MIDDLEBURY

Many consider Middlebury to be the heart of Addison County. The village is listed on the National Register of Historic Places, and offers a variety of residential neighborhoods as well as pastoral rural areas. A charming downtown is filled with independent retail shops, galleries, several restaurants, mainstay bakeries and coffee shops. In greater Middlebury you’ll find multiple grocery stores, a popular Co-op, hardware stores, and most of the services its residents might need to stay "local". It is the largest community in the county with a population of approximately 8,500 and covering 40 square miles. The town is also home to Middlebury College, a small liberal arts college with a global reputation.  Its idyllic campus has an international draw, with opportunities and sporting events for the greater community. Rikert Nordic Center is a quick 15 minute drive, while you'll find alpine skiing on the slopes of the Middlebury Snow Bowl just 20 minutes East.  Proximities:  North, you'll find Burlington International Airport an easy 50 minute drive, Montreal at 2.5 hrs North and Boston at 3.5 hrs South.

RECREATION: The Middlebury Parks and Recreation Department offers facilities and fields in multiple locations (tennis, basketball, an outdoor pool, and so much more), great programming for children and adults, summer camps, classes and events to connect you with your neighbors! Friends of Middlebury Youth Football League (MYFL), Middlebury Youth Lacrosse Club (MYLC) and Middlebury Amateur Hockey Association are popular outlets for the enthusiastic pre-High School clan. Green Mountain Adventures (an offshoot of Middlebury Mountaineer on Main Street), has created a host of guided experiences, and incredibly popular summer camps for kids. Eddy Farm School for Horse & Rider on South Street Extension is known for boarding, training and horsemanship summer camps. Mary Johnson Children's Center and Aurora Preschool supports Addison County children and their families with educational and recreational experiences in after-school programming, summer and vacation camps, and daytime learning opportunities. Middlebury Area Land Trust, better known as MALT, provides year-round youth programming and camps, as well as the Trail Around Middlebury (TAM), an incredible resource for all ages with 18 miles of footpath encircling the village and links to several hundred acres of town land, conserved properties and local landmarks. You’ll want to visit Frog Hollow Bikes for rentals, maps and recommendations for great local rides (as well as for maintenance, repair and sales!). And we cannot forget the Ralph Myhre Golf Course that offers the public incredible views from the edge of town on the Middlebury College campus from its beautiful 18-hole golf course.

RESOURCES/SERVICES/OPPORTUNITIES: Neighbors, Together is the local community action group comprised of reps from a cross-section of local businesses and organizations. Get involved! Mini Bury is a resource for parents offering info on events, activities, camps and classes in and around town. Elderly Services, Inc is a state-of-the-art adult day care facility offering a warm and safe place with abundant activities, services, meals and support and Eastview at Middlebury is our local 501c3 nonprofit corporation providing exceptional retirement living including cottage homes, apartments, residential care apartments and memory care studios all on 40 acres adjacent to Porter Medical Center. For local history and legend, visit the Henry Sheldon Museum of Vermont History and the Vermont Folklife Center. Musically inclined? The Middlebury Community Music Center has a fantastic line-up of classes, workshops, camps, lessons and opportunities for youth and adults. For music, stage performance, screenings, special events, a community gallery, lectures, classes, camps, look into the incredible offerings at the not-for-profit Town Hall Theater and also Addison County Parent/Child Center which provides great support and education to local families. Older children looking for a safe, alternative local hangout? Definitely check out Addison Central Teens! Want to take advantage of bus services/low cost transportation? Try the services of TVT (Tri-Valley Transit formerly ACTR), where you’ll benefit from bus routes around Middlebury, a Tri-Town Shuttle (Middlebury, Bristol, Vergennes), Snow Bowl shuttle, 116 Commuter, and Burlington and Rutland Link busses!

SCHOOLS/EDUCATION: The Addison Central School District (ACSD) is based in Middlebury and sees over Middlebury’s Elementary, Mary Hogan School, Middlebury Union Middle, and Middlebury Union High schools. The Patricia A. Hannaford Career Center provides personal and career enrichment programming for high school students, home-schooled students, as well as adults across the county. Bridge School offers an alternative private education in a converted barn on the outskirts of town for pre-schoolers through sixth grade. The Community College of Vermont offers satellite classrooms in the Battell Block in the center of town (one of 12 locations across the state), with classes for college credit across many disciplines. Of course we're also proud to have Middlebury College and all that it offers in our back yard.

