Winston Woods Homes

• 

  

  

  /20

  $263,500

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  209 Monroe Rd Unit 66, Bolingbrook, IL 60440

  Beautifully Maintained 3-Bedroom Townhome with fenced Backyard. Welcome to this exceptionally clean and move-in ready 3 bedroom, 2.5 bath townhome, offering both comfort and convenience. Step inside and you'll immediately notice the gleaming hardwood floors throughout, with Pergo flooring in two bedrooms and wood laminate in the third. The spacious living areas are enhanced by massive ceiling

  

  Beth Bellantuono

  Keller Williams Success Realty

  (331) 255-2882

  209 Monroe Rd Unit 66, Bolingbrook, IL 60440
• 

  Explore Winston Woods

• 

  

  

  /38

  $4,000 per month

  • 5 Beds
  • 3 Baths
  • 2,970 Sq Ft
  • House for Rent

  745 Feather Sound Dr, Bolingbrook, IL 60440

  Welcome to this beautifully maintained 5 -bedroom, 3 -bath home located in the desirable Feather Sound subdivision of Bolingbrook. With a 3-car garage, updated mechanicals, and modern amenities throughout, this home offers comfort, convenience, and style. Interior Features: Bright and open layout with a cozy fireplace on the main floor Full bath on first floor for added convenience

  Sean Cochran eXp Realty

  745 Feather Sound Dr, Bolingbrook, IL 60440
• 

  

  

  /20

  $273,500 Sold Sep 15, 2025

  • 2,156 Sq Ft
  • $127/SF
  • 16 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1971

  179 Roberts Rd, Bolingbrook, IL 60440

  Welcome to this beautifully maintained two-story townhome with full basement situated on a desirable Winston Village of Bolingbrook. Step into the inviting foyer that opens to updated wood laminate flooring throughout the main level. The spacious living room offers direct access to the backyard, perfect for relaxing or entertaining. Enjoy meals in the adjacent dining room featuring a large bay

  Melissa Kingsbury Redfin Corporation

  179 Roberts Rd, Bolingbrook, IL 60440
• 

  

  

  /41

  Est $587,938 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,723 Sq Ft

  865 Bonnie Brae Ln, Bolingbrook, IL 60440

  865 Bonnie Brae Ln, Bolingbrook, IL 60440
• 

  

  

  /28

  $437,000

  • 4 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  725 N Ashbury Ave, Bolingbrook, IL 60440

  Seller is motivated! Tucked away on a quiet street, this four-bedroom, two-and-a-half-bath home offers the perfect blend of privacy and convenience. Surrounded by mature trees and featuring a large fenced yard, this property provides a secluded, wooded feel rarely found in the Chicago suburbs. Step inside to discover a home filled with thoughtful updates: New roof (2024) for peace of mind

  Julie Riddle @properties Christie's International Real Estate

  725 N Ashbury Ave, Bolingbrook, IL 60440
• 

  

  /35

  $400,000 Sold Sep 10, 2025

  • 2,050 Sq Ft
  • $195/SF
  • 1 Day On Market

  • 3 Beds
  • 3 Baths
  • Built 1972

  725 N Pinecrest Rd, Bolingbrook, IL 60440

  Welcome to 725 N Pinecrest Rd-the one you've been waiting for! This beautifully updated T-raised ranch stands out with its unique layout and generous living space, all tucked into a prime location. The expansive main level features engineered hardwood floors, stainless steel appliances, a spacious dining area, and an open-concept living room perfect for hosting holidays or game nights with

  Jessica DeVries Southwestern Real Estate, Inc.

