Browse All Oswego IL 5 Bedroom Properties for Sale

5 Beds ⋅ 6 Baths ⋅ 12753973 MLS ⋅ NEW Status

Extraordinary Riverfront Retreat on Nearly 3 acres along the Fox River in Oswego. Frank Lloyd Wright-inspired architecture with extensive DESIGNER RENOVATIONS, LUXURY UPGRADES & MAJOR MECHANICAL IMPROVEMENTS. The home delivers the ultimate lifestyle - Walls of glass blending indoor/outdoor space, private boat launch, riverwalk, and two fire pit areas. Chef's kitchen: Custom RekMaker Cabinetry, JennAir appliances, double ovens/dishwashers/sinks, oversized island, built-in grill, commercial hood, adjoining wet bar. NanaWall Glass Wall Easily Opens dining room to the outdoors and a two-level patio Brickpaver patio - ideal for entertaining 75+ guests. Primary suite offers panoramic river views and a spa bath with steam shower, rain shower & soaking tub. A FIRST-FLOOR BEDROOM & ENSUITE FULL BATH are ideal for guests, a private office, and Generational Living. Lower level: radiant heated floors, rec room, wet bar, wine room, fitness room, full bath, hidden room, garage access. Radiant Heated 6 CAR GARAGE With New Boiler, Control4 Smart Home Automation, Sonos Audio, Kohler whole-house generator. New Architectural Roof. New HVAC. Newer tankless water heater. THE RIVERWOOD ESTATE is more than an exceptional home, it's a private riverfront legacy property where generations gather, celebrations become traditions, and memories are made for years to come. Welcome Home!

88 Riverwood Drive, Oswego

$649,990

5 Beds ⋅ 3 Baths ⋅ 12753311 MLS ⋅ NEW Status

Welcome to 1498 Vintage Dr. Oswego, Illinois a beautiful new home in our Sonoma Trails community. This home will be ready for a FALL MOVE IN! This homesite includes a fully sodded yard AND Landscaping package AND a FRONT PORCH. The exquisite Emerson plan offers 3,044 square feet of living space with 5 bedrooms, and 3 FULL baths, Loft plus a Flex Room great for a first-floor office or additional sitting area. Entertaining will be easy in this open-concept kitchen equipped with a GOURMET KITCHEN PACKAGE that not only provides ample kitchen storage but elevates the home to an entire new level of luxury. Kitchen boasts a large island with an overhang for stools, 42-inch designer cabinetry with crown molding and soft close drawers and doors PLUS butler pantry. Additionally, the kitchen features modern Kitchen Aid stainless-steel appliances, quartz countertops, and easy-to-maintain luxury vinyl plank flooring. The Emerson plan also features a full basement and a 3-car garage which provides ample storage for the entire home. The main bedroom suite has a large walk-in closet and private bath featuring a raised dual bowl vanity, luxury vinyl plank floors, quartz vanity top, large shower, and a linen closet. Convenient walk-in laundry room, 3 additional bedrooms with a full second bath and a linen closet complete the second floor. All Chicago homes include our America's Smart Home Technology. Photos are of similar home and model home. Actual home built may vary.

1498 Vintage Drive, Oswego

$654,990

5 Beds ⋅ 3 Baths ⋅ 12750432 MLS ⋅ ACTIVE Status

Welcome to 1486 Vintage Dr. Oswego, Illinois a beautiful new home in our Sonoma Trails community. This home is MOVE-IN READY! This homesite includes a fully sodded yard AND Landscaping package. The exquisite Emerson plan offers 3,044 square feet of living space with 5 bedrooms, and 3 FULL baths, Loft plus a Flex Room great for a first-floor office or additional sitting area. As you enter the home you are greeted by an impressive 2- story entry way and 9-foot ceilings throughout the first floor. Entertaining will be easy in this open-concept kitchen equipped with a GOURMET KITCHEN PACKAGE that not only provides ample kitchen storage but elevates the home to an entire new level of luxury. Kitchen boasts a large island with an overhang for stools, 42-inch designer cabinetry with crown molding and soft close drawers and doors PLUS butler pantry. Additionally, the kitchen features modern Kitchen Aid stainless-steel appliances, quartz countertops, and easy-to-maintain luxury vinyl plank flooring. Off of the kitchen is a bump out that allows for an oversized kitchen table and access to your backyard. Continuing onto the main level you will flow into your large Living area filled with natural light and room to spread out. A SPECIAL FEATURE of this home is a first-floor bedroom with adjacent full bathroom, a perfect space for out-of-town guests or multi-generational living. This home has it all with a full basement and a 3-car garage which provides ample storage for the entire home. The main bedroom suite has a large walk-in closet and private bath featuring a raised dual bowl vanity, luxury vinyl plank floors, quartz vanity top, large shower, and a linen closet. Convenient walk-in laundry room, 3 additional bedrooms with a full second bath and a linen closet complete the second floor. All Chicago homes include our America's Smart Home Technology. Exterior/interior photos of similar home, actual home as built may vary.

