Hillary Lafferty

3135 Book Rd Naperville, IL 60564

Two GREAT Agents, One AMAZING Team!

Hillary Lafferty – Realtor®, Carolyn & Hillary Homes

Hillary is a dedicated Realtor with Charles Rutenberg Realty and a proud co-leader of the Carolyn & Hillary Homes team. She serves Yorkville, Oswego, Naperville, and the southwest suburbs with a commitment to excellence and a client-first approach.

Known for her market knowledge, attention to detail, and genuine care, Hillary helps clients navigate every step of buying or selling with confidence. She takes pride in making the real estate process smooth from start to finish, ensuring her clients feel supported, informed, and excited about their next move.

Whether guiding first-time buyers, helping families settle into their forever home, or assisting sellers in achieving top value, Hillary combines proven strategies with local expertise to deliver results that exceed expectations.

 

Offices in Naperville and Yorkville

24w141 Hobson Road, Naperville
$4,950,000
7 Beds ⋅ 9 Baths ⋅ 12753503 MLS ⋅ ACTIVE Status
Nestled on 3 breathtaking acres of lush grounds and whimsical gardens, this impeccable Grand English Tudor Estate offers over 12,000 square feet of masterfully crafted living space. Conceived by engineer Ted Reitenbach and designed by the talented Barbara Grzelczyk, this magnificent home took three years for skilled craftsmen and artisans to create - built like no other here every detail bears witness to that devotion. A private gated entry leads to a stunning paver brick driveway with adjoining walkways and manicured gardens professionally designed, setting a grand tone before you even step inside. Step through grand 8 foot cherry wood cathedral doors into an opulent limestone foyer crowned by a breathtaking 250-pound antique chandelier with a built-in elevator mechanism for effortless elegance. Antique leaded glass windows with built-in blinds grace every first-floor window, while Pella windows with interior shades adorn the upper levels. Every hardware piece was handmade in Lithuania, and Perure hinges were selected for their unmatched Old World craftsmanship. The remaining chandeliers throughout are irreplaceable one-of-a-kind antique pieces that cannot be found or replicated, each adding timeless distinction to every space they illuminate. The formal dining room stuns with a hand-carved plaster ceiling and artisan-crafted leaded windows bathing the space in natural light. The distinguished library features soaring cathedral ceilings, custom-crafted light fixtures, and built-in cabinetry with grand mesh doors. The family room soars with 20-foot ceilings, 14 expansive windows, irreplaceable antique chandeliers, a majestic Chicago fire brick fireplace, and a dramatic second-story balcony overlook. Antique solid wide white oak floors flow beautifully throughout. Five magnificent fireplaces, every one crafted with authentic Chicago fire bricks, grace this extraordinary estate. This estate proudly features two full chef-caliber kitchens - seamlessly connected by a dumbwaiter elevator - making large-scale entertaining and multi-generational living truly effortless. The primary gourmet kitchen showcases French hand-glazed cabinetry, granite countertops, a professional Viking range with grill, griddle, convection oven and warming drawer, dual Sub-Zero refrigerators behind extraordinary handcrafted panels, and a charming limestone fireplace breakfast area. A true butler's pantry with an additional Sub-Zero walk-in refrigerator behind cherry paneling bridges the kitchen and formal dining room. Two expansive first-floor primary suites provide ideal accommodations for multi-generational living, in-law quarters, or distinguished guests. The walkout lower level is an entertainer's paradise: home theater, fitness room with sauna, wine cellar-ready room, billiards area, secret passageways, a second full chef-caliber kitchen, and generous storage. Outside, extensive patios, meandering garden paths, and enchanting landscaping create a storybook backdrop for grand entertaining, anchored by a beautifully crafted exterior storage building designed to match the manor architecture. The entire grounds are enclosed by a 6-foot wrought iron fence ensuring total privacy. Mechanical excellence includes three zoned HVAC systems a dedicated radiant heat boiler serving the basement, garage and front entrance steps, a state-of-the-art private water system, natural slate roof with copper gutters, and a smart home system. A once-in-a-generation opportunity for the discerning buyer who demands timeless elegance, unparalleled provenance, and the absolute finest in luxury living - nestled within one of the most coveted and sought-after communities in all of Chicagoland.