  725 N Pinecrest Rd, Bolingbrook, IL 60440
• 

  

  /23

  Est $390,641 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  533 N Ashbury Ave, Bolingbrook, IL 60440

  533 N Ashbury Ave, Bolingbrook, IL 60440
• 

  

  /18

  $435,000

  • 4 Beds
  • 2.5 Baths
  • 3,533 Sq Ft

  857 Bonnie Brae Ln, Bolingbrook, IL 60440

  Now is the perfect time to invest in a pool home before temperatures rise. Nestled in a tranquil and private interior setting in St. Andrews Woods. Natural oak hardwood floors t/o. Open floor plan, cathedral ceilings, oversized famly room w/ fire place, adjacent to this space is a spacious four-season sunroom. Updated bathrooms with granite flooring and shower enclosures. Wide staircases and

  Halina Verzani HomeSmart Connect LLC

  857 Bonnie Brae Ln, Bolingbrook, IL 60440
• 

  

  /18

  $252,000 Sold Sep 09, 2025

  • 1,460 Sq Ft
  • $173/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  207 Walker Dr, Bolingbrook, IL 60440

  A spacious and well-maintained home nestled in a quiet Bolingbrook neighborhood. This inviting residence offers 3 bedrooms, plus a den that has been converted into a 4th bedroom, providing flexible space for guests, an office, or a growing family. The main level features a bright and open layout with generous living and dining areas, a functional kitchen with ample cabinet space, and

  Eyaad Odeh Charles Rutenberg Realty of IL

  207 Walker Dr, Bolingbrook, IL 60440
• 

  

  /22

  Est $239,819 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,180 Sq Ft

  201 Monroe Rd, Bolingbrook, IL 60440

  201 Monroe Rd, Bolingbrook, IL 60440
• 

  

  /33

  $485,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,650 Sq Ft

  3 Charlestown Ct, Bolingbrook, IL 60440

  Welcome to your dream home! This stunning 5-bedroom, 3-bath raised ranch has been impeccably remodeled with modern elegance and comfort in mind. Step onto the charming covered front porch and into a welcoming foyer that sets the tone for the rest of this gorgeous home. The luxurious hardwood staircase leads you into bright, open living spaces filled with natural light. The beautiful features

  Arturas Strokovas Re/Max Millennium

  3 Charlestown Ct, Bolingbrook, IL 60440
• 

  

  /5

  $72,000 Sold Sep 08, 2025

  • Land
  • 0.35 Acre
  • $205,714 per Acre

  • 157 Days On Market

  829 Bonnie Brae Ln, Bolingbrook, IL 60440

  Build your dream home on this prime lot, ideally situated near Route 53 and major highways for easy access. Zoned R3, it's perfect for a single-family residence. The seller also has architectural designs available, which will be provided to the buyer at closing. Don't miss out on this fantastic opportunity!

  Janette Coss Realty of America, LLC

  829 Bonnie Brae Ln, Bolingbrook, IL 60440
• 

  

  /25

  Est $262,563 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  216 Douglass Way, Bolingbrook, IL 60440

  216 Douglass Way, Bolingbrook, IL 60440
• 

  

  /26

  $439,900 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440

  Welcome to this spacious 5 bedroom, 2.1 bath home nestled in one of Bolingbrook's most established neighborhoods, surrounded by mature trees and just minutes from the expressways. With 2104 square feet of living space, plus the basement, this home offers plenty of room to grow, including a large primary suite complete with its own cozy fireplace. The main level features a comfortable family

  Rebecca Kowalik john greene, Realtor

  800 N Ashbury Ave Unit 8, Bolingbrook, IL 60440
• 

  

  /31

  $443,000 Sold Sep 03, 2025

  • 2,600 Sq Ft
  • $170/SF
  • 70 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1993

  841 Bonnie Brae Ln, Bolingbrook, IL 60440

  Stunning Home in Highly Desirable St. Andrews Woods! Welcome to this captivating residence tucked away in the heart of St. Andrews Woods, one of Bolingbrook's most sought-after neighborhoods. Situated on nearly half an acre of lush, tree-lined property, this gem offers a rare combination of space, elegance, and natural beauty. From the moment you step inside, you'll feel the care and attention

