Browse All Oswego IL Properties with Pool for Sale

4 Beds ⋅ 4 Baths ⋅ 12787841 MLS ⋅ NEW Status

Tired of boring subdivision architecture? Looking for a little space between the neighbors but still enjoy the conveniences of being in-town? Want a floorplan that works great when hosting a crew but still has cozy components for the quieter life moments? Here is your UNICORN! It's rare to come across a home with this much character AND a magnificent 1.87 acre lot just one block to downtown Oswego, including a buildable lot! This mid-century modern home is surrounded by a wealth of trees plus it has a fenced in area with a firepit conveniently off of the deck. The main level is vast and the open floorplan is great for entertainment, including a recently remodeled eat-in Kitchen with a breakfast bar & table space, a sun drenched Four-season Room that maximizes the views, a spacious Living Room with one of two fireplaces, and a Den full of character that could easily be a 5th Bedroom. On the upper level there are 3 large Bedrooms set apart from the Master Sanctuary that includes a private balcony, two walk-in closets, and a beautifully tiled Bathroom. Additionally, the expansive finished lower level can be accessed from the Kitchen as well as the Garage, which ties into the 500 square foot workshop. Inside the second fenced portion of the yard is an 8' deep, 16x36 in-ground pool with newer mechanicals including a pump that was just installed in September 2026. This suburban oasis has the privacy you are looking for yet it is only blocks away from several parks and the Fox River trail. Please note there are two PINS with the Village of Oswego confirming that the front lot is buildable by connecting to city water and public sewer. New items include gutters, gutter guards & downspouts ('26), refrigerator ('26), hot water heater ('25), radon mitigation system ('23), high efficiency furnace & air conditioner ('22), pool heater & refurbished pool pump ('22), roof and siding ('19), the list goes on!

150 N Madison Street, Oswego

$425,000

4 Beds ⋅ 3 Baths ⋅ 12775191 MLS ⋅ CONTINGENT Status

Welcome to sought-after Windcrest of Oswego, where mature tree-lined streets, distinctive homes & spacious lots create a neighborhood that feels established and special - all just 1 mile from the Fox River Trail and 2 miles from downtown Oswego! Set on an impressive .41-acre lot with gorgeous mature trees, this 4-bedroom, 2.1-bath home offers something increasingly hard to find: space, privacy & peace - inside and out. Freshly painted and light-filled, the home features hardwood floors throughout the spacious bedrooms, brand new luxury vinyl in the family room and NO carpet anywhere! Eat-in kitchen with breakfast area, island with seating, abundant cabinetry & pantry! Cozy wood-burning fireplace in the family room, charming built-ins, 1st floor laundry, mudroom and a fabulous 3-season sunroom. Enjoy your own private retreat with an in-ground pool, huge fenced yard, fire pit, beautiful mature trees - plenty of room to swim, entertain, play or simply relax and enjoy the outdoors. All-electric home with a ducted heat-pump system providing heating & central air, plus individually controlled ductless heat-pump units in each bedroom for additional heating & cooling comfort. Newer windows, attached 2-car garage & unfinished basement offering plenty of storage and future possibilities. Nearby 2,000 square foot PLUS a basement, oversized lot, private in-ground pool, an incredible Oswego location and NO HOA! So much space, character, potential and value in one of Oswego's most established neighborhoods! Don't delay - schedule your showing today!