24w141 Hobson Road, Naperville
333 W Benton Avenue, Naperville
$3,700,000
4 Beds ⋅ 6 Baths ⋅ 12784038 MLS ⋅ ACTIVE Status
THE FINISHED DOWNTOWN NAPERVILLE ESTATE. For the buyer who wants the architecture, craftsmanship and lifestyle of a custom home - without the wait, uncertainty or disruption of building - 333 W Benton delivers a fully realized luxury residence in the heart of Downtown Naperville. Built in 2026 by award winning, high-end custom home Builder, highly sought after Architecture Group and exclusive Interior Designer, this exceptional 5 bedroom, 5.5 bath residence offers 5,645 total square feet of finished living space, with an extraordinary level of detail throughout. A truly exceptional custom residence, conceived for those who expect nothing less than extraordinary; no expense was spared to bring luxury and elegance with close vicinity to the center of it all. The design is intentionally timeless yet unmistakably contemporary, boasting soaring ceilings, lofted and beamed rooms, floor to ceiling windows, and an impeccable flow. The main level is designed for effortless everyday living and entertaining, featuring a private first-floor primary suite, dedicated office, designer kitchen with fully appointed scullery, laundry, mudroom and expansive outdoor living space. Upstairs, 3 additional spacious ensuite Bedrooms provide privacy for family and guests. The finished lower level expands the lifestyle with additional entertaining and recreational space, bedroom and full bath, creating the scale and flexibility expected of a true estate. Outdoor entertainment space includes a motorized screened Porch, grill area and open Patio on bluestone pavers. And then there is the address: Downtown Naperville. Restaurants, shopping, the Riverwalk, events and the energy of downtown are all part of everyday life. This is not a future home waiting to be built - it is a finished home - fully designed, fully constructed and ready to become yours.

333 W Benton Avenue, Naperville
115 S Webster Street, Naperville
$3,400,000
4 Beds ⋅ 6 Baths ⋅ 12727691 MLS ⋅ ACTIVE Status
An exceptional opportunity to make your dream of custom luxury living a reality in the heart of Downtown Naperville. 115 S. Webster is the southernmost homesite within The West End, an exclusive boutique community of just four luxury residences by Lakewest Homes. This to-be-built custom home offers buyers the rare opportunity to personalize finishes, fixtures, and design selections while securing one of downtown's most desirable addresses. Preliminary approvals with the City have been completed, and the foundation is currently being poured, allowing for an estimated nine-month build timeline from contract. Designed to blend contemporary architecture with timeless elegance, this custom residence will offer over 5,400 square feet of exceptional living space across four finished levels, featuring 5 bedrooms, 5 full bathrooms, 2 half bathrooms, a private elevator serving every floor, and a spectacular rooftop deck with sweeping views of Downtown Naperville. The chef-inspired kitchen is complemented by a fully appointed scullery, creating the perfect balance of beauty and function for everyday living and effortless entertaining. Thoughtfully designed for today's lifestyle, the home also includes a dedicated first-floor office, first-floor mudroom, and the convenience of laundry rooms on both the first and second floors. Premium appliances, designer finishes, expansive entertaining spaces, and seamless indoor-outdoor living complete this extraordinary custom residence. Ideally located just steps from Naperville's acclaimed restaurants, boutique shopping, and the iconic Riverwalk-and only half a block from Hugo's Frog Bar and the Apple Store-The West End offers an unmatched walkable luxury lifestyle. With only four homes in this exclusive development and limited opportunities remaining, now is the time to secure your homesite and begin creating a truly custom luxury residence.