  Deanna Mihalek Baird & Warner

  841 Bonnie Brae Ln, Bolingbrook, IL 60440
• 

  

  /30

  Est $291,296 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  535 Jordan Way, Bolingbrook, IL 60440

  535 Jordan Way, Bolingbrook, IL 60440
• 

  

  /25

  $479,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,650 Sq Ft

  5 Derbyshire Ct, Bolingbrook, IL 60440

  Your Dream Home Is Calling! This beautiful 5-bedroom, 3-bathroom home has been meticulously designed to balance style with everyday comfort. From the moment you step inside, you'll notice the thoughtful style choices-fresh paint, new waterproof luxury vinyl flooring, black finishes and recessed lighting that brightens every space. The open-concept main level is highlighted by a chef-inspired

  Damaris Hernandez Vista Real Estate LLC.

  5 Derbyshire Ct, Bolingbrook, IL 60440
• 

  

  /18

  $320,000 Sold Aug 28, 2025

  • 2,578 Sq Ft
  • $124/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  436 Cambridge Way, Bolingbrook, IL 60440

  Incredible Opportunity! Priced to sell, perfect for investors or homeowners with vision--Needs TLC and Strictly Sold AS-IS. This two-story home sits on a wooded corner lot and features a spacious three-car side-load garage. Step inside to a two-story open foyer. The large kitchen and breakfast area offer oak cabinetry. Enjoy the light-filled sun room which opens onto a custom wrap-around

  Christopher Grano Keller Williams Infinity

  436 Cambridge Way, Bolingbrook, IL 60440
• 

  

  /46

  Est $237,104 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,180 Sq Ft

  203 Diane Ln, Bolingbrook, IL 60440

  203 Diane Ln, Bolingbrook, IL 60440
• 

  

  /43

  $405,000 Open Sun 10AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft

  601 Derbyshire Ln, Bolingbrook, IL 60440

  Welcome to this beautifully updated 4 bedroom, 2 bath home situated on a spacious corner lot in the heart of Bolingbrook. Step inside to find fresh paint and brand new flooring throughout, creating a bright and modern feel. The home features a comfortable layout with plenty of natural light, generously sized bedrooms, and a convenient laundry area with a new washer and dryer. The expansive

  Maria Almaraz Midwest SignatureProperties Co

  601 Derbyshire Ln, Bolingbrook, IL 60440
• 

  /2

  $405,000 Sold Aug 22, 2025

  • 1,915 Sq Ft
  • $211/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  626 Derbyshire Ln, Bolingbrook, IL 60440

  Complete gut rehab with high quality finishes for this 2 story 4 bedrooms, 2.5 bathroom with partial finished basement on an oversized lot. New wood and carpet flooring 2025, all new paint 2025, all new windows 2025, new sliding patio door 2025, New bathrooms 2025, new landscaping 2025, new light fixtures 2025. All new interior doors 2025. Kitchen countertop 2025, kitchen backsplash 2025. Paver

  Nader Shahat Green Equities LLC

  626 Derbyshire Ln, Bolingbrook, IL 60440
• 

  

  /42

  Est $441,269 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  730 Victoria Ct, Bolingbrook, IL 60440

  730 Victoria Ct, Bolingbrook, IL 60440
• 

  

  /39

  $390,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,587 Sq Ft

  722 N Pinecrest Rd, Bolingbrook, IL 60440

  Don't miss the opportunity to see this beautiful 3 bedroom and 2 bath charming move-in-ready home. Large open concept offers dinning and living room with a view to the family room. The three bedrooms on first level are on one side of the house for more privacy. The main bedroom has its own full bathroom for convenience. Full Basement partially finished with a lot of potential. 4th bedroom in

  Eunice Garcia Kale Realty

  722 N Pinecrest Rd, Bolingbrook, IL 60440
• 

  