1486 Vintage Drive, Oswego

$649,990

5 Beds ⋅ 3 Baths ⋅ 12748333 MLS ⋅ ACTIVE Status

Welcome to 2302 La Cote Dr. Oswego, Illinois an new home in our Sonoma Trails community. This home site includes a XL fully sodded yard and landscaping package and will be ready for a winter move-in. The exquisite Emerson plan offers 3,044 square feet of living space with 5 bedrooms, 3 full baths, and loft. As you enter the home you are greeted by an impressive 2- story entry way and 9-foot ceilings throughout the first floor. Entertaining will be easy in this open-concept kitchen equipped with a GOURMET KITCHEN PACKAGE that not only provides ample kitchen storage but elevates the home to an entire new level of luxury. Kitchen boasts a large island with an overhang for stools, 42-inch designer cabinetry with crown molding and soft close drawers and doors PLUS butler pantry. Additionally, the kitchen features modern Kitchen Aid stainless-steel appliances, quartz countertops, and easy-to-maintain luxury vinyl plank flooring. Heading up the beautiful ROD IRON Staircase you will find that the main bedroom suite has a large walk-in closet and private bath featuring a raised dual bowl vanity, luxury vinyl plank floors, quartz vanity top, large shower, and a linen closet. Convenient walk-in laundry room, 3 additional bedrooms with a full second bath, Spacious Loft and a linen closet complete the second floor. All Chicago homes include our America's Smart Home Technology. This home is located in a amenity filled community, offering Pool, Pool House, Pickle Ball, 7 Parks and walking trails! Exterior/interior photos of similar home, actual home as built may vary.

2301 La Cote Drive, Oswego

$629,900

5 Beds ⋅ 3 Baths ⋅ 12747238 MLS ⋅ ACTIVE Status

About This Home: Turnkey luxury meets expansive suburban tranquility. Situated on a premium, north-facing corner lot in Oswego's prestigious Hudson Pointe community, this pristine 2024 Raleigh model offers 2,907 square feet of modern, move-in-ready living. Designed for buyers who want zero deferred maintenance, abundant natural light, and elevated comfort, this home delivers both style and profound practicality-backed by the ultimate peace of mind of transferable builder warranties. Expansive Outdoor Space: Set on a sprawling 13,900 sq. ft. side corner lot, this north-facing property is bathed in natural light. The massive open green space provides a rare sense of privacy and a blank canvas for your ultimate outdoor living oasis, starting with the welcoming front patio. The Hub of the Home: An open-concept gourmet kitchen featuring a massive center island, gleaming quartz countertops, a bright breakfast room, and premium stainless-steel appliances. It flows seamlessly into the family room-perfect for entertaining or daily life. Smart & Energy Efficient: Built for modern living, the home is wired for high-speed fiber internet and includes integrated smart home features (smart thermostat, video doorbell). High-efficiency HVAC and low-E windows keep utility costs low year-round. Main-Floor In-Law Suite & Flow: A highly sought-after, private main-floor bedroom is paired with a full bathroom featuring a convenient walk-in shower. Daily routines are a breeze with a dedicated mudroom/drop zone providing a seamless transition from the garage into the home. Wellness Retreat: The second-floor owner's suite functions as a private getaway, complete with an expansive walk-in closet and a spa-like en-suite bathroom featuring elegant quartz vanities and a luxurious shower with built-in seating. Three additional large bedrooms complete the upper level. EV-Ready 3-Car Garage & Upgraded Basement: The spacious 3-car garage is fully equipped with Wi-Fi-enabled openers and a 220-volt connection for fast electric vehicle charging. Inside, a massive full basement awaits your customization and is fully protected by an advanced filtration system and a dual sump pump system with a primary and secondary battery backup. Key Things to Know: Property Specs: 5 Beds | 3 Baths | 3-Car Garage | 2,907 Sq. Ft. Living Space | 13,900 Sq. Ft. Lot Premium Upgrades: North-facing corner lot with a brick facade, welcoming front patio, high-end quartz surfaces throughout, mudroom, and a 220V EV-ready garage. Future-Proof & Secure: Transferable builder warranties, dual sump pump backup system, advanced basement filtration, smart home integrations, and energy-efficient construction. Top-Tier Education: Located within the acclaimed Oswego School District 308 (Southbury Elementary, Murphy Junior High, Oswego East High School). Prime Location: Just 10 minutes to Route 59 amenities (Whole Foods, Costco, Amazon Fresh, LA Fitness). Steps away from Hudson Crossing Park's scenic Fox River trails, kayaking, and picnicking. Commuter Friendly: Easy access to Downtown Chicago via the nearby Metra rail, offering the perfect blend of a peaceful suburban retreat and urban accessibility. Tenant Occupied till end of October. Lease transfer to new owner possible! 24 Hours notice required for showings!