115 S Webster Street, Naperville
51 Ford Lane, Naperville
$3,275,000
5 Beds ⋅ 9 Baths ⋅ 12752990 MLS ⋅ ACTIVE Status
An extraordinary riverfront estate where timeless elegance meets resort-style living: set on two lots overlooking the DuPage River, this remarkable residence offers an exceptional combination of grand architecture, sophisticated finishes, and spectacular entertaining spaces unlike any other. From the moment you arrive, it is clear that this estate is solidly built, featuring a real stucco and stone exterior, simulated slate roof, copper gutters, multiple balconies, and professionally landscaped grounds. A private outdoor oasis provides an extraordinary setting for relaxation, providing an infinity pool with hot tub, basketball/volleyball court, shuffleboard court, putting green, firepit, outdoor bar, extensive landscape lighting, and stone stairs leading to the riverfront where you can kayak and fish right outside your own back door. Inside, refined craftsmanship and architectural detail unfold in every room. Enter though the custom carved double front door into the dramatic two-story foyer where a beautiful mural and crystal chandelier create a striking overhead scene and a custom travertine marble inlay create a beautiful pattern underfoot. A lovely double-sided stone fireplace is shared with the great room. Formal living and dining spaces are richly appointed with floor-to-ceiling wainscoting, crown molding, elegant chandeliers, columned entries, and soaring ceilings. At the heart of the home, the expansive chef's kitchen is as beautiful as it is functional, featuring an oversized center island with prep sink, butler's pantry with wine storage, custom bar with a hidden TV, and an impressive collection of premium commercial appliances including La Cornue, Viking, Thermador, Bosch, and GE Monogram. The kitchen flows naturally into the magnificent two-story great room, where multiple sets of patio doors bring the riverfront setting into view. A private office with wood inlay, a spacious mudroom with a laundry closet, a full bath, and a powder room complete the first level. A wood-paneled elevator serves all three levels of the home. The upper level is devoted to luxurious private spaces. The spectacular primary suite includes a sitting room with a custom fireplace, wet bar, and a private balcony. Four skylights illuminate the vaulted bath, which features heated travertine floors, marble countertops, double Jacuzzi tub, and an extraordinary double shower with rainfall showerheads, multiple body sprays, and handheld fixtures. The expansive walk-in closet doubles as a panic room and has custom organizers, safes and locking drawers, plus a mini fridge. Additional bedrooms each offer their own special features, including private baths, fireplaces, and balconies. The finished lower level rivals a private club, offering an impressive custom bar with seating for eight, lighted cabinetry, hammered copper sink, beer tap, kegerator, four mini-refrigerators, Viking ice maker, and more. Entertain in the spacious recreation and billiards rooms, or retreat to the dedicated theater with projector, screen, tiered seating for 12, and sound system. A custom wine cellar offers exceptional storage, while an additional bedroom and full bath provide accommodation for guests. Enjoy a private wellness experience every day in the spacious fitness room, offering a huge steam shower, a massage room/salon, and a private sauna. Step out and relax in the exterior bar/3-seasons room, and continue on to the infinity pool and hot tub. Equipped with extensive smart-home and lighting systems, oversized garage accommodations, heated walkways and driveway, whole-house generator, battery backup, and robust mechanical infrastructure throughout. This is more than an exceptional home-it is a destination. This is a rare opportunity to experience sophisticated riverfront living with the amenities, privacy, and craftsmanship offered by a true estate.