21 Partridge Square, Oswego

$625,000

4 Beds ⋅ 4 Baths ⋅ 12770275 MLS ⋅ CONTINGENT Status

Welcome to 204 Holly Lane in Gates Creek West, where spacious living, entertaining and a beautiful pond-side setting come together. Located in Oswego with Yorkville schools, this impressive two-story home offers flexible living space from top to bottom, along with an inground saltwater pool and tranquil views of the pond and fountain just beyond the backyard. A covered front porch and brick-accented exterior welcome you inside to a dramatic two-story foyer. The main level offers a private den, formal dining room and a beautifully designed sitting room featuring a built-in dry bar with wine cooler and beverage refrigerator-the perfect spot to unwind with an evening cocktail or gather with friends for conversation. At the heart of the home, the spacious kitchen provides abundant cabinetry and counter space and flows easily into the casual dining area and soaring two-story family room with fireplace and walls of windows. Step outside onto the raised composite deck overlooking the inground saltwater pool, mature backyard and pond beyond. Whether entertaining on a summer afternoon or simply listening to the fountain across the water, this backyard setting was made to be enjoyed. A first-floor laundry room adds everyday convenience. Upstairs, the generously sized primary suite features a vaulted ceiling, peaceful backyard views and a spacious en suite bath with dual vanity, soaking tub and separate shower. A concealed panic/safe room is located behind the smaller linen closet. Three additional well-sized bedrooms and another full bath complete the second level. The partially finished basement expands the possibilities even further with a recreation area, additional bedroom, wet bar and full bath-ideal for an in-law arrangement, extended-stay guests or additional living space. And golfers take note-the dedicated golf simulator, including the simulator equipment, stays with the home, creating your own year-round place to practice and play. With 5 bedrooms, 31/2 baths, multiple entertaining spaces, a three-car garage, inground saltwater pool, pond views and a versatile finished lower level, 204 Holly Lane offers the space to gather, retreat, entertain and enjoy home in every season. This is more than a house with great features-it's a home designed for how people actually live.

204 Holly Lane, Oswego

$644,900

4 Beds ⋅ 5 Baths ⋅ 12761395 MLS ⋅ ACTIVE Status

Welcome to a great house. Gates Creek West presents this spacious home with so much to offer. A large foyer welcomes you to this newer home w living room, separate dining room & eat-in kitchen w silver maple cabinets & granite counter-tops w large island. Kitchen opens to large family room w cathedral ceilings and wood burning fireplace and gas starter. First floor also features private office. 2nd floor boasts the master bedroom suite plus 3 large additional bedrooms. 4 full baths & additional 1/2 bath on first floor. Full finished Basement features a new and spacious bedroom, full bathroom, a fitness room and a recreational area. Large deck overlooks the in-ground pool, a new hot tub, and pergola for your enjoyment. New tear off roof. 3 car over-sized and heated garage w hot/cold water spicket. Beautifully landscaped yard has sprinkler system. House is located close to all amenities like schools and shopping centers near by. Show and sell today!