  /36

  $520,000 Sold Aug 20, 2025

  • 2,506 Sq Ft
  • $208/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1981

  5 Swan Cir, Bolingbrook, IL 60440

  Welcome to this rarely available, move-in ready gem located in the highly sought-after Feathersound subdivision. Nestled on a private, fenced cul-de-sac lot, this home sits on the largest parcel in the neighborhood-offering both space and privacy. Inside, you'll find four generously sized bedrooms with brand-new carpeting, including a luxurious primary suite featuring dual closets and a

  Laura Qualtier john greene, Realtor

  5 Swan Cir, Bolingbrook, IL 60440
• 

  

  /15

  Est $264,185 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,450 Sq Ft

  170 Tracy Way Unit 3, Bolingbrook, IL 60440

  170 Tracy Way Unit 3, Bolingbrook, IL 60440
• 

  

  /26

  $390,000

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  419 Charlestown Dr, Bolingbrook, IL 60440

  Wonderful 2 Story 4 bedroom house in Winston Woods! Main level has hardwood flooring throughout; updated kitchen includes granite counters and appliances, formal living and dining rooms; family room with stone fireplace and sliding door to back yard. Upper level has master suite w walk-in closet & private bath; 3 additional nicely sized bedrooms & updated bathrooms. Partially finished basement

  Andrew Preze RE/MAX Professionals

  419 Charlestown Dr, Bolingbrook, IL 60440
• 

  

  /18

  $225,000 Sold Aug 20, 2025

  • 1,692 Sq Ft
  • $133/SF
  • 6 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1972

  210 Diane Ln, Bolingbrook, IL 60440

  Spacious 2 bedroom townhome with a private fenced yard. Updated baths, finished basement. New furnace and A/C. Light and bright first floor with eat-in kitchen, dining room, living room, half bath. Slider to the patio and yard. Upstairs primary bedroom with huge walk-in closet and second bedroom also with ample closet space and a full bath. Come for the home - Enjoy the lifestyle! Close to

  Sandra Hannan ICandy Realty LLC

  210 Diane Ln, Bolingbrook, IL 60440
• 

  

  /48

  Est $524,999 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,527 Sq Ft

  885 Bonnie Brae Ln, Bolingbrook, IL 60440

  885 Bonnie Brae Ln, Bolingbrook, IL 60440
• 

  

  /20

  $270,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  149 Thomas Rd, Bolingbrook, IL 60440

  Beautiful Fordham Model Townhome! Freshly painted throughout with a great first-floor layout. A spacious den/office greets you just off the entry, and the large, bright living and dining room with bay window is perfect for entertaining. The oversized primary suite features a charming bay window, an 8x8 walk-in closet, private bath, and dressing room. Enjoy a private, fenced backyard for relaxing

  Irene Burciaga Baird & Warner

  149 Thomas Rd, Bolingbrook, IL 60440
• 

  

  /39

  $355,000 Sold Aug 18, 2025

  • 2,516 Sq Ft
  • $141/SF
  • 8 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1972

  553 N Ashbury Ave, Bolingbrook, IL 60440

  Welcome to this spacious split-level home in the Bolingbrook area offering comfort, functionality, and room to grow! With 5 bedrooms and 3 full bathrooms, this well-maintained home features a generous layout that includes a bright living room, formal dining room, and a kitchen ready for your personal touch. The inviting family room provides great space for gatherings, while the separate laundry

  Joe Castillo RE/MAX Mi Casa

  553 N Ashbury Ave, Bolingbrook, IL 60440
• 

  

  /30

  Est $284,642 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  206 Porter Ln, Bolingbrook, IL 60440

  206 Porter Ln, Bolingbrook, IL 60440
• 

  

  /14

  $274,900 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  514 Jill Ln, Bolingbrook, IL 60440

