Historic & Antique Homes

This search features single-family homes built before 1945. Properties are listed by price in order from high to low. You may change your sort order below, and you can refine your search by checking or unchecking the search criteria (or sliding the criteria bar) along the right side of this page.

414 - 416 Dorset Hollow Road Dorset VT 05251

Dorset, VT414 - 416 Dorset Hollow Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4830516

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,672

Incredible privacy with access to all village amenities, this estate with sweeping mountain views on 19 secluded acres in Dorset Hollow, is just 1/3 mile to the village. Stone pillars greet as one gently climbs a meandering drive to this historic 1930's "Enfield” house moved to this site where it received renewed foundation and life. A private sanctuary, this exceptional location offers a unique lifestyle opportunity supporting the sporting land lover, pets, or agricultural interest over a mix of open fields and hardwood forest. A 2004 restoration opened up the circular floor plan offering gathering spaces centered around a well-appointed country kitchen featuring a large marble island and great room with vaulted ceilings, enhanced architectural interests with natural light and fireplace. The dining room extends to the outside deck and leads to an additional living room. All gathering spaces boast wood burning fireplaces! The main level master suite features a private wood paneled study with fireplace, marble tile bath and views. The center hall staircase leads to 2 additional bedrooms and baths. The lower level offers a private bedroom suite with its own entry, as well as, the garage, laundry room and ample storage. In addition to all of this, a charming one bedroom guest cottage with fieldstone fireplace offers ideal guest lodgings or an income opportunity. The possibilities are endless with space to expand with additional buildings and other land improvements.

Listed by Steven Bryant of TPW Real Estate

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$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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389 Cobble Hill Road Londonderry VT 05148

Londonderry, VT389 Cobble Hill Road

Price$999,500

Est. Mortgage: $/month

MLS Number 4763028

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,227

In the heart of the desirable Mountain towns of Vermont, Cobble Hill Farm offers complete privacy and stunning views of Glebe Mountain. The farm is sited at the end of a dirt road on 149 acres with ancient stone walls that crisscross the land, a spring-fed pond and trails throughout the property. The residence is a c1790s Noah's Ark design, a style of Cape architecture unique to the area. The addition includes a magnificent great room with a 15 ft. ceiling and a floor-to-ceiling stone fireplace. The farmhouse is 3,227 square feet in estate-condition and was last renovated about 25 years ago. There are highly skilled design/builders in the area who have a sensitivity to historic homes and the requirements of 21st century families. The house has good bones and all the elements to support the value - end of the road privacy, views, historic house and a very convenient location. The trails connect into a 32 km network of trails run by the Viking Nordic Center and the location is within walking distance to Lowell Lake. Cobble Hill Farm is 2.8 miles from the center of Londonderry, 8 miles from the nationally renowned Weston Playhouse, 10 miles from Bromley, 17 miles from Stratton and 19 miles from Manchester.

Listed by Dia Jenks and T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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1841 Dorset West Road Dorset VT 05251

Dorset, VT1841 Dorset West Road

Price$995,000

Est. Mortgage: $/month

MLS Number 4820606

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 3,984

Tastefully and extensively renovated 1840's historic Dorset West Road residence and carriage house embodying the charm and picturesque beauty of Vermont. Imagine taking in the mountain and meadow views from a rocking chair on the marble porch or relaxing by a year-round babbling brook on a sunny day or picking your own produce from the organic garden! The residence was formally and forever known as The Marble West Inn and also lends itself to a perfect family home with 8 bedrooms and baths, formal and casual living rooms, study, a commercial kitchen, spacious dining room and multiple fireplaces. The carriage house has an additional 3 bedrooms, 3 baths and a four-season porch overlooking the brook. This is a rare opportunity for the discerning purchaser.

Listed by Andy Reed and Elena Atwill of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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Historic Weston Village Home

41 Lawrence Hill Road Weston VT 05161

Weston, VT41 Lawrence Hill Road

Price$749,900

Est. Mortgage: $/month

MLS Number 4825595

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 4,492

This gorgeous historic/vintage house has been very well cared for and updated as appropriate --the wide pine wood floors and weathered beams immediately give a warm and classic feel. With approximately 4500 square feet of finished living space spread out over 2 and half stories, this is a very special and comfortable property. The sixteen rooms are amazing. A huge master bedroom/master bedroom suite on the second floor is impressive. With a great number bedrooms and a loft area this home provides opportunities for large families and friends to gather. It is only a few hundred yards from the village green, the specialty shops in Weston, and the Weston Playhouse. This is a special Weston property and a must see spectacular home.