404 Heatherwood Drive, Oswego

$1,200,000

7 Beds ⋅ 6 Baths ⋅ 12750633 MLS ⋅ ACTIVE Status

Some homes you see. This one, you feel the moment you step inside. This extraordinary 7-bedroom, 6-bath waterfront estate brings extensive renovations, exceptional craftsmanship, and true resort-style living together on a truly remarkable property. Set along Waubonsie Creek, this expansive home offers incredible flexibility for everyday living, entertaining, multi-generational needs, and guests. The main level has been beautifully transformed with new oak hardwood flooring, fresh paint, updated lighting and plumbing fixtures, and impeccable trim work throughout. At the heart of the home is a completely renovated kitchen, thoughtfully redesigned with wall-to-ceiling custom cabinetry, integrated lighting, quartz countertops, double ovens, and a spacious eat-in area overlooking the pool. Direct access to the screened-in porch creates a seamless connection between indoor and outdoor living. Formal living and dining spaces provide an elegant backdrop for entertaining, while the dramatic two-story family room fills with natural light and centers around a striking masonry fireplace, framing views of the yard and pool beyond. Down the hall, a second fireplace warms the library, creating an inviting retreat for quiet mornings or evening conversation. The first-floor primary suite is a private sanctuary, crowned by soaring coffered, 10-foot ceilings. The completely renovated spa-inspired bath is where the home truly indulges - an oversized walk-in shower, a stand-alone soaking tub, heated floors, and custom tile, sinks, and vanity come together for a retreat that rivals any five-star escape. A custom lower staircase and all-new carpeting further elevate the home's impressive interior. A brand-new mudroom, designed specifically with poolside living in mind, offers direct access to the pool along with custom benches, built-in drawers for pool towels, a new dog wash, new tile and lighting, and an oversized pantry closet. Upstairs, five bedrooms provide exceptional space and versatility, many crowned with soaring vaulted ceilings. One features a private en-suite bath and walk-in closet, while another includes a custom built-in bunk bed, ideal for children, grandkids, or overnight guests. The remaining bedrooms are complemented by a beautifully updated shared full bathroom, including a newly renovated hall bathroom. The walk-out lower level expands the possibilities even further. A separate suite with a bedroom, full closet, and full bath offers outstanding potential for multi-generational living, an in-law arrangement, or extended-stay guests. The spacious recreation area gathers around the home's third masonry fireplace, with abundant storage and a renovated wine room featuring new wine shelving and custom tile. Outside, the property becomes a private oasis with an in-ground pool, large screened-in porch, dog run, waterfront setting, and expansive grounds designed for both relaxation and entertaining. Car enthusiasts will appreciate the home's exceptional five-car garage capacity. The three-car side-load garage features brand-new epoxy flooring, while the walk-out lower level provides an additional two-car tandem garage, creating tremendous flexibility for vehicles, recreational equipment, storage, or workshop space. A turnaround driveway adds everyday convenience. Additional highlights include Pella windows, several new appliances, and extensive updates throughout the home. The village is also installing a new parkway walkway in front of the property that will connect to a larger path system, adding even more appeal for those who enjoy walking, biking, and the outdoors. The home was converted to the new 2" city water in September (with the well kept intact to serve the pool and irrigation needs). This is more than a home. It is a waterfront estate designed for the way you want to live, with exceptional entertaining possibilities, resort-style outdoor living, and thoughtful craftsmanship at every turn. Schedule today

3663 Wolf Road, Oswego

$525,000

4 Beds ⋅ 3 Baths ⋅ 12722695 MLS ⋅ ACTIVE Status

A best buy in Deerpath Creek and the true definition of real estate done right is found here! These owners hate to leave (job transfer) and have done absolutely everything in this home with quality and craftsmanship in mind! You'll appreciate all the high end finishes the moment you walk in the door! Enjoy summers here because this home also features a custom in-ground SALT WATER swimming pool with all the bells and whistles, pool heater, cleaner and supplies (new salt water chlorinator too)! Inside you'll find an open main level floorplan, updated main level kitchen with custom Brakur cabinets, granite counters and upgraded interior trim finishes. On the 2nd floor you'll notice the large secondary bedroom sizes along with a primary master suite with dual closets and a private bath. In the finished basement (perfect for an in-law setup), you'll find more quality trim work, a full 2nd kitchen, family room with a custom stone fireplace, bonus room and a large storage room (could easily be converted to another full bath with minimal work). Newer items include a new AC (2025), new furnace (2023), new refrigerator, new dish washer, high end windows, Anderson patio door, front door, insulated & reinforced garage door, water softener, water heater, and a Culligan reverse osmosis system! Outside you'll enjoy a well planned, professionally landscaped lot with a fenced-in rear yard, extensive concrete & paver patio finishes, side concrete storage apron and a large, 10x14 custom storage/pool shed with a concrete floor! All this on a rare Deerpath Creek lot that is one of the few that is not part of the association, which means no rules and regulations and no association fees! Don't forget that this home is just a short walk to Prairie Point Elementary, Prairie Point Park & Oswego Park District Splash Pad too! This one checks all the boxes and is priced aggressivley for a hassle free sale!