51 Ford Lane, Naperville
1076 Parkside Road, Naperville
$2,499,900
5 Beds ⋅ 6 Baths ⋅ 12721451 MLS ⋅ ACTIVE Status
Experience exceptional new construction living in this custom-built luxury residence offering nearly 4,800 square feet above grade, plus a finished basement, thoughtfully designed for modern living and effortless entertaining by Naperville's Mart Design Co, the leading remodeling company in Naperville. Situated on a beautiful 1/2 acre homesite in Naperville, this home seamlessly blends timeless architecture with today's most sought-after floor plan. A welcoming front porch leads into a grand foyer where soaring 10-foot ceilings, expansive living spaces, and abundant natural light create an immediate sense of elegance. The heart of the home is an impressive open-concept great room that flows seamlessly into the chef's kitchen and casual dining area, creating the perfect setting for both everyday living and entertaining. The gourmet kitchen is designed to impress with an oversized island, spacious walk-in pantry, separate butler's pantry, premium appliances, and generous custom cabinetry. The main level also features a private study, formal dining room, expansive mudroom, powder room, and a highly desirable first-floor guest suite complete with its own full bath, offering the ideal setup for multigenerational living, overnight guests, or a second private home office. The second level is equally impressive, featuring a luxurious primary retreat with dual walk-in closets and a spa-inspired bath complete with dual vanities, a freestanding soaking tub, oversized shower, and private water closet. Four additional spacious bedrooms, multiple well-appointed bathrooms, a large loft, and a convenient second-floor laundry room complete the upper level. The finished basement expands the home's living space even further, providing endless possibilities for a recreation room, home theater, fitness area, game room, additional guest accommodations, or all of the above. Outside, enjoy a covered rear outdoor living area overlooking the backyard, offering the perfect extension of the home's entertaining space. An attached three-car garage provides ample room for vehicles, storage, and hobbies. Built with luxury, comfort, and functionality in mind, this exceptional new construction home offers the rare combination of timeless design, generous living spaces, and modern conveniences in one of Naperville's most desirable locations.

1076 Parkside Road, Naperville
1046 Sylvan Circle, Naperville
$2,495,000
4 Beds ⋅ 5 Baths ⋅ 12763552 MLS ⋅ ACTIVE Status
1046 Sylvan Circle presents an extraordinary opportunity to enjoy refined luxury living in one of Downtown Naperville's most distinctive residential settings on over a half acre. Privately nestled within the sought-after Sylvan Circle community, this remarkable home offers an exceptional balance of sophistication, and everyday comfort in a peaceful setting surrounded by mature trees and beautifully established residences. Positioned on an impressive fully fenced half-acre homesite with expansive 100 x 200 dimensions and among the largest backyard settings in the neighborhood, this exceptional property provides ample space for a future pool, sport court, or the outdoor sanctuary of your dreams. Offering approximately 4,500 square feet above grade in addition to an expansive 2,315-square-foot finished lower level, the home delivers remarkable scale while maintaining an inviting and comfortable feel throughout. Extensive recent improvements have elevated both the interior and exterior, including a beautifully limewashed facade, professionally painted black exterior windows, refreshed landscaping with lava rock accents, meticulously maintained mature trees, and a new roof and skylights completed in 2025. Outdoor spaces have been thoughtfully designed with Bluestone walkways, a classic brick paver patio, fire-pit with gas line, and beautifully layered landscaping featuring mature plantings and seasonal color that create a serene outdoor experience. Designed for both entertaining and everyday living, the kitchen combines functionality and style with an oversized island, custom cabinetry with integrated storage solutions and built-ins, walk-in pantry, marble backsplash, designer lighting, Series 7 Viking six-burner range with griddle and double ovens, separate French-Door oven, additional convection/microwave oven, and Jenn-Air professional-grade refrigeration. Adjacent living spaces are equally impressive, including a beautifully enhanced family room featuring custom picture-frame moldings, a private first-floor office with French doors, and a bright sunroom retreat complete with mounted television and views of the surrounding grounds. Upstairs, the primary suite has been transformed into a remarkable wellness-inspired sanctuary featuring a newly reimagined spa experience with bespoke wet-room design, luxurious marble finishes, new his-and-her vanities, updated lighting, a spacious shower with multiple body sprays, and a soaking tub thoughtfully integrated into a seamless spa-like setting designed for daily relaxation. Three additional generously sized bedrooms, including one ensuite, feature vaulted ceilings and oversized closets. Additional updates include beautifully refreshed secondary bath, a redesigned hall bath with new shower and tub wrapped in tile extending to the ceiling, updated powder room, custom closet enhancements, fresh paint throughout, new carpeting throughout nearly the entire home and basement (2025), and premium hypoallergenic carpet padding with moisture-resistant membrane protection. Significant mechanical investments include two top-of-the-line Carrier Infinity furnaces and air conditioning systems delivering exceptional year-round comfort and efficiency. The finished lower level features a fifth bedroom, full bath, and private garage staircase access, creating flexibility for guests, related living arrangements, or entertaining. Completing this exceptional offering is an oversized three-car garage with direct lower-level access and a location just moments from Downtown Naperville, the Riverwalk, bike paths, Green Park, train, boutique shopping, acclaimed restaurants, and all in award-winning District 203 schools including Prairie Elementary, Washington Junior High, and Naperville North High School. Renovated in 2023, and then over $400,000 of updates in this past year, this truly exceptional residence offers elevated living, remarkable improvements, and a lifestyle rarely found in downtown Naperville!

