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Woodstock VT Real Estate

Once named the “Prettiest Small Town in America” Woodstock is the shire town of Windsor County, Vermont. Its picturesque village has won awards for its beautiful scenery and streetscapes making it a year-round destination. The town of Woodstock hosts several annual events and festivals including December’s Wassail Weekend in which the town transforms into a winter wonderland with lights, decorations, and charm. Woodstock is home to a welcoming, tight-knit community that embraces the town’s unique character. 

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353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4934539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 10
  • Square Feet 11,470

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

Listed by Christopher Lang of LandVest,Inc/Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Square Feet 5,412
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley of Williamson Group Sothebys Intl. Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Bedrooms 6
  • Square Feet 5,142
  • Construction Existing
  • Bathroom 8

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

Listed by Carol Wood and Danny Kogut of Williamson Group Sothebys Intl. Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 15
  • Square Feet 10,206

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer's market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

311 Densmore Hill Road Woodstock VT 05048

Woodstock, VT311 Densmore Hill Road

Price$3,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4932341

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,456

This extraordinary 115 acre property, located in the towns of Woodstock & Hartland, offers the perfect mosaic of qualities that buyers are looking for. The acreage is unencumbered and presents the perfect opportunity for a family estate, future development or equestrian opportunities with grass covered hillsides, trail systems and the GMHA just 3 miles away. The diverse topography of the property with trails throughout has an easily accessible summit offering a unique homesite location with spectacular unobstructed panoramic long range views that can be captured from sunrise to sunset. For the winter sports enthusiast, you have it all right here. The extensive trail systems can be combined for snowmobiles, nordic or alpine skiing. The level of stewardship is evident from the maintenance of the extensive trail systems, existing structures and grounds to the main pond that is deep and well stocked. The structures include a very comfortable two story cottage with long vista views, a large barn/garage, two stall horse barn with run-in and a split rail fenced area. There is also a three sided oversize pole barn currently being used for equipment storage located at the end of one of the trails. The property is accessed off a municipal road via (3) gated entry points. A gazebo at the summit takes in nearly 360 degree long range views providing the idyllic setting for a substantial residence. The properties captivating views and trailed woodlands stand ready to implant your vision.

Listed by Roger Danyew of Diamond Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4 Bond Street Woodstock VT 05091

Woodstock, VT4 Bond Street

Price$3,250,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4877059

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5

4 Bond Street stands in a prominent but discrete location in the center of the village of Woodstock, VT. Distinguished on many levels, the property represents an incredible opportunity for the next owner to take stewardship of what is undeniably a unique historical American architectural treasure. The multi-generational home of the Billings family, 4 Bond Street has been home to both a Governor and a Chief Justice of the Green Mountain State. The legacy of the family is significant in the historic preservation and land conservation of the area. The first period brick Federal has been modified and expanded over the last two centuries but still retains much of its original historic character through the preservation of its defining architectural materials, design, adornments, and room proportions. Quarter sawn, clear white oak floors, waxed to show their extraordinary beauty and durability over the last 200 years grace the interior. Preserved period mouldings, chair rails, built-in cabinetry and bookshelves can be found throughout. Set on over one and a quarter acre with frontage on the Kedron Brook, the property is unique for its setting and size. A detached three car barn/garage sits at a pleasant distance from the main house. 4 Bond Street is a once in a lifetime opportunity to take stewardship of a rare historical asset as well as an opportunity to make an extraordinary home in the heart of one of America's most beautiful villages.

Listed by Richard Higgerson and Laird Bradley of Williamson Group Sothebys Intl. Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

144 & 232 Town Farm Road Woodstock VT 05071

Woodstock, VT144 & 232 Town Farm Road

Price$2,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4937127

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 3,748

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock. The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, tennis court and smokehouse, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. The houses and studio invite thoughtful renovation to meet the quality of the site: its woodlands, hayfields, and farm pond, threaded by trails and farm roads to high meadows with valley views. The beauty of the land, authenticity, and character distinguish this generational offering. No showings November 24-26

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

89 Academy Circle Woodstock VT 05071

Woodstock, VT89 Academy Circle

Price$2,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4936765

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,139

Knoll Brook Bend is one of the premier landmark homes in the historic village of South Woodstock , Vt. Sitting up on a hill looking out over the village and bordered by the lovely Kedron Brook it is truly breathtaking. The original features have been left intact while updating the home with modern conveniences. The stone work and landscaping enhance the grounds in keeping with the Federal architectural style of the 1831 house. The living room with wall of bookcases and fireplace offers a beautiful place for entertaining . The large chef's kitchen makes cooking for a large or small crowd a joy . This is Village living at its best . Walk to the Kedron Inn for dinner at the Ransom Tavern , take a swim in the Kedron pond or pick up lunch at the country store. Only 5 minutes into Woodstock. Skiing at Six, and Killington minutes away . Green Mountain Horse Association is within walking distance to observe world class horse events . There are year round actives to enjoy whatever ones interests are from music to live theater and all types of arts events .

