Martha's Vineyard Historic Homes

Explore available historic homes on Martha's Vineyard. These beautiful properties were built between 1700 and 1930. You may find homes that have been completely renovated, others lovingly maintained with recent upgrades, and some that are ready for projects. View current real estate listings for historic houses below.

Historic Homes for Sale Martha's Vineyard

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40 Grove Avenue Vineyard Haven MA

Vineyard Haven, MA40 Grove Avenue

Price$2,500,000

Est. Mortgage: $/month

MLS Number 35851

  • Residential
  • Square Feet 5000
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

This wonderful combination of old and new sits in a historic spot formerly known as Holmes Hole, home to many sea captains. This is a gardener's eden with an oversized lot filled with perennials, a spectacular pool surrounded by cutting flowers, small cabana, and a charming fish pond. Enjoy water views from your large deck or take a short walk to the sandy beach at the end of the lane. Totaling 5000 sq. ft., boasting 4 bedrooms and several bathrooms, this partially renovated house with an addition was done with a discerning eye and master workmanship. The newer section includes a fabulous master suite with peeks of the water. The downstairs focuses on a magnificent yard and pool, with formal and informal areas to enjoy all seasons. The older bungalow section of the house also enjoys peeks of the water and charm of years gone by. This is a truly unique and whimsical spot in a great neighborhood near the Vineyard Haven Yacht Club, downtown Vineyard Haven, and the West Chop woods. Do not miss this rare opportunity to enjoy the best of both worlds.

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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74 North Water Street Edgartown MA

Edgartown, MA74 North Water Street

Price$3,750,000

Est. Mortgage: $/month

MLS Number 35817

  • Residential
  • Square Feet 3360
  • Bedrooms 7
  • Bathroom 3
  • Half Bath 1

The Captain Henry Pease II House, dating back to the 1830's, has been nicely maintained and restored to preserve most of the historic details and character. Many nice features include beautiful wide planked pine floors, original molding, built-ins, finish details and six fireplaces. The spacious eat in kitchen has been tastefully renovated with modern amenities that include french doors that lead out to a brick patio and a private and beautifully maintained yard. The perfect spot for summer dining and entertaining. Upon entering the front entrance, there is an entryway with a curved staircase, a traditional front parlor, family room and formal dining room, each with fireplace. The second floor includes 2 guest bedrooms, each with fireplace, that share a full bath. The master has it's own en-suite bath with shower and soaking tub, fireplace and access to a second floor summer porch that offers nice water views of the Edgartown Harbor. A perfect spot for relaxing. A finished third floor with an additional 2 bedrooms and full bath. Easy access to the Edgartown Harbor, the Village and the Lighthouse.

Listed by Karen M. Overtoom R.E.

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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277 North Road Chilmark MA

Chilmark, MA277 North Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 35612

  • Residential
  • Square Feet 2914
  • Bedrooms 6
  • Bathroom 3
  • Half Bath 1

With a sweeping entrance through an expansive farm field, walking and riding trails, woodlands, pond, beach access, and total privacy, this feels like one of the exclusive home associations on the island, but this is yours all unto your own. Almost 70 acres of storied history, seclusion and a mile of stone walls throughout the property exude the authentic character of this long beloved farm in Chilmark. Past the antique post and beam barn, a granite bridge over Roaring Brook leads you to the back meadows and a beautiful ridgeline with strong views of the Vineyard Sound and the Elizabeth Islands. From this rise, the vista over the open meadows surrounding the ridge out to the rolling treetops of the north shore is equally enchanting and a landscape like no other on the island. Ride horses on the extensive trails throughout the property and out to the Sound for a swim. Even on your way to your beach, the Vineyard's past whispers to you as you pass the old brickyard. This is an extraordinary situation in which to create your island estate. This is the place James Cagney loved “beyond words” for the freedom and peace it provided. (PLEASE NOTE: There are 2 houses and a detached bedroom which are not habitable as is.)

