Culture & Shopping. Home will be sold AS IS

922 Marvel Avenue, Woodstock

$185,000

4 Beds ⋅ 2 Baths ⋅ 12004036 MLS ⋅ CLOSED Status

431 W Judd Street, Woodstock

$229,000

3 Beds ⋅ 1 Baths ⋅ 11989744 MLS ⋅ CLOSED Status

This is a recently renovated 3 bedroom home located in the Historic District of Woodstock, just two blocks away from the Square. The house features original hardwood floors, millwork, and interior doors, adding to its charm and character. You can enjoy the beautiful sunrise from the back porch and watch the sunset from the front porch swing. Additionally, there is a detached one-car garage and a spacious side yard, as well as a patio closer to the house. What makes this property unique is its zoning classification, B2C, which allows for the small building on the property to be used for a business, office, or workshop. This provides great flexibility for those looking to combine living and working in the same location.

124 N Madison Street, Woodstock

$411,000

4 Beds ⋅ 4 Baths ⋅ 11799764 MLS ⋅ CLOSED Status

415 W South Street, Woodstock

$310,000

4 Beds ⋅ 3 Baths ⋅ 11765058 MLS ⋅ CLOSED Status

The charm of Woodstock's Victorian areas near the square with the upgrades of a recent complete rehab including wiring, electric panel, plumbing, HVAC, insulation, counters and cabinets, carpet and hardwood floors, windows, roof, and siding, foundations and sidewalks, landscaping and deck. 3 blocks to the historic Square and 5 blocks to the train station. Massive master bedroom suite. Lots of windows. Many of the original hand-blown glass panes are preserved in the entry. Special efforts were made to reflect the period of the house by preserving the original window sizes, refinishing the original newel, post, and rail of the stairway, and finding "new" hardwood flooring that appears to come from the local sawmill of the 1870s. The rocks in the rock gardens and the day lilies around the building were placed dug and from the original home. This beautiful home is located on the block where Ground Hog Day was filmed. one block from the Bed and Breakfast, and yes momentarily is seen in the street scenes. The home also has unique features of "tandemness", there are 2 basements, 2 laundry setups, 2 furnaces, 2 AC, and 2 driveways which create energy savings as well as the security of backup, and convenience.

359 S Madison Street, Woodstock

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Woodstock Real Estate & Homes With Historic/Period Mlwk

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