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

19 the Green Woodstock VT 05091

Woodstock, VT19 the Green

Price$2,250,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4928047

  • Residential Single Family
  • Bedrooms 6
  • Square Feet 4,454
  • Construction Existing
  • Bathroom 7

THE OTIS SKINNER HOUSE - Once owned by famed stage actor Otis Skinner, this historic Woodstock village home has been lovingly and comprehensively updated by its current owners. The spacious gourmet kitchen is a home chef's dream with a stunning Lacanche range, dual dishwashers, a brand new Sub-Zero refrigerator, ample counter space, and abundant storage. Redesigned and renovated in 2011 around a central windowed "tower," the home overlooks the Ottauquechee River and the covered bridge; Pella casements welcome in stunning sunset views and the sounds of water journeying to the Connecticut. With at least six flexible bedroom spaces - including a third-floor guest suite - a formal office, and multiple common spaces, this home accommodates a houseful as comfortably as it provides a cozy home for just a few. From the copper roof to the central air on the second and third floors to excellent heating systems, 19 the Green is well designed to greet every New England season. Beautifully situated on Woodstock's fabled Green and a short stroll from shops and restaurants, the Otis Skinner house enjoys the best of two worlds - the home may be situated at the heart of the village, but it truly lives on the burbling banks of the Ottauquechee.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2 Border Lane Woodstock VT 05091

Woodstock, VT2 Border Lane

Price$2,250,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4939125

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 5,897

This sun-soaked estate offers everything you could dream of in a Vermont property. Privacy without isolation, plenty of acreage for outdoor activities, and a short walk to the “Currier & Ives” town of Woodstock, VT, with its chic shops, top-notch restaurants, and sports facilities. Meticulous attention to detail during recent renovations has rendered this home a delightful marriage of country charm and contemporary convenience. The kitchen boasts marble countertops, inlaid cupboards, an induction cooktop, a sub-zero refrigerator, and a Cove dishwasher. This eat-in kitchen opens to a roomy but intimate family room and leads to a formal dining room. The spacious center hall opens to a sunken living room that enjoys dramatic long-range views from one perspective and lovely short-range views from another, making this home a rare find, particularly for an in-town property. There are two options for the primary bedroom, one is upstairs, and the other is on the ground level. There is a guest room upstairs and one on the first floor. All four bedrooms are ensuite. The basement has ample storage space and is perfect for a large rec room, in addition to a separate studio/workshop, and laundry room/exercise room, and bathroom. Border Lane is a highly coveted address for good reason. Matteport and video tour available. Call for an appointment to see this one of a kind property.

Listed by Jennifer Falvey of KW Vermont Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

26 The Green Woodstock VT 05091

Woodstock, VT26 The Green

Price$2,150,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4933190

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,864

The Historic Daughter's of the American Revolution (DAR) Mansion was constructed in 1807 by Tilley Parker to serve as housing for Vermont's early legislature & tavern. A master preservationist undertook a complete restoration of the original dwelling in 1995 with an architecturally sympathetic addition using original materials combined with elements crafted using authentic hand tools. The result blends the patina of an antique structure with an aesthetically elegant kitchen, baths & modern mechanical systems offering the best of yesterday & today. Living & dining rooms feature wide board floors, antique brick fireplaces, crown moldings & chair rails, all enclosed by airy 9+ foot high ceilings. The library is warmed by a 3rd fireplace, flanked by hand-made mahogany bookshelves & raised paneling for a gracious comfortable retreat. Generous country kitchen is outfitted with professional style appliances, granite surfaces & custom cherry cabinets & opens into a comfortable family gathering room framed floor to ceiling with windows flooding the space with warm natural light throughout the year. Upstairs accommodations include 2 guest bedrooms, each with fireplace & private bath, as well as a master bedroom suite with dressing area, bath accented by marble & tile and a spacious bedroom with elevated tray ceiling. Two finished rooms on the lower level with bathroom provide space for seasonal gatherings or a media/exercise room. Walk to all Village amenities!

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5250 West Woodstock Road Woodstock VT 05091

Woodstock, VT5250 West Woodstock Road

Price$1,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4918791

  • Residential Single Family
  • Bathroom 9
  • Bedrooms 9
  • Construction Existing
  • Square Feet 4,502

The iconic Farmhouse Inn overlooking the Ottauquechee River is located west of Woodstock Village within 15- and 30-minutes' drive of the Killington and Okemo ski resorts, respectively. Known locally as the Robinson Farm, after the family that build the handsome home and legendary barn shortly after the turn of the 20th Century. The property has been converted by the present owners into a gracious and authentic rural farm environment for vacations, weddings, and other events large and small. The historic 1905 Farmhouse Inn offers accommodation in the 7 Guest Rooms, all with private baths and gracious gathering rooms on the first floor. A 2-bedroom Innkeeper's quarters provides private living space. The Red Barn was constructed in the style of a 'bank barn' with grade level entry points to the different levels of the barn where they served a variety of agricultural purposes. The massive timber frame is exposed on all levels with the upper two having been adapted for the event venue hosting up to 150 guests. The White Barn accommodates 50 guests for smaller ceremonies and other events with a wide deck providing a place of seasonal outdoor dining. 13 acres of open land and convenient location offer the potential to create a farm-to-table restaurant, direct-to-consumer shop selling local and regional goods or an immersive Agri-tourism guest experience. Less hospitality-oriented uses as a gentleman's farm or niche farm producing or marketing local goods are great options as well.

Listed by Rachel Arsenault and Laird Bradley of Williamson Group Sothebys Intl. Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2023 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 31, 2023 3:54 AM EST.

 

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