Listed by Chuck Sweetman of Mary Mitchell Miller Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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698 Vermont RT 11 Route Chester VT 05143

Chester, VT698 Vermont RT 11 Route

Price$699,000

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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282 Ways Lane Manchester VT 05254

Manchester, VT282 Ways Lane

Price$695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4838023

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,654

A wonderful opportunity to own a historic Manchester Village home on a 1.2 acre bucolic setting within walking distance to stores, restaurants and hiking trails. This turn-key home has been lovingly renovated over the recent years to include updated windows, kitchen appliances, washer/dryer, and bathrooms while maintaining the original charm and character of the home. There are beautiful moldings throughout, wide pine floors, and two wood burning fireplaces. The main floor has a spacious kitchen with a sitting area and a wood burning fireplace perfect for lounging, a dining room, a den/office, and a light filled living room including the second fireplace. On the second floor you will find three generously sized bedrooms and an extra room which could be used as a nursery, an office, or whatever you may need. Finally, the backyard presents an expansive marble patio, beautiful gardens enclosed by a stonewall, and an old Vermont barn.

Listed by Katherine Zilkha of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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2206 Green Mountain Turnpike Chester VT 05143
Active With Contract

MLS Number 4832641

  • Residential Single Family
  • Construction Existing
  • Bedrooms 12
  • Bathroom 12
  • Square Feet 6,976

Now is your chance to own a charming colonial in a picturesque Vermont town! Take advantage of a rare opportunity to purchase what is currently operating as a Bed and Breakfast on the historic Green Mountain Turnpike (a peaceful country road) in beautiful Chester, Vermont. This grand 230 year old former stagecoach Inn and tavern, which sits on 35 acres of woods, meadow, and lawn, has retained the charm of an earlier time and offers many original features, including wide plank pine floors, Rumford fireplaces, hand-hewn beams, a beehive oven, authentic Moses Eaton stenciling (hidden near a secret third staircase), and Chester's first hot water bathtub. The residence features nine bright and spacious guestrooms, all with their own private baths and great views, as well as a spacious owner's quarters, an Inn office and a lovely stone garage. Enjoy meals in the comfortable country dining room, relax on the back porch and in the guest parlor by the fireplace while mingling with loved ones. There is plenty of space for all to enjoy inside and out. You will love the beautiful natural surroundings in every season, including a private, spring-fed pond and acres of meadow, woods and paths for hiking, swimming, ice skating, snowshoeing and cross-country skiing-right on the premises! The setting is quiet, serene, peaceful, and only minutes away from the Village of Chester. Opportunity calls! This property has not been offered for sale for over 20 years.

Listed by Hergenrother Realty Group and Terri Naroian of KW Vermont

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$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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244 Main Street Chester VT 05143

Chester, VT244 Main Street

Price$425,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4816260

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 4,475

One of the most beloved properties in the town of Chester. There are very few homes that possess the history and character of this historic 1820 Victorian beauty. It has been cared for and had been run as a family owned Inn for nearly three decades. It's now ready for it's next chapter in which many possibilities exist. The main house has six bedrooms on the second floor each with it's own private bathroom. On the first floor you'll find a country kitchen, formal dining room, large front living room and a den that's ideal for a home office with fiber optic internet. You will also find gorgeous hardwood floors, original interior oak trim and a grand stairway leading up to the second floor. A classic front porch that gazes across to the town green. Connected to the house is a barn that had been used for retail space with a lovely one bedroom apartment above it. The property also features a carriage house which like the home is also on the National Historic Register. The carriage house still has the original horse stalls from back in the day. At the back of the property is a private 3 bedroom cottage ideal for a guest house. So many possibilities exist. Located across from the vibrant town green with its retail stores and restaurants. Just a short drive to several major ski areas including Okemo, Stratton, Magic and Bromley.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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 Colburn Road Chester VT 05143

Chester, VT60 Colburn Road

Price$369,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4816948

  • Residential Single Family
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 1,584

Have you ever dreamed of operating your own farm in a picturesque Vermont town? Take advantage of this rare opportunity to expand on this spacious stone structure, situated on 102 acres, surrounded by open fields, woodlands, and the Williams River. Recovering from a fire in 2012, the interior has been reconstructed and ready for you to craft it into the home you've always desired! Enjoy the variety of agriculture embedded on the land, including 13+/- acres of crop fields + orchards! Pick from the organic blueberry farm and host many delicious meals featuring lots of flavor from your garlic + herb gardens! Find serenity in your established perennial gardens, or skip rocks along the trout pond with friends and family. Nature is no stranger to this residence as the land features a large 30x70 chicken coop and honey bees to pollinate the gardens! Adventurer at heart? This amazing location is only minutes away from the Okemo Mountain Resort and offers private access to the V.A.S.T. snowmobile trail! Bordering 30+ acres of preserved habitat, you will love the ease of country living in this historic 2-story home. Schedule your showing, today!