702 West Point Way, Oswego

$625,000

5 Beds ⋅ 4 Baths ⋅ 12745106 MLS ⋅ ACTIVE Status

This meticulously designed masterpiece epitomizes model-quality elegance, offering an unparalleled living experience. Guests are received on a covered front porch before stepping into a grand, two-story foyer. To the right, a sophisticated formal living room centers around a crackling fireplace, while an exquisite formal dining room resides to the left. Rich hardwood paths flow seamlessly into a breathtaking family room, where a second fireplace serves as a focal point against a backdrop of sweeping backyard & pond views. The kitchen is a masterclass in culinary luxury, anchoring the home with stainless steel appliances, dual ovens, and an abundance of artistry cabinetry and premium countertops. A breakfast room transitions effortlessly to the outdoor patio, while a main-level executive study-versatile enough to serve as a sixth bedroom-enjoys access to an adjacent bath. The upper level is configured with a versatile loft perfect for remote studies or relaxation. Accommodations include a junior suite with a private wardrobe and en suite bath, alongside three additional generous sized bedrooms. The primary retreat is an expansive haven of indulgence, boasting dual walk-in closets and a spa-inspired bath complete with double vanities, a shower, and a deep soaking tub. Below, a massive, deep-pour basement with nine-foot ceilings and roughed in plumbing for bath and kitchen stands ready for your custom finishing ideas. A tandem three-car garage with storage loft easily accommodates your toys, big and small! Outside, the professionally landscaped, lush grounds frame a premium paver patio overlooking tranquil pond views. Situated within Southbury-a premier community boasting premium pools, a pickleball court, sand volleyball & walking paths-this home offers close proximity to popular District 308 schools- Southbury Elementary, Traughber, Oswego High School and major local amenities for shopping & dining.

233 Willington Way, Oswego

$620,000

5 Beds ⋅ 4 Baths ⋅ 12744077 MLS ⋅ ACTIVE Status

New Price! Welcome to your dream home in Churchill Club with a full finished basement! 705 Wilmore! This charming Spectacular Bid model has been updated throughout with 6 Br, 3 1/2 baths, 3 car garage and 4593 sf of finished living space and 4715 total sf. The FIRST FLOOR features hardwood flooring, 9' ceilings, front Living room & Dining room which lead to the gorgeous remodeled GOURMET KITCHEN. Your resident Chef will love the newer maple cabinets with 50" upper cabinets, 9' tall pantry wall cabinet, soft-close doors & cabinets, granite counters, new lighting, 2025 stainless appliances, Samsung 5-burner stove, French-style 4-door refrigerator, Whirlpool built-in microwave, dishwasher, 38"x60" Granite island workspace with cabinet storage & extra seating. The kitchen is open to the breakfast nook & butler pantry with a wall of cabinets & wine refrigerator. The GREAT ROOM has a 2-story ceiling, wood-burning fireplace with gas starter, SGD to backyard and is adjacent to Bedroom-5/den with double door entry & overlooking the backyard. The main hall has two wall closets & half bath. The SECOND FLOOR features the Master Bedroom Suite with vaulted ceiling, carpet, ceiling fan, fabulous 12x12 WIC, Master Bath Suite with granite double sink vanity, soaking tub, separate shower, ceramic tile & linen closet. The rest of the floor has three more bedrooms--two have access to the front balcony. The hall bath has granite double sink vanity, separate shower/tub & lavatory; second floor laundry room with Samsung W/D, cabinets & counter space; the loft has a closet and overlooks the Great room. The FINISHED BASEMENT has a spacious family room with Luxury Vinyl Plank (LVP) flooring. wet bar, 2 wine refrigerators, cabinets, shelving & bar seating. Also a full bath with LED lighting & full-size shower. Bedroom-6 has LVP flooring, wall closet & escape window. The flex room is open to your ideas. The storage room has a waterline for an extra refrigerator & the mechanical room has the furnace, 2-50 gal HWH, sump pump with battery back up. The GARAGE is a 3-car Tandem, drywalled & built-in cabinet storage. OUTSIDE is 2025 new front walk & back patio with sealed & stained stamped concrete & repainted front facade. CHURCHILL CLUB AMENITIES include a fabulous clubhouse with party room, fitness center, tennis, volleyball & basketball courts, pools, bike paths & walking trails. There are 3 on-site schools: Churchill Elementary, Plank Jr High & Brokow Early Learning. Oswego East High school is less than a mile away. Shopping & Dining are just minutes away at Rt 34 & Douglas. You cannot beat the convenience of all the amenities and a fabulous move-in ready home too!

