4 Beds • 5 Baths · 3,696 Sq. Ft.
55750 County Road 33
Middlebury, IN 46540
Bright Star Real Estate Services LLC
205 Greenfield Drive
Middlebury, IN
$1,200,000
Middlebury, IN 46540 · Highland Woods
MLS# IRM202629033
Listed 31 days ago
Welcome to this extraordinary custom all-brick estate nestled in the heart of Middlebury's prestigious Highland Woods subdivision. Perched atop the area's rolling hills, this exceptional Town & Country-built residence offers more than 6,000 square feet of beautifully finished living space and has been completely transformed with over $800,000 in luxurious updates completed within the past two years. Step inside the stunning foyer and discover impeccable craftsmanship and designer finishes throughout. The inviting lodge-inspired family room features a striking stone fireplace, while the spectacular custom kitchen is a true showpiece with premium finishes, abundant storage, and a hidden butler's pantry. The adjoining buffet and beverage area makes entertaining effortless, whether hosting holidays in the formal dining room or enjoying casual meals in the bright breakfast area overlooking your private back yard. You will love the spacious mudroom/laundry room. The perfect "drop spot" for coats, or backpacks. The main-level den/office with gorgeous custom woodwork provides the perfect work-from-home space. Upstairs, the luxurious primary suite features dual walk-in closets and a spa-inspired bath with a soaking tub and oversized tiled shower. Three additional bedrooms include a Jack-and-Jill bath with a walk-in shower and a third full bath with tub. The lower level is designed for entertaining with a custom kitchen, stone accents, a spacious family room with a second fireplace, bar area, two additional bedrooms, a fourth full bath, and a stunning wine room where fireside entertaining is at your fingertips for game nights, gatherings, or relaxing with friends. Outside, enjoy a private backyard surrounded by mature trees and abundant wildlife, along with a newly constructed deck ideal for outdoor living and entertaining. Beyond its beautiful finishes, this home offers peace of mind with new roof, windows, updated mechanicals, and a heated three-car attached garage. Every detail has been thoughtfully updated, and nothing has been overlooked. This is a rare opportunity to own one of Middlebury's finest homes.
Estimate principal and interest for this listing.
$240,000
Estimated monthly payment
$6,068/mo
Estimate only — not MLS listing data. Does not include taxes, insurance, or other costs. Rates change daily.
Listed by Coldwell Banker Real Estate Group. Contact 574-522-2822.
4 Beds • 5 Baths · 3,696 Sq. Ft.
55750 County Road 33
Middlebury, IN 46540
Bright Star Real Estate Services LLC
5 Beds • 4 Baths · 3,333 Sq. Ft.
53660 Forest Lakes Drive
Middlebury, IN 46540-8971
R1 Property Group LLC
4 Beds • 2 Baths · 2,055 Sq. Ft.
209 Bristol Avenue
Middlebury, IN 46540
Cressy & Everett- Elkhart


Listings displayed by Mark Dietel Realty
Based on information submitted to the MLS GRID as of September 22, 2026 at 7:16 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
IRMLS is the source of this listing information as distributed by MLS GRID.
The compilations of listings and each individual listing are © 2026 MLS GRID. All rights reserved. The listing content is owned by the MLS GRID and is protected by federal copyright law.
IDX information is provided exclusively for consumers' personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by IRMLS as amended from time to time.
Some IDX listings have been excluded from this website.
Please report suspected listing-data inaccuracies to Mark Dietel Realty. Contact us or call (317) 426-9911.
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MIBOR Broker Listing Cooperative® Disclaimer
© 2026 MIBOR REALTOR® Association
IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed accurate by the Broker Listing Cooperative® listing service.
Listings courtesy of MIBOR Broker Listing Cooperative as distributed by MLS GRID
IDX information is provided exclusively for consumers' personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.
Based on information submitted to the Broker Listing Cooperative listing service as of September 22, 2026 at 7:16 AM EDT. All data is obtained from various sources and may not have been verified by broker or Broker Listing Cooperative listing service. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Based on information submitted to the MLS GRID as of September 22, 2026 at 7:16 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


Listings displayed by Mark Dietel Realty
Based on information submitted to the MLS GRID as of September 22, 2026 at 7:16 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
IRMLS is the source of this listing information as distributed by MLS GRID.
The compilations of listings and each individual listing are © 2026 MLS GRID. All rights reserved. The listing content is owned by the MLS GRID and is protected by federal copyright law.
IDX information is provided exclusively for consumers' personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by IRMLS as amended from time to time.
Some IDX listings have been excluded from this website.
Please report suspected listing-data inaccuracies to Mark Dietel Realty. Contact us or call (317) 426-9911.
Copyright complaints: DMCA notice.
MIBOR Broker Listing Cooperative® Disclaimer
© 2026 MIBOR REALTOR® Association
IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed accurate by the Broker Listing Cooperative® listing service.
Listings courtesy of MIBOR Broker Listing Cooperative as distributed by MLS GRID
IDX information is provided exclusively for consumers' personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.
Based on information submitted to the Broker Listing Cooperative listing service as of September 22, 2026 at 7:16 AM EDT. All data is obtained from various sources and may not have been verified by broker or Broker Listing Cooperative listing service. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Based on information submitted to the MLS GRID as of September 22, 2026 at 7:16 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.