For abundant general information covering all of Addison County, you’ll want to visit the Addison County Chamber of Commerce’s site. You’ll find info on many of the organizations and businesses mentioned here, and so many more; it’s member-centric but the Chamber’s website provides extensive and invaluable info nonetheless. Of course, if you’re setting up shop in the area, it’s a connection you’ll want to make for networking, referrals, classes and smart opportunities, so be sure to stop by the Chamber offices and introduce yourself! Of course, we’re proud to spread the word on all things local, so while you’re wandering through charming downtown of Middlebury please do stop by to see us at 34 Main Street. We’ll answer questions, provide recommendations for our favorite nearby hot spots, and connect you with our friends and neighbors who will be happy to get to know you!

View all current listings available in Middlebury, VT below. To learn more about the town of Middlebury, click here.

Area: 39.23 mi²

Population: 8,501

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88 Mainelli Road Middlebury VT 05753

MLS Number 5021979

  • Commercial
  • Address 88 Mainelli Road
  • Square Feet 11,694
  • Acreage 4.43
  • Area VT-Addison

Rare opportunity to own a diversified, multi-tenanted commercial investment property in Middlebury. Located in the Middlebury Industrial Park, 88 Mainelli Road is an 11,694 SF building located on approximately 4.43 acres. Originally built circa 1979, an addition was added in 2015. Three tenants currently occupy the entire building. Champlain Valley Creamery has roughly 1,680 SF, the Appalachian Gap Distillery occupies about 6,374 SF and The Friday Group, a consulting firm, has roughly 3,320 SF of office space (there is also a 320 SF mechanical room). The property is serviced by municipal water and sewer and has an active 36kW PV solar array owned by AllEarth Services. Ample land for additional building development. Please call broker to discuss in greater detail and for financial information.

Listed by Duncan Harris of The Kingsland Company

$
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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Court Street Middlebury VT 05753
Pending

MLS Number 4922137

  • Commercial
  • Address 5 Court Street
  • Year Built 1880
  • Square Feet 8,553
  • Acreage 0.1

Seller has authorized the Listing Agency to offer compensation to a Buyer Agency of 3% of the contract sale price. Such compensation must be included in any offer to purchase.  A prominent feature in downtown Middlebury since 1814, this structure was the replacement of the original courthouse in this location, and built in 1883.To quote Glen Andres in the Walking Tour of Middlebury, "This replacement, by Clinton Smith of Middlebury, was described in the Middlebury Register in 1883 as of "mixed architecture with Queen Anne features,"and declared the handsomest courthouse in the state. The facade is both picturesque and ordered. Its asymmetric massing and variety of detail in stone, brick, wood, slate, and glazing are held in line by articulating brick panels and "structure."This was very up-to-date design for Vermont. The panel-brick style (as it since has been dubbed) was just being popularized by leading architects in Boston, New York, and Philadelphia. Yet the courthouse is hardly a pure import. Its architect was local, and he has put the stamp of his personality and craftsmanship on its design. He also has maintained a sensitivity to its setting. Vigorous in its detail, the 1883 courthouse remains a good neighbor to the earlier structures on Court Square, prominent, but not too assertive for the good of its surroundings." Currently used for office space, many of the original architectural details are intact! The property includes an elevator, and is fully up to date with fire safety including a sprinkler system.Three floors of office space, and a full basement that has plenty of storage, and all the mechanicals. Own a piece of Middlebury history!