705 Wilmore Drive, Oswego

$790,000

5 Beds ⋅ 5 Baths ⋅ 12743965 MLS ⋅ CONTINGENT Status

A little bit country, a little bit city - all on over an acre. Tucked in Old Reserve Hills on a private 1-acre lot, this stately home gives you room to breathe and space between you and your neighbors, while still sitting inside the Oswego city limits. Surrounded by farmland views but minutes from everyday convenience - the best of both worlds, literally.~~~Step inside and the two-story foyer stops you. Twenty-foot ceilings, a wall of Palladian windows, and a Great Room that just pours with natural light. Hardwood floors carry you through the main level, past a formal living room and dining room built for entertaining.~~~Here's the flex that sets this one apart: a main-floor in-law suite with its own full bath, an adjoining sitting area, and private exterior access to the patio. Full independence, total privacy - whether it's for extended household members, guests, or a home office that feels like its own wing.~~~The kitchen means business. A center island with a breakfast bar, wine rack, and beverage fridge anchors the space, while granite counters and Thomasville 42" cabinets give it a rich, custom feel. Cabinets wrap around the corner, connecting a butler pantry to the kitchen workspace - and combined with the walk-in pantry, storage is never a question. Recessed lighting keeps it bright, and cooking is set up for real work: built-in dual ovens, a gas cooktop, and a stainless Broan range hood, plus a full-size fridge and full-size freezer that give the whole space a genuinely commercial feel.~~~Upstairs, four bedrooms and a loft. The primary suite is the showstopper - triple tray ceiling with inset crown, and a bathroom that feels like a spa: oversized shower with dual sprayers, separate soaking tub, a huge split-sink vanity with a makeup station, tulip lighting, and a cathedral ceiling overhead. Plus a walk-in closet with built-ins that's a room of its own. One secondary bedroom has its own private bath; the other two share a jack-and-jill.~~~Then there's the backyard. One acre, fresh landscaping, and an in-ground pool with diving board and slide - the summer headquarters. A brick paver patio and pergola with TV round it out for long evenings outside. And the three-car side-load garage is a home for trucks and SUVs: 32.5' wide, 23.5' deep, with 8-foot insulated doors.~~~The bones are built to last - 2x6 construction, steel H-beam supports, tornado ties on every joist, insulated interior walls for quiet, and dual-zone HVAC for comfort on every level. Bellagio two-panel wood doors and vinyl-clad Thermopane windows throughout. Students attend Hunt Club, Traughber, and Oswego High School. Room to breathe, built to last - and waiting for you.

5320 Goldenrod Drive, Oswego

$499,900

5 Beds ⋅ 4 Baths ⋅ 12675936 MLS ⋅ ACTIVE Status

212 Mondovi Drive, Oswego

$499,900

5 Beds ⋅ 3 Baths ⋅ 12702588 MLS ⋅ CONTINGENT Status

Welcome to your DREAMIEST DREAM HOME! Close QUICK! This home is available NOW!!.....Absolutely pristine Silver Charm model in the highly sought-after Churchill Club community! Offering 2,800+ sq. ft. of beautifully maintained living space, this exceptional home combines space, luxury, and an unbeatable lifestyle.||| Features: 5 Bedrooms | 3 Full Bathrooms | Full Basement with Bathroom Rough-In | Dual Staircase | Main-Level Bedroom & Full Bath- (perfect for extended family needing main level living) | 9' Ceilings | Gourmet Kitchen Upgrade | 42" Maple Cabinets | Built-In Cooktop | Double Oven | Prep Island | Breakfast Bar | Formal Living Room | Formal Dining Room | Mudroom | Recessed Lighting | Ceiling Fans & Lighting in All Bedrooms | Gorgeous Spa-Inspired Primary Bath | Private Backyard with No Rear Neighbors | Huge Backyard | Paver Patio | Oak Railings | New Roof (2019)||||Churchill Club Lifestyle: Junior Olympic-Size Pool | Water Slides | Kiddie Pool | Splash Pad | Pickleball Courts | Sand Volleyball | Parks | Walking & Bike Paths | Three On-Site Schools | Walk to Shopping, Restaurants, and Everyday Conveniences |Vacation year-round in your dream home while enjoying one of Oswego's premier resort-style communities. Luxury, location, and lifestyle all come together at 432 Bluegrass Parkway. Welcome home!