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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87 Bellevue Avenue Vineyard Haven MA

Vineyard Haven, MA87 Bellevue Avenue

Price$3,600,000

Est. Mortgage: $/month

MLS Number 35371

  • Residential
  • Square Feet 2398
  • Bedrooms 5
  • Bathroom 2
  • Half Bath 2

This extraordinary waterfront home sits on a bluff overlooking the desirable Lagoon Pond, with views spanning to Eastville Point Beach and Vineyard Haven Harbor beyond. This home is sited on 1.57 acres of landscaped lawn with brilliant green oak trees and features 120 feet of frontage on Lagoon Pond. A stunning example of the perfect blend of historic charm and modern amenities, this classic Victorian style home was built in the 1870s as part of the Innisfail Inn, a summer resort that attracted famous actors, operetta stars, and musicians, who spent their days enjoying the ocean breeze and perfecting their craft with informal concerts on the wrap-around porch. This home has been thoughtfully renovated to include updated amenities. The kitchen was expanded; an eight-hundred-square-foot master bedroom suite including private bath, a walk-through closet, an office alcove, and air conditioning was added; and the porch was enlarged to wrap around the new living space. The interior of the house radiates happiness, with cheerful accents of color grounded by crisp white paint. Yet the vintage character of the home remains with original exposed joists, board walls, and open ceilings, keeping the feel of the Victorian cottage intact. In Celtic, Innisfail means "the abode of peace and rest", an accurate translation to convey the tranquility and beauty of this property. This is a rare opportunity to own a lovingly maintained home with a long and storied history, but most importantly, this elegant home is the perfect property for generations of gatherings for family and friends. This home directly abuts the vacant land for sale at 0 Howard Street. A buyer looking to keep the same feel and privacy that 87 Bellevue currently holds, should also consider buying the adjacent land with almost 150 feet of Lagoon frontage and a 4-bedroom septic in place.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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24 William Street Vineyard Haven MA

Vineyard Haven, MA24 William Street

Price$1,500,000

Est. Mortgage: $/month

MLS Number 34698

  • Residential
  • Square Feet 2036
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.31

A desirable and coveted location on historic William Street in Vineyard Haven. This delightful Greek Revival home has been well maintained over the years and offers a spacious yard, award winning flower gardens and a detached 2 car garage. This 4 bedroom antique features a nice floor plan with formal entertaining areas and cozy living spaces with oversized windows, multiple fireplaces and old-world charm such as wide board antique pine flooring, original molding, doors, and decorative windows throughout. The perfect In-Town location with easy access to downtown Vineyard Haven restaurants, shops, beaches and ferry.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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 Beach Plum Lane Chilmark MA

Chilmark, MA100 Beach Plum Lane

Price$8,500,000

Est. Mortgage: $/month

MLS Number 35399

  • Residential
  • Square Feet 2140
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.3

Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound and the village of Menemsha. This property, once featured on the cover of Architectural Digest, dates to the 1930's and was lovingly renovated and restored by the current owner and Joseph Dick, a well-known and respected architect on the Cape and Islands. The main house features two bedrooms, two baths, living and dining rooms with water views, fireplace, well-appointed kitchen, outdoor rain shower, and a front porch which provides a front row seat to those magical Menemsha sunsets and the Elizabeth Islands. The guest house has one bedroom and bath, large, open living and dining areas, an ample kitchen, and an outdoor shower. Adjacent to the guest house is a detached, one bedroom cottage. A cottage at the rear of the property contains an office with wide water views and a lower level space currently configured as a personal gym. The last of the five cottages on the property is used for storage of seasonal furnishings. Expansion of the main house is possible with permitting. The property has been approved for a five bedroom septic system (see listing broker for conditions). Mature landscaping, specimen trees and lush perennial gardens surround the property and delight the senses with vivid colors and welcoming floral scents. A short stroll on a deeded path takes one to the historic fishing village of Menemsha, it's seafood and craft shops and the calm waters at Menemsha Beach. A video tour of this property can be found here: https://vimeo.com/video/358902170

Listed by Russell Maloney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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10 Duck Pond Lane Aquinnah MA

Aquinnah, MA10 Duck Pond Lane

Price$1,700,000

Est. Mortgage: $/month

MLS Number 35274

  • Residential
  • Square Feet 2444
  • Bedrooms 5
  • Bathroom 6
  • Acreage 3.2

The property was a historic farm, though it is run as a B&B now. It is surrounded by stone walls, pond and stream. Ocean views from all the bedrooms with decks. Full stone foundation on first floor. Heartwood southern pine floors upstairs and bathrooms in each room.