1046 Sylvan Circle, Naperville
610 Sunset Drive, Naperville
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 12762715 MLS ⋅ ACTIVE Status
CUSTOM BUILD OPPORTUNITY in Naperville's East Highlands Neighborhood with PRIME Lot and A+ location on Sunset Drive, which is a beautiful tree lined street, just steps to Highlands Elementary School and steps to the Riverwalk and Downtown Naperville! BUYER CAN CUSTOMIZE AND MAKE SELECTIONS. Established Local Builder delivers an awesome homebuilding experience, seamless design process, luxury finishes, thoughtful functionality & unparalleled attention to detail. Builder includes the best building materials and modern building processes: Engineered Zip System from Huber Engineered Woods, Pella Windows, James Hardie Siding, Fully Custom Cabinetry, High End Luxury Appliances, Beautiful Millwork, Professional Landscaping, Concrete Driveway, True Masonry Fireplace - The difference is in the details!!!! Nationally Recognized District 203 Schools: Highlands Elementary, Kennedy Jr, and Naperville Central High School. Looking to build Fully Custom? Bring your architect and design team or we can recommend some of our favorites and the builder can perfectly execute everything you can dream up!!! Builder has built over 400 custom homes in the Naperville, is wonderful to work with and has an impeccable reputation in the community. Builder Warranty Included!

610 Sunset Drive, Naperville
70 Forest Avenue, Naperville
$2,299,000
5 Beds ⋅ 5 Baths ⋅ 12761014 MLS ⋅ ACTIVE Status
Exclusive Half-Acre Retreat in the Heart of Downtown Naperville Set on one of Naperville's most coveted cul-de-sacs, this exceptional Forest Avenue estate offers the rare combination of privacy, space, and walk-to-town convenience. Positioned on a 1/2-acre lot with no homes directly behind, it overlooks open green space and a brand-new neighborhood park-perfect for outdoor entertaining, play, or future pool plans. This timeless 6,129 sq ft home spans three exquisitely finished levels, with a 1,300 sq ft finished third floor and an unfinished basement ready to realize your personal vision. Boasting 5 bedrooms, 4.5 baths, and a 4-car garage, it's designed for modern luxury living. Step inside to a grand foyer with fireplace that flows seamlessly into a spacious chef's kitchen with breakfast nook, opening to a bright bonus room overlooking the backyard. The first-floor turreted office with private entrance is ideal for professional meetings without compromising family life, while the second-floor turret off the primary suite offers a private sitting room or secondary office retreat. Dual laundry rooms on the first and second floors enhance convenience. The finished third floor provides unparalleled flexibility-perfect for a playroom, media room, additional office, or guest suite. The unfinished basement invites you to design a personal recreation space, gym, or additional living quarters. Deep pour/ high ceilings totaling 1674 sq ft. Enjoy a true walk-to-everything lifestyle-just blocks from Centennial Beach, the Riverwalk, West Greens Park, and downtown dining and shopping, as well as all three award-winning District 203 schools: Naper Elementary, Washington Junior High, and Naperville North High School. Commuters will appreciate the short walk or bike ride to the Metra for easy access to Chicago. This Forest Avenue masterpiece combines timeless elegance, modern convenience, and unmatched location, making it one of downtown Naperville's most exclusive offerings.

