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

$4,950,000
7 Beds ⋅ 9 Baths ⋅ 12753503 MLS ⋅ NEW 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
$3,950,000
4 Beds ⋅ 6 Baths ⋅ 12750568 MLS ⋅ NEW Status
Gorgeous brand NEW construction in DOWNTOWN Naperville built by Muellner Construction, Moment Design Architecture Group and Grooters Interior Design. No expense was spared to bring luxury and elegance with close vicinity to the center of it all. With 5,645 total square feet of living space, the Primary suite, Office, Laundry, Scullery and Mud Room are some of the extras on the main level, with 3 additional ensuite bedrooms on the second level. The Basement boasts a central Media Room, side rooms being conveyed as an Exercise/Craft Room and Game Room, plus a Bedroom with full Bath. Outdoor entertainment space includes a motorized screen Porch, grill area and open Patio on bluestone pavers. So much to be enjoyed.

333 W Benton Avenue, 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
$2,799,000
4 Beds ⋅ 6 Baths ⋅ 12715590 MLS ⋅ ACTIVE Status
Welcome to 917 Jackson Street, where luxury, space, and an unbeatable location come together in the true heart of downtown Naperville. Nestled on a quiet cul-de-sac, but just steps from the Riverwalk, award-winning restaurants such as Hugo Frog Bar and Ramsay's Kitchen, boutique shopping, parks, and all that vibrant downtown Naperville has to offer, this exceptional home delivers the lifestyle you've been waiting for. Located in the highly sought-after Naperville District 203 school district, this home offers an exceptional combination of location, convenience, and lifestyle. Boasting 5 spacious bedrooms and a rare 4-car garage, this home provides incredible flexibility for guests, hobbies, or entertaining. The beautifully renovated kitchen is the centerpiece of the home, featuring all-new top-of-the-line appliances including a Sub-Zero fridge, premium finishes, and a thoughtfully designed layout that blends style and functionality. The fully finished basement offers valuable additional living space with endless possibilities, including a recreation area, home office, guest space, or potential in-law arrangement. With tons of storage space throughout, this home provides the perfect balance of comfort and practicality. Step outside to your own private backyard retreat. Designed for year-round enjoyment, the beautiful outdoor space features a spacious patio, built-in fireplace, and inviting surroundings-perfect for relaxing evenings, entertaining friends, and creating lasting memories. Offering exceptional space, luxury updates, abundant storage, a walkable downtown location, and access to the acclaimed District 203 schools, 917 Jackson Street is a rare opportunity to experience the very best of downtown Naperville living.

917 Jackson Avenue, Naperville
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 12721550 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
$2,595,500
5 Beds ⋅ 8 Baths ⋅ 12734369 MLS ⋅ ACTIVE Status
Welcome to an absolutely incredible 2.65-acre estate in Naperville, offering the space, privacy, amenities, and character that are nearly impossible to duplicate. This impressive three-story home features approximately 8,800 square feet of living space, 5 bedrooms, 7.5 bathrooms, and exceptional indoor and outdoor entertaining spaces. The home has been thoughtfully updated while maintaining the character and scale that make it so special. At the center of the home is a brand-new kitchen, beautifully finished with today's modern look and designed for both everyday living and entertaining. Just off the main kitchen is an additional kitchen and prep area, perfect for entertaining, holidays, family gatherings, and larger events. The main level features beautiful hardwood flooring, incredible natural light, and multiple gathering spaces. The spacious living room offers a fireplace, while the sunken family room makes a statement with its dramatic stone fireplace, hardwood floors, exposed wood beams, skylights, and direct patio access. The formal dining room provides plenty of room for entertaining along with a wet bar and beverage refrigerator. Dual staircases lead upstairs to an incredible 1,100-square-foot primary suite featuring its own fireplace, large covered private balcony overlooking the grounds, cedar-lined walk-in closet, and impressive private bath. Four additional generously sized bedrooms offer en-suite baths and cedar-lined closets, providing exceptional space and privacy for family and guests. The flexible floor plan also provides possibilities for an in-law, guest, or live-in suite. The lower level has been completely refinished with today's modern finishes, creating another incredible level of living and entertaining space. It includes an exercise room, sauna, wet bar, full bath, fireplace, wine cellar, and direct access to the indoor pool area. One of my favorite features of this home is the 12-foot-deep heated indoor swimming pool and whirlpool, located inside an approximately 33' x 44' enclosed pool room. Skylights and ceiling fans fill the space with natural light, while the professionally charred cedar vaulted ceiling gives the room an amazing, one-of-a-kind look. A central dehumidification system, basement access, and nearby half bath make this an incredible year-round space. Outside is just as impressive. The tennis and pickleball courts have been completely redone, giving you your own private recreation area right at home. Multiple patios and four balconies provide plenty of places to relax, entertain, and enjoy the beautiful 2.65-acre setting. Additional features include a huge three-car garage, three driveway entrances, Pella windows with inlaid blinds, more than 40 skylights, five fireplaces, a sunroom, and a beautiful tree-lined circular driveway that creates an incredible first impression as you approach the home. This is not your typical Naperville home. Where else are you going to find 2.65 acres, approximately 8,800 square feet, a brand-new kitchen plus an additional entertaining kitchen, a newly refinished lower level, an indoor pool and whirlpool, redone tennis and pickleball courts, multiple patios and balconies, and this kind of privacy? Located in highly acclaimed Naperville School District 203, with convenient access to shopping, dining, and expressways. There is simply too much to list. This is one of those homes you need to see in person to truly appreciate everything it has to offer. YOU CAN CONNECT TO COUNTY WATER AND SEWER FOR APPROX. $20K.

23W735 Hobson 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
$2,324,000
6 Beds ⋅ 7 Baths ⋅ 12754560 MLS ⋅ NEW Status
Privately situated on a tree-lined cul-de-sac, this extraordinary custom brick and stone estate offers timeless elegance, exceptional craftsmanship, and resort-style living. The residence features 6 en-suite bedrooms, 3 fireplaces, 2 executive offices, and a heated 6-car tandem garage, plus a private-entry guest residence ideal for multi-generational living. A dramatic two-story foyer, Brazilian cherry floors, custom millwork, and a gourmet Viking-appointed kitchen showcase the home's refined design. The luxurious primary suite includes a private sitting room, fireplace, and wet bar, while a versatile third-floor retreat offers endless possibilities. Outside, enjoy a beautifully landscaped private sanctuary with expansive entertaining spaces. The walk-out lower level features a climate-controlled 1,000-bottle wine cellar and abundant potential for customization. An exceptional legacy estate where luxury, privacy, and timeless sophistication converge.

616 Driftwood Court, Naperville
$2,299,000
5 Beds ⋅ 5 Baths ⋅ 12710318 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
$2,295,000
4 Beds ⋅ 5 Baths ⋅ 12541311 MLS ⋅ ACTIVE Status
*** Located in the Woods Of Rivermist*** Welcome to this charming home located in a peaceful cul-de-sac in Naperville. The entire home has been professionally designed and renovated. Great large home office. possible 5th bedroom in the lower level. New Front doors just installed different from pictures. Nothing is original. Sought after district 203 schools. Award winning schools - Kingsley-Lincoln and Naperville Central. Newer Wood shingle roof and HVAC. This spacious property boasts an inviting open floor plan with abundant natural light. The kitchen features modern appliances and ample counter space, appropriate for culinary enthusiasts. The living area extends to a beautifully landscaped backyard, appropriate for outdoor gatherings. Enjoy a serene primary suite with a luxurious bathroom and walk-in closet. Conveniently located near schools, parks, and shopping centers.

203 Settlers Court, Naperville
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