432 Bluegrass Parkway, Oswego

$589,005

5 Beds ⋅ 3 Baths ⋅ 12691340 MLS ⋅ ACTIVE Status

** BRICK FRONT OPTION * IN LAW SUITE WITH 2ND FLOOR LAUNDRY OPTION * SPECIAL FINANCING OFFERS AVAILABLE!! READY FOR FALL DELIVERY!!!! Homesite# 0107 Discover the Raleigh, a home expertly planned to combine style and everyday comfort. This spacious layout offers four bedrooms, two and a half bathrooms, and a dedicated study to suit your lifestyle. The main level features a seamless flow between the family room, kitchen, and breakfast room, creating an open and inviting space perfect for both relaxing and entertaining. The chef-inspired kitchen boasts stainless steel appliances, sleek 42" cabinetry, elegant quartz countertops, and a large island that serves as both a functional workspace and gathering spot. The owner's suite, located upstairs, is a true retreat featuring two generous walk-in closets and a spa-like en-suite bathroom with dual sinks and a deluxe shower. Three additional bedrooms share a full bathroom, and the main-level laundry room adds ease to your daily routine. An Open to Below lookout from the second level creates a dramatic and airy connection to the other rooms below, enhancing the home's spacious feel. A standard three-car garage provides ample parking and storage. Exterior will be OCEANSIDE color siding with GRAYSTONE color brick. (pic for reference ONLY) *Photos are not this actual home* Discover Reserve at Hummel Trails, a vibrant master-planned community offering brand-new homes in Oswego, Illinois-where modern living meets everyday convenience and natural beauty. Designed with lifestyle in mind, this inviting neighborhood features a scenic pond and community park, creating the perfect setting for relaxing evenings, outdoor play, and gathering with friends and family. Ideally located just minutes from the bustling Route 59 corridor in Naperville, Illinois, residents enjoy quick access to top-tier shopping, dining, and entertainment. Everyday errands and weekend plans are effortless with nearby destinations like Whole Foods Market, Amazon Fresh, LA Fitness, and Costco. Families benefit from highly regarded Oswego Community Unit School District 308, with convenient access to Southbury Elementary, Traughber Junior High, and Oswego East High School. For outdoor enthusiasts, Wolf's Crossing Community Park is just moments away, offering playgrounds, a splash pad, fitness areas, and open green space for year-round recreation. At Reserve at Hummel Trails, you're not just buying a new home-you're stepping into a connected, amenity-rich community designed to elevate your everyday life."

188 Blazing Star Trail, Oswego

$599,586

5 Beds ⋅ 3 Baths ⋅ 12686263 MLS ⋅ CONTINGENT Status

5 BEDROOMS * SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FALL DELIVERY! Homesite #0127. Discover the Raleigh, a home expertly planned to combine style and everyday comfort. This spacious layout offers four bedrooms, two and a half bathrooms, a dedicated study to suit your lifestyle, in addition to an In-Law suite with a second floor laundry upgrade. The main level features a seamless flow between the family room, kitchen, and breakfast room, creating an open and inviting space perfect for both relaxing and entertaining. The chef-inspired kitchen boasts stainless steel appliances, sleek 42" cabinetry, elegant quartz countertops, and a large island that serves as both a functional workspace and gathering spot. The owner's suite, located upstairs, is a true retreat featuring two generous walk-in closets and a spa-like en-suite bathroom with dual sinks and a deluxe shower. Three additional bedrooms share a full bathroom, and the main-level laundry room adds ease to your daily routine. An Open to Below lookout from the second level creates a dramatic and airy connection to the other rooms below, enhancing the home's spacious feel. A standard three-car garage provides ample parking and storage. Exterior will be GREYSTONE color siding with Graystone color brick. (pic for reference ONLY). *Photos are not this actual home* Welcome to Hudson Pointe II, a beautifully designed master-planned community offering brand-new homes in the heart of Oswego, Illinois. Perfectly blending comfort, convenience, and natural beauty, this neighborhood is ideal for families and individuals seeking a balanced lifestyle. Right within the community, residents can enjoy a well-maintained park for leisurely play and gatherings, as well as a serene pond that enhances the peaceful atmosphere of Hudson Pointe II. Just 10 minutes from the Naperville Route 59 corridor, Hudson Pointe II places premier shopping, dining, and entertainment within easy reach. Access top destinations like Whole Foods, Amazon Fresh Market, LA Fitness, and Costco, along with a variety of local restaurants and entertainment spots. Families will appreciate the top-rated Oswego School District 308, with students attending Southbury Elementary, Murphy Junior High, and Oswego East High School-all conveniently located within a 10-minute drive. Outdoor enthusiasts will love the close proximity to Wolf's Crossing Community Park, offering an array of recreational features including playgrounds, an outdoor fitness area, a splash pad, and more-perfect for year-round family fun. At Hudson Pointe II, you're not just buying a home-you're joining a thoughtfully planned community where modern living meets natural charm and everyday convenience.