Listed by IPJ Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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103 Court Street Middlebury VT 05753

Middlebury, VT103 Court Street

Price$871,000

Est. Mortgage: $/month

MLS Number 4980065

  • Residential Single Family
  • Full Bath 3
  • Address 103 Court Street
  • Construction Existing
  • Bedrooms 5

Discover the BEST home office in VT perfect spot to run a business and raise a family! With opportunity in this spacious five-bedroom, three-bathroom home situated on a sprawling 2.4-acre lot. In walking distance to all 3 public schools. Two bedrooms grace the main floor, offering convenience and flexibility, while the second floor hosts an impressive trio of bedrooms, including a luxurious primary bedroom suite. Step into the primary suite and indulge in the expansive bathroom, featuring a jacuzzi tub and a separate shower. The suite is complete with a generously sized walk-in closet, offering both style and functionality. The fully walk-out basement presents a myriad of possibilities within its mixed-use zoning. Whether you envision a chiropractic office, daycare, apartments, attorney's office, architect's studio, or even a chic hair salon, this versatile space is ready to transform according to your vision. Previously utilized as a chiropractic office, the potential for this space is boundless. The property is strategically located right off Court Street, the main road, ensuring easy access for clients and customers. Ample parking further enhances the property's appeal, making it a versatile canvas for various ventures. This property is not just a home; it's an opportunity waiting to be seized. Explore the potential of this unique residence and its versatile spaces that cater to a myriad of possibilities. Large living space and large office space! Come see today!

Listed by Kelly Laliberte of Wallace Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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103 Court Street Middlebury VT 05753

MLS Number 4980086

  • Commercial
  • Address 103 Court Street
  • Year Built 1995
  • Square Feet 5,280
  • Acreage 2.4

Discover the perfect blend of comfort and opportunity in this spacious five-bedroom, three-bathroom home situated on a sprawling 2.4-acre lot. The main living space welcomes you with an open concept design, providing ample room for a growing family. Two bedrooms grace the main floor, offering convenience and flexibility, while the second floor hosts an impressive trio of bedrooms, including a luxurious primary bedroom suite. Step into the primary suite and indulge in the expansive bathroom, featuring a jacuzzi tub and a separate shower. The suite is complete with a generously sized walk-in closet, offering both style and functionality. The fully walk-out basement presents a myriad of possibilities within its mixed-use zoning. Whether you envision a chiropractic office, daycare, apartments, attorney's office, architect's studio, or even a chic hair salon, this versatile space is ready to transform according to your vision. Previously utilized as a chiropractic office, the potential for this space is boundless. Convenience meets visibility, as the property is strategically located right off Court Street, the main road, ensuring easy access for clients and customers. Ample parking further enhances the property's appeal, making it a versatile canvas for various ventures. This property is not just a home; it's an opportunity waiting to be seized. Explore the potential of this unique residence and its versatile spaces that cater to a myriad of possibilities. Schedule your viewing!

Listed by Kelly Laliberte of Wallace Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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45 Court St.(route 7) Street Middlebury VT 05753

MLS Number 4999647

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3

Historic Victorian Multifamily Home with Owner-Occupied Potential in Downtown Middlebury, VT Step into history with this charming Victorian multifamily home, built in 1840, located in the heart of downtown Middlebury. This well-maintained property features three distinct units, offering a unique opportunity for owner-occupancy with rental income. Live in Comfort, Earn with Ease o Owner's Apartment: Spacious and inviting, the 1620 square foot upstairs apartment offers the perfect blend of historic charm and modern convenience. o Rental Income: Collect a monthly rental income of $5840 from the fully leased apartments. Property Highlights o Investment Opportunity: With a continuous occupancy history, this property ensures a solid return on investment. o Recent Upgrades: Enjoy modern living with recent renovations and open concept designs, seamlessly blending contemporary comfort with historic charm. o Prime Location: Located within walking distance to local shops, restaurants, and cultural attractions, making it highly desirable for tenants. o Well-Maintained: The property has been carefully maintained to preserve its historic character while incorporating modern amenities. This is a rare opportunity to live in a historic gem while benefiting from a steady rental income in a high-demand market. Experience the vibrant community of Middlebury and secure a sound investment.