Listed by Gay Head Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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31 Lamberts Cove Road Vineyard Haven MA

MLS Number 35174

  • Residential
  • Square Feet 5732
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 3

Tashmoo Farm, originally built before the Revolutionary War, has been meticulously and tastefully restored to preserve the historic character and grandeur. This gracious home is in pristine condition and now features 6 bedrooms, 5 full baths, 3 half baths, several sitting rooms, a more formal living room, dining room and family room. All new heating and A/C. The newly renovated kitchen includes 2 Sub Zero refrigerators, a Bosche dishwasher, Thermador double ovens and a five burner stove top. Many complimenting features include original moldings, 7 fireplaces, wide pine and fir floors and all new windows. A har-tru tennis court, gunite pool and a delightful pool house were added in the late 1990's. The pool house is accessible to both tennis and pool through oversized doors that lead to private patios covered by a pergola. It's is well equipped for entertaining with grill area and wet bar, a changing room and full bath. Beautifully landscaped grounds with expansive lawns overlooking rolling meadows, extensive perennial gardens surrounded by stone walls offers exceptional privacy. Access to Lake Tashmoo and the association dock.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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26 North Summer Street Edgartown MA

Edgartown, MA26 North Summer Street

Price$3,985,000

Est. Mortgage: $/month

MLS Number 34778

  • Residential
  • Square Feet 4360
  • Bedrooms 8
  • Bathroom 5
  • Half Bath 1

Located in the heart of historic downtown Edgartown on a prime commercial street lies this beautiful 1820's Colonial building on nearly 15,000 sq. ft. of property. There is substantial frontage on North Summer Street just a half block from Main Street. In addition, the rear of the property fronts the entire rear length of the town parking area that also offers entrances to a number of commercial businesses, including Espresso Love, Isola Restaurant and the Edgartown Cinemas. This property has tremendous potential to offer the many usages allowed in the Edgartown B1 district and could provide a wonderful mix of retail, office and residential uses. Please call to preview this unique opportunity.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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125 Main Street Vineyard Haven MA

Vineyard Haven, MA125 Main Street

Price$1,700,000

Est. Mortgage: $/month

MLS Number 33936

  • Residential
  • Square Feet 2770
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.18

Located at the edge of Downtown Vineyard Haven, this 3-bedroom home sits overlooking Vineyard Sound and Owen Park. The home dates back to 1870 and has been impeccably maintained by each generation of the same family since it was constructed. Owen Park abuts this property on two sides. This historic park in the heart of Vineyard Haven is one of the few public docks and access points to the water as well as to Vineyard Haven Harbor. It is enjoyed by sailors coming and going, families visiting the beach, and the site of the occasional summer concert under the gazebo. The house has been meticulously maintained and is a glimpse back in history. There are even photos inside of the house with a horse and buggy out from before Main Street was paved. All of the large pane windows are original and still have the distinctive “wavy” glass. The grand staircase that greets you when you enter the front door has not changed and neither have many of the wide plank wood floors. While a new owner will be looking to make updates to this home, the history, character, and location are one of a kind. This landmark Vineyard Haven property will continue to offer accessibility to town, open space, and the water for years to come. It is just waiting for the next owner to put their mark on it.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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1153 Main Street Vineyard Haven MA

Vineyard Haven, MA1153 Main Street

Price$10,499,000

Est. Mortgage: $/month

MLS Number 33535

  • Residential
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6
  • Half Bath 1

This three-story shingle-style air conditioned home on Vineyard Sound, an easy walk to the West Chop Club, epitomizes the relaxed elegance of late 19th-century seaside living. Beautifully restored and decorated, the 5,345-sf house ideally located on a peaceful private road, includes eight bedrooms, multiple formal and informal gathering areas, and wide porches with spectacular water views. A superb example of traditional coastal New England architecture with its cedar shingles and abundance of windows, gables, and gambrels, this meticulously maintained house was built in 1897 and renovated in the early 1990s, paying tribute to its historical detail while adding many amenities. A spacious gourmet kitchen, outfitted with high-end appliances, adjoins a casual dining/lounging area and connects through a butler's pantry to the formal dining room. Two living rooms, one with a large fireplace, comfortably accommodate a large gathering. The expansive master suite includes a balcony with water views, brick fireplace, spacious master bath, and adjoining sitting room and office. The .59-acre property makes the most of its dramatic setting with graceful perennial gardens, open lawns, and most importantly 2 possible sites for a pool. A private path leads to the West Chop Trust's north shore beach for lazy days in the sun, tide rides, and fishing. Just two miles from the center of Vineyard Haven, a West Chop classic similar to this home rarely comes on the market, and provides the perfect setting to create memories of your own for generations to come.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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93 South Water Street Edgartown MA

Edgartown, MA93 South Water Street

Price$7,500,000

Est. Mortgage: $/month

MLS Number 33715

  • Residential
  • Square Feet 5207
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 1