701 Erwin Street, Oswego

$1,099,000

5 Beds ⋅ 4 Baths ⋅ 12684348 MLS ⋅ ACTIVE Status

Welcome to 14 Abbeyfeale Drive, an extraordinary executive estate nestled on 2.2 beautifully landscaped acres in one of Oswego's most prestigious settings. Offering over-the-top quality, exceptional craftsmanship, and luxurious amenities throughout, this stunning move-in-ready residence features 5 bedrooms, a private office, 4 full bathrooms, a deep-pour finished basement, and an oversized 4-car garage. From the moment you enter, the grand two-story foyer with its elegant chandelier sets the tone for the sophistication found throughout the home. Rich premium walnut hardwood flooring spans the main level, complemented by solid wood paneled doors, custom millwork, and detailed trim surrounding every door and window. Picturesque windows adorned with plantation shutters flood the home with natural light while showcasing breathtaking views of the surrounding property. Designed for both everyday living and entertaining, the custom chef's kitchen is a true showpiece featuring high-end finishes, abundant workspace, and a large center island complete with a prep sink. The adjacent family room offers built-in shelving, a grand fireplace, and spectacular views of the backyard oasis. The thoughtfully designed main level includes a first-floor bedroom and full bathroom, ideal for guests or multi-generational living. Two separate staircases lead to the second floor, including a discreet secondary staircase equipped with a chairlift for added accessibility. Upstairs, you'll find four generously sized bedrooms, including a luxurious primary suite that serves as a private retreat. The owner's suite features a cozy fireplace sitting area, spacious walk-in closet, and spa-inspired bathroom with heated floors. Every bathroom in the home, except the basement bath, offers the comfort of heated flooring. One secondary bedroom also provides convenient access to additional attic storage. The finished deep-pour basement expands the living space with a dedicated theater room, large office or potential guest suite, full bathroom, recreation area, television lounge, expansive utility room, and an oversized storage room with built-in shelving. Step outside and discover your own private resort. The meticulously maintained grounds feature professional landscaping, a paver patio with fire pit, expansive wood deck, outdoor speaker system, and a dedicated area to practice your golf swing. Sports enthusiasts will appreciate the private pickleball court, while the expansive yard offers endless opportunities for recreation and relaxation. With oversized bedrooms, exceptional attention to detail, premium finishes, and an unmatched blend of luxury and functionality, 14 Abbeyfeale Drive presents a rare opportunity to own one of Oswego's finest executive homes.

14 Abbeyfeale Drive, Oswego

$598,000

5 Beds ⋅ 4 Baths ⋅ 12667759 MLS ⋅ ACTIVE Status

WELCOME TO THIS LOVELY AND ELEGANT HOME. 9 FEET CEILING, 4 BEDROOM + FIRST FLOOR DEN AND 2nd LOFT, *** SUNROOM***, OVER 3450 SQ FT, 3.1 BATH, *** 3 CAR GARAGE***, *** LOOKOUT BASEMENT***, FIREPLACE. TWO STORY FOYER AND LIVING ROOM, A GOURMET KITCHEN w/ISLAND, HARDWOOD FLOORS, HUGE MASTER BEDROOM SUITE WITH *** SITTING AREA ***, WALKIN CLOSET AND LUXURY MASTER BATH WITH SEPERATE SHOWER AND WHIRLPOOL TUB. TWO BEDROOMS WITH JACK AND JILL. 4TH BEDROOM SUITE, LARGE LAUNDRY ROOM, CLUB HOUSE, PARK, PLAYGROUND, POOL, POND. Elementary school in the subdivision. OVER 100+ SHOPPING STORES WITHIN MINUTES.

607 Mansfield Way, Oswego

$1,150,000

5 Beds ⋅ 5 Baths ⋅ 12644617 MLS ⋅ ACTIVE Status

Welcome to the historic Gaylord House & Gardens, a truly extraordinary estate where timeless character, modern comfort, and endless possibilities come together on just over 5 picturesque acres. Originally built in 1865, this property is rich in local history and offers a rare opportunity to own a one-of-a-kind country retreat with unmatched charm, ample acreage, and exceptional special use potential. Every detail of this remarkable home showcases timeless craftsmanship and thoughtful livability. With 5 bedrooms and 4.5 bathrooms, the home offers a generous and well balanced layout designed to accommodate comfortable living and entertaining. Original woodwork, hardwood flooring, and stunning architectural details have been beautifully preserved throughout. Multiple living spaces create a warm and inviting atmosphere, highlighted by two wood burning fireplaces, a finished attic, walkout basement, private elevator, wine cellar, and screened in patio. A thoughtfully integrated 2008 addition expands the home while honoring its original character and architectural integrity. The vintage 1901 piano located in the dining room is also included with the sale, adding yet another touch of timeless elegance. Outside, the scenic grounds are surrounded by mature trees, open green space, and protective security fencing that lines the property, offering both beauty and privacy while creating an ideal setting for pets and children. The property features a large barn ideal for gatherings or events, a chicken barn, two workshops, a machine shed, and two spacious pastures, making it perfectly suited for horses, hobby farming, entertaining, or recreational use. Electric service is available to all exterior structures. Whether you are envisioning a private estate, boutique event venue, bed and breakfast, or peaceful countryside homestead, this property offers incredible potential. The property is zoned R3 SU, offering additional flexibility and opportunity for a variety of uses. Known as the Gaylord House & Gardens, this exceptional property combines historic significance with the serenity of country living while remaining conveniently close to shopping, dining, and everyday amenities. The opportunity to own an estate of this caliber and one of Kendall County's most distinctive landmark properties is truly once in a lifetime. Experience the beauty, presence and endless potential by scheduling your private showing today.