Listed by Deborah Fortier of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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45 Court Street Middlebury VT 05753

Middlebury, VT45 Court Street

Price$697,000

Est. Mortgage: $/month

MLS Number 4999633

  • Multifamily
  • Address 45 Court Street
  • Units 3
  • Bathroom 3
  • Acreage 0.2

Collect $5840 per month from fully leased apartments ! Historic Victorian Multifamily Home in Downtown Middlebury, VT Discover a piece of history with this charming Victorian multifamily home, built in 1840, located in the heart of downtown Middlebury. This well-maintained property features three distinct units: a 1-bedroom and a 2-bedroom on the ground level, and a spacious 2-bedroom with large bonus rooms on the upper floors. All apartments are fully leased with quality tenants generating $5840 income per month. All tenants have an on time payment history. Property Highlights Investment Opportunity: This property offers a solid return on investment in a high-demand rental market. Recent Upgrades: Enjoy modern living with renovated lower-level apartments with open concept designs, blending contemporary comfort with historic charm. Prime Location: Situated within walking distance to local shops, restaurants, and cultural attractions, making it highly desirable for tenants. Well-Maintained: The property has been carefully maintained to preserve its historic character while incorporating modern amenities. This is a rare opportunity to own a historic gem in Middlebury, offering both stability and growth potential. Don't miss out on this exceptional investment in a vibrant community. For more information or to schedule a viewing, contact us today!

Listed by Deborah Fortier of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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60-62 Main Street Middlebury VT 05753

MLS Number 5013590

  • Commercial
  • Address 60-62 Main Street
  • Year Built 1900
  • Square Feet 4,986
  • Area VT-Addison

OWN A PIECE OF HISTORY ON MAIN ST. IN MIDDLEBURY! Commercial building in the heart of Middlebury comprises a vibrant retail store, Buy Again Alley, an architect's office, a one-bedroom apartment, two studio apartments, and a space opening onto Frog Alley in the rear that has been an office and retail space. With nearly 5,000 square feet, the options are numerous. Renovation will be needed. Superb location in the midst of a thriving business district with Middlebury College less than a quarter mile away. This is a building worthy of significant investment for a lifetime of income.

Listed by Jeff Olson and k. Cory Foote of BHHS Vermont Realty Group/Middlebury

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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60-62 Main Street Middlebury VT 05753

Middlebury, VT60-62 Main Street

Price$599,000

Est. Mortgage: $/month

MLS Number 5022266

  • Multifamily
  • Address 60-62 Main Street
  • Units 3
  • Bathroom 3
  • Acreage 0.04

OWN A PIECE OF HISTORY ON MAIN STREET IN MIDDLEBURY! Commercial building in the heart of downtown Middlebury comprises a vibrant retail store, Buy Again Alley, an architect's office, a one bedroom apartment, two studio apartments, and a space opening onto Frog Alley in the rear that has been used as an office and retail space. With nearly 5,000 square feet, the options are numerous. Renovation will be needed. Superb location in the midst of a thriving business district with Middlebury College less than a quarter mile away. This is a building worthy of significant investment for a lifetime of income. Potential to increase the number of residential units.

Listed by k. Cory Foote and Jeff Olson of BHHS Vermont Realty Group/Vergennes

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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70 Fields Road Middlebury VT 05753

Middlebury, VT70 Fields Road

Price$599,000

Est. Mortgage: $/month

Pending

MLS Number 5032355

  • Residential Single Family
  • Full Bath 2
  • Address 70 Fields Road
  • Construction Existing
  • Bedrooms 4

Seller has authorized the Listing Agency to offer compensation to a Buyer Agency of 3% of the contract sale price. Such compensation must be included in any offer to purchase.  Bright and sunny days ahead for you in this two-story village home. The simple elegance of a home with the right rooms in the right places! A semi-formal dining room space for large gatherings around the table, a delightful living room where you cozy up near the gas fireplace (it's as easy as flipping a light switch!) and a large eat-in kitchen adjacent to a more casual sitting area lets everyone in the household share about their day and enjoy one another's company! Upstairs you'll find a primary suite with a private bath including a large jetted tub and stall shower, three additional bedrooms and a 2nd bathroom. In the lower level of the house, half of the space is finished and currently serves as a bit of a media suite/exercise room with plenty of natural light from the large window wells - make it what you want! The other half is perfectly suited for storage, laundry and mechanicals and is even plumbed for an additional bathroom should you need that in your future. Top things off with roof mounted solar panels that reduce electric costs to just about the monthly maintenance fee!! Convenience is a key factor with a direct entry into the house/mudroom and a guest bath on the main level. In the neighborhood you'll find access to the Trail Around Middlebury, banks, playing fields, the Middlebury Recreation Center, grocery stores, shopping and fitness studios! Offers due by Thursday, March 20 @ 4pm