236 Isleview Drive, Oswego

$540,000

4 Beds ⋅ 3 Baths ⋅ 12726943 MLS ⋅ CONTINGENT Status

Buyer financing fell through, great opportunity for you! Move-in ready and beautifully updated 4-bedroom home situated on a fully fenced lot overlooking a peaceful farm field. This spacious home offers a wonderful floor plan with a finished basement and oversized 3-car garage. The updated kitchen features granite countertops, farmhouse sink, newer stainless-steel appliances, abundant 42-inch cabinetry and generous prep space, opening to a bright south-facing sunroom. The main level also offers a family room, living room, dining room and convenient mudroom. Gray-washed hardwood floors, updated lighting and an electric fireplace add warmth and style. Upstairs are 4 spacious bedrooms, including the luxurious owner's suite with walk-in closet and private bath featuring a Jacuzzi tub, separate shower and dual vanity. The finished basement includes a separate room with built-in closet, ideal for a 5th bedroom, office or flex space, plus a large crawl space for storage. Enjoy exceptional outdoor living with a newly built multi-level deck, concrete patio, heated above-ground pool and fully fenced yard with peaceful views. Recent updates include roof (2019), windows (2013), central A/C (2015) and 2-speed high-efficiency furnace (2016). Conveniently located near schools, shopping, dining, parks and all that Oswego has to offer. Don't miss this exceptional home!

437 Raintree Drive, Oswego

$875,000

4 Beds ⋅ 4 Baths ⋅ 12701760 MLS ⋅ ACTIVE Status

Welcome to this exceptional custom-built two-story home situated on a beautiful 3.5-acre corner lot, offering the perfect combination of privacy, comfort, and space to enjoy both indoor and outdoor living. With approximately 2,400 square feet of above-grade living space plus a fully finished basement, this thoughtfully designed five-bedroom, three-and-a-half-bath residence provides flexibility for a variety of lifestyles. The inviting eat-in kitchen is the heart of the home and features a center island, breakfast nook, pantry, and a full complement of new appliances. Whether preparing everyday meals or entertaining guests, this space offers abundant storage, generous workspace, and an open, welcoming atmosphere. Just off the kitchen, the convenient laundry room includes a second pantry for even more storage, while a nearby half bath adds everyday functionality. A see-through fireplace creates a warm and inviting connection between the kitchen and the spacious family room, where soaring vaulted ceilings and a dramatic wall of eight west-facing windows fill the home with natural light and showcase beautiful backyard views. The adjoining dining room provides an elegant setting for holiday gatherings, family celebrations, and dinner parties. The main-level primary suite offers a peaceful retreat complete with a private en-suite bathroom. Upstairs, you'll find three generously sized bedrooms and a full bath, providing comfortable accommodations with separation from the main living areas. The fully finished basement expands the home's living space with an additional bedroom featuring an egress window, a full bathroom, a dedicated weight room, and flexible space that can be used for recreation, hobbies, media, or guests. Step outside to discover an outdoor setting designed for relaxation and entertainment. The spacious patio overlooks the beautifully maintained backyard and features a built-in swimming pool and an in-ground trampoline, creating the perfect space for enjoying warm summer days, hosting gatherings, or simply relaxing while taking in the peaceful surroundings. The expansive 3.5-acre corner lot offers room to roam, garden, play, or simply enjoy the privacy of country-style living. Adding even more value is the impressive 30-by-40-foot outbuilding complete with electricity, making it ideal for a workshop, hobby space, equipment storage, recreational vehicles, or countless other possibilities. This custom home combines quality craftsmanship, generous living spaces, abundant storage, and exceptional outdoor amenities in a setting that is both peaceful and practical. From the soaring ceilings and abundant natural light to the finished basement, backyard oasis, and versatile outbuilding, every detail has been thoughtfully designed to maximize comfort and functionality. This rare property offers the opportunity to enjoy spacious living on acreage while creating lasting memories for years to come. Schedule your private showing today and experience everything this remarkable property has to offer. Asking price $875,000.

3 Settlers Lane, Oswego

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Oswego Homes with Pool

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Browse All Oswego IL Properties with Pool for Sale

Oswego Homes with Pool

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