1542 Plainfield Road, Oswego

$649,990

5 Beds ⋅ 3 Baths ⋅ 12641560 MLS ⋅ PENDING Status

Welcome to 2314 Hirsch Rd. Oswego, Illinois a beautiful new home in our Sonoma Trails community. This home will be ready for a FALL MOVE IN! This homesite includes a fully sodded yard AND Landscaping package. The exquisite Emerson plan offers 3,044 square feet of living space with 5 bedrooms, and 3 FULL baths, Loft plus a Flex Room great for a first-floor office or additional sitting area. Entertaining will be easy in this open-concept kitchen equipped with a GOURMET KITCHEN PACKAGE that provides ample kitchen storage. Kitchen boasts a large island with an overhang for stools, 42-inch designer cabinetry with crown molding and soft close drawers and doors PLUS butler pantry. Additionally, the kitchen features modern Kitchen Aid stainless-steel appliances, quartz countertops, and easy-to-maintain luxury vinyl plank flooring. A SPECIAL FEATURE of this home is a first-floor bedroom with adjacent full bathroom, a perfect space for out-of-town guests or multi-generational living. The Emerson plan also features a full basement and a 3-car garage. The main bedroom suite has a large walk-in closet and private bath featuring a raised dual bowl vanity, luxury vinyl plank floors, quartz vanity top, large shower, and a linen closet. Convenient walk-in laundry room, 3 additional bedrooms with a full second bath. All Chicago homes include our America's Smart Home Technology. Exterior/interior photos of similar home, actual home as built may vary.

2314 Hirsch Road, Oswego

$615,000

5 Beds ⋅ 3 Baths ⋅ 12635458 MLS ⋅ CONTINGENT Status

*Photos are not this actual home*

516 Fridley Avenue, Oswego

$1,499,000

5 Beds ⋅ 4 Baths ⋅ 12526887 MLS ⋅ ACTIVE Status

Private 14.4-Acre Creekfront Estate | 4,800+ Sq Ft | Designed for Living, Creating & Expanding! Welcome to 1502 Cherry Rd - a one-of-a-kind estate where privacy, space, and luxury converge on over 14 pristine acres in Oswego, IL. Designed for those who demand the extraordinary, this stunning ranch offers a lifestyle rarely found at any price. Step inside and discover a thoughtfully designed floor plan centered around two main-level master suites - ideal for multigenerational living, long-term guests, or a private owner's retreat. The Finished Room Over Garage (FROG) adds even more versatility, whether you envision a home office, media room, playroom, or additional guest suite. The property's crown jewel is its unmatched garage and storage infrastructure. A 4-car attached garage paired with a massive pole barn delivers the kind of space that car collectors, hobbyists, equipment owners, and entrepreneurs dream about. Bring your classics, your toys, your tools - there is room for all of it. Outdoors, over 14 acres of picturesque land surround you with room to roam, entertain, or simply breathe. The estate's natural setting provides the seclusion of country living while remaining just minutes from everyday conveniences in Oswego and a short drive to the greater Chicagoland area. Additional highlights include a thoughtful ranch layout, generous living spaces, and a character and quality that must be experienced in person to be fully appreciated. This is not just a home - it is a private retreat built for a buyer who has earned the best. Schedule your private showing today.

1502 Cherry Road, Oswego

$579,605

5 Beds ⋅ 3 Baths ⋅ 12628764 MLS ⋅ PRICE CHANGE Status

SPECIAL FINANCING OFFERS AVAILABLE!! READY FOR FALL DELIVERY!!!! Homesite# 0058 "Discover the Raleigh, a home expertly planned to combine style and everyday comfort. This spacious layout offers four bedrooms, two and a half bathrooms, and a dedicated study to suit your lifestyle. The main level features a seamless flow between the family room, kitchen, and breakfast room, creating an open and inviting space perfect for both relaxing and entertaining. The chef-inspired kitchen boasts stainless steel appliances, sleek 42" cabinetry, elegant quartz countertops, and a large island that serves as both a functional workspace and gathering spot. The owner's suite, located upstairs, is a true retreat featuring two generous walk-in closets and a spa-like en-suite bathroom with dual sinks and a deluxe shower. Three additional bedrooms share a full bathroom, and the main-level laundry room adds ease to your daily routine. An Open to Below lookout from the second level creates a dramatic and airy connection to the other rooms below, enhancing the home's spacious feel. A standard three-car garage provides ample parking and storage. Exterior will be OCEANSIDE color siding with GRAYSTONE color brick. (pic for reference ONLY) *Photos are not this actual home* Discover Reserve at Hummel Trails, a vibrant master-planned community offering brand-new homes in Oswego, Illinois-where modern living meets everyday convenience and natural beauty. Designed with lifestyle in mind, this inviting neighborhood features a scenic pond and community park, creating the perfect setting for relaxing evenings, outdoor play, and gathering with friends and family. Ideally located just minutes from the bustling Route 59 corridor in Naperville, Illinois, residents enjoy quick access to top-tier shopping, dining, and entertainment. Everyday errands and weekend plans are effortless with nearby destinations like Whole Foods Market, Amazon Fresh, LA Fitness, and Costco. Families benefit from highly regarded Oswego Community Unit School District 308, with convenient access to Southbury Elementary, Traughber Junior High, and Oswego East High School. For outdoor enthusiasts, Wolf's Crossing Community Park is just moments away, offering playgrounds, a splash pad, fitness areas, and open green space for year-round recreation. At Reserve at Hummel Trails, you're not just buying a new home-you're stepping into a connected, amenity-rich community designed to elevate your everyday life."