  This 3-bedroom, 2.1-bath townhome with a first-floor den in Bolingbrook's desirable Winston Village offers 1,460 square feet of comfortable living space in a prime location. The kitchen and all three bathrooms were tastefully updated about nine years ago, along with upgrades such as a new furnace, A/C, water heater, windows, sliding glass door, and both front and garage doors. More recent

  Rob Hayes Platinum Partners Realtors

  514 Jill Ln, Bolingbrook, IL 60440
• 

  

  /56

  $475,000 Sold Aug 08, 2025

  • 2,609 Sq Ft
  • $182/SF
  • 79 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  868 Bonnie Brae Ln, Bolingbrook, IL 60440

  Stunning 4-Bedroom Home in Desirable Saint Andrews Woods Welcome to Saint Andrews Woods! Homes in this sought-after neighborhood rarely become available, and this gorgeous 4-bedroom property is on the market for the first time. Freshly painted with new carpet and flooring, this move-in-ready home is waiting for its next owner. Step into the bright, open foyer that leads to a spacious living

  Lynda Mottola @properties Christie's International Real Estate

  868 Bonnie Brae Ln, Bolingbrook, IL 60440
• 

  

  /28

  Est $360,176 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,915 Sq Ft

  634 N Pinecrest Rd, Bolingbrook, IL 60440

  634 N Pinecrest Rd, Bolingbrook, IL 60440
• 

  

  /23

  $285,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  208 Porter Ln, Bolingbrook, IL 60440

  Gorgeous, 4 bdrm, 2 1/2 bath AND a den! Finished basement. 4th bedroom is in the basement. Home shows beautifully. Maple cabinets, recessed lighting, Wood floor throughout. Close to elementary school. Not far from shopping, restaurants, and much more! You can still have an amazing home in Bolingbrook without breaking the bank! Grab your agent and come see your forever home! **Property taxes do

  Sean Cochran eXp Realty

  208 Porter Ln, Bolingbrook, IL 60440
• 

  

  /39

  $517,500 Sold Aug 01, 2025

  • 2,249 Sq Ft
  • $230/SF
  • 42 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1994

  857 Bluestem Dr, Bolingbrook, IL 60440

  Welcome to this bright updated house conveniently located in Bolingbrook. Close to major highways,shopping and nice restaurants, yet a quiet and private location next to the magnificent park and nature. The second floor features 3 good sized bedrooms, master suite bath has separate bath and shower, and a walk-in closet. Basement is nice and dry, never had water issues, waiting for your

  Hui Li Charles Rutenberg Realty of IL

  857 Bluestem Dr, Bolingbrook, IL 60440
• 

  

  /18

  Est $246,985 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  599 Eric Way, Bolingbrook, IL 60440

  599 Eric Way, Bolingbrook, IL 60440
• 

  

  /5

  $149,000

  • Land
  • 0.32 Acre
  • $465,625 per Acre

  792 Bonnie Brae Ct, Bolingbrook, IL 60440

  Vacant wooded lot approximately .33 of acre in prestigious St. Andrews Woods in Bolingbrook

  Jonathan Minerick Homecoin.com

  792 Bonnie Brae Ct, Bolingbrook, IL 60440
• 

  

  /38

  $558,000 Sold Jun 30, 2025

  • 3,226 Sq Ft
  • $173/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  405 Cambridge Way, Bolingbrook, IL 60440

  Step into timeless charm and solid craftsmanship with this one-of-a-kind 4-bedroom, 3-bath timber frame home-an architectural gem that blends classic style with modern comfort. From the moment you arrive, the beauty of this home shines through, offering character, warmth, and the kind of attention to detail that makes every day feel special. At the heart of the home is a soaring two-story brick

  Katherine Rubis Berkshire Hathaway HomeServices Chicago

  405 Cambridge Way, Bolingbrook, IL 60440
• 

  /2

  Est $545,561 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,933 Sq Ft

  1 Ennis Ct, Bolingbrook, IL 60440

  1 Ennis Ct, Bolingbrook, IL 60440

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