70 Forest Avenue, Naperville
3947 Caliente Circle, Naperville
$2,275,000
5 Beds ⋅ 6 Baths ⋅ 12622927 MLS ⋅ ACTIVE Status
It's YOUR turn to own Overstreet Builders' most admired home; The Kensington. The striking facade boasts a huge porch, black stone, Hardie panels, cedar accents, tons of windows & 8' glass doors-exuding luxury. Own extra cars/toys? A 4-car garage has an excess of storage. Pavers lead to a side-entry & for easy clean up inside, epoxy floors. Mature landscaping & irrigation ensure a turnkey experience. Be enamored w/ a floor-to-ceiling glass entry. Gigantic Pella windows flood the home with sunshine, showcasing every detail. From foyer to family, kitchen to garden room, this is an entertainment hub. The covered patio serve station w/ built in grill & fridge, paving stone / granite peninsula transitions from in- to outdoor living. ADDL UPGRADES-A modern stair w/ horizontal spindles, square posts, handrails, starter step & curbed stringer greets you. For changing lifestyles or multigen living, flexibility is key. Our flex room has 8' glass doors & crown molding. Use as a living room, office or toy room. The dining room w/ striking ceiling & accent wall spills into the kitchen so guests feel connected. A magnificent tile, wood & concrete framed linear F.P. in the family accentuates the back-lit ceiling. A 1st floor private-in-law suite is a must. The kitchen displays exquisite Quartzite complimented w/ metallic tiles for some shine. The wet bar houses wine racks, glass displays, Miele wine ref & sink so guests can grab something to sip on! PLUS white, ceiling height cabinets, soft close drawers/hinges, modern full overlay doors & chic gold pulls throughout-all on trend. 4x10'6 island w/ seating; perfect for baking, hosting & daily use! Recently added Miele appliances (w/ built-in coffee maker!) complete this chef-inspired kitchen. Our working pantry is a "2-fer"-workspace & pantry. Pass grilled treats in or drinks out. The microwave & beverage fridge are conveniently housed here w/ room for addl gadgets. No more kitchen clutter! Luxury shelves hide behind a pocket door. Another Overstreet staple is the garden room, offering a vaulted ceiling, more floor to ceiling windows, an 8' 3-pane slider inviting you to the outdoor oasis. The mudroom is larger than most bedrooms! It has 8' lockers w/ cubbies above & below, huge closet & desk. 2ND FLR DETAILS-Extravagant primary suite: linear windows, custom ceilings, Brakur closet shelving w/ island & W/D. An elegant spa w/ glass-enclosed wet room to relax & rejuvenate. Back-lit niches, floor to ceiling tile, gold fixtures, U by Moen, speakers, TONS of storage, mirror surrounds & natural light. Talk about wow-factor! 9' hall ceilings; 10-11' vaults in every room, a balcony, impressive J&J bath, en-suite & all walk-in closets. Hallway w/ HW floors, a backlit niche & beautiful views of the 2-story foyer & family. Even the laundry has extras-huge closet, built in sink, folding counter & cabinetry galore. 2050 sqft of flexible finished basement space-lounge, entertain or game. Use 3 rooms as bedrooms, gym, office or theater options. Fully equipped w/ a kitchenette & oversized full bath w/ 4x5 shower. There's a 2nd staircase w/ garage access. Endless possibilities! Upgrades throughout inc-Wide-plank white oak HWF, countertops, carpet/tile, plumbing fixtures, trim details, 8' doors, stylish lighting & more. Smart home features are a staple in luxury homes! An Elon platform integrates automation: security w/ cameras, audio, lighting, thermostats & more. Plus a generator-it's got it all! Photos are great but you MUST see it in person! Every detail-from architectural design to carefully curated finishes-are showcased with exceptional craftsmanship for which Overstreet is known for. Opportunities to own an OB model are extremely rare - don't miss your chance! Listing agent / Overstreet can provide more info. Contract handled through Overstreet.

3947 Caliente Circle, Naperville
23W735 Hobson Road, Naperville
$2,250,000
5 Beds ⋅ 8 Baths ⋅ 12779451 MLS ⋅ ACTIVE Status

23W735 Hobson Road, Naperville
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