Listed by Hergenrother Realty Group and Daniel Preston of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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662 Main Street Chester VT 05143

Chester, VT662 Main Street

Price$349,000

Est. Mortgage: $/month

MLS Number 4828399

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,195

Located in the heart of the village, just a short distance from the historic Chester Green you will find this absolute gem of a home and property. This is a wonderfully cared for 3 bedroom, 3 bathroom family home that boasts refinished hardwood floors and freshly painted rooms. The first floor has a large kitchen with tons of counter space and cabinets as well as a brand new gas range. You'll find a lovely formal dining room with a built in china cabinet. Off the dining room is a den ideal for a home office or study. The living room features and abundance windows facing the front yard that allows for great sunlight all throughout the day. You will also find a full bath and laundry room on the first floor as well as a four season sky lit sunroom off the kitchen that opens out to the back wrap around deck. The second floor features a large primary bedroom with new flooring and its own private bath with walk in closet and a soaking tub. You'll also have fantastic view of the beautiful pastures of neighboring Buttonwood farm. There are two other good sized bedrooms and an additional bathroom rounding out the second floor. All on a level village lot with a classic New England front porch to relax and watch the world go by. Property also boasts a one car garage and a nice private back yard. Conveniently located close to 4 major ski resorts and a short distance to all town amenities. This sweet village home is move in ready and waiting for it's next chapter.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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475 Flamstead Road Chester VT 05143

Chester, VT475 Flamstead Road

Price$325,000

Est. Mortgage: $/month

MLS Number 4834088

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 2,187

This is a beautiful farmhouse setting, located just a 1/2 mile from the center of historic Chester. This 62 acre property provides spectacular views of the Vermont countryside from anywhere in the front yard. Renovate the existing farmhouse, or build your own VT dream home. There's a new horse barn, several acres of pasture and an outdoor riding arena.

Listed by Christopher Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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49 Maple Hill Road Mount Holly VT 05758

Mount Holly, VT49 Maple Hill Road

Price$285,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4832183

  • Residential Single Family
  • Village Belmont
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Back on the Market! This Antique Village home is the perfect Vermont getaway. With broadband, high-speed internet and The Belmont Village community close by, including the Belmont General Store, Belmont Town Museum and charming local library this 3 bedroom family home offers tremendous historic character with todays conveniences. Stainless steel appliances and marble counters in the kitchen, newly-refinished floors, a sunny mudroom with slate tile floors and large storage closet. The beautiful living room has exposed beams, a new woodstove (to be installed in January) and direct access to a private backyard deck. All bedrooms are on the 2nd floor with another large full bath with bathtub. Fantastic closet space throughout. Snowmobile trail access is right from the house and it's a short drive to Okemo, Bromley, Stratton, Weston, Manchester and Woodstock.

Listed by Gail Beardmore and Rachael Hyjek of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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463 Main Street Chester VT 05143

Chester, VT463 Main Street

Price$275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4820846

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 1,821

Sweet opportunity to be located on Main Street in lovely Chester village. This is a great place to call home...you can tell the time of day by who is walking the 3 mile loop around the village! This home is in excellent condition. The attached shed and two story barn is going to make some hobbyist or woodworker a happy camper. The building is loaded with character...take a good look at the porch detail. From the driveway, you would walk into the attached shed with the entry that doubles as a mudroom. The large kitchen is big enough to be an eat-in kitchen and it has a great walk-in pantry. There is a full dining room and then through the French doors to the living room with antique bay window. There are two front bedrooms, one with a 3/4 bath. Upstairs there are three more bedrooms and two more 3/4 baths. There is a door to the unfinished attic over the barn. The home is partially furnished. The gardens are spectacular. If you don't wish to maintain them, the owner can share names of landscapers who would do that for you. There is a giant backyard with a super flat lawn. Enjoy it as it is, set up yard games or plant a vegetable garden. Have a look at the video. This is a special village property and it's ready for you!

Listed by Betty McEnaney of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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100 Benedict Road Dorset VT 05253

Dorset, VT100 Benedict Road

Price$169,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4817333

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,280

Historic East Dorset. A three bedroom, 2 bath home, first floor master, seated on a level lot, with easy access to Route 7A. The only lot on the street with access directly from 7A and Benedict Road. Homestead with 2 outbuildings. Once these buildings are down, they are down forever. Restore these buildings and use them as you need. Apply for a zoning variance and open up a small business. You have the parking already in place. OR, do as investors say, buy the lowest priced house in the neighbor and fix it up, and realize the largest equity on the street. Drive down Benedict Road and you'll see a street in transition. Speckled on the street are older homes restored to perfection. If you have the time, talent and are looking for a project, check out this estate. Home has new windows, new master bathroom, new sliding glass door, Move in to the house and rebuild the outbuildings? Put in a renter and fix up the outbuildings. too many options, come see for yourself how this estate can work for you.

Listed by Lynn Rawson and Adrienne Sherwood of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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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33 100 N Route Jamaica VT 05155

Jamaica, VT33 100 N Route

Price$155,000

Est. Mortgage: $/month

MLS Number 4680489

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,329

Charming historical farmhouse with barn located within minutes of the mountains! On the first floor you will find a full kitchen with walk-in pantry and soapstone sink next to separate dining and living rooms. A bathroom, master bedroom and full washer/dryer set can also be found on the main level. The second story has 2 bedrooms, one enjoys a spacious sitting room or office space. Upstairs has 2 large closets with plenty of storage space for all of your gear. Potential for Residential or Commercial use - check with Town of Jamaica. Change of Use would require Act 250 Approval. The Winhall River borders the lot and it is located in a Flood Zone.

Listed by Annie Bessette and Peggy O'Neill of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 2021
* 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 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 January 20, 2021.