Located within Edgartown's charming Historic District and offering magical views across a tidal pond to Edgartown Harbor, lies this unique 5 bedroom residence. The home underwent a complete renovation in 2010 preserving every historic detail while introducing a fresh and stylish flair. The first floor offers a gourmet kitchen, family room, dining room and large living room with fireplace and French doors leading to the harbor facing deck. The 2nd floor offers 4 bedrooms and 3 baths. There is an entire wing offering an dramatic master bedroom suite with a 20 foot high, cathedral ceiling, an office, sitting room and luxurious bathroom. The lower level offers a second living space, bathroom and walkout to the covered grill area, exterior shower and pool / terrace area. Complimenting the property is a 2-car garage and perfectly landscaped lot which stretches from South Water Street to the waters edge, all located less than three blocks from Main Street.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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108 William Street Vineyard Haven MA

Vineyard Haven, MA108 William Street

Price$2,500,000

Est. Mortgage: $/month

MLS Number 31993

  • Residential
  • Square Feet 5534
  • Bedrooms 7
  • Bathroom 6
  • Acreage 0.657

Beautiful property inside and out at a great price point. This majestic harbor view property offers living at its best in a vibrant area of well maintained and preserved period homes just one block to Main Street plus Owen Park deep water dock, beach, bandstand, and boat moorings. Enjoy all the benefits with the village mere steps away, clay tennis courts around the corner, and two blocks to Tisbury school. The Steamship ferry dock is ultra convenient for commuters and excursions to the mainland. Located in the heart of William Street, this Bracketed-Italianate style gem is known as the Capt. Benjamin Cromwell House and was carefully sited on the highest point of the property in 1873. Perfectly proportioned cross gable and cupola, impeccably renovated and updated throughout, features include 6 bedrooms, 5 baths, chef's kitchen, oil heat, a/c, spacious finished third floor loft with soaring peaks. Don't forget the adorable cabin guest house with its climbing roses plus a two car garage while overlooking the .66 acre manicured grounds. Skip over to Owen Park to your dinghy or kayak, grab a morning swim or stretch on the beach, or simply soak up a magical sunrise or reflective sunset while the sea ebbs and flows. As the captain of the old Island Line transportation service with steam-powered side-wheelers, the Eagle's Wing and later the Monohansett, this property was an emblem of the Captain's success and enhanced by its prominent physical setting with surrounding decorative caste iron fencing. The architectural details, water views, spacious veranda, gleaming wood floors, 9' ceilings, crown molding, and more will captivate the attention of the most discerning buyer. The historic port of Holmes Hole became Vineyard Haven in 1871 and later Tisbury. William Street was the second street laid out by the village in 1831 and has consistently maintained its look. Truly a rare, in-town, luxury opportunity, in turn-key condition - a property which needs to be seen to be appreciated. Furnishings negotiable separately.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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54 Mayhew Norton Road West Tisbury MA

West Tisbury, MA54 Mayhew Norton Road

Price$1,150,000

Est. Mortgage: $/month

MLS Number 33055

  • Residential
  • Square Feet 1747
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.6

This lovely, unique home, nestled at the top of enchanting Indian Hill road, is warm with country charm and historic character. Recent extensive renovations include new windows, kitchen, bathroom and heating system, making this home comfortable for year round living. A covered porch welcomes you into the country kitchen complete with custom cabinets, soapstone counter tops and stainless steel appliances. The sun filled living room and wood paneled dining room each have fireplaces, beautiful wide pine floors and exposed timber ceilings. A cathedral post and beam addition houses the master bedroom suite with its own private bath, study and laundry. On the opposite end, is a second bright new bedroom and a charming renovated bathroom. The upper floor is its own separate sanctuary with a dormer ceiling bedroom and skylit sitting area. The heated walk out basement features exposed granite foundation walls and a beehive oven. A few steps from the house is the post and beam “Studio” which can also be used as an office and guest bedroom. The timber frame garage is spacious enough for a workshop and for storing bikes, surfboards and kayaks all conveniently accessible from the driveway. This 1.6 acre property is surrounded by pastoral beauty with mature trees, rolling hills and stone walls, all within a short distance of the trails of Cedar Tree Neck and hundreds of acres of conservation land. https://my.matterport.com/show/?m=qBmD4PmVsCP

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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508 North Road Chilmark MA

Chilmark, MA508 North Road

Price$750,000

Est. Mortgage: $/month

MLS Number 32266

  • Residential
  • Square Feet 900
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.1

Historically known as the Cooper Gallery, this endearing icon of Menemsha has remained in the same family for years. A 3 bedroom cottage with a wonderful location, centrally located to all things Menemsha has to offer. Large Kitchen space with dining space, spacious living room, full bathroom and a bedroom make up the first floor plus a large deck space. Upstairs is two bright bedrooms with skylights.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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