Listed by IPJ Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1676 Case Street Middlebury VT 05753

Middlebury, VT1676 Case Street

Price$498,500

Est. Mortgage: $/month

Pending

MLS Number 5025791

  • Residential Single Family
  • Full Bath 1
  • Address 1676 Case Street
  • Construction Existing
  • Bedrooms 2

This well-maintained home has lovely mountain views and 10 acres of open land which would be nice for growing anything (it has good soil!) or for pasturing whatever animals you might like. The major bonus of the property is the approximately 1000 Sq.Ft of finished heated space in the garage. There is even a 3/4 bath and a place to cook in this space. It has had a variety of uses over the years, the most recent being as a space for playing and enjoying music. There is also a significant amount of storage space in this building. This property is set well back from the road so it is quieter and more private than you might anticipate for being in this location.

Listed by Nancy Foster of Champlain Valley Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1282 Painter Road Middlebury VT 05753

Middlebury, VT1282 Painter Road

Price$449,000

Est. Mortgage: $/month

Pending

MLS Number 5029109

  • Residential Single Family
  • Full Bath 1
  • Address 1282 Painter Road
  • Construction Existing
  • Bedrooms 2

Seller has authorized the Listing Agency to offer compensation to a Buyer Agency of 3% of the contract sale price. Such compensation must be included in any offer to purchase.  This sweet home is ready for you to move right in! Located just a couple miles outside of downtown Middlebury, on just under an acre of land with lovely views of the Green Mountains. When you drive up you will notice the well cared for property boasts a standing seam roof, newer windows and fiber cement siding- all low maintenance! Inside you will be delighted by the custom, eat in kitchen with yellow birch cabinets, granite counters and stainless appliances. A door from the kitchen leads out to the fantastic screened in porch, with deck beyond- great for warmer weather entertaining and relaxing! Back to the living room- hardwood floors and and a wood stove keeps the house cozy if needed. Radiant floor heating in both the kitchen and bath add to the coziness! The primary bedroom has a sleeping and sitting area- in a previous life it was two separate bedrooms. The second bedroom is nearby, as well as the full bath with tile shower and yellow birch cabinets in there as well. An attached, one car garage leads you into the house to a great mudroom/laundry room- a much needed space in Vermont! Don't forget the basement- that houses the utilities and is excellent for storage. The spacious yard has plenty of room for gardens, and currently a yurt holds residence and provides studio, office, music or meditation space. The owner will remove this structure if the new owner does not have use for it. Come take a look and you will be happy that you did!

Listed by IPJ Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Stonecrop Road Middlebury VT 05753

Middlebury, VT33 Stonecrop Road

Price$430,000

Est. Mortgage: $/month

Pending

MLS Number 5028305

  • Residential Single Family
  • Full Bath 1
  • Address 33 Stonecrop Road
  • Construction Pre-Construction
  • Bedrooms 3

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater and more will be at your fingertips. This three bedroom, end unit townhome will be ready for occupancy in the summer of 2025. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole house ventilation system. Step inside the open concept first floor living area which enjoys plenty of natural light from the many windows. The generous kitchen features an oversized island with seating, energy star appliances, and direct access to a private deck, perfect for morning coffee or evening grilling. The kitchen transitions seamlessly into spacious dining and living areas making entertaining a breeze. A powder room on this level is great for guests. Upstairs you will find a primary suite with spacious walk-in closet and en-suite bath featuring a double vanity, complemented by 2 other bedrooms and bath. The lower level provides private garage parking, gear- friendly mudroom and washer and dryer. A partially finished bonus room and utility space round out that level. Future community amenities will include green space, community garden, access to trails and more. Inquire for more details!

Listed by IPJ Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated March 23, 2025 8:08 PM EDT