158 Blazing Star Trail, Oswego

$605,000

5 Beds ⋅ 3 Baths ⋅ 12627383 MLS ⋅ CONTINGENT Status

702 Erwin Street, Oswego

$414,000

5 Beds ⋅ 3 Baths ⋅ 12621935 MLS ⋅ ACTIVE Status

Designed for effortless living, this home offers a functional, practical floor plan with tastefully refreshed updates! You'll appreciate the efficient use of space, and worry-free lifestyle, ideal for those looking to simplify without compromising comfort. With no basement to worry about, you'll enjoy low maintenance, no concerns about flooding or moisture, and a home that's easy to navigate and easy to care for. A classic white picket fence sets the tone, leading to an oversized covered front porch including ceiling fans, custom porch furniture, inviting you to share this perfect cozy porch in the morning with coffee or relaxing in the evenings. Step inside to see a two-story foyer that offers a bright, open-concept layout with stylish wood laminate flooring throughout the main level. Fresh paint throughout the home creates a light, neutral backdrop offering a true blank canvas for buyers to bring their own style and vision to life. Just off the entry, a versatile room with custom French doors offers the perfect flexible space for a home office, den, or playroom, tailored to today's versatile needs. Designed for both everyday living and entertainment, the spacious living and family rooms flow seamlessly together. The family room opens to a generously sized eat-in kitchen featuring abundant cabinetry and counter space, a center island with electric and storage, pantry with a custom sliding barn door, fresh paint, and a few new appliances that include microwave and dishwasher. The main level is completed by a convenient half bath and a functional laundry/mudroom with direct access to the attached two-car garage and asphalt driveway. Upstairs, you'll find five generously sized bedrooms, including a spacious primary master suite with vaulted ceilings, a walk-in closet, and a private bath with double sinks and a separate shower. An additional full hallway bathroom also offers another full shower, double sink, and vanity for ample storage. New trim, updated electrical with new outlets, light switches and hardware all around the home. Enjoy peace of mind with major updates, including a brand-new furnace (February 2026), roof, paint, and more! HOME WARRANTY included ! Low HOA. Step outside to the oversized backyard complete with a concrete patio, pergola, fully fenced yard including a dedicated dog run! Kid friendly/family-oriented neighborhood, close to elementary school, three parks and walkable to downtown restaurants, bars, coffee shops and village events. With ten total rooms and a thoughtfully designed layout, this move-in-ready home offers the perfect balance of simplicity, functionality and community. Don't miss the opportunity to make it yours!

123 Eisenhower Drive, Oswego

$649,990

5 Beds ⋅ 3 Baths ⋅ 12564530 MLS ⋅ PENDING Status

Welcome to 1440 Vintage Dr. Oswego, Illinois a beautiful new home in our Sonoma Trails community. This home will be ready for a summer MOVE IN! This homesite includes a fully sodded yard AND Landscaping package. The exquisite Emerson plan offers 3,044 square feet of living space with 5 bedrooms, and 3 FULL baths, Loft plus a Flex Room great for a first-floor office or additional sitting area. As you enter the home you are greeted by an impressive 2- story entry way and 9-foot ceilings throughout the first floor. Entertaining will be easy in this open-concept kitchen equipped with a GOURMET KITCHEN PACKAGE that not only provides ample kitchen storage but elevates the home to an entire new level of luxury. Kitchen boasts a large island with an overhang for stools, 42-inch designer cabinetry with crown molding and soft close drawers and doors PLUS butler pantry. Additionally, the kitchen features modern Kitchen Aid stainless-steel appliances, quartz countertops, and easy-to-maintain luxury vinyl plank flooring. This home has it all with a full LOOK OUT BASEMENT and a 3-car garage which provides ample storage for the entire home. The main bedroom suite has a large walk-in closet and private bath featuring a raised dual bowl vanity, luxury vinyl plank floors, quartz vanity top, large shower, and a linen closet. Convenient walk-in laundry room, 3 additional bedrooms with a full second bath and a linen closet complete the second floor. All Chicago homes include our America's Smart Home Technology. Exterior/interior photos of similar home, actual home as built may vary.

1440 Vintage Drive, Oswego

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